메뉴 건너뛰기




Volumn 4, Issue 11, 2012, Pages 1409-1438

Macrocycles in new drug discovery

Author keywords

[No Author keywords available]

Indexed keywords

BETA SECRETASE 1; BETA SECRETASE INHIBITOR; CD135 ANTIGEN; CILENGITIDE; CYCLIN DEPENDENT KINASE 2 INHIBITOR; CYCLIN DEPENDENT KINASE INHIBITOR; CYCLOSPORIN A; EPOTHILONE B; HEAT SHOCK PROTEIN 90 INHIBITOR; IXABEPILONE; JANUS KINASE 2 INHIBITOR; MACROCYCLIC COMPOUND; MOLECULAR SCAFFOLD; PACRITINIB; PHOSPHOTRANSFERASE INHIBITOR; PROTEIN TYROSINE KINASE INHIBITOR; RADICICOL; REBECCAMYCIN; RENIN INHIBITOR; RUBOXISTAURIN; STAUROSPORINE; TANESPIMYCIN; TEMSIROLIMUS; ZEARALENONE;

EID: 84864679725     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.12.93     Document Type: Review
Times cited : (381)

References (99)
  • 1
    • 46449115901 scopus 로고    scopus 로고
    • The exploration of macrocycles for drug discovery - An underexploited structural class
    • DOI 10.1038/nrd2590, PII NRD2590
    • Driggers EM, Hale SP, Lee J, Terrett NK. The exploration of macrocycles for drug discovery - an underexploited structural class. Nat. Rev. Drug Discov. 7(7), 608-624 (2008). (Pubitemid 351927725)
    • (2008) Nature Reviews Drug Discovery , vol.7 , Issue.7 , pp. 608-624
    • Driggers, E.M.1    Hale, S.P.2    Lee, J.3    Terrett, N.K.4
  • 2
    • 77955607298 scopus 로고    scopus 로고
    • Macrocycles in medicinal chemistry and drug discovery
    • Oyelere AK. Macrocycles in medicinal chemistry and drug discovery. Curr. Top. Med. Chem. 10(14), 1359-1360 (2010).
    • (2010) Curr. Top. Med. Chem. , vol.10 , Issue.14 , pp. 1359-1360
    • Oyelere, A.K.1
  • 3
    • 79953777824 scopus 로고    scopus 로고
    • Macrocycles are great cycles: Applications, opportunities, and challenges of synthetic macrocycles in drug discovery
    • Marsault E, Peterson ML. Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery. J. Med. Chem. 54(7), 1961-2004 (2011).
    • (2011) J. Med. Chem. , vol.54 , Issue.7 , pp. 1961-2004
    • Marsault, E.1    Peterson, M.L.2
  • 4
    • 77955600915 scopus 로고    scopus 로고
    • Advances in the development of macrocyclic inhibitors of hepatitis C virus NS3-4A protease
    • Avolio S, Summa V. Advances in the development of macrocyclic inhibitors of hepatitis C virus NS3-4A protease. Curr. Top. Med. Chem. 10(14), 1403-1422 (2010).
    • (2010) Curr. Top. Med. Chem. , vol.10 , Issue.14 , pp. 1403-1422
    • Avolio, S.1    Summa, V.2
  • 5
    • 77955615249 scopus 로고    scopus 로고
    • Chemoinformatic analysis of biologically active macrocycles
    • Brandt W, Haupt VJ, Wessjohann LA. Chemoinformatic analysis of biologically active macrocycles. Curr. Top. Med. Chem. 10(14), 1361-1379 (2010).
    • (2010) Curr. Top. Med. Chem. , vol.10 , Issue.14 , pp. 1361-1379
    • Brandt, W.1    Haupt, V.J.2    Wessjohann, L.A.3
  • 6
    • 77955625804 scopus 로고    scopus 로고
    • Macrocycle molecules for the management of systemic infections: The clarithromycin paradigm
    • Giamarellos-Bourboulis EJ. Macrocycle molecules for the management of systemic infections: the clarithromycin paradigm. Curr. Top. Med. Chem. 10(14), 1470-1475 (2010).
    • (2010) Curr. Top. Med. Chem. , vol.10 , Issue.14 , pp. 1470-1475
    • Giamarellos-Bourboulis, E.J.1
  • 9
    • 77955638589 scopus 로고    scopus 로고
    • Recent advances in the medicinal chemistry of novel erythromycinderivatized antibiotics
    • Ying L, Tang D. Recent advances in the medicinal chemistry of novel erythromycinderivatized antibiotics. Curr. Top. Med. Chem. 10(14), 1441-1469 (2010).
    • (2010) Curr. Top. Med. Chem. , vol.10 , Issue.14 , pp. 1441-1469
    • Ying, L.1    Tang, D.2
  • 11
    • 15444377930 scopus 로고    scopus 로고
    • What can a chemist learn from nature's macrocycles? - A brief, conceptual view
    • DOI 10.1007/s11030-005-1314-x
    • Wessjohann LA, Ruijter E, Garcia-Rivera D, Brandt W. What can a chemist learn from nature's macrocycles? A brief, conceptual view. Mol. Divers. 9(1), 171-186 (2005). (Pubitemid 40394851)
    • (2005) Molecular Diversity , vol.9 , Issue.1-3 , pp. 171-186
    • Wessjohann, L.A.1    Ruijter, E.2    Garcia-Rivera, D.3    Brandt, W.4
  • 12
    • 77951729433 scopus 로고    scopus 로고
    • FDA approval summary: Temsirolimus as treatment for advanced renal cell carcinoma
    • Kwitkowski VE, Prowell TM, Ibrahim A et al. FDA approval summary: temsirolimus as treatment for advanced renal cell carcinoma. Oncologist 15(4), 428-435 (2010).
    • (2010) Oncologist , vol.15 , Issue.4 , pp. 428-435
    • Kwitkowski, V.E.1    Prowell, T.M.2    Ibrahim, A.3
  • 15
    • 45549107234 scopus 로고    scopus 로고
    • Novel cytotoxic agents: Epothilones
    • Goodin S. Novel cytotoxic agents: epothilones. Am. J. Health Syst. Pharm. 65(10, Suppl. 3), S10-S15 (2008).
