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Literature DB >> 19703770

Structure-activity relationship and improved hydrolytic stability of pyrazole derivatives that are allosteric inhibitors of West Nile Virus NS2B-NS3 proteinase.

Shyama Sidique¹, Sergey A Shiryaev, Boris I Ratnikov, Ananda Herath, Ying Su, Alex Y Strongin, Nicholas D P Cosford.

Abstract

West Nile Virus (WNV) is a potentially deadly mosquito-borne flavivirus which has spread rapidly throughout the world. Currently there is no effective vaccine against flaviviral infections. We previously reported the identification of pyrazole ester derivatives as allosteric inhibitors of WNV NS2B-NS3 proteinase. These compounds degrade rapidly in pH 8 buffer with a half life of 1-2h. We now report the design, synthesis and in vitro evaluation of pyrazole derivatives that are inhibitors of WNV NS2B-NS3 proteinase with greatly improved stability in the assay medium.

Entities: CellLine Chemical Disease Gene Species

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Year: 2009 PMID： 19703770 PMCID： PMC2776708 DOI： 10.1016/j.bmcl.2009.07.150

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

11 in total

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Authors: K M van der Meulen; M B Pensaert; H J Nauwynck
Journal: Arch Virol Date: 2005-01-19 Impact factor: 2.574

Review 2. West Nile virus: Uganda, 1937, to New York City, 1999.

Authors: C G Hayes
Journal: Ann N Y Acad Sci Date: 2001-12 Impact factor: 5.691

3. Functional characterization of cis and trans activity of the Flavivirus NS2B-NS3 protease.

Authors: Aloke K Bera; Richard J Kuhn; Janet L Smith
Journal: J Biol Chem Date: 2007-03-02 Impact factor: 5.157

Review 4. West Nile Virus NS2B/NS3 protease as an antiviral target.

Authors: K J Chappell; M J Stoermer; D P Fairlie; P R Young
Journal: Curr Med Chem Date: 2008 Impact factor: 4.530

5. Substrate inhibition kinetic model for West Nile virus NS2B-NS3 protease.

Authors: Suzanne M Tomlinson; Stanley J Watowich
Journal: Biochemistry Date: 2008-10-15 Impact factor: 3.162

Review 6. West Nile virus.

Authors: Grant L Campbell; Anthony A Marfin; Robert S Lanciotti; Duane J Gubler
Journal: Lancet Infect Dis Date: 2002-09 Impact factor: 25.071

7. Identification and characterization of 3-substituted pyrazolyl esters as alternate substrates for cathepsin B: the confounding effects of DTT and cysteine in biological assays.

Authors: Michael C Myers; Andrew D Napper; Nuzhat Motlekar; Parag P Shah; Chun-Hao Chiu; Mary Pat Beavers; Scott L Diamond; Donna M Huryn; Amos B Smith
Journal: Bioorg Med Chem Lett Date: 2007-07-05 Impact factor: 2.823

8. Identification and biochemical characterization of small-molecule inhibitors of west nile virus serine protease by a high-throughput screen.

Authors: Niklaus H Mueller; Nagarajan Pattabiraman; Camilo Ansarah-Sobrinho; Prasanth Viswanathan; Theodore C Pierson; R Padmanabhan
Journal: Antimicrob Agents Chemother Date: 2008-07-07 Impact factor: 5.191

9. Potent cationic inhibitors of West Nile virus NS2B/NS3 protease with serum stability, cell permeability and antiviral activity.

Authors: Martin J Stoermer; Keith J Chappell; Susann Liebscher; Christina M Jensen; Chun H Gan; Praveer K Gupta; Wei-Jun Xu; Paul R Young; David P Fairlie
Journal: J Med Chem Date: 2008-08-26 Impact factor: 7.446

10. Discovery of a non-peptidic inhibitor of west nile virus NS3 protease by high-throughput docking.

Authors: Dariusz Ekonomiuk; Xun-Cheng Su; Kiyoshi Ozawa; Christophe Bodenreider; Siew Pheng Lim; Zheng Yin; Thomas H Keller; David Beer; Viral Patel; Gottfried Otting; Amedeo Caflisch; Danzhi Huang
Journal: PLoS Negl Trop Dis Date: 2009-01-13

18 in total

1. Structural and functional parameters of the flaviviral protease: a promising antiviral drug target.

Authors: Sergey A Shiryaev; Alex Y Strongin
Journal: Future Virol Date: 2010-09-01 Impact factor: 1.831

2. Virtual ligand screening of the National Cancer Institute (NCI) compound library leads to the allosteric inhibitory scaffolds of the West Nile Virus NS3 proteinase.

Authors: Sergey A Shiryaev; Anton V Cheltsov; Katarzyna Gawlik; Boris I Ratnikov; Alex Y Strongin
Journal: Assay Drug Dev Technol Date: 2010-11-04 Impact factor: 1.738

3. Structure-guided fragment-based in silico drug design of dengue protease inhibitors.

Authors: Tim Knehans; Andreas Schüller; Danny N Doan; Kassoum Nacro; Jeffrey Hill; Peter Güntert; M S Madhusudhan; Tanja Weil; Subhash G Vasudevan
Journal: J Comput Aided Mol Des Date: 2011-02-23 Impact factor: 3.686

Review 4. Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review.

Authors: Khalid Karrouchi; Smaail Radi; Youssef Ramli; Jamal Taoufik; Yahia N Mabkhot; Faiz A Al-Aizari; M'hammed Ansar
Journal: Molecules Date: 2018-01-12 Impact factor: 4.411

5. Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides.

Authors: Gary A Molander; DaWeon Ryu; Mona Hosseini-Sarvari; Rammohan Devulapally; Dave G Seapy
Journal: J Org Chem Date: 2013-06-25 Impact factor: 4.354

6. Characterization of the Zika virus two-component NS2B-NS3 protease and structure-assisted identification of allosteric small-molecule antagonists.

Authors: Sergey A Shiryaev; Chen Farhy; Antonella Pinto; Chun-Teng Huang; Nicole Simonetti; Annie Elong Ngono; Antimone Dewing; Sujan Shresta; Anthony B Pinkerton; Piotr Cieplak; Alex Y Strongin; Alexey V Terskikh
Journal: Antiviral Res Date: 2017-04-29 Impact factor: 5.970