Literature DB >> 21381765

3-Hydroxypyrimidine-2,4-diones as an inhibitor scaffold of HIV integrase.

Jing Tang1, Kasthuraiah Maddali, Mathieu Metifiot, Yuk Y Sham, Robert Vince, Yves Pommier, Zhengqiang Wang.   

Abstract

Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (INIs). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure-activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.

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Year:  2011        PMID： 21381765      PMCID： PMC3072462          DOI： 10.1021/jm1014378

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  48 in total

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Authors:  Richard A Friesner; Jay L Banks; Robert B Murphy; Thomas A Halgren; Jasna J Klicic; Daniel T Mainz; Matthew P Repasky; Eric H Knoll; Mee Shelley; Jason K Perry; David E Shaw; Perry Francis; Peter S Shenkin
Journal:  J Med Chem       Date:  2004-03-25       Impact factor: 7.446

2.  HIV-1 integrase pharmacophore model derived from diverse classes of inhibitors.

Authors:  Gabriela Iurcu Mustata; Alessandro Brigo; James M Briggs
Journal:  Bioorg Med Chem Lett       Date:  2004-03-22       Impact factor: 2.823

3.  Rationally designed dual inhibitors of HIV reverse transcriptase and integrase.

Authors:  Zhengqiang Wang; Eric M Bennett; Daniel J Wilson; Christine Salomon; Robert Vince
Journal:  J Med Chem       Date:  2007-07-04       Impact factor: 7.446

4.  Estimation of binding free energies for HIV proteinase inhibitors by molecular dynamics simulations.

Authors:  T Hansson; J Aqvist
Journal:  Protein Eng       Date:  1995-11

5.  Presence of an inducible HIV-1 latent reservoir during highly active antiretroviral therapy.

Authors:  T W Chun; L Stuyver; S B Mizell; L A Ehler; J A Mican; M Baseler; A L Lloyd; M A Nowak; A S Fauci
Journal:  Proc Natl Acad Sci U S A       Date:  1997-11-25       Impact factor: 11.205

Review 6.  Novel integrase inhibitors for HIV.

Authors:  Nicole Prada; Martin Markowitz
Journal:  Expert Opin Investig Drugs       Date:  2010-09       Impact factor: 6.206

7.  Beta-diketo acid pharmacophore hypothesis. 1. Discovery of a novel class of HIV-1 integrase inhibitors.

Authors:  Raveendra Dayam; Tino Sanchez; Omoshile Clement; Robert Shoemaker; Shizuko Sei; Nouri Neamati
Journal:  J Med Chem       Date:  2005-01-13       Impact factor: 7.446

Review 8.  Elvitegravir: a new HIV integrase inhibitor.

Authors:  Kazuya Shimura; Eiichi N Kodama
Journal:  Antivir Chem Chemother       Date:  2009-10-19

Review 9.  HIV-1 IN inhibitors: 2010 update and perspectives.

Authors:  Christophe Marchand; Kasthuraiah Maddali; Mathieu Métifiot; Yves Pommier
Journal:  Curr Top Med Chem       Date:  2009       Impact factor: 3.295

10.  Virus evolution reveals an exclusive role for LEDGF/p75 in chromosomal tethering of HIV.

Authors:  Anneleen Hombrouck; Jan De Rijck; Jelle Hendrix; Linos Vandekerckhove; Arnout Voet; Marc De Maeyer; Myriam Witvrouw; Yves Engelborghs; Frauke Christ; Rik Gijsbers; Zeger Debyser
Journal:  PLoS Pathog       Date:  2007-03       Impact factor: 6.823
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  16 in total

1.  Microwave assisted organic synthesis (MAOS) of small molecules as potential HIV-1 integrase inhibitors.

Authors:  Stefania Ferro; Sara De Grazia; Laura De Luca; Rosaria Gitto; Caterina Elisa Faliti; Zeger Debyzer; Alba Chimirri
Journal:  Molecules       Date:  2011-08-11       Impact factor: 4.411

2.  6-Cyclohexylmethyl-3-hydroxypyrimidine-2,4-dione as an inhibitor scaffold of HIV reverase transcriptase: Impacts of the 3-OH on inhibiting RNase H and polymerase.

Authors:  Jing Tang; Karen A Kirby; Andrew D Huber; Mary C Casey; Juan Ji; Daniel J Wilson; Stefan G Sarafianos; Zhengqiang Wang
Journal:  Eur J Med Chem       Date:  2017-01-30       Impact factor: 6.514

3.  3-Hydroxypyrimidine-2,4-diones as Selective Active Site Inhibitors of HIV Reverse Transcriptase-Associated RNase H: Design, Synthesis, and Biochemical Evaluations.