    • (2008) Am. J. Health Syst. Pharm. , vol.65 , Issue.10 SUPPL. 3
    • Goodin, S.1
  • 16
    • 56049127901 scopus 로고    scopus 로고
    • Ixabepilone: A novel microtubulestabilizing agent for the treatment of metastatic breast cancer
    • Goodin S. Ixabepilone: a novel microtubulestabilizing agent for the treatment of metastatic breast cancer. Am. J. Health Syst. Pharm. 65(21), 2017-2026 (2008).
    • (2008) Am. J. Health Syst. Pharm. , vol.65 , Issue.21 , pp. 2017-2026
    • Goodin, S.1
  • 17
    • 33746377987 scopus 로고    scopus 로고
    • Inhibitors of the HSP90 molecular chaperone: Attacking the master regulator in cancer
    • DOI 10.2174/156802606777812004
    • Mcdonald E, Workman P, Jones K. Inhibitors of the HSP90 molecular chaperone: attacking the master regulator in cancer. Curr. Top. Med. Chem. 6(11), 1091-1107 (2006). (Pubitemid 44110922)
    • (2006) Current Topics in Medicinal Chemistry , vol.6 , Issue.11 , pp. 1091-1107
    • McDonald, E.1    Workman, P.2    Jones, K.3
  • 18
    • 80755140046 scopus 로고    scopus 로고
    • SB1518, a novel macrocyclic pyrimidinebased JAK2 inhibitor for the treatment of myeloid and lymphoid malignancies
    • Hart S, Goh KC, Novotny-Diermayr V et al. SB1518, a novel macrocyclic pyrimidinebased JAK2 inhibitor for the treatment of myeloid and lymphoid malignancies. Leukemia 25(11), 1751-1759 (2011).
    • (2011) Leukemia , vol.25 , Issue.11 , pp. 1751-1759
    • Hart, S.1    Goh, K.C.2    Novotny-Diermayr, V.3
  • 19
    • 84858848013 scopus 로고    scopus 로고
    • Results of a Phase 2 study of pacritinib (SB1518), a novel oral JAK2 inhibitor, in patients with primary, post-polycythemia vera, and post-essential thrombocythemia myelofibrosis
    • San Diego Convention Center, San Diego, CA, USA, 10-13 December
    • Komrojki RS, Wadleigh M, Seymour JF et al. Results of a Phase 2 study of pacritinib (SB1518), a novel oral JAK2 inhibitor, in patients with primary, post-polycythemia vera, and post-essential thrombocythemia myelofibrosis. Presented at: 53rd ASH Annual Meeting and Exposition. San Diego Convention Center, San Diego, CA, USA, 10-13 December 2011.
    • (2011) 53rd ASH Annual Meeting and Exposition
    • Komrojki, R.S.1    Wadleigh, M.2    Seymour, J.F.3
  • 20
    • 84862908102 scopus 로고    scopus 로고
    • Discovery of kinase spectrum selective macrocycle (16E)-14-methyl-20- oxa5,7,14,26-tetraazatetracyc lo19.3.1.1(2,6).1(8,12)heptacosa- 1(25),2(26),3,5,8(27),9,11,16,21,23- decaene (SB1317/TG02), a potent inhibitor of cyclin dependent kinases (CDKs), janus kinase 2 (JAK2), and Fms-like tyrosine kinase-3 (FLT3) for the treatment of cancer
    • William AD, Lee ACH, Goh KC et al. Discovery of kinase spectrum selective macrocycle (16E)-14-methyl-20- oxa5,7,14,26-tetraazatetracyc lo19.3.1.1(2,6).1(8,12)heptacosa- 1(25),2(26),3,5,8(27),9,11,16,21,23- decaene (SB1317/TG02), a potent inhibitor of cyclin dependent kinases (CDKs), janus kinase 2 (JAK2), and Fms-like tyrosine kinase-3 (FLT3) for the treatment of cancer. J. Med. Chem. 55(1), 169-196 (2012).
    • (2012) J. Med. Chem. , vol.55 , Issue.1 , pp. 169-196
    • William, A.D.1    Lee, A.C.H.2    Goh, K.C.3
  • 21
    • 79952741178 scopus 로고    scopus 로고
    • Cilengitide: The first anti-angiogenic small molecule drug candidate. design, synthesis and clinical evaluation
    • Mas-Moruno C, Rechenmacher F, Kessler H. Cilengitide: the first anti-angiogenic small molecule drug candidate. design, synthesis and clinical evaluation. Anticancer Agents Med. Chem. 10(10), 753-768 (2010).
    • (2010) Anticancer Agents Med. Chem. , vol.10 , Issue.10 , pp. 753-768
    • Mas-Moruno, C.1    Rechenmacher, F.2    Kessler, H.3
  • 22
    • 78049253211 scopus 로고    scopus 로고
    • Cilengitide in newly diagnosed glioblastoma with MGMT promoter methylation: Protocol of a multicenter, randomized, open-label, controlled phase III trial (CENTRIC)
    • Stupp R, Van Den Bent MJ, Erridge SC et al. Cilengitide in newly diagnosed glioblastoma with MGMT promoter methylation: Protocol of a multicenter, randomized, open-label, controlled phase III trial (CENTRIC). J. Clin. Oncol. 28(15s), TPS152 (2010).
    • (2010) J. Clin. Oncol. , vol.28 , Issue.15 S
    • Stupp, R.1    Van Den Bent, M.J.2    Erridge, S.C.3
  • 23
    • 79953782257 scopus 로고    scopus 로고
    • Potent anti-tumor activity of a macrocycle-quinoxalinone class pan-Cdk inhibitor in vitro and in vivo
    • Hirai H, Takahashi-Suziki I, Shimomura T et al. Potent anti-tumor activity of a macrocycle-quinoxalinone class pan-Cdk inhibitor in vitro and in vivo. Invest. New Drugs 29(4), 534-543 (2011).
