메뉴 건너뛰기




Volumn 16, Issue 7, 2014, Pages 359-366

Privileged structures as peptide backbone constraints: Polymer-supported stereoselective synthesis of benzimidazolinopiperazinone peptides

Author keywords

iminiums; peptidomimetics; privileged structure; solid phase synthesis

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; PEPTIDE; PIPERAZINE DERIVATIVE; POLYMER;

EID: 84904284340     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co500023k     Document Type: Article
Times cited : (17)

References (45)
  • 1
    • 70350173842 scopus 로고    scopus 로고
    • Peptidomimetics A Versatile Route to Biologically Active Compounds
    • Grauer, A.; König, B. Peptidomimetics A Versatile Route to Biologically Active Compounds Eur. J. Org. Chem. 2009, 5099-5111
    • (2009) Eur. J. Org. Chem. , pp. 5099-5111
    • Grauer, A.1    König, B.2
  • 2
    • 44949231073 scopus 로고    scopus 로고
    • Peptidomimetics, A Synthetic Tool of Drug Discovery
    • Vagner, J.; Qu, H.; Hruby, V. J. Peptidomimetics, A Synthetic Tool of Drug Discovery Curr. Opin. Chem. Biol. 2008, 12, 292-296
    • (2008) Curr. Opin. Chem. Biol. , vol.12 , pp. 292-296
    • Vagner, J.1    Qu, H.2    Hruby, V.J.3
  • 3
    • 0036783393 scopus 로고    scopus 로고
    • Design, Synthesis, and Application of Peptide Secondary Structure Mimetics
    • Eguchi, E.; Kahn, M. Design, Synthesis, and Application of Peptide Secondary Structure Mimetics Mini-Rev. Med. Chem. 2002, 2, 447-462
    • (2002) Mini-Rev. Med. Chem. , vol.2 , pp. 447-462
    • Eguchi, E.1    Kahn, M.2
  • 4
    • 0034778418 scopus 로고    scopus 로고
    • Solid-phase syntheses of β-turn analogues to mimic or disrupt protein - Protein interactions
    • DOI 10.1021/ar9901523
    • Burgess, K. Solid-Phase Syntheses of β-Turn Analogues to Mimic or Disrupt Protein-Protein Interactions Acc. Chem. Res. 2001, 34, 826-835 (Pubitemid 32999607)
    • (2001) Accounts of Chemical Research , vol.34 , Issue.10 , pp. 826-835
    • Burgess, K.1
  • 5
    • 3142781225 scopus 로고    scopus 로고
    • Small-molecule inhibitors of protein-protein interactions: Progressing towards the dream
    • Arkin, M. R.; Wells, J. A. Small-Molecule Inhibitors of Protein-Protein Interactions: Progressing Towards the Dream Nat. Rev. Drug Discovery 2004, 3, 301-317 (Pubitemid 38499758)
    • (2004) Nature Reviews Drug Discovery , vol.3 , Issue.4 , pp. 301-317
    • Arkin, M.R.1    Wells, J.A.2
  • 6
    • 0041312697 scopus 로고    scopus 로고
    • Diversity of protein-protein interactions
    • DOI 10.1093/emboj/cdg359
    • Nooren, I. M.; Thornton, J. M. Diversity of Protein-Protein Interactions EMBO J. 2003, 22, 3486-3492 (Pubitemid 36898326)
    • (2003) EMBO Journal , vol.22 , Issue.14 , pp. 3486-3492
    • Nooren, I.M.A.1    Thornton, J.M.2
  • 7
    • 23044496736 scopus 로고    scopus 로고
    • Protein-protein interactions in human disease
    • DOI 10.1016/j.sbi.2005.06.001, PII S0959440X0500117X, Membranes/Engineering and Desing
    • Ryan, D. P.; Matthews, J. M. Protein-Protein Interactions in Human Disease Curr. Opin. Struct. Biol. 2005, 15, 441-446 (Pubitemid 41073836)
    • (2005) Current Opinion in Structural Biology , vol.15 , Issue.4 , pp. 441-446
    • Ryan, D.P.1    Matthews, J.M.2
  • 8
    • 49549083915 scopus 로고    scopus 로고
    • Peptide-Mediated Interactions in Biological Systems: New Discoveries and Applications
