메뉴 건너뛰기




Volumn 53, Issue 24, 2010, Pages 8716-8726

Design, synthesis, and evaluation of dibenzo[ c,h ][1,6]naphthyridines as topoisomerase i inhibitors and potential anticancer agents

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DIBENZO[C,H][1,6]NAPHTHYRIDINE DERIVATIVE; DNA TOPOISOMERASE INHIBITOR; HETEROCYCLIC COMPOUND; INDENOISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 78650395550     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101048k     Document Type: Article
Times cited : (77)

References (39)
  • 1
    • 0030014783 scopus 로고    scopus 로고
    • DNA Topoisomerases
    • Wang, J. C. DNA Topoisomerases Annu. Rev. Biochem. 1996, 65, 635-692
    • (1996) Annu. Rev. Biochem. , vol.65 , pp. 635-692
    • Wang, J.C.1
  • 2
    • 15844383117 scopus 로고    scopus 로고
    • Friction and Torque Govern the Relaxation of DNA Supercoils by Eukaryotic Topoisomerase IB
    • Koster, D. A.; Croquette, V.; Dekker, C.; Shuman, S.; Dekker, N. H. Friction and Torque Govern the Relaxation of DNA Supercoils by Eukaryotic Topoisomerase IB Nature 2005, 434, 671-674
    • (2005) Nature , vol.434 , pp. 671-674
    • Koster, D.A.1    Croquette, V.2    Dekker, C.3    Shuman, S.4    Dekker, N.H.5
  • 3
    • 67650682519 scopus 로고    scopus 로고
    • DNA Topoisomerase i Inhibitors: Chemistry, Biology, and Interfacial Inhibition
    • Pommier, Y. DNA Topoisomerase I Inhibitors: Chemistry, Biology, and Interfacial Inhibition Chem. Rev. 2009, 109, 2894-2902
    • (2009) Chem. Rev. , vol.109 , pp. 2894-2902
    • Pommier, Y.1
  • 4
    • 0032489634 scopus 로고    scopus 로고
    • Crystal Structures of Human Topoisomerase i in Covalent and Noncovalent Complexes with DNA
    • Redinbo, M. R.; Stewart, L.; Kuhn, P.; Champoux, J. J.; Hol, W. G. J. Crystal Structures of Human Topoisomerase I in Covalent and Noncovalent Complexes with DNA Science 1998, 279, 1504-1513
    • (1998) Science , vol.279 , pp. 1504-1513
    • Redinbo, M.R.1    Stewart, L.2    Kuhn, P.3    Champoux, J.J.4    Hol, W.G.J.5
  • 5
    • 7144248725 scopus 로고
    • Plant Antitumor Agents. I. The Isolation and Structure of Camptothecin, a Novel Alkaloidal Leukemia and Tumor Inhibitor from Camptotheca acuminata
    • Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K. H.; McPhail, A. T.; Sim, G. A. Plant Antitumor Agents. I. The Isolation and Structure of Camptothecin, a Novel Alkaloidal Leukemia and Tumor Inhibitor from Camptotheca acuminata J. Am. Chem. Soc. 1966, 88, 3888-3890
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 3888-3890
    • Wall, M.E.1    Wani, M.C.2    Cook, C.E.3    Palmer, K.H.4    McPhail, A.T.5    Sim, G.A.6
  • 6
    • 33749034730 scopus 로고    scopus 로고
    • Topoisomerase i Inhibitors: Camptothecins and beyond
    • Pommier, E. Topoisomerase I Inhibitors: Camptothecins and Beyond Nat. Rev. Cancer 2006, 6, 789-802
    • (2006) Nat. Rev. Cancer , vol.6 , pp. 789-802
    • Pommier, E.1
  • 7
    • 0017889598 scopus 로고
    • Total Synthesis of Nitidine Chloride
    • Cushman, M.; Cheng, L. Total Synthesis of Nitidine Chloride J. Org. Chem. 1978, 43, 286-288
    • (1978) J. Org. Chem. , vol.43 , pp. 286-288
    • Cushman, M.1    Cheng, L.2
  • 8
    • 0007565558 scopus 로고
