De novo design and in-silico studies of novel 1-phenyl-2,3,4,9-tetrahydro- 1H-pyrido[3,4-b]indole-3-carboxylicacid derivatives as HIV-1 reverse transcriptase inhibitors

Medicinal Chemistry Research

Volumn 23, Issue 8, 2014, Pages 3662-3670

  Penta, Ashok ^a   Chander, Subhash ^a   Ganguly, S ^b   Murugesan, S ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

^b BIRLA INSTITUTE OF TECHNOLOGY   (India)

Author keywords

AIDS; Autodock; Docking; HIV 1 reverse transcriptase; Molecular properties

Indexed keywords

1 PHENYL 2,3,4,9 TETRAHYDRO 1H PYRIDO[3,4 B]INDOLE 3 CARBOXYLIC ACID; ANTIVIRUS AGENT; BENZENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; EFAVIRENZ; INDOLE DERIVATIVE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; PYRIDINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; TNK 651; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; COMPUTER MODEL; DRUG DESIGN; ENERGY; ENZYME ACTIVE SITE; HYDROGEN BOND; MOLECULAR DOCKING; MOLECULAR INTERACTION;

EID: 84904433499     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-014-0945-9     Document Type: Article

References (24)

1. Adachi J, Mizoi Y, Naito T, Ogawa Y, Getani Y, Nihomiya I (1991) Identification of tetrahydro-β-carboline-3-carboxylic acid in foodstuffs, human urine and human milk. J Nutr 121:646-652
2. Audia JE, Evrard DA, Murdoch GR, Droste JJ, Nissen JS, Schenck KW, Fludzinski P, Lucaites VL, Nelson DL, Cohen ML (1996) Potent, selective tetrahydro- β-carboline antagonists of the serotonin 2B (5HT2B) contractile receptor in the rat stomach fundus. J Med Chem 39:2773-2780 (Pubitemid 26240346)
3. Bethune MP (2010) Non-nucleoside reverse transcriptase inhibitors (NNRTIs), their discovery, development and use in the treatment of HIV-1 infection: a review of the last 20 years (1989-2009). Antivir Res 85:75-90
4. Brossi A, Focella A, Teitel S (1973) Alkaloids in mammalian tissues. 3. Condensation of L-tryptophan and L-5-hydroxytryptophan with formaldehyde and acetaldehyde. J Med Chem 16:418-420
5. Chong P, Sebahar P, Youngman M, Garrido D, Zhang H, Eugene L, Robert ST, Wang NL, Ferris RG, Edelstein M, Weaver K, Mathis A, Peat A (2012) Rational design of potent non-nucleoside inhibitors of HIV-1 reverse transcriptase. J Med Chem 55:10601-10609
6. Daisy P, Suveena S, Rajalakshmi M, Lilly V (2011) Ligand based virtual screening on natural compounds for discovering active ligands. Der Pharm Chem 3:51-57
7. Daugan A, Grondin P, Ruault C, Gouville ACLMD, Coste H, Kirilovsky J, Hyafil F, Labaudiniere R (2003) The discovery of tadalafil: a novel and highly selective PDE5 Inhibitor. 1: 5,6,11,11a-tetra0068ydro-1H-imidazo[1′, 5′:1,6]pyrido[3,4-b]indole- 1,3(2H)-dione analogues. J Med Chem 46:4525-4532 (Pubitemid 37238753)
8. Deveau AM, Labroli A, Dieckhaus CM, Barthen MT, Smith KS, Macdonald TL (2001) The synthesis of amino-acid functionalized β-carbolines as topoisomerase II inhibitors. Bioorg Med Chem Lett 11:1251-1255 (Pubitemid 32434345)
9. Gharbia MA, Patel UR, Moyer JA, Muth EA (1987) Psychotropic agents: synthesis and antipsychotic activity of substituted β-carbolines. J Med Chem 30:1100-1105 (Pubitemid 17120795)
10. Glennon RA, Hong SS, Bondarev M, Law H, Dukat M, Rakhit S, Power P, Fan E, Kinneau D, Kamboj R, Teitler M, Davis KH, Smith C (1996) Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J Med Chem 39:314-322 (Pubitemid 26027037)