    • Petsalaki, E.; Russell, R. B. Peptide-Mediated Interactions in Biological Systems: New Discoveries and Applications Curr. Opin. Biotechnol. 2008, 19, 344-350
    • (2008) Curr. Opin. Biotechnol. , vol.19 , pp. 344-350
    • Petsalaki, E.1    Russell, R.B.2
  • 10
    • 0037648871 scopus 로고    scopus 로고
    • Design of β-turn based therapeutic agents
    • DOI 10.2174/1381612033454900
    • Kee, S.; Jois, S. D. S. Design of β-Turn Based Therapeutic Agents Curr. Pharm. Des. 2003, 9, 1209-1224 (Pubitemid 36582256)
    • (2003) Current Pharmaceutical Design , vol.9 , Issue.15 , pp. 1209-1224
    • Suat Kee, K.1    Jois, S.D.S.2
  • 11
    • 39049124587 scopus 로고    scopus 로고
    • Privileged scaffolds targeting reverse-turn and helix recognition
    • DOI 10.1517/14728222.12.1.101
    • Che, Y.; Marshall, G. R. Privileged Scaffolds Targeting Reverse-Turn and Helix Recognition Expert Opin. Ther. Targets 2008, 12, 101-114 (Pubitemid 351247166)
    • (2008) Expert Opinion on Therapeutic Targets , vol.12 , Issue.1 , pp. 101-114
    • Che, Y.1    Marshall, G.R.2
  • 14
    • 0027744344 scopus 로고
    • 6-Substituted benzimidazoles as new nonpeptide angiotensin II receptor antagonists: Synthesis, biological activity, and structure-activity relationships
    • DOI 10.1021/jm00077a007
    • Ries, U. J.; Mihm, G.; Narr, B.; Hasselbach, K. M.; Wittneben, H.; Entzeroth, M.; van Meel, J. C.; Wienen, W.; Hauel, N. H. 6-Substituted Benzimidazoles as New Nonpeptide Angiotensin II Receptor Antagonists: Synthesis, Biological Activity, and Structure-Activity Relationships J. Med. Chem. 1993, 36, 4040-4051 (Pubitemid 24024676)
    • (1993) Journal of Medicinal Chemistry , vol.36 , Issue.25 , pp. 4040-4051
    • Ries, U.J.1    Mihm, G.2    Narr, B.3    Hasselbach, K.M.4    Wittneben, H.5    Entzeroth, M.6    Van Meel, J.C.A.7    Wienen, W.8    Hauel, N.H.9
  • 16
    • 1242339542 scopus 로고    scopus 로고
    • Synthesis and biological evaluations of novel benzimidazoles as potential antibacterial agents
    • DOI 10.1016/j.bmcl.2003.12.051
    • He, Y.; Yang, J.; Wu, B.; Risen, L.; Swayze, E. E. Synthesis and Biological Evaluations of Novel Benzimidazoles as Potential Antibacterial Agents Bioorg. Med. Chem. Lett. 2004, 14, 1217-1220 (Pubitemid 38229860)
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , Issue.5 , pp. 1217-1220
    • He, Y.1    Yang, J.2    Wu, B.3    Risen, L.4    Swayze, E.E.5
  • 17
    • 50949121863 scopus 로고    scopus 로고
    • Synthesis and Cytotoxicity Evaluation of Some Benzimidazole-4,7-diones as Bioreductive Anticancer Agents
    • Gellis, A.; Kovacic, H.; Boufatah, N.; Vanelle, P. Synthesis and Cytotoxicity Evaluation of Some Benzimidazole-4,7-diones as Bioreductive Anticancer Agents Eur. J. Org. Chem. 2008, 43, 1858-1864
    • (2008) Eur. J. Org. Chem. , vol.43 , pp. 1858-1864
    • Gellis, A.1    Kovacic, H.2    Boufatah, N.3    Vanelle, P.4
  • 18
    • 84876818552 scopus 로고    scopus 로고
    • Benzimidazole Derivatives as Potential Anticancer Agents
    • Rashedy, A. E.; Aboul-Enein, Y. Benzimidazole Derivatives as Potential Anticancer Agents Mini.-Rev. Med. Chem. 2013, 13, 399-407
    • (2013) Mini.-Rev. Med. Chem. , vol.13 , pp. 399-407
    • Rashedy, A.E.1    Aboul-Enein, Y.2
  • 19
    • 0025486534 scopus 로고
    • The Benzimidazole Anthelmintic AgentsA Review
