Literature DB >> 29259750

Design and Synthesis of Piperazine Sulfonamide Cores Leading to Highly Potent HIV-1 Protease Inhibitors.

Christopher J Bungard1, Peter D Williams1, Jurgen Schulz1, Catherine M Wiscount1, M Katharine Holloway1, H Marie Loughran1, Jesse J Manikowski1, Hua-Poo Su1, David J Bennett1, Lehua Chang2, Xin-Jie Chu2, Alejandro Crespo2, Michael P Dwyer2, Kartik Keertikar2, Gregori J Morriello2, Andrew W Stamford2, Sherman T Waddell2, Bin Zhong3, Bin Hu3, Tao Ji3, Tracy L Diamond1, Carolyn Bahnck-Teets1, Steven S Carroll1, John F Fay1, Xu Min1, William Morris2, Jeanine E Ballard1, Michael D Miller1, John A McCauley1.   

Abstract

Using the HIV-1 protease binding mode of MK-8718 and PL-100 as inspiration, a novel aspartate binding bicyclic piperazine sulfonamide core was designed and synthesized. The resulting HIV-1 protease inhibitor containing this core showed an 60-fold increase in enzyme binding affinity and a 10-fold increase in antiviral activity relative to MK-8718.

Entities:  

Year:  2017        PMID： 29259750      PMCID： PMC5733263          DOI： 10.1021/acsmedchemlett.7b00386

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  9 in total

1.  Regioselective ring-opening of amino acid-derived chiral aziridines: an easy access to cis-2,5-disubstituted chiral piperazines.

Authors:  Krishnananda Samanta; Gautam Panda
Journal:  Chem Asian J       Date:  2011-01-03

Review 2.  Recent Progress in the Development of HIV-1 Protease Inhibitors for the Treatment of HIV/AIDS.

Authors:  Arun K Ghosh; Heather L Osswald; Gary Prato
Journal:  J Med Chem       Date:  2016-01-22       Impact factor: 7.446

3.  Discovery of MK-8718, an HIV Protease Inhibitor Containing a Novel Morpholine Aspartate Binding Group.

Authors:  Christopher J Bungard; Peter D Williams; Jeanine E Ballard; David J Bennett; Christian Beaulieu; Carolyn Bahnck-Teets; Steve S Carroll; Ronald K Chang; David C Dubost; John F Fay; Tracy L Diamond; Thomas J Greshock; Li Hao; M Katharine Holloway; Peter J Felock; Jennifer J Gesell; Hua-Poo Su; Jesse J Manikowski; Daniel J McKay; Mike Miller; Xu Min; Carmela Molinaro; Oscar M Moradei; Philippe G Nantermet; Christian Nadeau; Rosa I Sanchez; Tummanapalli Satyanarayana; William D Shipe; Sanjay K Singh; Vouy Linh Truong; Sivalenka Vijayasaradhi; Catherine M Wiscount; Joseph P Vacca; Sheldon N Crane; John A McCauley
Journal:  ACS Med Chem Lett       Date:  2016-05-09       Impact factor: 4.345

4.  PL-100, a novel HIV-1 protease inhibitor displaying a high genetic barrier to resistance: an in vitro selection study.

Authors:  Serge Dandache; Craig A Coburn; Maureen Oliveira; Timothy J Allison; M Katharine Holloway; Jinzi J Wu; Brent R Stranix; Chandra Panchal; Mark A Wainberg; Joseph P Vacca
Journal:  J Med Virol       Date:  2008-12       Impact factor: 2.327

Review 5.  Investigational protease inhibitors as antiretroviral therapies.

Authors:  Narasimha M Midde; Benjamin J Patters; Pss Rao; Theodore J Cory; Santosh Kumar
Journal:  Expert Opin Investig Drugs       Date:  2016-08-02       Impact factor: 6.206

6.  Cleavage of HIV-1 gag polyprotein synthesized in vitro: sequential cleavage by the viral protease.

Authors:  S Erickson-Viitanen; J Manfredi; P Viitanen; D E Tribe; R Tritch; C A Hutchison; D D Loeb; R Swanstrom
Journal:  AIDS Res Hum Retroviruses       Date:  1989-12       Impact factor: 2.205

7.  Expedite protocol for construction of chiral regioselectively N-protected monosubstituted piperazine, 1,4-diazepane, and 1,4-diazocane building blocks.

Authors:  François Crestey; Matthias Witt; Jerzy W Jaroszewski; Henrik Franzyk
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

8.  Active human immunodeficiency virus protease is required for viral infectivity.

Authors:  N E Kohl; E A Emini; W A Schleif; L J Davis; J C Heimbach; R A Dixon; E M Scolnick; I S Sigal
Journal:  Proc Natl Acad Sci U S A       Date:  1988-07       Impact factor: 11.205

9.  Structure at 2.5-A resolution of chemically synthesized human immunodeficiency virus type 1 protease complexed with a hydroxyethylene-based inhibitor.

