Synthesis and biological evaluation of 5H-indolo [3,2- b][1,5]benzothiazepine derivatives, designed as conformationally constrained analogues of the human immunodeficiency virus type 1 reverse transcriptase inhibitor L-737, 126

Antiviral Chemistry and Chemotherapy

Volumn 9, Issue 2, 1998, Pages 139-148

  Silvestri, R ^a   Artico, M ^a   Bruno, B ^a   Massa, S ^b   Novellino, E ^c   Greco, G ^d   Marongiu, M E ^e   Pani, A ^e   De Montis, A ^e   La Colla, P ^e  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

^c UNIVERSITY OF SALERNO   (Italy)

^d UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^e UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

5H indolo 3,2 b 1,5 benzothiazepine derivatives; Anti HIV agents; NNRTIs

Indexed keywords

BENZOTHIADIAZINE DERIVATIVE; L 737126; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONFORMATIONAL TRANSITION; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROLYSIS; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION;

EID: 0031899273     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632029800900205     Document Type: Article

References (21)

1. Artico M (1996) Non-nuclcoside anti-HIV-1 reverse transcriptase inhibitors (NNRTIs): a chemical survey from lead compounds to selected drugs for clinical trials. Farmaco 51:305-331.
2. Artico M, Silvestri R, Pagnozzi E, Stefancich G, Massa S, Loi AG, Putzolu M, Corrias S, Spiga MG & La Colla P (1996a) Pyrrolo[l,2-b][l,2,5]benzothiadiazepines (PBTDs): a novel class of non-nucleoside reverse transcriptase inhibitors. Bioorganic and Medicinal Chemistry 4:837-850.
3. Artico M, Silvestri R, Massa S, Loi AG, Corrias S, Piras G & La Colla P (1996b) 2-Sulfonyl-4-chloroanilino moiety: a potent pharmacophorc for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones. Journal of Medicinal Chemistry 39:522-530.
4. Bernstein FC, Koetzle TF, Williams GJB, Mcycr EF Jr, Brice MD, Rodgers JR, Kennard O, Shimanouchi T & Tasumi T (1997) The protein data bank: a computer based archival file for macromolecular structures. Journal of Molecular Biology 112:535-542.
5. Chimirri A, Grasso S, Monforte AM, Monforte P & Zappalà M (1991) Anti-HIV agents. I. Synthesis and in vitro evaluation of novel lH,3H-thiazolo[3,4-a]benzimidazoles. Farmaco 46:817-823.
6. Clark M, Cramer RD III & Van Opdenbosch N (1989) Validation of the general purpose Tripos 5.2 force field. Journal of Computational Chemistry 10:982-1012.
7. De Clercq E (1995a) Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. Journal of Medicinal Chemistry 38:2491-2516.
8. De Clercq E (1995b) Antiviral therapy of human immunodeficiency virus infections. Clinical Microbiology Reviews 8:200-239.
9. Ding J, Das K, Moereels H, Koymans L, Andries K, Janssen PAJ, Hughes SH & Arnold E (1995) Structure of HIV-1 RT/TIBO R86183 complex reveals similarity in the binding of diverse nonnuclcoside inhibitors. Nature Structural Biology 2:407-415.
10. Gasteigcr J ScMarsili M (1980) Iterative partial equalization of orbital clcctronegativity - a rapid access to atomic charges. Tetrahedron 36:3219-3228.
11. Giannotti D, Viti G, Nannicini R, Pestellini V & Bellarosa D (1995) Synthesis and anti-HIV-1 activity of new thiadiazepindioxides. Bioorganic & Medicinal Chemistry Letters 5:1461-1466.
12. Hargrave KD, Proudfoot JR, Grozinger KG, Cullen E, Kapadia SR, Patel UR, Fuchs VU, Mauldin SC, Vitous J, Behnke ML, Klunder JM, Pal K, Skiles JW, McNeil DW, Rose JM, Chow GC, Skoog MT, Wu JC, Schmidt G, Engel WW, Eberlein WG, Saboe TD, Campbell SJ, Rosenthal AS & Adams J (1991) Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. l. Tricyclic pyridobenzo- and dipyridodiazepinones. Journal of Medicinal Chemistry 34:2231-2241.
13. Heath-Brown B & Philpott PG (1965) Studies in the indole series. Part III.The Japp-Klingemmann reaction. Journal of the Chemical Society 7185-7193.
14. Kukla MJ, Breslin HJ, Pauwels R, Fedde CL, Miranda M, Scott MK, Sherill RG, Raeymaekers A, Van Gelder J, Andries K, Janssen MAC, De Clercq E & Janssen PAJ (1991) Synthesis and HIV-1 activity of 4,5,6,7-tetrahydro-5-mcthylimidazo[4,5,ljk][l,4]benzodiazepin-2(lH)-one (TIBO) derivatives. Journal of Medicinal Chemistry 34:746-751.
15. Palmer PJ.Trigg RB & Warrington JV (1971) Benzothiazolines as antitubercolous agents. Journal of Medicinal Chemistry 14:248-251.
16. Pauwels R, Balzarini J, Baba M, Snoeck R, Schols D, Herdewijn P, Desmyter J & Dc Clercq E (1988) Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. Journal of Virological Methods 20:309-321.
17. Ren J, Esnouf R, Garmaen E, Somers D, Ross C, Kirby I, Keeling J, Darby G, Jones T, Stuart D & Stammers D (1995) High resolution structures of HIV-1 RT from four RT-inhibitor complexes. Nature Structural Biology 2:293-302.
18. Terret NK, Bojanic D, Mcrson JR & Stephenson PT (1992) Imidazo[2′,3′:6,5]dipyrido[3,2-b:2')3'-e]-l,4-diazepines: nonnucleoside HIV-1 reverse transcriptase inhibitors with greater enzyme affinity than nevirapine. Bioorganic and Medicinal Chemistry Letters 2:1745-1750.
19. Tramontano E & Cheng Y-C (1992) HIV-1 reverse transcriptase inhibition by dipyridodiazepinone derivative: BI-RG-587. Biochemical Pharmacology 43:1371-1376.
20. Trapani G, Franco M, Latrofa A, Genchi G, Siro Brigiani G, Mazzoccoli M, Persichella M, Serra M, Biggio G & Liso G (1994) Synthesis and anticonvulsant activity of some 1,2,3,3a-tetrahydropyrrolo[2,l-b]benzothiazol-l-ones and pyrrolo[2,l-b]thiazole analogues. European Journal of Medicinal Chemistry 29:197-204.
21. Williams TM, Ciccarone TM, MacTough SC, Rooney CS, Balani SK, Condra JH, Emini EA, Goldman ME, Greenlee WJ, Kauffman LR, O'Brien JA, Sardana VV, Schleif WA, Theoharides AD & Anderson PS (1993) 5-Chloro-3-(pnenylsulfonyl)indole-2-carboxamide: a novel non-nucleoside inhibitor of HIV-1 reverse transcriptase. Journal of Medicinal Chemistry 36:1291-1294.