Synthesis of quinolin-2-one alkaloid derivatives and their inhibitory activities against HIV-1 reverse transcriptase

Molecules

Volumn 16, Issue 9, 2011, Pages 7649-7661

  Cheng, Pi ^a,c   Gu, Qiong ^b   Liu, Wei ^a   Zou, Jian Feng ^a   Ou, Yang Yong ^c   Luo, Zhong Yong ^c   Zeng, Jian Guo ^a,c  

^a HUNAN AGRICULTURAL UNIVERSITY   (China)

^b SUN YAT SEN UNIVERSITY   (China)

^c Hunan Engineering Research Center of Botanical Extract   (China)

Author keywords

Activity; Alkaloid; HIV 1 RT; Quinolin 2 one; Synthesis

Indexed keywords

ALKALOID; QUINOLONE DERIVATIVE; RNA DIRECTED DNA POLYMERASE;

ARTICLE; BINDING SITE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; DRUG ANTAGONISM; ENZYME ASSAY; ENZYMOLOGY; HUMAN IMMUNODEFICIENCY VIRUS 1; PROTEIN BINDING; PROTEIN MOTIF; SYNTHESIS;

ALKALOIDS; ALLOSTERIC SITE; AMINO ACID MOTIFS; COMPUTER SIMULATION; ENZYME ASSAYS; HIV REVERSE TRANSCRIPTASE; HIV-1; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROTEIN BINDING; QUINOLONES;

EID: 80053290788     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16097649     Document Type: Article

References (18)