    • Stereoselective Oxidation by Thionyl Chloride Leading to the Indeno[1,2- c ]isoquinoline System
    • Cushman, M.; Cheng, L. Stereoselective Oxidation by Thionyl Chloride Leading to the Indeno[1,2- c ]isoquinoline System J. Org. Chem. 1978, 43, 3781-3783
    • (1978) J. Org. Chem. , vol.43 , pp. 3781-3783
    • Cushman, M.1    Cheng, L.2
  • 9
    • 0031815336 scopus 로고    scopus 로고
    • Protein-Linked DNA Strand Breaks Induced by NSC 314622, a Novel Noncamptothecin Topoisomerase i Poison
    • Kohlhagen, G.; Paull, K.; Cushman, M.; Nagafuji, P.; Pommier, Y. Protein-Linked DNA Strand Breaks Induced by NSC 314622, a Novel Noncamptothecin Topoisomerase I Poison Mol. Pharmacol. 1998, 54, 50-58
    • (1998) Mol. Pharmacol. , vol.54 , pp. 50-58
    • Kohlhagen, G.1    Paull, K.2    Cushman, M.3    Nagafuji, P.4    Pommier, Y.5
  • 10
    • 0029960812 scopus 로고    scopus 로고
    • Eukaryotic DNA Topoisomerase I: Genome Gatekeeper and Its Intruders, Camptothecins
    • Pommier, Y. Eukaryotic DNA Topoisomerase I: Genome Gatekeeper and Its Intruders, Camptothecins Semin. Oncol. 1996, 23, 3-10
    • (1996) Semin. Oncol. , vol.23 , pp. 3-10
    • Pommier, Y.1
  • 11
    • 77954187741 scopus 로고    scopus 로고
    • DNA Topoisomerases and Their Poisoning by Anticancer and Antibacterial Drugs
    • Pommier, Y.; Leo, E.; Zhang, H.; Marchand, C. DNA Topoisomerases and Their Poisoning by Anticancer and Antibacterial Drugs Chem. Biol. 2010, 17, 421-433
    • (2010) Chem. Biol. , vol.17 , pp. 421-433
    • Pommier, Y.1    Leo, E.2    Zhang, H.3    Marchand, C.4
  • 14
    • 66849113688 scopus 로고    scopus 로고
    • The Indenoisoquinoline Noncamptothecin Topoisomerase i Inhibitors: Update and Perspectives
    • Pommier, Y.; Cushman, M. The Indenoisoquinoline Noncamptothecin Topoisomerase I Inhibitors: Update and Perspectives Mol. Cancer Ther. 2009, 8, 1008-1014
    • (2009) Mol. Cancer Ther. , vol.8 , pp. 1008-1014
    • Pommier, Y.1    Cushman, M.2
  • 16
  • 17
    • 0346996356 scopus 로고    scopus 로고
    • Design, Synthesis, and Biological Evaluation of Indenoisoquinoline Topoisomerase i Inhibitors Featuring Polyamine Side Chains on the Lactam Nitrogen
    • Nagarajan, M.; Xiao, X.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. Design, Synthesis, and Biological Evaluation of Indenoisoquinoline Topoisomerase I Inhibitors Featuring Polyamine Side Chains on the Lactam Nitrogen J. Med. Chem. 2003, 46, 5712-5724
    • (2003) J. Med. Chem. , vol.46 , pp. 5712-5724
    • Nagarajan, M.1    Xiao, X.2    Antony, S.3    Kohlhagen, G.4    Pommier, Y.5    Cushman, M.6
  • 19
    • 34247613433 scopus 로고    scopus 로고
    • Investigation of the Lactam Side Chain Length Necessary for Optimal Indenoisoquinoline Topoisomerase i Inhibition and Cytotoxicity in Human Cancer Cell Cultures
    • Morrell, A.; Placzek, M. S.; Steffen, J. D.; Antony, S.; Agama, K.; Pommier, Y.; Cushman, M. Investigation of the Lactam Side Chain Length Necessary for Optimal Indenoisoquinoline Topoisomerase I Inhibition and Cytotoxicity in Human Cancer Cell Cultures J. Med. Chem. 2007, 50, 2040-2048
    • (2007) J. Med. Chem. , vol.50 , pp. 2040-2048
    • Morrell, A.1    Placzek, M.S.2    Steffen, J.D.3    Antony, S.4    Agama, K.5    Pommier, Y.6    Cushman, M.7
  • 20