Authors:  M Jaskólski; A G Tomasselli; T K Sawyer; D G Staples; R L Heinrikson; J Schneider; S B Kent; A Wlodawer
Journal:  Biochemistry       Date:  1991-02-12       Impact factor: 3.162
  9 in total
  8 in total

1.  Design, Synthesis and X-Ray Structural Studies of Potent HIV-1 Protease Inhibitors Containing C-4 Substituted Tricyclic Hexahydro-Furofuran Derivatives as P2 Ligands.

Authors:  Arun K Ghosh; Satish Kovela; Ashish Sharma; Dana Shahabi; Ajay K Ghosh; Denver R Hopkins; Monika Yadav; Megan E Johnson; Johnson Agniswamy; Yuan-Fang Wang; Shin-Ichiro Hattori; Nobuyo Higashi-Kuwata; Manabu Aoki; Masayuki Amano; Irene T Weber; Hiroaki Mitsuya
Journal:  ChemMedChem       Date:  2022-03-04       Impact factor: 3.540

2.  Design and Synthesis of Highly Potent HIV-1 Protease Inhibitors Containing Tricyclic Fused Ring Systems as Novel P2 Ligands: Structure-Activity Studies, Biological and X-ray Structural Analysis.

Authors:  Arun K Ghosh; Prasanth R Nyalapatla; Satish Kovela; Kalapala Venkateswara Rao; Margherita Brindisi; Heather L Osswald; Masayuki Amano; Manabu Aoki; Johnson Agniswamy; Yuan-Fang Wang; Irene T Weber; Hiroaki Mitsuya
Journal:  J Med Chem       Date:  2018-05-15       Impact factor: 7.446

3.  Structural Analysis of Potent Hybrid HIV-1 Protease Inhibitors Containing Bis-tetrahydrofuran in a Pseudosymmetric Dipeptide Isostere.

Authors:  Linah N Rusere; Gordon J Lockbaum; Mina Henes; Sook-Kyung Lee; Ean Spielvogel; Desaboini Nageswara Rao; Klajdi Kosovrasti; Ellen A Nalivaika; Ronald Swanstrom; Nese Kurt Yilmaz; Celia A Schiffer; Akbar Ali
Journal:  J Med Chem       Date:  2020-08-03       Impact factor: 7.446

4.  Design, synthesis, and X-ray studies of potent HIV-1 protease inhibitors incorporating aminothiochromane and aminotetrahydronaphthalene carboxamide derivatives as the P2 ligands.

Authors:  Arun K Ghosh; Ravindra D Jadhav; Hannah Simpson; Satish Kovela; Heather Osswald; Johnson Agniswamy; Yuan-Fang Wang; Shin-Ichiro Hattori; Irene T Weber; Hiroaki Mitsuya
Journal:  Eur J Med Chem       Date:  2018-09-18       Impact factor: 6.514

Review 5.  Drug Design Strategies to Avoid Resistance in Direct-Acting Antivirals and Beyond.

Authors:  Ashley N Matthew; Florian Leidner; Gordon J Lockbaum; Mina Henes; Jacqueto Zephyr; Shurong Hou; Desaboini Nageswara Rao; Jennifer Timm; Linah N Rusere; Debra A Ragland; Janet L Paulsen; Kristina Prachanronarong; Djade I Soumana; Ellen A Nalivaika; Nese Kurt Yilmaz; Akbar Ali; Celia A Schiffer
Journal:  Chem Rev       Date:  2021-01-07       Impact factor: 60.622

6.  Inhibition of HIV-1 Protease by Carpobrotus edulis (L.).

Authors:  Beauty E Omoruyi; David I Ighodaro; Anthony J Afolayan; Graeme Bradley
Journal:  Evid Based Complement Alternat Med       Date:  2020-06-07       Impact factor: 2.629

7.  Sulfonylation of 1,4-Diazabicyclo[2.2.2]octane: Charge-Transfer Complex Triggered C-N Bond Cleavage.

Authors:  Ying Fu; Qin-Shan Xu; Quan-Zhou Li; Ming-Peng Li; Chun-Zhao Shi; Zhengyin Du
Journal:  ChemistryOpen       Date:  2019-01-28       Impact factor: 2.911

8.  Synthesis, in silico study (DFT, ADMET) and crystal structure of novel sulfamoyloxy-oxazolidinones: Interaction with SARS-CoV-2.

Authors:  Abdeslem Bouzina; Malika Berredjem; Sofiane Bouacida; Khaldoun Bachari; Christelle Marminon; Marc Le Borgne; Zouhair Bouaziz; Yousra Ouafa Bouone
Journal:  J Mol Struct       Date:  2022-02-05       Impact factor: 3.841
  8 in total

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