    • (2011) Invest. New Drugs , vol.29 , Issue.4 , pp. 534-543
    • Hirai, H.1    Takahashi-Suziki, I.2    Shimomura, T.3
  • 24
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • DOI 10.1016/S0169-409X(00)00129-0, PII S0169409X00001290
    • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 46(1-3), 3-26 (2001). (Pubitemid 33653411)
    • (2000) Advanced Drug Delivery Reviews , vol.46 , Issue.1-3 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 25
    • 33751106653 scopus 로고    scopus 로고
    • New approaches to molecular cancer therapeutics
    • DOI 10.1038/nchembio840, PII NCHEMBIO840
    • Collins I, Workman P. New approaches to molecular cancer therapeutics. Nat. Chem Biol. 2(12), 689-700 (2006). (Pubitemid 44764211)
    • (2006) Nature Chemical Biology , vol.2 , Issue.12 , pp. 689-700
    • Collins, I.1    Workman, P.2
  • 26
    • 84942886311 scopus 로고    scopus 로고
    • Compound properties and drug quality
    • Wermuth C (Ed.). Academic Press, London, UK
    • Lipinski CA. Compound properties and drug quality. In: In The Practice of Medicinal Chemistry (Second Edition). Wermuth C (Ed.). Academic Press, London, UK, 341 (2003).
    • (2003) The Practice of Medicinal Chemistry (Second Edition) , pp. 341
    • Lipinski, C.A.1
  • 30
    • 52049109838 scopus 로고    scopus 로고
    • Natural products in drug discovery
    • Harvey AL. Natural products in drug discovery. Drug Discov. Today 13(19-20), 894-901 (2008).
    • (2008) Drug Discov. Today , vol.13 , Issue.19-20 , pp. 894-901
    • Harvey, A.L.1
  • 31
    • 84882530434 scopus 로고    scopus 로고
    • Conformational restriction and/or steric hindrance in medicinal chemistry
    • Academic Press, London, UK
    • Mann A. Conformational restriction and/or steric hindrance in medicinal chemistry. In: The Practice Of Medicinal Chemistry, Wermuth CG (Ed.). Academic Press, London, UK (2008).
    • (2008) The Practice of Medicinal Chemistry, Wermuth CG (Ed.)
    • Mann, A.1
  • 32
    • 79959243001 scopus 로고    scopus 로고
    • Thermodynamics of ligand binding and efficiency
    • Reynolds CH, Holloway MK. Thermodynamics of ligand binding and efficiency. ACS Med. Chem. Lett. 2(6), 433-437 (2011).
    • (2011) ACS Med. Chem. Lett. , vol.2 , Issue.6 , pp. 433-437
    • Reynolds, C.H.1    Holloway, M.K.2
  • 33
    • 77953631827 scopus 로고    scopus 로고
    • A medicinal chemist's guide to molecular interactions
    • Bissantz C, Kuhn B, Stahl M. A medicinal chemist's guide to molecular interactions. J. Med. Chem. 53(14), 5061-5084 (2010).
    • (2010) J. Med. Chem. , vol.53 , Issue.14 , pp. 5061-5084
    • Bissantz, C.1    Kuhn, B.2    Stahl, M.3
  • 34
    • 77949347414 scopus 로고    scopus 로고
    • Hydrophobicity - Shake flasks, protein folding and drug discovery
    • Sarkar A, Kellogg GE. Hydrophobicity - shake flasks, protein folding and drug discovery. Curr. Top Med. Chem. 10(1), 67-83 (2010).
    • (2010) Curr. Top Med. Chem. , vol.10 , Issue.1 , pp. 67-83
    • Sarkar, A.1    Kellogg, G.E.2
  • 35
    • 0036266270 scopus 로고    scopus 로고
    • Changes in motion vs. bonding in positively vs. negatively cooperative interactions
    • Williams DH, Calderone CT, O'Brien DP, Zerella R. Changes in motion vs. bonding in positively vs. negatively cooperative interactions. Chem. Comm. (12), 1266-1267 (2002). (Pubitemid 34594554)
    • (2002) Chemical Communications , Issue.12 , pp. 1266-1267
    • Williams, D.H.1    Calderone, C.T.2    O'Brien, D.P.3    Zerella, R.4
  • 36
    • 78649233754 scopus 로고    scopus 로고
    • Thermodynamic and structural effects of macrocyclic constraints in protein-ligand interactions
    • DeLorbe JE, Clements JH, Whiddon BB, Martin SF. Thermodynamic and structural effects of macrocyclic constraints in protein-ligand interactions. ACS Med. Chem. Lett. 1(8), 448-452 (2010).
    • (2010) ACS Med. Chem. Lett. , vol.1 , Issue.8 , pp. 448-452
    • Delorbe, J.E.1    Clements, J.H.2    Whiddon, B.B.3    Martin, S.F.4
  • 39
    • 42949157650 scopus 로고    scopus 로고
    • Macrocyclic aminopyrimidines as multitarget CDK and VEGF-R inhibitors with potent antiproliferative activities
    • Lücking U, Siemeister G, Schäfer M et al. Macrocyclic aminopyrimidines as multitarget CDK and VEGF-R inhibitors with potent antiproliferative activities. ChemMedChem 2(1), 63-77 (2007).
    • (2007) ChemMedChem , vol.2 , Issue.1 , pp. 63-77
    • Lücking, U.1    Siemeister, G.2    Schäfer, M.3
  • 40
    • 38149041702 scopus 로고    scopus 로고
    • Structurebased design and synthesis of novel macrocyclic pyrazolo1,5-a1,3,5triazine compounds as potent inhibitors of protein kinase CK2 and their anticancer activities
    • Nie Z, Perretta C, Erickson P et al. Structurebased design and synthesis of novel macrocyclic pyrazolo1,5-a1,3,5triazine compounds as potent inhibitors of protein kinase CK2 and their anticancer activities. Bioorg. Med. Chem. Lett. 18(2), 619-623 (2008).