1. Mehellou, Y.; Clercq, E.D. Twenty-six years of anti-HIV drug discovery: Where do we stand and where do we go? J. Med. Chem. 2010, 53, 521-538.
2. Ragno, R.; Coluccia, A.; Regina, G.L.; Martino, G.D.; Piscitelli, F.; Lavecchia, A.; Novellino, E.; Bergamini, A.; Ciaprini, C.; Sinistro, A.; et al. Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide. J. Med. Chem. 2006, 49, 3172-3184. (Pubitemid 43830516)
3. Barreca, M.L.; Rao, A.; Luca, L.D.; Iraci, N.; Monforte, A.; Maga, G.; Clercq, E.D.; Pannecouque, C.; Balzarini, J.; Chimirri, A. Discovery of novel benzimidazolones as potent non-nucleoside reverse transcriptase inhibitors active against wild-type and mutant HIV-1 strains. Bioorg. Med. Chem. Lett. 2007, 17, 1956-1960. (Pubitemid 46367661)
4. Regina, G.L.; Coluccia, A.; Piscitelli, F.; Bergamini, A.; Sinistro, A.; Cavazza, A.; Maga, G.; Samuele, A.; Zanoli, S.; Novellino, E.; et al. Indolyl aryl sulfones as HIV-1 non-nucleoside reverse transcriptase inhibitors: Role of two halogen atoms at the indole ring in developing new analogues with improved antiviral activity. J. Med. Chem. 2007, 50, 5034-5038. (Pubitemid 47525483)
5. Jones, L.H.; Allan, G.; Barba, O.; Burt, C.; Corbau, R.; Dupont, T.; Knochel, T.; Irving, S.; Middleton, D. S.; Mowbray, C. E.; et al. Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays. J. Med. Chem. 2009, 52, 1219-1923.
6. Freeman, G.A.; Andrews, C.W., III.; Hopkins, A.L.; Lowell, G.S.; Schaller, L.T.; Cowan, J.R.; Gonzales, S.S.; Koszalka, G.W.; Hazen, R.J.; Boone, L.R.; et al. Design of non-nucleoside inhibitors of HIV-1 reverse transcriptase with improved drug resistance properties. 2. J. Med. Chem. 2004, 47, 5923-5936. (Pubitemid 39507334)
7. Barreca, M.L.; Rao, A.; Luca, L.D.; Zappalà, M.; Monforte, A.; Maga, G.; Pannecouque, C.; Balzarini, J.; Clercq, E.D.; Chimirri, A.; Monforte, P. Computational strategies in discovering novel non-nucleoside inhibitors of HIV-1 RT. J. Med. Chem. 2005, 48, 3433-3437. (Pubitemid 40628061)
8. Monforte, A.; Logoteta, P.; Ferro, S.; Luca, L.D.; Iraci, N.; Maga, G.; Clercq, E.D.; Pannecouque, C.; Chimirri, A. Design, synthesis, and structure-activity relationships of 1,3-dihydrobenzimidazol-2-one analogues as anti-HIV agents. Bioorg. Med. Chem. Lett. 2009, 17, 5962-5967.
9. Mccormick, J.L.; McKee, T.C.; Cardellina, J.H., II.; Boyd, M.R. HIV inhibitory natural products. 26. quinoline alkaloids from Euodia roxburghiana. J. Nat. Prod. 1996, 59, 469-471.
10. Guillemont, J.; Benjahad, A.; Oumouch, S.; Decrane, L.; Palandjian, P.; Vernier, D.; Queguiner, L.; Andries, K.; Béthune, M.; Hertogs, K.; et al. Synthesis and biological evaluation of C-5 methyl substituted 4-arylthio and 4-aryloxy-3-Iodopyridin-2(1H)-one type anti-HIV agents. J. Med. Chem. 2009, 52, 7473-7487.
11. Mowbray, C.E.; Burt, C.; Corbau, R.; Perros, M.; Tran, I.; Stupple, P.A.; Webster, R.; Wood, A. Pyrazole NNRTIs 1: Design and initial optimisation of a novel template. Bioorg. Med. Chem. Lett. 2009, 19, 5599-5602.
12. Xu. B.; Sun. Y.; Guo, Y.; Cao, Y.; Yu, T. Synthesis and biological evaluation of N4-(hetero)arylsulfonylquinoxalinones as HIV-1 reverse transcriptase inhibitors. Bioorg. Med. Chem. 2009, 17, 2767-2774.
13. Ren, J.; Chamberlain, P.P.; Stamp, A.; Short, S.A.; Weaver, K.L.; Romines, K.R.; Hazen, R.; Freeman, A.; Ferris, R.G.; Andrew, C.W.; et al. Structural basis for the improved drug resistance profile of new generation benzophenone non-nucleoside HIV-1 reverse transcriptase inhibitors. J. Med. Chem. 2008, 51, 5000-5008.
14. O'llah, E.; Rufchahi, M. Synthesis of 6-chloro and 6-fluoro-4-hydroxyl-2- quinolone and their azo disperse dyes. Chin. Chem. Lett. 2010, 21, 542-546.
15. Zhu, Q.; Reza, F.; Yang, Z.; Anthony, A.; Liu, Y.; Joon, C.H.; Richard, W. 4-Thio substituted quinoline and naphthyridine compounds. Patent EP 2,061,466, 2009.
16. Whisler, M.C.; MacNeil, S.; Snieckus, V.; Beak, P. Beyond thermodynamic acidity: A perspective on the complex-induced proximity effect (CIPE) in deprotonation reactions. Angew. Chem. Int. Ed. Engl. 2004, 43, 2206-2225. (Pubitemid 39257757)
17. Hewawasam, P.; Fan, W.; Knipe, J.; Moon, S.L.; Boissard, C.G.; Gribkoff, V.K.; Starrett, J.E. The synthesis and structure-activity relationships of 4-aryl-3-aminoquinolin-2-ones: A new class of calcium-dependent, large conductance, potassium (maxi-K) channel openers targeted for post-stroke neuroprotection. Bioorg. Med. Chem. Lett. 2002, 12, 1779-1783. (Pubitemid 34626909)
18. Ren, J.; Milton, J.; Weaver, K.L.; Short, S.A.; Stuart, D.I. Structural basis for the resilience of efavirenz (DMP-266) to drug resistance mutations in HIV-1 reverse transcriptase. Structure 2000, 8, 1089-1094 (Pubitemid 32667472)