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Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays.

Jones LH, Allan G, Barba O, Burt C, Corbau R, Dupont T, Knöchel T, Irving S, Middleton DS, Mowbray CE, Perros M, Ringrose H, Swain NA, Webster R, Westby M, Phillips C
J Med Chem 52 1219-23 (2009)
Cited: 26 times
EuropePMC logo PMID: 19175319

Abstract

A major problem associated with non-nucleoside reverse transcriptase inhibitors (NNRTIs) for the treatment of HIV is their lack of resilience to mutations in the reverse transcriptase (RT) enzyme. Using structural overlays of the known inhibitors efavirenz and capravirine complexed in RT as a starting point, and structure-based drug design techniques, we have created a novel series of indazole NNRTIs that possess excellent metabolic stability and mutant resilience.

Reviews - 2jle mentioned but not cited (1)

  1. Molecular Docking Studies of HIV-1 Resistance to Reverse Transcriptase Inhibitors: Mini-Review. Tarasova O, Poroikov V, Veselovsky A. Molecules 23 E1233 (2018)

Articles - 2jle mentioned but not cited (7)

  1. What do docking and QSAR tell us about the design of HIV-1 reverse transcriptase nonnucleoside inhibitors? Paneth A, Płonka W, Paneth P. J Mol Model 23 317 (2017)
  2. Binding property of HIV p24 and Reverse transcriptase by chalcones from Pongamia pinnata seeds. Mathaiyan M, Suresh A, Balamurugan R. Bioinformation 14 279-284 (2018)
  3. Aryl Substituted Benzimidazolones as Potent HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors. Pribut N, Basson AE, van Otterlo WAL, Liotta DC, Pelly SC. ACS Med Chem Lett 10 196-202 (2019)
  4. Assessment of Nonnucleoside Inhibitors Binding to HIV-1 Reverse Transcriptase Using HYDE Scoring. Paneth A, Płonka W, Paneth P. Pharmaceuticals (Basel) 12 E64 (2019)
  5. LigTMap: ligand and structure-based target identification and activity prediction for small molecular compounds. Shaikh F, Tai HK, Desai N, Siu SWI. J Cheminform 13 44 (2021)
  6. Human adenovirus DNA polymerase is evolutionarily and functionally associated with human telomerase reverse transcriptase based on in silico molecular characterization that implicate abacavir and zidovudine. Fatoki TH. Front Bioinform 3 1123307 (2023)
  7. Modeling and Analysis of HIV-1 Pol Polyprotein as a Case Study for Predicting Large Polyprotein Structures. Hao M, Imamichi T, Chang W. Int J Mol Sci 25 1809 (2024)


Reviews citing this publication (6)

  1. HIV-1 NNRTIs: structural diversity, pharmacophore similarity, and implications for drug design. Zhan P, Chen X, Li D, Fang Z, De Clercq E, Liu X. Med Res Rev 33 Suppl 1 E1-72 (2013)
  2. "Old Dogs with New Tricks": exploiting alternative mechanisms of action and new drug design strategies for clinically validated HIV targets. Kang D, Song Y, Chen W, Zhan P, Liu X. Mol Biosyst 10 1998-2022 (2014)
  3. Structure-based design of anti-infectives. Agarwal AK, Fishwick CW. Ann N Y Acad Sci 1213 20-45 (2010)
  4. Efavirenz a nonnucleoside reverse transcriptase inhibitor of first-generation: Approaches based on its medicinal chemistry. Bastos MM, Costa CCP, Bezerra TC, da Silva FC, Boechat N. Eur J Med Chem 108 455-465 (2016)
  5. Recent advances in the structure-based rational design of TNKSIs. Zhan P, Song Y, Itoh Y, Suzuki T, Liu X. Mol Biosyst 10 2783-2799 (2014)
  6. Fragment-based approaches to anti-HIV drug discovery: state of the art and future opportunities. Huang B, Kang D, Zhan P, Liu X. Expert Opin Drug Discov 10 1271-1281 (2015)

Articles citing this publication (12)

  1. Lersivirine, a nonnucleoside reverse transcriptase inhibitor with activity against drug-resistant human immunodeficiency virus type 1. Corbau R, Mori J, Phillips C, Fishburn L, Martin A, Mowbray C, Panton W, Smith-Burchnell C, Thornberry A, Ringrose H, Knöchel T, Irving S, Westby M, Wood A, Perros M. Antimicrob Agents Chemother 54 4451-4463 (2010)
  2. Pyrazole NNRTIs 4: selection of UK-453,061 (lersivirine) as a development candidate. Mowbray CE, Burt C, Corbau R, Gayton S, Hawes M, Perros M, Tran I, Price DA, Quinton FJ, Selby MD, Stupple PA, Webster R, Wood A. Bioorg Med Chem Lett 19 5857-5860 (2009)
  3. Drug hybridization strategies: before or after lead identification? Fraga CA. Expert Opin Drug Discov 4 605-609 (2009)
  4. Hybrid diarylbenzopyrimidine non-nucleoside reverse transcriptase inhibitors as promising new leads for improved anti-HIV-1 chemotherapy. Zeng ZS, He QQ, Liang YH, Feng XQ, Chen FE, De Clercq E, Balzarini J, Pannecouque C. Bioorg Med Chem 18 5039-5047 (2010)
  5. Construction of a tetracyclic butterfly-like scaffold: palladium-catalyzed heck/arylation cascade. Kim KH, Lee HS, Kim SH, Kim SH, Kim JN. Chemistry 16 2375-2380 (2010)
  6. Letter Comparison of the non-nucleoside reverse transcriptase inhibitor lersivirine with its pyrazole and imidazole isomers. Jones LH, Allan G, Corbau R, Middleton DS, Mowbray CE, Newman SD, Phillips C, Webster R, Westby M. Chem Biol Drug Des 77 393-397 (2011)
  7. Revealing the drug-resistant mechanism for diarylpyrimidine analogue inhibitors of HIV-1 reverse transcriptase. Zhang H, Qin F, Ye W, Li Z, Ma S, Xia Y, Jiang Y, Zhu J, Li Y, Zhang J, Chen HF. Chem Biol Drug Des 78 427-437 (2011)
  8. Synthesis of isoflavene-thiosemicarbazone hybrids and evaluation of their anti-tumor activity. Yee EMH, Brandl MB, Black DS, Vittorio O, Kumar N. Bioorg Med Chem Lett 27 2454-2458 (2017)
  9. Synthesis of quinolin-2-one alkaloid derivatives and their inhibitory activities against HIV-1 reverse transcriptase. Cheng P, Gu Q, Liu W, Zou JF, Ou YY, Luo ZY, Zeng JG. Molecules 16 7649-7661 (2011)
  10. Novel fluorine-containing DAPY derivatives as potent HIV-1 NNRTIs: a patent evaluation of WO2014072419. Meng Q, Liu N, Huang B, Zhan P, Liu X. Expert Opin Ther Pat 25 1477-1486 (2015)
  11. Unprecedented rearrangement of 2-(2-aminoethyl)-1-aryl-3,4-dihydropyrazino[1,2-b]indazole-2-ium 6-oxides to 2,3-dihydro-1H-imidazo[1,2-b]indazoles. Kocí J, Oliver AG, Krchnák V. J Org Chem 75 502-505 (2010)
  12. Synthesis and anti-human immunodeficiency virus type 1 activity of (E)-N-phenylstyryl-N-alkylacetamide derivatives. Cheng P, Chen JJ, Huang N, Wang RR, Zheng YT, Liang YZ. Molecules 14 3176-3186 (2009)


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