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , Issue.2 , pp. 619-623
    • Nie, Z.1    Perretta, C.2    Erickson, P.3
  • 41
    • 79952804851 scopus 로고    scopus 로고
    • Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry
    • Ishikawa M, Hashimoto Y. Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry. J. Med. Chem. 54(6), 1539-1554 (2011).
    • (2011) J. Med. Chem. , vol.54 , Issue.6 , pp. 1539-1554
    • Ishikawa, M.1    Hashimoto, Y.2
  • 42
    • 71049126548 scopus 로고    scopus 로고
    • Escape from flatland: Increasing saturation as an approach to improving clinical success
    • Lovering F, Bikker J, Humblet C. Escape from flatland: increasing saturation as an approach to improving clinical success. J. Med. Chem. 52(21), 6752-6756 (2009).
    • (2009) J. Med. Chem. , vol.52 , Issue.21 , pp. 6752-6756
    • Lovering, F.1    Bikker, J.2    Humblet, C.3
  • 43
    • 77952320391 scopus 로고    scopus 로고
    • Macrocyclic BACE inhibitors: Optimization of a micromolar hit to nanomolar leads
    • Huang Y, Strobel ED, Ho CY et al. Macrocyclic BACE inhibitors: optimization of a micromolar hit to nanomolar leads. Bioorg. Med. Chem. Lett. 20(10), 3158-3160 (2010).
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , Issue.10 , pp. 3158-3160
    • Huang, Y.1    Strobel, E.D.2    Ho, C.Y.3
  • 46
    • 1942453243 scopus 로고    scopus 로고
    • Ligand efficiency: A useful metric for lead selection
    • DOI 10.1016/S1359-6446(04)03069-7, PII S1359644604030697
    • Hopkins AL, Groom CR, Alex A. Ligand efficiency: a useful metric for lead selection. Drug Discov. Today 9(10), 430-431 (2004). (Pubitemid 38510559)
    • (2004) Drug Discovery Today , vol.9 , Issue.10 , pp. 430-431
    • Hopkins, A.L.1    Groom, C.R.2    Alex, A.3
  • 47
    • 34247352907 scopus 로고    scopus 로고
    • Novel bis(indolyl)maleimide pyridinophanes that are potent, selective inhibitors of glycogen synthase kinase-3
    • DOI 10.1016/j.bmcl.2007.02.059, PII S0960894X07002569
    • Zhang H-C, Boñaga LVR, Ye H, Derian CK, Damiano BP, Maryanoff BE. Novel bis(indolyl)maleimide pyridinophanes that are potent, selective inhibitors of glycogen synthase kinase-3. Bioorg. Med. Chem. Lett. 17(10), 2863-2868 (2007). (Pubitemid 46636245)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.10 , pp. 2863-2868
    • Zhang, H.-C.1    Bonaga, L.V.R.2    Ye, H.3    Derian, C.K.4    Damiano, B.P.5    Maryanoff, B.E.6
  • 49
  • 50
    • 70350509085 scopus 로고    scopus 로고
    • Synthesis of a resorcylic acid lactone (RAL) library using fluorous-mixture synthesis and profile of its selectivity against a panel of kinases
    • Jogireddy R, Dakas P-Y, Valot G, Barluenga S, Winssinger N. Synthesis of a resorcylic acid lactone (RAL) library using fluorous-mixture synthesis and profile of its selectivity against a panel of kinases. Chem. Eur. J. 15(43), 11498-11506 (2009).
    • (2009) Chem. Eur. J. , vol.15 , Issue.43 , pp. 11498-11506
    • Jogireddy, R.1    Dakas, P.-Y.2    Valot, G.3    Barluenga, S.4    Winssinger, N.5
  • 51
    • 29444460171 scopus 로고    scopus 로고
    • Concise synthesis of pochonin A, an HSP90 inhibitor
    • DOI 10.1021/ol052263+
    • Moulin E, Barluenga S, Winssinger N. Concise synthesis of pochonin A, an HSP90 inhibitor. Org. Lett. 7(25), 5637-5639 (2005). (Pubitemid 43010817)
    • (2005) Organic Letters , vol.7 , Issue.25 , pp. 5637-5639
    • Moulin, E.1    Barluenga, S.2    Winssinger, N.3
  • 52
    • 33845213862 scopus 로고    scopus 로고
    • Diversity-oriented synthesis of pochonins and biological evaluation against a panel of kinases
    • DOI 10.1002/chem.200600553
    • Moulin E, Barluenga S, Totzke F, Winssinger N. Diversity-oriented synthesis of pochonins and biological evaluation against a panel of kinases. Chem. Eur. J. 12(34), 8819-8834 (2006). (Pubitemid 44852467)
    • (2006) Chemistry - A European Journal , vol.12 , Issue.34 , pp. 8819-8834
    • Moulin, E.1    Barluenga, S.2    Totzke, F.3    Winssinger, N.4
  • 53
    • 78650513498 scopus 로고    scopus 로고
    • Design and synthesis of potent macrocyclic renin inhibitors
    • Sund C, Belda O, Wiktelius D et al. Design and synthesis of potent macrocyclic renin inhibitors. Bioorg. Med. Chem. Lett. 21(1), 358-362 (2011).
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , Issue.1 , pp. 358-362
    • Sund, C.1    Belda, O.2    Wiktelius, D.3
  • 54
    • 58149194055 scopus 로고    scopus 로고
    • Structure-activity relationship and metabolic stability studies of backbone cyclization and N-methylation of melanocortin peptides
    • Linde Y, Ovadia O, Safrai E et al. Structure-activity relationship and metabolic stability studies of backbone cyclization and N-methylation of melanocortin peptides. Peptide Sci. 90(5), 671-682 (2008).