    • McKellar, Q. A.; Scott, E. W. The Benzimidazole Anthelmintic AgentsA Review J. Vet. Pharmacol. Ther. 1990, 13, 223-247
    • (1990) J. Vet. Pharmacol. Ther. , vol.13 , pp. 223-247
    • McKellar, Q.A.1    Scott, E.W.2
  • 20
    • 0026060039 scopus 로고
    • Lansoprazole, A Novel Benzimidazole Proton Pump Inhibitor, and its Related Compounds Have Selective Activity against Helicobacter pylori
    • Iwahi, T.; Satoh, H.; Nakao, M.; Iwasaki, T.; Yamazaki, T.; Kubo, K.; Tamura, T.; Imada, A. Lansoprazole, A Novel Benzimidazole Proton Pump Inhibitor, and its Related Compounds Have Selective Activity against Helicobacter pylori Antimicrob. Agents Chemother. 1991, 35, 490-496
    • (1991) Antimicrob. Agents Chemother. , vol.35 , pp. 490-496
    • Iwahi, T.1    Satoh, H.2    Nakao, M.3    Iwasaki, T.4    Yamazaki, T.5    Kubo, K.6    Tamura, T.7    Imada, A.8
  • 25
    • 0034625424 scopus 로고    scopus 로고
    • New developments in the chemistry of N-acyliminium ions and related intermediates
    • DOI 10.1016/S0040-4020(00)00159-9, PII S0040402000001599
    • Speckamp, W. N.; Moolenaar, M. J. New Developments in the Chemistry of N -Acyliminium Ions and Related Intermediates Tetrahedron 2000, 56, 3817-3856 (Pubitemid 30422385)
    • (2000) Tetrahedron , vol.56 , Issue.24 , pp. 3817-3856
    • Speckamp, W.N.1    Moolenaar, M.J.2
  • 26
    • 63549142605 scopus 로고    scopus 로고
    • Intermolecular Addition Reactions of N-Acyliminium Ions (Part I)
    • Yazici, A.; Pyne, S. G. Intermolecular Addition Reactions of N-Acyliminium Ions (Part I) Synthesis 2009, 339-368
    • (2009) Synthesis , pp. 339-368
    • Yazici, A.1    Pyne, S.G.2
  • 27
    • 63549102143 scopus 로고    scopus 로고
    • Intermolecular Addition Reactions of N-Acyliminium Ions (Part II)
    • Yazici, A.; Pyne, S. G. Intermolecular Addition Reactions of N-Acyliminium Ions (Part II) Synthesis 2009, 513-541
    • (2009) Synthesis , pp. 513-541
    • Yazici, A.1    Pyne, S.G.2
  • 28
    • 84872519641 scopus 로고    scopus 로고
    • Regioselective Incorporation of Backbone Constrains Compatible with Traditional Solid-Phase Peptide Synthesis
    • La Venia, A.; Lemrova, B.; Krchnak, V. Regioselective Incorporation of Backbone Constrains Compatible with Traditional Solid-Phase Peptide Synthesis ACS Comb. Sci. 2013, 15, 59-72
    • (2013) ACS Comb. Sci. , vol.15 , pp. 59-72
    • La Venia, A.1    Lemrova, B.2    Krchnak, V.3
  • 29
    • 84874964175 scopus 로고    scopus 로고
    • Polymer-Supported Stereoselective Synthesis of Tetrahydro-2 H -oxazolo[3,2- a ]pyrazin-5(3 H)-ones
    • La Venia, A.; Dolensky, B.; Krchnak, V. Polymer-Supported Stereoselective Synthesis of Tetrahydro-2 H -oxazolo[3,2- a ]pyrazin-5(3 H)-ones ACS Comb. Sci. 2013, 15, 162-167
    • (2013) ACS Comb. Sci. , vol.15 , pp. 162-167
    • La Venia, A.1    Dolensky, B.2    Krchnak, V.3
  • 30
    • 84863622646 scopus 로고    scopus 로고
    • Polymer-Supported Stereoselective Synthesis of Benzimidazolinopiperazinones
    • Cankarova, N.; Krchnak, V. Polymer-Supported Stereoselective Synthesis of Benzimidazolinopiperazinones J. Org. Chem. 2012, 77, 5687-5695
    • (2012) J. Org. Chem. , vol.77 , pp. 5687-5695
    • Cankarova, N.1    Krchnak, V.2
  • 31
    • 84875001174 scopus 로고    scopus 로고
    • Polymer-Supported Stereoselective Synthesis of (1 S,5 S)-6-Oxa-3,8-diazabicyclo[3.2.1]octanes