11. Glennon RA, Grella B, Tyacke RJ, Lau A, Westaway J, Hudson AL (2004) Binding of β-carbolines at imidazoline I2 receptors: a structure-affinity investigation. Bioorg Med Chem Lett 14:999-1002 (Pubitemid 38167629)
12. Guzman F, Cain M, Larscheid P, Hagen T, Cook JM, Schweri M, Skolnick P, Paul SM (1984) Biomimetic approach to potential benzodiazepine-receptor agonists and antagonists. J Med Chem 27:564-570 (Pubitemid 14149264)
13. Herraiz T (2007) Identification and occurrence of β-carboline alkaloids in raisins and inhibition of monoamine oxidase (MAO). J Agric Food Chem 55:8534-8540
14. Herraiz T, Chaparro C (2005) Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors. Biochem Biophys Res Commun 326:378-386 (Pubitemid 39593558)
15. Herraiz T, González D, Azpilicueta AC, Aran VJ, Guillen VJ (2010) β-carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). Food Chem Toxicol 48:839-845
16. Hopkins AL, Ren J, Esnouf RM, Willcox BE, Jones EY, Ross C, Miyasaka T, Walker RT, Tanaka H, Stammers DK, Stuart DI (1996) Complexes of HIV-1 reverse transcriptase with inhibitors of the HEPT series reveal conformational changes relevant to the design of potent non-nucleoside inhibitors. J Med Chem 39:1589-1600
17. Hou T, Wang J, Zhang W, Xu X (2007) ADME evaluation in drug discovery. 6. Can oral bioavailability in humans be effectively predicted by simple molecular property-based rules? J Chem Inf Model 47:460-463 (Pubitemid 46615948)
18. Kumar KA, Prathyusha LT, Umamaheshwari M, Sivashanmugam T, Subhadradevi V, Jagannath P, Madeswaran A, Salesheir F (2012) Design, admet and docking studies on some novel chalcone derivatives as soluble epoxide hydrolase enzyme inhibitors. J Chil Chem Soc 57:1442-1446
19. Li D, Zhan P, De Clercq E, Liu X (2012) Strategies for the design of HIV-1 non-nucleoside reverse transcriptase inhibitors: lessons from the development of seven representative paradigms. J Med Chem 55:3595-3613
20. Masanda VH, Patila KN, Jawarkarb RD, Haddac TB, Youssoufi MH, Alafeefy AA (2011) Exploring interactions of 2-amino-6-aryl-sulfonyl benzonitrile derivatives as non-nucleoside reverse transcriptase inhibitors of HIV-1 using docking studies. J Comput Method Mol Des 1:39-48
21. Paul AJ, Janssen PAJ, Lewi PJ, Arnold E, Daeyaert F, Jonge M, Heeres J, Koymans L, Vinkers M, Guillemont J, Pasquier E, Kukla M, Ludovici D, Andries K, Be0 thune MPD, Pauwels R, Das K, Clark AD, Frenkel YV, Hughes SH, Medaer B, Knaep FD, Bohets H, Clerck FD, Lampo A, Williams P, Stoffels P (2005) In search of a novel anti-HIV drug: multidisciplinary coordination in the discovery of 4-[[4-[[4-[(1E)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino] benzonitrile (R278474, rilpivirine). J Med Chem 48:1901-1909 (Pubitemid 40396320)
22. Sobhani AM, Ebrahimi SA, Mahmoudian M (2002) An in-vitro evaluation of human DNA topoisomerase I inhibition by Peganum harmala L. seeds extract and its β-carboline alkaloids. J Pharm Pharm Sci 5:19-23 (Pubitemid 34463347)
23. Sun LQ, Zhu L, Qian K, Qin B, Huang L, Chen CH, Lee KH, Xie L (2012) Design, synthesis and preclinical evaluations of novel 4-substituted 1,5-diarylanilines as potent HIV-1 non-nucleoside reverse transcriptase inhibitor (NNRTI) drug candidates. J Med Chem 55:7219-7229
24. Valdez RH, Tonin LTD, Nakamura TU, Filho BPD, Diaz JAM, Sarragiotto MH, Nakamura CV (2009) Biological activity of 1,2,3,4-tetrahydro-β-carboline-3- carboxamides against Trypanosoma cruzi. Acta Trop 110:7-14