Utility of 5-(furan-2-yl)-3-(p-tolyl)-4,5-dihydro-1 H-pyrazole-1-carbothioamide in the synthesis of heterocyclic compounds with antimicrobial activity

Abdou O Abdelhamid; Ibrahim E El Sayed; Yasser H Zaki; Ahmed M Hussein; Mangoud M Mangoud; Mona A Hosny

doi:10.1186/s13065-019-0566-y

Utility of 5-(furan-2-yl)-3-(p-tolyl)-4,5-dihydro-1 H-pyrazole-1-carbothioamide in the synthesis of heterocyclic compounds with antimicrobial activity

BMC Chem. 2019 Apr 1;13(1):48. doi: 10.1186/s13065-019-0566-y. eCollection 2019 Dec.

Authors

Abdou O Abdelhamid¹, Ibrahim E El Sayed², Yasser H Zaki³, Ahmed M Hussein³, Mangoud M Mangoud⁴, Mona A Hosny⁵

Affiliations

¹ 1Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613 Egypt.
² 2Department of Chemistry, Faculty of Science, El Menoufia University, Shebin El Koom, 32511 Egypt.
³ 3Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef, 62514 Egypt.
⁴ Environmental Research Department, National Center for Social and Criminological Research, IbnKhaldoun Square, Mohandesin, Zamalek, Giza, 11561 Egypt.
⁵ 5Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo, 11757 Egypt.

Abstract

Background: Pyrazolines show different biological activities. In recent years, interest in the chemistry of hydrazonoyl halides has been renewed. 1,3,4-Thiadiazoles are one of the most common heterocyclic pharmacophores with a wide range of biological activities.

Results: Ethyl 2-(5-(furan-2-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methyl-thiazole-5-carboxylate, 2-(5-(furan-2-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one, and 1-(2-(5-(furan-2-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazol-5-yl)ethan-1-one were synthesized from the reaction of 5-(furan-2-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide with different halogenated compounds. Thiazole, 1,3,4-thiadiazole and pyrano[2,3-d]thiazole derivatives were also synthesized. The structures of the newly synthesized compounds were elucidated based on elemental analysis, spectral data, and alternative synthetic routes whenever possible. Additionally, the newly synthesized compounds were screened for antimicrobial activity against various microorganisms.

Conclusions: A new series of novel functionalized 1,3,4-thiadiazoles, 1,3-thiazoles, and pyrazoline-containing moieties were synthesized using hydrazonoyl halides as precursors and evaluated for their in vitro antibacterial, and antifungal activities. The antimicrobial results of the examined compounds revealed promising results and some derivatives have activities similar to the references used.

Keywords: 1,3,4-Thiadiazoles; Antimicrobials; Hydrazonoyl halides; Pyrano[2,3-d]thiazoles; Thiazoles; Urea derivatives.