Novel Sulfamethoxazole Ureas and Oxalamide as Potential Antimycobacterial Agents

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F17%3A10365056" target="_blank" >RIV/00216208:11160/17:10365056 - isvavai.cz</a>

Result on the web

<a href="http://www.mdpi.com/1420-3049/22/4/535/htm" target="_blank" >http://www.mdpi.com/1420-3049/22/4/535/htm</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules22040535" target="_blank" >10.3390/molecules22040535</a>

Result language

angličtina

Original language name

Novel Sulfamethoxazole Ureas and Oxalamide as Potential Antimycobacterial Agents

Original language description

Infections caused by Mycobacterium tuberculosis (Mtb.) and nontuberculous mycobacteria (NTM) are considered to be a global health problem; current therapeutic options are limited. Sulfonamides have exhibited a wide range of biological activities including those against mycobacteria. Based on the activity of 4-(3-heptylureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide against NTM, we designed a series of homologous sulfamethoxazole-based n-alkyl ureas (C-1-C-12), as well as several related ureas and an oxalamide. Fifteen ureas and one oxalamide were synthesized by five synthetic procedures and characterized. They were screened for their activity against Mtb. and three NTM strains (M. avium, M. kansasii). All of them share antimycobacterial properties with minimum inhibitory concentration (MIC) values starting from 2 mu M. The highest activity showed 4,4&apos;-[carbonylbis(azanediyl)]bis[N-(5-methylisoxazol-3-yl)benzenesulfonamide] with MIC of 2-62.5 mu M (i.e., 1.07-33.28 mu g/mL). Among n-alkyl ureas, methyl group is optimal for the inhibition of both Mtb. and NTM. Generally, longer alkyls led to increased MIC values, heptyl being an exception for NTM. Some of the novel derivatives are superior to parent sulfamethoxazole. Several urea and oxalamide derivatives are promising antimycobacterial agents with low micromolar MIC values.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

30104 - Pharmacology and pharmacy

Project

<a href="/en/project/GJ17-27514Y" target="_blank" >GJ17-27514Y: Peptide Drug Delivery Systems Targeting Macrophages for Antimycobacterial Active Compounds</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Molecules

ISSN

1420-3049

e-ISSN

—

Volume of the periodical

22

Issue of the periodical within the volume

4

Country of publishing house

CH - SWITZERLAND

Number of pages

13

Pages from-to

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UT code for WoS article

000404517800033

EID of the result in the Scopus database

2-s2.0-85017023796