    • 17144371295 scopus 로고    scopus 로고
    • Structures of Three Classes of Anticancer Agents bound to the Human Topoisomerase I-DNA Covalent Complex
    • Staker, B. L.; Feese, M. D.; Cushman, M.; Pommier, Y.; Zembower, D.; Stewart, L.; Burgin, A. B. Structures of Three Classes of Anticancer Agents bound to the Human Topoisomerase I-DNA Covalent Complex J. Med. Chem. 2005, 48, 2336-2345
    • (2005) J. Med. Chem. , vol.48 , pp. 2336-2345
    • Staker, B.L.1    Feese, M.D.2    Cushman, M.3    Pommier, Y.4    Zembower, D.5    Stewart, L.6    Burgin, A.B.7
  • 22
    • 0013018788 scopus 로고
    • Synthesis of Indoles and Isoquinolones from Phenylmalonate Heterocycles
    • Stadbauer, W.; Kappe, T. Synthesis of Indoles and Isoquinolones from Phenylmalonate Heterocycles Monatsh. Chem. 1984, 115, 467-475
    • (1984) Monatsh. Chem. , vol.115 , pp. 467-475
    • Stadbauer, W.1    Kappe, T.2
  • 23
    • 56049121230 scopus 로고    scopus 로고
    • Thermal Reaction of 3a H,5 H -Thiazolo[5,4- c ]quinoline-2,4-diones - An Easy Pathway to 4-Amino-1 H -quinolin-2-ones and Novel 6 H -Thiazolo[3,4- c ]quinazoline-3,5-Diones
    • Mrkvicka, V.; Klasek, A.; Kimmel, R.; Pevec, A.; Kosmrlj, J. Thermal Reaction of 3a H,5 H -Thiazolo[5,4- c ]quinoline-2,4-diones-an Easy Pathway to 4-Amino-1 H -quinolin-2-ones and Novel 6 H -Thiazolo[3,4- c ]quinazoline-3,5- Diones ARKIVOC (Gainesville, FL, U. S.) 2008, 14, 289-302
    • (2008) ARKIVOC (Gainesville, FL, U. S.) , vol.14 , pp. 289-302
    • Mrkvicka, V.1    Klasek, A.2    Kimmel, R.3    Pevec, A.4    Kosmrlj, J.5
  • 24
    • 0032514855 scopus 로고    scopus 로고
    • Multilevel Selectivity in the Mild and High-Yielding Chlorosilane-Induced Cleavage of Carbamates to Isocyanates
    • Chong, P. Y.; Janicki, S. Z.; Petillo, P. A. Multilevel Selectivity in the Mild and High-Yielding Chlorosilane-Induced Cleavage of Carbamates to Isocyanates J. Org. Chem. 1998, 63, 8515-8521
    • (1998) J. Org. Chem. , vol.63 , pp. 8515-8521
    • Chong, P.Y.1    Janicki, S.Z.2    Petillo, P.A.3
  • 25
    • 5844262332 scopus 로고
    • Synthetical Experiments Related to Indole Alkaloids
    • Potts, K. T.; Robinson, R. Synthetical Experiments Related to Indole Alkaloids J. Chem. Soc. 1955, 2675-2686
    • (1955) J. Chem. Soc. , pp. 2675-2686
    • Potts, K.T.1    Robinson, R.2
  • 26
    • 33748542524 scopus 로고
    • Allylic Strain in Six-Membered Rings
    • Johnson, F. Allylic Strain in Six-Membered Rings Chem. Rev. 1968, 68, 375-413
    • (1968) Chem. Rev. , vol.68 , pp. 375-413
    • Johnson, F.1
  • 27
    • 33947483396 scopus 로고
    • Steric Interference in Allylic and Pseudoallylic Systems. I. Two Stereochemical Theorems
    • Johnson, F. Steric Interference in Allylic and Pseudoallylic Systems. I. Two Stereochemical Theorems J. Am. Chem. Soc. 1965, 87, 5492-5493
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 5492-5493
    • Johnson, F.1
  • 28
    • 23044459095 scopus 로고    scopus 로고
    • A Facile Method to Transform trans-4-Carboxy-3,4-dihydro-3-phenyl-1(2 H)-isoquinolones to Indeno[1,2- c ]isoquinolines
    • Xiao, X.; Cushman, M. A Facile Method to Transform trans-4-Carboxy-3,4- dihydro-3-phenyl-1(2 H)-isoquinolones to Indeno[1,2- c ]isoquinolines J. Org. Chem. 2005, 70, 6496-6498
