New chalcone-sulfonamide hybrids exhibiting anticancer and antituberculosis activity

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

New chalcone-sulfonamide hybrids exhibiting anticancer and antituberculosis activity

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

New chalcone-sulfonamide hybrids exhibiting anticancer and antituberculosis activity

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10606 - Microbiology

Projekt

<a href="/cs/project/EF16_027%2F0007990" target="_blank" >EF16_027/0007990: Mezinárodní mobilita výzkumných pracovníků Mikrobiologického ústavu AV ČR, v. v. i.</a><br>

Návaznosti

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

Rok uplatnění

2019

Kód důvěrnosti údajů

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

Název periodika

European Journal of Medicinal Chemistry

ISSN

0223-5234

e-ISSN

—

Svazek periodika

176

Číslo periodika v rámci svazku

AUG 15

Stát vydavatele periodika

FR - Francouzská republika

Počet stran výsledku

11

Strana od-do

50-60

Kód UT WoS článku

000472686100005

EID výsledku v databázi Scopus

2-s2.0-85065432965