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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

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • 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

  • 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