    • (2008) Peptide Sci , vol.90 , Issue.5 , pp. 671-682
    • Linde, Y.1    Ovadia, O.2    Safrai, E.3
  • 55
    • 25444447991 scopus 로고    scopus 로고
    • Cyclic peptides, a chemical genetics tool for biologists
    • Horswill AR, Benkovic SJ. Cyclic peptides, a chemical genetics tool for biologists. Cell Cycle 4(4), 552-555 (2005). (Pubitemid 41359779)
    • (2005) Cell Cycle , vol.4 , Issue.4 , pp. 552-555
    • Horswill, A.R.1    Benkovic, S.J.2
  • 56
    • 78650515510 scopus 로고    scopus 로고
    • Novel 2,3,4,5-tetrahydro-benzodazepine derivatives of 2,4-diaminopyrimidine, selective and orally bioavailable ALK inhibitors with antitumor efficacy in ALCL mouse models
    • Mesaros EF, Burke JP, Parrish JD et al. Novel 2,3,4,5-tetrahydro- benzodazepine derivatives of 2,4-diaminopyrimidine, selective and orally bioavailable ALK inhibitors with antitumor efficacy in ALCL mouse models. Bioorg. Med. Chem. Lett. 21(1), 463-466 (2011).
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , Issue.1 , pp. 463-466
    • Mesaros, E.F.1    Burke, J.P.2    Parrish, J.D.3
  • 57
    • 84855857003 scopus 로고    scopus 로고
    • Design, synthesis, and anaplastic lymphoma kinase (ALK) inhibitory activity for a novel series of 2,4,8,22-tetraazatetracyclo14.3.1.13,7.19,13 docosa-1(20),3(22),4,6,9(21),10,12,16,18- nonaene macrocycles
    • Breslin HJ, Lane BM, Ott GR et al. Design, synthesis, and anaplastic lymphoma kinase (ALK) inhibitory activity for a novel series of 2,4,8,22-tetraazatetracyclo14.3.1.13,7.19,13 docosa-1(20),3(22),4,6,9(21),10,12, 16,18- nonaene macrocycles. J. Med. Chem. 55(1), 449-464 (2011).
    • (2011) J. Med. Chem. , vol.55 , Issue.1 , pp. 449-464
    • Breslin, H.J.1    Lane, B.M.2    Ott, G.R.3
  • 58
    • 79960342165 scopus 로고    scopus 로고
    • Discovery of a stable macrocyclic o-aminobenzamide Hsp90 inhibitor which significantly decreases tumor volume in a mouse xenograft model
    • Zapf CW, Bloom JD, Li Z et al. Discovery of a stable macrocyclic o-aminobenzamide Hsp90 inhibitor which significantly decreases tumor volume in a mouse xenograft model. Bioorg. Med. Chem. Lett. 21(15), 4602-4607 (2011).
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , Issue.15 , pp. 4602-4607
    • Zapf, C.W.1    Bloom, J.D.2    Li, Z.3
  • 59
    • 79957861042 scopus 로고    scopus 로고
    • Discovery of a macrocyclic o-aminobenzamide Hsp90 inhibitor with heterocyclic tether that shows extended biomarker activity and in vivo efficacy in a mouse xenograft model
    • Zapf CW, Bloom JD, Mcbean JL et al. Discovery of a macrocyclic o-aminobenzamide Hsp90 inhibitor with heterocyclic tether that shows extended biomarker activity and in vivo efficacy in a mouse xenograft model. Bioorg. Med. Chem. Lett. 21(12), 3627-3631 (2011).
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , Issue.12 , pp. 3627-3631
    • Zapf, C.W.1    Bloom, J.D.2    McBean, J.L.3
  • 60
    • 79953281151 scopus 로고    scopus 로고
    • Design and SAR of macrocyclic Hsp90 inhibitors with increased metabolic stability and potent cell-proliferation activity
    • Zapf CW, Bloom JD, Mcbean JL et al. Design and SAR of macrocyclic Hsp90 inhibitors with increased metabolic stability and potent cell-proliferation activity. Bioorg. Med. Chem. Lett. 21(8), 2278-2282 (2011).
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , Issue.8 , pp. 2278-2282
    • Zapf, C.W.1    Bloom, J.D.2    McBean, J.L.3
  • 61
    • 79956157504 scopus 로고    scopus 로고
    • Macrocyclic lactams as potent Hsp90 inhibitors with excellent tumor exposure and extended biomarker activity
    • Zapf CW, Bloom JD, Mcbean JL et al. Macrocyclic lactams as potent Hsp90 inhibitors with excellent tumor exposure and extended biomarker activity. Bioorg. Med. Chem. Lett. 21(11), 3411-3416 (2011).
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , Issue.11 , pp. 3411-3416
    • Zapf, C.W.1    Bloom, J.D.2    McBean, J.L.3
  • 62
    • 67650741952 scopus 로고    scopus 로고
    • Discovery of novel 2-aminobenzamide inhibitors of heat shock protein 90 as potent, selective and orally active antitumor agents
    • Huang KH, Veal JM, Fadden RP et al. Discovery of novel 2-aminobenzamide inhibitors of heat shock protein 90 as potent, selective and orally active antitumor agents. J. Med. Chem. 52(14), 4288-4305 (2009).
    • (2009) J. Med. Chem. , vol.52 , Issue.14 , pp. 4288-4305
    • Huang, K.H.1    Veal, J.M.2    Fadden, R.P.3
  • 63
    • 77950582432 scopus 로고    scopus 로고
    • Conformational refinement of hydroxamatebased histone deacetylase inhibitors and exploration of 3-piperidin-3-ylindole analogues of dacinostat (LAQ824)
    • Cho YS, Whitehead L, Li J et al. Conformational refinement of hydroxamatebased histone deacetylase inhibitors and exploration of 3-piperidin-3-ylindole analogues of dacinostat (LAQ824). J. Med. Chem. 53(7), 2952-2963 (2010).
