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https://doi.org/10.2478/acph-2014-0023

Design, synthesis, and pharmacological screening of β-amino-, thiadiazole/thiadiazine-phosphonate based triazole motifs as antimicrobial/cytotoxic agents

WAFAA M. ABDOU ; Chemical Industries Division, National Research Centre, D-12311, Dokki, Cairo, Egypt
NEVEN A. GANOUB ; Chemical Industries Division, National Research Centre, D-12311, Dokki, Cairo, Egypt
EMAN SABRYZRINKA ; Chemical Industries Division, National Research Centre, D-12311, Dokki, Cairo, Egypt

Puni tekst: engleski, pdf (478 KB) str. 267-284 preuzimanja: 387* citiraj
APA 6th Edition
ABDOU, W.M., GANOUB, N.A. i SABRYZRINKA, E. (2014). Design, synthesis, and pharmacological screening of β-amino-, thiadiazole/thiadiazine-phosphonate based triazole motifs as antimicrobial/cytotoxic agents. Acta Pharmaceutica, 64 (3), 267-284. https://doi.org/10.2478/acph-2014-0023
MLA 8th Edition
ABDOU, WAFAA M., et al. "Design, synthesis, and pharmacological screening of β-amino-, thiadiazole/thiadiazine-phosphonate based triazole motifs as antimicrobial/cytotoxic agents." Acta Pharmaceutica, vol. 64, br. 3, 2014, str. 267-284. https://doi.org/10.2478/acph-2014-0023. Citirano 27.06.2019.
Chicago 17th Edition
ABDOU, WAFAA M., NEVEN A. GANOUB i EMAN SABRYZRINKA. "Design, synthesis, and pharmacological screening of β-amino-, thiadiazole/thiadiazine-phosphonate based triazole motifs as antimicrobial/cytotoxic agents." Acta Pharmaceutica 64, br. 3 (2014): 267-284. https://doi.org/10.2478/acph-2014-0023
Harvard
ABDOU, W.M., GANOUB, N.A., i SABRYZRINKA, E. (2014). 'Design, synthesis, and pharmacological screening of β-amino-, thiadiazole/thiadiazine-phosphonate based triazole motifs as antimicrobial/cytotoxic agents', Acta Pharmaceutica, 64(3), str. 267-284. doi: https://doi.org/10.2478/acph-2014-0023
Vancouver
ABDOU WM, GANOUB NA, SABRYZRINKA E. Design, synthesis, and pharmacological screening of β-amino-, thiadiazole/thiadiazine-phosphonate based triazole motifs as antimicrobial/cytotoxic agents. Acta Pharm. [Internet]. 2014 [pristupljeno 27.06.2019.];64(3):267-284. doi: https://doi.org/10.2478/acph-2014-0023
IEEE
W.M. ABDOU, N.A. GANOUB i E. SABRYZRINKA, "Design, synthesis, and pharmacological screening of β-amino-, thiadiazole/thiadiazine-phosphonate based triazole motifs as antimicrobial/cytotoxic agents", Acta Pharmaceutica, vol.64, br. 3, str. 267-284, 2014. [Online]. doi: https://doi.org/10.2478/acph-2014-0023

Sažetak
Three different series of phosphonate derivatives, β-amino- and fused thiadiazolo/thiadiazine-phosphonates have been synthesized using addition and/or addition-cyclization protocol of Horner-Wadsworth-Emmons (HWE) reagents to 1,2,4-triazole-3-thiols. The design of potentially antimicrobial and anticancer phosphor esters relied on the results of computer-assisted molecular modeling. All synthesized phosphonates were evaluated for their in vitro antimicrobial activities while anticancer properties were determined for eight out of twenty new phosphonates. The tested phosphonates, except for compounds that have a nitrile moiety, exhibited from moderate to significant antimicrobial activity. Nevertheless, the most active compounds were fused thiadiazole-phosphonates, which inhibited the growth of both Gram-negative and Gram-positive bacteria better than β-aminophosphonates and fused thiadiazolophosphonates. In parallel, the antitumor activity screenings of selected phosphonates from each series and the substrate 1 was also tested. Their antitumor properties against ten carcinoma cell lines, including breast (MCF7, MDA-MB- 231/ATCC, MDA-MB-435, BT-549), ovarian (IGROVI, OVCAR-3, SK-OV-3), prostate (PX-3, PU-145), and liver (HEPG2) were investigated. The results showed that all synthesized compounds reflected remarkable antitumor activity against breast (especially MDA-MB-231/ATCC and BT-549), and prostate carcinoma cell lines (PC-3 and DU-145), whereas a moderate to good effect on ovarian and liver cancer cells was observed.

Ključne riječi
β-amino/thiadiazolo/thiadiazino-phosphonates; 1,2,4-triazole-3-thiols; Horner-Wadsworth-Emmons reagents; in vitro antimicrobial/antineoplastic activity

Hrčak ID: 121067

URI
https://hrcak.srce.hr/121067

Posjeta: 522 *