New chalcone-sulfonamide hybrids exhibiting anticancer and antituberculosis activity
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388971%3A_____%2F19%3A00508040" target="_blank" >RIV/61388971:_____/19:00508040 - isvavai.cz</a>
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0223523419304222?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0223523419304222?via%3Dihub</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.ejmech.2019.05.013" target="_blank" >10.1016/j.ejmech.2019.05.013</a>
Alternative languages
Result language
angličtina
Original language name
New chalcone-sulfonamide hybrids exhibiting anticancer and antituberculosis activity
Original language description
New sulfonamides 5/6 derived from 4-methoxyacetophenone I were synthesized by N-sulfonation reaction of ammonia (3) and aminopyrimidinone (4) with its sulfonyl chloride derivative 2. Sulfonamides 5 and 6 were used as precursors of two new series of chalcones 8a-f and 9a-f, which were obtained through Claisen-Schmidt condensation with aromatic aldehydes 7a-f. Compounds 5/6, 8a-d, 8f, 9a-d, and 9f were screened by the US National Cancer Institute (NCI) at 10 mu M against sixty different human cancer cell lines (one-dose trial). Chalcones 8b and 9b satisfied the pre-determined threshold inhibition criteria and were selected for screening at five different concentrations (100, 10, 1.0, 0.1, and 0.01 mu M). Compound 8b exhibited remarkable GI(50) values ranging from 0.57 to 12.4 mu M, with cytotoxic effects being observed in almost all cases, especially against the cell lines K-562 of Leukemia and LOX IMVI of Melanoma with Gl(50) = 0.57 and 1.28 mu M, respectively. Moreover, all compounds were screened against Mycobacterium tuberculosis H37Rv, chalcones 8a-c and 9a-c were the most active showing MIC values between 14 and 42 mu M, and interestingly they were devoid of antibacterial activity against Mycobacterium smegmatis and Staphylococcus aureus. These antituberculosis hits showed however low selectivity, being equally inhibitory to M. tuberculosis and mammalian T3T cells. The chalcone-sulfonamide hybrids 8a-f and 9a-f resulted to be appealing cytotoxic agents with significant antituberculosis activity. (C) 2019 Elsevier Masson SAS. All rights reserved.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10606 - Microbiology
Result continuities
Project
<a href="/en/project/EF16_027%2F0007990" target="_blank" >EF16_027/0007990: International mobility of researchers of the Institute of Microbiology of the CAS, v. v. i.</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Medicinal Chemistry
ISSN
0223-5234
e-ISSN
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Volume of the periodical
176
Issue of the periodical within the volume
AUG 15
Country of publishing house
FR - FRANCE
Number of pages
11
Pages from-to
50-60
UT code for WoS article
000472686100005
EID of the result in the Scopus database
2-s2.0-85065432965