    • (2010) J. Med. Chem. , vol.53 , Issue.7 , pp. 2952-2963
    • Cho, Y.S.1    Whitehead, L.2    Li, J.3
  • 66
    • 79960178510 scopus 로고    scopus 로고
    • Discovery of the macrocycle 11-(2-pyrrolidin- 1-yl-ethoxy)-14,19-dioxa-5, 7,26-triaza-tetracy clo19.3.1.1(2,6).1(8,12)heptacosa- 1(25),2(26),3,5,8,10, 12(27),16,21,23-decaene (SB1518), a potent janus kinase 2/Fms-like tyrosine kinase-3 (JAK2/FLT3) inhibitor for the treatment of myelofibrosis and lymphoma
    • William AD, Lee ACH, Blanchard SP et al. Discovery of the macrocycle 11-(2-pyrrolidin- 1-yl-ethoxy)-14,19-dioxa-5,7,26-triaza-tetracy clo19.3.1.1(2,6).1(8,12)heptacosa- 1(25),2(26),3,5,8,10,12(27),16,21,23-decaene (SB1518), a potent janus kinase 2/Fms-like tyrosine kinase-3 (JAK2/FLT3) inhibitor for the treatment of myelofibrosis and lymphoma. J. Med. Chem. 54(13), 4638-4658 (2011).
    • (2011) J. Med. Chem. , vol.54 , Issue.13 , pp. 4638-4658
    • William, A.D.1    Lee, A.C.H.2    Blanchard, S.P.3
  • 67
    • 33750482579 scopus 로고    scopus 로고
    • Conformational flexibility, internal hydrogen bonding, and passive membrane permeability: Successful in silico prediction of the relative permeabilities of cyclic peptides
    • DOI 10.1021/ja063076p
    • Rezai T, Bock JE, Zhou MV, Kalyanaraman C, Lokey RS, Jacobson MP. Conformational flexibility, internal hydrogen bonding, and passive membrane permeability: successful in silico prediction of the relative permeabilities of cyclic peptides. J. Am. Chem. Soc. 128(43), 14073-14080 (2006). (Pubitemid 44657500)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.43 , pp. 14073-14080
    • Rezai, T.1    Bock, J.E.2    Zhou, M.V.3    Kalyanaraman, C.4    Lokey, R.S.5    Jacobson, M.P.6
  • 68
    • 33644644973 scopus 로고    scopus 로고
    • Testing the conformational hypothesis of passive membrane permeability using synthetic cyclic peptide diastereomers
    • DOI 10.1021/ja0563455
    • Rezai T, Yu B, Millhauser GL, Jacobson MP, Lokey RS. Testing the conformational hypothesis of passive membrane permeability using synthetic cyclic peptide diastereomers. J. Am. Chem. Soc. 128(8), 2510-2511 (2006). (Pubitemid 43327908)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.8 , pp. 2510-2511
    • Rezai, T.1    Yu, B.2    Millhauser, G.L.3    Jacobson, M.P.4    Lokey, R.S.5
  • 70
    • 0025054575 scopus 로고
    • Reinvestigation of the conformation of cyclosporin A in chloroform
    • Kessler H, Köck M, Wein T, Gehrke M. Reinvestigation of the conformation of cyclosporin A in chloroform. Helv. Chim. Acta 73(7), 1818-1832 (1990). (Pubitemid 20353191)
    • (1990) Helvetica Chimica Acta , vol.73 , Issue.7 , pp. 1818-1832
    • Kessler, H.1    Kock, M.2    Wein, T.3    Gehrke, M.4
  • 71
    • 0026476589 scopus 로고
    • Conformation of cyclosporin A in polar solvents
    • Ko SY, Dalvit C. Conformation of cyclosporin A in polar solvents. Int. J. Pept. Protein Res. 40(5), 380-382 (1992).
    • (1992) Int. J. Pept. Protein Res. , vol.40 , Issue.5 , pp. 380-382
    • Ko, S.Y.1    Dalvit, C.2
  • 72
    • 78650746852 scopus 로고    scopus 로고
    • Methods for the synthesis of macrocycle libraries for drug discovery
    • Terrett NK. Methods for the synthesis of macrocycle libraries for drug discovery. Drug Discov. Today: Technologies 7(2), e97-e104 (2010).
    • (2010) Drug Discov. Today: Technologies , vol.7 , Issue.2
    • Terrett, N.K.1
  • 73
    • 80055009977 scopus 로고    scopus 로고
    • Comparison of diffusion coefficients for matched pairs of macrocyclic and linear molecules over a drug-like molecular weight range
    • Bogdan AR, Davies NL, James K. Comparison of diffusion coefficients for matched pairs of macrocyclic and linear molecules over a drug-like molecular weight range. Org. Biomol. Chem. 9(22), 7727-7733 (2011).
    • (2011) Org. Biomol. Chem. , vol.9 , Issue.22 , pp. 7727-7733
    • Bogdan, A.R.1    Davies, N.L.2    James, K.3
  • 74
    • 84859716448 scopus 로고    scopus 로고
    • Targeting the Hsp90 molecular chaperone with novel macrolactams. synthesis, structural, binding, and cellular studies
    • Day JEH, Sharp SY, Rowlands MG et al. Targeting the Hsp90 molecular chaperone with novel macrolactams. synthesis, structural, binding, and cellular studies. ACS Chem. Biol. 6(12), 1339-1347 (2011).
    • (2011) ACS Chem. Biol. , vol.6 , Issue.12 , pp. 1339-1347
    • Day, J.E.H.1    Sharp, S.Y.2    Rowlands, M.G.3
  • 75
    • 60849093178 scopus 로고    scopus 로고
    • Discovery of ixabepilone
    • Hunt JT. Discovery of ixabepilone. Mol. Cancer Ther. 8(2), 275-281 (2009).
