Synthesis and molecular modeling study of new trimeric quinoline derivatives

Bioorganic Chemistry

Volumn 39, Issue 4, 2011, Pages 143-150

  Saugues, Emmanuelle ^a,b   Nauton, Lionel ^a,b   Théry, Vincent ^a,b   Anizon, Fabrice ^a,b   Moreau, Pascale ^a,b  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b CNRS   (France)

Author keywords

Quinoline; Suzuki coupling

Indexed keywords

2,2',2'' TRIETHOXY 5',5'' DIISOPROPYL 3,7':3,7'' TERQUINOLINE; 2,2',2'' TRIETHOXY 5,5',5'' TRIISOPROPYL 3,7':3,7'' TERQUINOLINE; 5',5'' DIISOPROPYL 2,2',2'' TRIPROPOXY 3,7':3,7'' TERQUINOLINE; 5,5' DIISOPROPYL 2,2',2'' TRIETHOXY 3,7':3,7'' TERQUINOLINE; 5,5' DIISOPROPYL 2,2',2'' TRIPROPOXY 3,7':3,7'' TERQUINOLINE; 5,5',5'' TRIISOPROPYL 2,2',2'' TRIPROPOXY 3,7':3,7'' TERQUINOLINE; PROTEIN BAK; PROTEIN BCL XL; QUINOLINE DERIVATIVE; TRIMERIC QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATIONAL TRANSITION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SUZUKI REACTION;

BCL-2 HOMOLOGOUS ANTAGONIST-KILLER PROTEIN; BCL-X PROTEIN; BINDING SITES; MODELS, MOLECULAR; POLYMERIZATION; PROTO-ONCOGENE PROTEINS C-BCL-2; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80053052485     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2011.07.001     Document Type: Article

References (15)

1. E. Ramesh, R.D.R.S. Manian, R. Raghunathan, S. Sainath, and M. Raghunathan Synthesis and antibacterial property of quinolines with potent DNA gyrase activity Bioorg. Med. Chem. 17 2009 660 666
2. R. Musiol, J. Jampilek, K. Kralova, D.R. Richardson, D. Kalinowski, B. Podeszwa, J. Finster, H. Niedbala, A. Palka, and J. Polanski Investigating biological activity spectrum for novel quinoline analogues Bioorg. Med. Chem. 15 2007 1280 1288 (Pubitemid 46038140)
3. S.K. Srivastava, A. Jha, S.K. Agarwal, R. Mukherjee, and A.C. Burman Synthesis and structure-activity relationships of potent antitumor active quinoline and naphthyridine derivatives Anti-Cancer Agents Med. Chem. 7 2007 685 709 (Pubitemid 350237773)
4. L.-P. Guan, Q.-H. Jin, G.-R. Tian, K.-Y. Chai, and Z.-S. Quan Synthesis of some quinoline-2(1H)-one and 1,2,4-triazolo [4,3-a] quinoline derivatives as potent anticonvulsants J. Pharm. Pharmaceut. Sci. 10 2007 254 262 (Pubitemid 47078767)
5. 3 receptor antagonists J. Med. Chem. 48 2005 306 311 (Pubitemid 40105269)
6. M.T. Vazquez, M. Romero, and M.D. Pujol Synthesis of novel 2,3-dihydro-1,4-dioxino[2,3-g]quinoline derivatives as potential antitumor agents Bioorg. Med. Chem. 12 2004 949 956 (Pubitemid 38251287)
7. Y.-Q. Fang, R. Karisch, and M. Lautens Efficient syntheses of KDR kinase inhibitors using a Pd-catalyzed tandem C-N/Suzuki coupling as the key step J. Org. Chem. 72 2007 1341 1346
8. L and Mcl-1 Bioorg. Med. Chem. 16 2008 7443 7449
9. S. Broch, F. Anizon, and P. Moreau First synthesis of 3,6′- and 3,7′-biquinoline derivatives Synthesis 2008 2039 2044 (Pubitemid 351999963)
10. S. Broch, B. Aboab, F. Anizon, and P. Moreau Synthesis and in vitro antiproliferative activities of quinoline derivatives Eur. J. Med. Chem. 45 2010 1657 1662
11. S. Broch, H. Hénon, A.-L. Debaud, M.-L. Fogeron, N. Bonnefoy-Bérard, F. Anizon, and P. Moreau Synthesis and biological activities of new di- and trimeric quinoline derivatives Bioorg. Med. Chem. 18 2010 7132 7143
12. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision D.01, Gaussian, Inc., Wallingford, CT, 2004.
13. L-Bak peptide complex: recognition between regulators of apoptosis Science 275 1997 983 986 (Pubitemid 27087715)
14. Sybylx1.3, Tripos International, 1699 South Hanley Rd., St. Louis, Missouri, 63144, USA.
15. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin UCSF chimera - a visualization system for exploratory research and analysis J. Comput. Chem. 25 2004 1605 1612