Nitroimidazoles Part 9. Synthesis, molecular docking, and anticancer evaluations of piperazine-tagged imidazole derivatives-Reference-Cited by-同舟云学术

Nitroimidazoles Part 9. Synthesis, molecular docking, and anticancer evaluations of piperazine-tagged imidazole derivatives

Published:2021-04-14 Issue:5 Volume:76 Page:293-302
ISSN:1865-7117
Container-title:Zeitschrift für Naturforschung B
language:en
Short-container-title:

Author:

Al-Soud Yaseen A.¹,Al-Ahmad Ala’a H.¹,Abu-Qatouseh Luay²,Shtaiwi Amneh³,Alhelal Kafa’ A. S.¹,Al-Suod Hossam H.¹,Alsawakhneh Sondos O.¹,Al-Qawasmeh Raed A.⁴⁵

Affiliation:

1. Department of Chemistry, Faculty of Science , Al al-Bayt University , Al-Mafraq 25113 , Jordan

2. Faculty of Pharmacy , University of Petra , Amman , Jordan

3. School of Pharmacy , Middle East University , Queen Alia Airport Street , Amman 11118 , Jordan

4. Department of Chemistry, College of Sciences , University of Sharjah , Sharjah 27272 , UAE

5. Department of Chemistry , The University of Jordan , Amman 11942 , Jordan

Abstract

Abstract New piperazine-tagged imidazole derivatives were synthesized via reaction of 1-alkyl/aryl-5-bromo-2-alkyl-4-nitro-1H-imidazoles 1–3 with piperazine nucleophiles. Nine selected compounds were assessed for their antiproliferative inhibition potency against five human cancer cell lines (MCF-7, PC3, Du145, HepG2 and Dermal/Fibroblast). Compounds 7 and 10 are the most potent anticancer agents on HepG2 cell line with IC50 values of (5.6 ± 0.5 µm) and (29.6 ± 7.6 µm) respectively, and on MCF-7 with IC50 values of (32.1 ± 5.6 µm) and (46.2 ± 8.2 µm) respectively. The molecular docking of compounds 7 and 10 has been studied, and the results reveal that the newly designed piperazine-tagged imidazole derivatives bind to the hydrophobic pocket and polar contact with high affinity.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/znb-2020-0200/pdf

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