    • (2009) Mol. Cancer Ther. , vol.8 , Issue.2 , pp. 275-281
    • Hunt, J.T.1
  • 76
    • 8744279305 scopus 로고    scopus 로고
    • Strategies for total and diversity-oriented synthesis of natural product(-like) macrocycles
    • DOI 10.1007/b96883, Natural Product Synthesis I: Targets, Methods, Concepts
    • Wessjohann LA, Ruijter E. Strategies for total and diversity-oriented synthesis of natural product(-like) macrocycles. In: Natural Product Synthesis I. Mulzer J (Ed.). Springer, Heidelberg, Berlin, Germany, 137-184 (2005). (Pubitemid 44423480)
    • (2005) Topics in Current Chemistry , vol.243 , pp. 137-184
    • Wessjohann, L.A.1    Ruijter, E.2
  • 77
    • 0035914011 scopus 로고    scopus 로고
    • Formation of macrocycles via ring-closing olefin metathesis
    • DOI 10.1021/jo0158480
    • Lee CW, Grubbs RH. Formation of macrocycles via ring-closing olefin metathesis. J. Org. Chem. 66(21), 7155-7158 (2001). (Pubitemid 32983107)
    • (2001) Journal of Organic Chemistry , vol.66 , Issue.21 , pp. 7155-7158
    • Choon Woo Lee1    Grubbs, R.H.2
  • 78
    • 36549022964 scopus 로고    scopus 로고
    • Synthesis of macrocyclic urea kinase inhibitors
    • DOI 10.1055/s-2007-991083
    • Tao Z-F, Sowin TJ, Lin N-H. Synthesis of macrocyclic urea kinase inhibitors. Synlett 18, 2855-2858 (2007). (Pubitemid 350189836)
    • (2007) Synlett , Issue.18 , pp. 2855-2858
    • Tao, Z.-F.1    Sowin, T.J.2    Lin, N.-H.3
  • 79
    • 78649254350 scopus 로고    scopus 로고
    • Grand challenge commentary: Accessing new chemical space for 'undruggable' targets
    • Dandapani S, Marcaurelle LA. Grand challenge commentary: accessing new chemical space for 'undruggable' targets. Nat. Chem. Biol. 6(12), 861-863 (2010).
    • (2010) Nat. Chem. Biol. , vol.6 , Issue.12 , pp. 861-863
    • Dandapani, S.1    Marcaurelle, L.A.2
  • 80
    • 80455177350 scopus 로고    scopus 로고
    • Synthesis of macrocyclic natural products by catalystcontrolled stereoselective ring-closing metathesis
    • Yu M, Wang C, Kyle AF et al. Synthesis of macrocyclic natural products by catalystcontrolled stereoselective ring-closing metathesis. Nature 479(7371), 88-93 (2011).
    • (2011) Nature , vol.479 , Issue.7371 , pp. 88-93
    • Yu, M.1    Wang, C.2    Kyle, A.F.3
  • 81
    • 84860420690 scopus 로고    scopus 로고
    • Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents
    • Kim MJ, Lee SH, Park SO et al. Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents. Bioorg. Med. Chem. 19(18), 5468-5479 (2011).
    • (2011) Bioorg. Med. Chem. , vol.19 , Issue.18 , pp. 5468-5479
    • Kim, M.J.1    Lee, S.H.2    Park, S.O.3
  • 82
    • 33845481603 scopus 로고    scopus 로고
    • Chemistry and biology of resorcylic acid lactones
    • DOI 10.1039/b610344h
    • Winssinger N, Barluenga S. Chemistry and biology of resorcylic acid lactones. Chem. Commun. (1), 22-36 (2007). (Pubitemid 44913078)
    • (2007) Chemical Communications , Issue.1 , pp. 22-36
    • Winssinger, N.1    Barluenga, S.2
  • 83
    • 70350511755 scopus 로고    scopus 로고
    • Divergent syntheses of resorcylic acid lactones: L-783277, LL-Z1640- 2, and hypothemycin
    • Dakas P-Y, Jogireddy R, Valot G, Barluenga S, Winssinger N. Divergent syntheses of resorcylic acid lactones: L-783277, LL-Z1640- 2, and hypothemycin. Chem. Eur. J. 15(43), 11490-11497 (2009).
    • (2009) Chem. Eur. J. , vol.15 , Issue.43 , pp. 11490-11497
    • Dakas, P.-Y.1    Jogireddy, R.2    Valot, G.3    Barluenga, S.4    Winssinger, N.5
  • 84
    • 33750884444 scopus 로고    scopus 로고
    • Synthesis of cyclic peptides constrained with biarylamine linkers using Buchwald-Hartwig C-N coupling
    • DOI 10.1021/jo061366i
    • Balraju V, Iqbal J. Synthesis of cyclic peptides constrained with biarylamine linkers using Buchwald-Hartwig C-N coupling. J. Org. Chem. 71(23), 8954-8956 (2006). (Pubitemid 44721971)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.23 , pp. 8954-8956
    • Balraju, V.1    Iqbal, J.2
  • 85
    • 79961098414 scopus 로고    scopus 로고
    • Synthesis of 5-iodo- 1,2,3-triazole-containing macrocycles using copper flow reactor technology
    • Bogdan AR, James K. Synthesis of 5-iodo- 1,2,3-triazole-containing macrocycles using copper flow reactor technology. Organic Letters 13(15), 4060-4063 (2011).
    • (2011) Organic Letters , vol.13 , Issue.15 , pp. 4060-4063
    • Bogdan, A.R.1    James, K.2
  • 86
    • 79956097468 scopus 로고    scopus 로고
    • CuAAC macrocyclization: High intramolecular selectivity through the use of copper-tris(triazole) ligand complexes
    • Chouhan G, James K. CuAAC macrocyclization: high intramolecular selectivity through the use of copper-tris(triazole) ligand complexes. Org. Lett. 13(10), 2754-2757 (2011).
    • (2011) Org. Lett. , vol.13 , Issue.10 , pp. 2754-2757
    • Chouhan, G.1    James, K.2
  • 87
    • 84861048815 scopus 로고    scopus 로고
    • Continuous flow synthesis. A pharma perspective
    • Malet Sanz L, Susanne F. Continuous flow synthesis. a pharma perspective. J. Med. Chem. 55(9), 4062-4098 (2012).
    • (2012) J. Med. Chem. , vol.55 , Issue.9 , pp. 4062-4098
    • Malet Sanz, L.1    Susanne, F.2
  • 88
    • 79959580534 scopus 로고    scopus 로고
    • Contemporary strategies for peptide macrocyclization
    • White CJ, Yudin AK. Contemporary strategies for peptide macrocyclization. Nat. Chem. 3(7), 509-524 (2011).