    • Schütznerova, E.; Oliver, A. G.; Zajicek, J.; Krchnak, V. Polymer-Supported Stereoselective Synthesis of (1 S,5 S)-6-Oxa-3,8- diazabicyclo[3.2.1]octanes Eur. J. Org. Chem. 2013, 3158-3165
    • (2013) Eur. J. Org. Chem. , pp. 3158-3165
    • Schütznerova, E.1    Oliver, A.G.2    Zajicek, J.3    Krchnak, V.4
  • 32
    • 11144325118 scopus 로고    scopus 로고
    • Controlled microwave heating in modern organic synthesis
    • DOI 10.1002/anie.200400655
    • Kappe, C. O. Controlled Microwave Heating in Modern Organic Synthesis Angew. Chem., Int. Ed. 2004, 43, 6250-6284 (Pubitemid 40036603)
    • (2004) Angewandte Chemie - International Edition , vol.43 , Issue.46 , pp. 6250-6284
    • Kappe, C.O.1
  • 33
    • 33644853780 scopus 로고    scopus 로고
    • The Impact of Microwave Synthesis on Drug Discovery
    • Kappe, C. O.; Dallinger, D. The Impact of Microwave Synthesis on Drug Discovery Nat. Rev. Drug Discovery 2006, 5, 51-63
    • (2006) Nat. Rev. Drug Discovery , vol.5 , pp. 51-63
    • Kappe, C.O.1    Dallinger, D.2
  • 34
    • 1542752259 scopus 로고    scopus 로고
    • Microwave-Assisted Solid-Phase Synthesis (MASS): Parallel and Combinatorial Chemical Library Synthesis
    • Al-Obeidi, F.; Austin, R. E.; Okonya, J. F.; Bond, D. R. Microwave-Assisted Solid-Phase Synthesis (MASS): Parallel and Combinatorial Chemical Library Synthesis Mini.-Rev. Med. Chem. 2003, 3, 449-460
    • (2003) Mini.-Rev. Med. Chem. , vol.3 , pp. 449-460
    • Al-Obeidi, F.1    Austin, R.E.2    Okonya, J.F.3    Bond, D.R.4
  • 35
    • 45949123116 scopus 로고
    • Solid-Phase Synthesis of Protected Peptide Fragments using a Trialkoxydiphenyl-methylester Resin
    • Rink, H. Solid-Phase Synthesis of Protected Peptide Fragments using a Trialkoxydiphenyl-methylester Resin Tetrahedron Lett. 1987, 28, 3787-3790
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3787-3790
    • Rink, H.1
  • 36
    • 53049110370 scopus 로고    scopus 로고
    • Solid-Phase Synthesis of Difficult Peptide Sequences at Elevated Temperatures: A Critical Comparison of Microwave and Conventional Heating Technologies
    • Bacsa, B.; Horváti, K.; Bosze, S.; Andreae, F.; Kappe, C. O. Solid-Phase Synthesis of Difficult Peptide Sequences at Elevated Temperatures: A Critical Comparison of Microwave and Conventional Heating Technologies J. Org. Chem. 2008, 73, 7532-7542
    • (2008) J. Org. Chem. , vol.73 , pp. 7532-7542
    • Bacsa, B.1    Horváti, K.2    Bosze, S.3    Andreae, F.4    Kappe, C.O.5
  • 37
    • 84876420160 scopus 로고    scopus 로고
    • Fast and Effective Reduction of Nitroarenes by Sodium Dithionite under PTC Conditions: Application in Solid-Phase Synthesis
    • Kaplanek, R.; Krchňák, V. Fast and Effective Reduction of Nitroarenes by Sodium Dithionite under PTC Conditions: Application in Solid-Phase Synthesis Tetrahedron Lett. 2013, 54, 2600-2603
    • (2013) Tetrahedron Lett. , vol.54 , pp. 2600-2603
    • Kaplanek, R.1    Krchňák, V.2
  • 39
    • 34948865727 scopus 로고    scopus 로고
    • Superacid promoted reactions of N-acyliminium salts and evidence for the involvement of superelectrophiles
    • DOI 10.1039/b708760h
    • Zhang, Y.; De Schepper, D. J.; Gilbert, T. M.; Sai, K. K.; Klumpp, D. A. Superacid Promoted Reactions of N-Acyliminium Salts and Evidence for the Involvement of Superelectrophiles Chem. Commun. 2007, 4032-4034 (Pubitemid 47524972)