    • (2005) J. Org. Chem. , vol.70 , pp. 6496-6498
    • Xiao, X.1    Cushman, M.2
  • 30
    • 0001581736 scopus 로고
    • Total Synthesis of (±)-14-Epicorynoline, (±)-Corynoline, and (+)-6-Oxocorynoline
    • Cushman, M.; Abbaspour, A.; Gupta, Y. P. Total Synthesis of (±)-14-Epicorynoline, (±)-Corynoline, and (+)-6-Oxocorynoline J. Am. Chem. Soc. 1983, 105, 2873-2879
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2873-2879
    • Cushman, M.1    Abbaspour, A.2    Gupta, Y.P.3
  • 31
    • 0000198424 scopus 로고
    • Total Synthesis of (±)-Corydalic Acid Methyl-Ester
    • Cushman, M.; Wong, W. C. Total Synthesis of (±)-Corydalic Acid Methyl-Ester J. Org. Chem. 1984, 49, 1278-1280
    • (1984) J. Org. Chem. , vol.49 , pp. 1278-1280
    • Cushman, M.1    Wong, W.C.2
  • 32
    • 27644486549 scopus 로고    scopus 로고
    • Synthesis of cis-isoquinolonic acids containing boronate esters
    • DOI 10.1055/s-2005-872124, M01905SS
    • Zhang, H. W.; Vogels, C. M.; Wheaton, S. L.; Baerlocher, F. J.; Decken, A.; Westcott, S. A. Synthesis of cis-Isoquinolonic Acids Containing Boronate Esters Synthesis 2005, 2739-2743 (Pubitemid 41551525)
    • (2005) Synthesis , Issue.16 , pp. 2739-2743
    • Zhang, H.1    Vogels, C.M.2    Wheaton, S.L.3    Baerlocher, F.J.4    Decken, A.5    Westcott, S.A.6
  • 34
    • 33144472888 scopus 로고    scopus 로고
    • Synthesis of Benz[d]indeno[1,2-b]pyran-5,11-diones: Versatile Intermediates for the Design and Synthesis of Topoisomerase i Inhibitors
    • Morrell, A.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. Synthesis of Benz[d]indeno[1,2-b]pyran-5,11-diones: Versatile Intermediates for the Design and Synthesis of Topoisomerase I Inhibitors Bioorg. Med. Chem. Lett. 2006, 16, 1846-1849
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 1846-1849
    • Morrell, A.1    Antony, S.2    Kohlhagen, G.3    Pommier, Y.4    Cushman, M.5
  • 36
    • 78650411871 scopus 로고    scopus 로고
    • SYBYL 7.3, Tripos International: St. Louis.
    • SYBYL 7.3, Tripos International: St. Louis.
  • 38
    • 0028906786 scopus 로고
    • Some Practical Considerations and Applications of the National Cancer Institute in Vitro Anticancer Drug Discovery Screen
    • Boyd, M. R.; Paull, K. D. Some Practical Considerations and Applications of the National Cancer Institute In Vitro Anticancer Drug Discovery Screen Drug Development Res. 1995, 34, 91-109
    • (1995) Drug Development Res. , vol.34 , pp. 91-109
    • Boyd, M.R.1    Paull, K.D.2
  • 39
    • 0033605675 scopus 로고    scopus 로고
    • Induction of Reversible Complexes between Eukaryotic DNA Topoisomerase i and DNA-containing Oxidative Base Damages. 7,8-Dihydro-8-Oxoguanine and 5-Hydroxycytosine
    • Pourquier, P.; Ueng, L.-M.; Fertala, J.; Wang, D.; Park, H.-J.; Essigmann, J. M.; Bjornsti, M.-A.; Pommier, Y. Induction of Reversible Complexes between Eukaryotic DNA Topoisomerase I and DNA-containing Oxidative Base Damages. 7,8-Dihydro-8-Oxoguanine and 5-Hydroxycytosine J. Biol. Chem. 1999, 274, 8516-8523
    • (1999) J. Biol. Chem. , vol.274 , pp. 8516-8523
    • Pourquier, P.1    Ueng, L.-M.2    Fertala, J.3    Wang, D.4    Park, H.-J.5    Essigmann, J.M.6    Bjornsti, M.-A.7    Pommier, Y.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.