    • (2011) Nat. Chem. , vol.3 , Issue.7 , pp. 509-524
    • White, C.J.1    Yudin, A.K.2
  • 89
    • 56449110342 scopus 로고    scopus 로고
    • Translation of DNA into a library of 13,000 synthetic small-molecule macrocycles suitable for in vitro selection
    • Tse BN, Snyder TM, Shen Y, Liu DR. Translation of DNA into a library of 13,000 synthetic small-molecule macrocycles suitable for in vitro selection. J. Am. Chem. Soc. 130(46), 15611-15626 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , Issue.46 , pp. 15611-15626
    • Tse, B.N.1    Snyder, T.M.2    Shen, Y.3    Liu, D.R.4
  • 90
    • 84055221862 scopus 로고    scopus 로고
    • Optimization of the potency and pharmacokinetic properties of a macrocyclic ghrelin receptor agonist (part I): Development of ulimorelin (TZP-101) from hit to clinic
    • Hoveyda HR, Marsault E, Gagnon R et al. Optimization of the potency and pharmacokinetic properties of a macrocyclic ghrelin receptor agonist (part I): development of ulimorelin (TZP-101) from hit to clinic. J. Med. Chem. 54(24), 8305-8320 (2011).
    • (2011) J. Med. Chem. , vol.54 , Issue.24 , pp. 8305-8320
    • Hoveyda, H.R.1    Marsault, E.2    Gagnon, R.3
  • 91
    • 79952662135 scopus 로고    scopus 로고
    • Discovery of MK-1220: A macrocyclic inhibitor of hepatitis C virus NS3/4A Protease with improved preclinical plasma exposure
    • Rudd MT, Mccauley JA, Butcher JW et al. Discovery of MK-1220: a macrocyclic inhibitor of hepatitis C virus NS3/4A Protease with improved preclinical plasma exposure. ACS Med. Chem. Lett. 2(3), 207-212 (2011).
    • (2011) ACS Med. Chem. Lett. , vol.2 , Issue.3 , pp. 207-212
    • Rudd, M.T.1    McCauley, J.A.2    Butcher, J.W.3
  • 92
    • 79955613841 scopus 로고    scopus 로고
    • Molecular obesity, potency and other addictions in drug discovery
    • Hann MM. Molecular obesity, potency and other addictions in drug discovery. MedChemComm 2(5), 349-355 (2011).
    • (2011) MedChemComm , vol.2 , Issue.5 , pp. 349-355
    • Hann, M.M.1
  • 93
    • 33746637660 scopus 로고    scopus 로고
    • Current development of mTOR inhibitors as anticancer agents
    • DOI 10.1038/nrd2062, PII NRD2062
    • Faivre S, Kroemer G, Raymond E. Current development of mTOR inhibitors as anticancer agents. Nat. Rev. Drug Discov. 5(8), 671-688 (2006). (Pubitemid 44151605)
    • (2006) Nature Reviews Drug Discovery , vol.5 , Issue.8 , pp. 671-688
    • Faivre, S.1    Kroemer, G.2    Raymond, E.3
  • 94
    • 0029842109 scopus 로고    scopus 로고
    • Structure of the FKBP12-rapamycin complex interacting with the binding domain of human FRAP
    • Choi J, Chen J, Schreiber SL, Jon C. Structure of the FKBP12-rapamycin complex interacting with the binding domain of human FRAP. Science 273, 239-242 (1996). (Pubitemid 26285890)
    • (1996) Science , vol.273 , Issue.5272 , pp. 239-242
    • Choi, J.1    Chen, J.2    Schreiber, S.L.3    Clardy, J.4
  • 95
    • 14844338576 scopus 로고    scopus 로고
    • Much anticipated - The bioactive conformation of epothilone and its binding to tubulin
    • DOI 10.1002/anie.200462241
    • Heinz DW, Schubert W-D, Höfle G. Much anticipated - the bioactive conformation of epothilone and its binding to tubulin. Angew. Chem. Int. Ed. Engl. 44(9), 1298-1301 (2005). (Pubitemid 40352555)
    • (2005) Angewandte Chemie - International Edition , vol.44 , Issue.9 , pp. 1298-1301
    • Heinz, D.W.1    Schubert, W.-D.2    Hofle, G.3
  • 96
    • 3843053396 scopus 로고    scopus 로고
    • The binding mode of epothilone A on alpha,beta-tubulin by electron crystallography
    • DOI 10.1126/science.1099190
    • Nettles JH, Li H, Cornett B, Krahn JM, Snyder JP, Downing KH. The binding mode of epothilone A on α,β-tubulin by electron crystallography. Science 305(5685), 866-869 (2004). (Pubitemid 39038421)
    • (2004) Science , vol.305 , Issue.5685 , pp. 866-869
    • Nettles, J.H.1    Li, H.2    Cornett, B.3    Krahn, J.M.4    Snyder, J.P.5    Downing, K.H.6
  • 97
    • 79955566051 scopus 로고    scopus 로고
    • Route to three-dimensional fragments using diversityoriented synthesis
    • Hung AW, Ramek A, Wang Y et al. Route to three-dimensional fragments using diversityoriented synthesis. Proc. Natl Acad. Sci. USA 108(17), 6799-6804 (2011).
    • (2011) Proc. Natl Acad. Sci. USA , vol.108 , Issue.17 , pp. 6799-6804
    • Hung, A.W.1    Ramek, A.2    Wang, Y.3
  • 98
    • 70350409235 scopus 로고    scopus 로고
    • The impact of aromatic ring count on compound developability - Are too many aromatic rings a liability in drug design? Drug Discov
    • Ritchie TJ, Macdonald SJF. The impact of aromatic ring count on compound developability - are too many aromatic rings a liability in drug design? Drug Discov. Today 14(21-22), 1011-1020 (2009).
    • (2009) Today , vol.14 , Issue.21-22 , pp. 1011-1020
    • Ritchie, T.J.1    MacDonald, S.J.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.