Authors:  Jing Tang; Feng Liu; Eva Nagy; Lena Miller; Karen A Kirby; Daniel J Wilson; Bulan Wu; Stefan G Sarafianos; Michael A Parniak; Zhengqiang Wang
Journal:  J Med Chem       Date:  2016-03-08       Impact factor: 7.446

4.  Double-Winged 3-Hydroxypyrimidine-2,4-diones: Potent and Selective Inhibition against HIV-1 RNase H with Significant Antiviral Activity.

Authors:  Sanjeev Kumar V Vernekar; Jing Tang; Bulan Wu; Andrew D Huber; Mary C Casey; Nataliya Myshakina; Daniel J Wilson; Jayakanth Kankanala; Karen A Kirby; Michael A Parniak; Stefan G Sarafianos; Zhengqiang Wang
Journal:  J Med Chem       Date:  2017-05-31       Impact factor: 7.446

5.  N-Substituted Quinolinonyl Diketo Acid Derivatives as HIV Integrase Strand Transfer Inhibitors and Their Activity against RNase H Function of Reverse Transcriptase.

Authors:  Luca Pescatori; Mathieu Métifiot; Suhman Chung; Takashi Masoaka; Giuliana Cuzzucoli Crucitti; Antonella Messore; Giovanni Pupo; Valentina Noemi Madia; Francesco Saccoliti; Luigi Scipione; Silvano Tortorella; Francesco Saverio Di Leva; Sandro Cosconati; Luciana Marinelli; Ettore Novellino; Stuart F J Le Grice; Yves Pommier; Christophe Marchand; Roberta Costi; Roberto Di Santo
Journal:  J Med Chem       Date:  2015-05-26       Impact factor: 7.446

6.  3-Hydroxypyrimidine-2,4-Diones as Novel Hepatitis B Virus Antivirals Targeting the Viral Ribonuclease H.

Authors:  Andrew D Huber; Eleftherios Michailidis; Jing Tang; Maritza N Puray-Chavez; Maria Boftsi; Jennifer J Wolf; Kelsey N Boschert; Megan A Sheridan; Maxwell D Leslie; Karen A Kirby; Kamalendra Singh; Hiroaki Mitsuya; Michael A Parniak; Zhengqiang Wang; Stefan G Sarafianos
Journal:  Antimicrob Agents Chemother       Date:  2017-05-24       Impact factor: 5.191

7.  Structural and inhibition studies of the RNase H function of xenotropic murine leukemia virus-related virus reverse transcriptase.

Authors:  Karen A Kirby; Bruno Marchand; Yee Tsuey Ong; Tanyaradzwa P Ndongwe; Atsuko Hachiya; Eleftherios Michailidis; Maxwell D Leslie; Daniel V Sietsema; Tracy L Fetterly; Christopher A Dorst; Kamalendra Singh; Zhengqiang Wang; Michael A Parniak; Stefan G Sarafianos
Journal:  Antimicrob Agents Chemother       Date:  2012-01-17       Impact factor: 5.191

8.  6-Biphenylmethyl-3-hydroxypyrimidine-2,4-diones potently and selectively inhibited HIV reverse transcriptase-associated RNase H.

Authors:  Lei Wang; Jing Tang; Andrew D Huber; Mary C Casey; Karen A Kirby; Daniel J Wilson; Jayakanth Kankanala; Michael A Parniak; Stefan G Sarafianos; Zhengqiang Wang
Journal:  Eur J Med Chem       Date:  2018-07-17       Impact factor: 6.514

9.  3-Hydroxypyrimidine-2,4-dione-5-N-benzylcarboxamides Potently Inhibit HIV-1 Integrase and RNase H.

Authors:  Bulan Wu; Jing Tang; Daniel J Wilson; Andrew D Huber; Mary C Casey; Juan Ji; Jayakanth Kankanala; Jiashu Xie; Stefan G Sarafianos; Zhengqiang Wang
Journal:  J Med Chem       Date:  2016-06-17       Impact factor: 7.446

10.  Cutting into the Substrate Dominance: Pharmacophore and Structure-Based Approaches toward Inhibiting Human Immunodeficiency Virus Reverse Transcriptase-Associated Ribonuclease H.

Authors:  Lei Wang; Stefan G Sarafianos; Zhengqiang Wang
Journal:  Acc Chem Res       Date:  2019-12-27       Impact factor: 22.384
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