Document Detail

Indolylarylsulfones as HIV-1 non-nucleoside reverse transcriptase inhibitors: new cyclic substituents at indole-2-carboxamide.
MedLine Citation:
PMID:  21366296     Owner:  NLM     Status:  MEDLINE    
New indolylarylsulfone derivatives bearing cyclic substituents at indole-2-carboxamide linked through a methylene/ethylene spacer were potent inhibitors of the WT HIV-1 replication in CEM and PBMC cells with inhibitory concentrations in the low nanomolar range. Against the mutant L100I and K103N RT HIV-1 strains in MT-4 cells, compounds 20, 24-26, 36, and 40 showed antiviral potency superior to that of NVP and EFV. Against these mutant strains, derivatives 20, 24-26, and 40 were equipotent to ETV. Molecular docking experiments on this novel series of IAS analogues have also suggested that the H-bond interaction between the nitrogen atom in the carboxamide chain of IAS and Glu138:B is important in the binding of these compounds. These results are in accordance with the experimental data obtained on the WT and on the mutant HIV-1 strains tested.
Giuseppe La Regina; Antonio Coluccia; Andrea Brancale; Francesco Piscitelli; Valerio Gatti; Giovanni Maga; Alberta Samuele; Christophe Pannecouque; Dominique Schols; Jan Balzarini; Ettore Novellino; Romano Silvestri
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2011-03-02
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  54     ISSN:  1520-4804     ISO Abbreviation:  J. Med. Chem.     Publication Date:  2011 Mar 
Date Detail:
Created Date:  2011-03-17     Completed Date:  2011-06-17     Revised Date:  2014-02-06    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1587-98     Citation Subset:  IM    
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MeSH Terms
Anti-HIV Agents / chemical synthesis*,  chemistry,  pharmacology
Benzoxazines / pharmacology
Cells, Cultured
HIV Reverse Transcriptase / chemistry
HIV-1 / drug effects*,  genetics
Indoles / chemical synthesis*,  chemistry,  pharmacology
Leukocytes, Mononuclear / drug effects,  virology
Models, Molecular
Molecular Conformation
Nevirapine / pharmacology
Protein Binding
Pyridazines / pharmacology
Reverse Transcriptase Inhibitors / chemical synthesis*,  chemistry,  pharmacology
Structure-Activity Relationship
Sulfones / chemical synthesis*,  chemistry,  pharmacology
Reg. No./Substance:
0/Anti-HIV Agents; 0/Benzoxazines; 0/Indoles; 0/Pyridazines; 0/Reverse Transcriptase Inhibitors; 0/Sulfones; 0C50HW4FO1/etravirine; 99DK7FVK1H/Nevirapine; EC Reverse Transcriptase; JE6H2O27P8/efavirenz

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