    • (2007) Chemical Communications , Issue.39 , pp. 4032-4034
    • Zhang, Y.1    DeSchepper, D.J.2    Gilbert, T.M.3    Sai, K.K.S.4    Klumpp, D.A.5
  • 40
    • 45249102900 scopus 로고    scopus 로고
    • Evolution of natural product scaffolds by acyl- and arylnitroso hetero-diels-alder reactions: New chemistry on pipeline
    • DOI 10.1021/jo8004827
    • Krchňák, V.; Waring, K. R.; Noll, B.; Moellmann, U.; Dahse, H.-M.; Miller, M. J. Evolution of Natural Product Scaffolds by Acyl- and Arylnitroso Hetero Diels-Alder Reactions: New Chemistry on Piperine J. Org. Chem. 2008, 73, 4559-4567 (Pubitemid 351842472)
    • (2008) Journal of Organic Chemistry , vol.73 , Issue.12 , pp. 4559-4567
    • Krchnak, V.1    Waring, K.R.2    Noll, B.C.3    Moellmann, U.4    Dahse, H.-M.5    Miller, M.J.6
  • 41
    • 84863758389 scopus 로고    scopus 로고
    • Piperazine Amide Linker for Cyclative Cleavage from Solid Support: Traceless Synthesis of Dihydroquinoxalin-2-ones
    • Neagoie, C.; Krchňák, V. Piperazine Amide Linker for Cyclative Cleavage from Solid Support: Traceless Synthesis of Dihydroquinoxalin-2-ones ACS Comb. Sci. 2012, 13, 399-402
    • (2012) ACS Comb. Sci. , vol.13 , pp. 399-402
    • Neagoie, C.1    Krchňák, V.2
  • 42
    • 0000585031 scopus 로고    scopus 로고
    • Solid-Phase Synthesis of Heterocycles Containing an 1-Acyl-3- oxopiperazine Skeleton
    • Vojkovsky, T.; Weichsel, A.; Patek, M. Solid-Phase Synthesis of Heterocycles Containing an 1-Acyl-3-oxopiperazine Skeleton J. Org. Chem. 1998, 63, 3162-3163
    • (1998) J. Org. Chem. , vol.63 , pp. 3162-3163
    • Vojkovsky, T.1    Weichsel, A.2    Patek, M.3
  • 43
    • 0033616089 scopus 로고    scopus 로고
    • Solid-phase synthesis and structural analysis of bicyclic β-turn mimetics incorporating functionality at the i to i + 3 positions [11]
    • DOI 10.1021/ja992203x
    • Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. Solid-Phase Synthesis and Structural Analysis of Bicyclic β-Turn Mimetics Incorporating Functionality at the i to i + 3 Position J. Am. Chem. Soc. 1999, 121, 12204-12205 (Pubitemid 30027805)
    • (1999) Journal of the American Chemical Society , vol.121 , Issue.51 , pp. 12204-12205
    • Eguchi, M.1    Lee, M.S.2    Nakanishi, H.3    Stasiak, M.4    Lovell, S.5    Kahn, M.6
  • 44
    • 0035847512 scopus 로고    scopus 로고
    • Solid-phase synthesis and solution structure of bicyclic β-turn peptidomimetics: Diversity at the i position
    • DOI 10.1016/S0040-4039(00)02248-6, PII S0040403900022486
    • Eguchi, M.; Lee, M. S.; Stasiak, M.; Kahn, M. Solid-Phase Synthesis and Solution Structure of Bicyclic β-Turn Peptidomimetics: Diversity at the i Position Tetrahedron Lett. 2001, 42, 1237-1239 (Pubitemid 32149781)
    • (2001) Tetrahedron Letters , vol.42 , Issue.7 , pp. 1237-1239
    • Eguchi, M.1    Lee, M.S.2    Stasiak, M.3    Kahn, M.4
  • 45
    • 0032542074 scopus 로고    scopus 로고
    • The Domino Blocks: A Simple Solution for Parallel Solid-Phase Organic Synthesis
    • Krchňák, V.; Padera, V. The Domino Blocks: A Simple Solution for Parallel Solid-Phase Organic Synthesis Bioorg. Med. Chem. Lett. 1998, 22, 3261-3264
    • (1998) Bioorg. Med. Chem. Lett. , vol.22 , pp. 3261-3264
    • Krchňák, V.1    Padera, V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.