Design, Synthesis, and Evaluation of Thiol-Activated Sources of Sulfur Dioxide (SO2) as Antimycobacterial Agents

Here, 2,4-dinitrophenylsulfonamides with tunable cysteine-activated SO2 release profiles with half-lives of SO2 release varying from 2 to 63 min are reported. N-Benzyl-2,4-dinitrobenzenesulfonamide (6), which is prepared in one step from commercial sources, had a potency (MIC = 0.15 μM) of inhibitin...

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Bibliographic Details
Published inJournal of medicinal chemistry Vol. 55; no. 1; pp. 553 - 557
Main Authors Malwal, Satish R, Sriram, Dharmarajan, Yogeeswari, Perumal, Konkimalla, V. Badireenath, Chakrapani, Harinath
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 12.01.2012
Amer Chemical Soc
Subjects
Antitubercular Agents - chemical synthesis
Antitubercular Agents - chemistry
Antitubercular Agents - pharmacology
Cell Survival - drug effects
Chemistry, Medicinal
Cysteine - metabolism
HEK293 Cells
Humans
Kinetics
Life Sciences & Biomedicine
Microbial Sensitivity Tests
Mycobacterium tuberculosis - drug effects
Mycobacterium tuberculosis - metabolism
Pharmacology & Pharmacy
Science & Technology
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
Sulfonamides - pharmacology
Sulfur Dioxide - metabolism
MYCOBACTERIUM-TUBERCULOSIS
SYSTEM
MECHANISM
JS-K
THERAPEUTIC AGENTS
INHALATION
NITRIC-OXIDE
MEAT-PRODUCTS
FRESH
SULFITE
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Summary:Here, 2,4-dinitrophenylsulfonamides with tunable cysteine-activated SO2 release profiles with half-lives of SO2 release varying from 2 to 63 min are reported. N-Benzyl-2,4-dinitrobenzenesulfonamide (6), which is prepared in one step from commercial sources, had a potency (MIC = 0.15 μM) of inhibiting Mycobacterium tuberculosis (Mtb) higher than the clinical agent isoniazid (MIC = 0.37 μM).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-2623
1520-4804
DOI:10.1021/jm201023g