Microwave-assisted synthesis of new 2-aryl and 2-alkylimidazolones and evaluation of their in vitro anticancer activity and their in vivo toxicity on zebrafish embryos
Herein we describe the synthesis of five new 2-aryl and 2-alkylimidazolone derivatives via an effective one-pot synthetic strategy assisted by microwave irradiations which allowed us to access the desired product in a reduced time reaction compared to the thermal heating and a slightly better yield...
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| Published in | Chemical papers Vol. 75; no. 6; pp. 2549 - 2560 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Cham
Springer International Publishing
01.06.2021
Springer Nature B.V Versita (Central European Science Journals) |
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| Abstract | Herein we describe the synthesis of five new 2-aryl and 2-alkylimidazolone derivatives via an effective one-pot synthetic strategy assisted by microwave irradiations which allowed us to access the desired product in a reduced time reaction compared to the thermal heating and a slightly better yield (48% compared to 45%). The new imidazolone derivatives were evaluated for their anticancer activity in vitro against MCF-7, MDA-MB-231 and HepG2 cell lines. The results showed good cytotoxic effects for some of these derivatives on both MCF-7 and HepG2 cell lines in the range of 5.7–11.3 µM. Among the synthesized derivatives,
2ab
and
2b
showed the strongest activity with IC
50
values of 7 and 5.7 µM (MCF-7) and 6.2 and 8.6 µM (HepG2), respectively. The cytotoxic activities of these derivatives were moderate compared to those of doxorubicin. However, this product showed higher toxicity in vivo on the development of zebrafish embryos than the synthesized imidazolones. These derivatives at high concentrations exhibited some morphological abnormalities on the embryos. |
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| AbstractList | Herein we describe the synthesis of five new 2-aryl and 2-alkylimidazolone derivatives via an effective one-pot synthetic strategy assisted by microwave irradiations which allowed us to access the desired product in a reduced time reaction compared to the thermal heating and a slightly better yield (48% compared to 45%). The new imidazolone derivatives were evaluated for their anticancer activity in vitro against MCF-7, MDA-MB-231 and HepG2 cell lines. The results showed good cytotoxic effects for some of these derivatives on both MCF-7 and HepG2 cell lines in the range of 5.7-11.3 mu M. Among the synthesized derivatives, 2ab and 2b showed the strongest activity with IC50 values of 7 and 5.7 mu M (MCF-7) and 6.2 and 8.6 mu M (HepG2), respectively. The cytotoxic activities of these derivatives were moderate compared to those of doxorubicin. However, this product showed higher toxicity in vivo on the development of zebrafish embryos than the synthesized imidazolones. These derivatives at high concentrations exhibited some morphological abnormalities on the embryos. Herein we describe the synthesis of five new 2-aryl and 2-alkylimidazolone derivatives via an effective one-pot synthetic strategy assisted by microwave irradiations which allowed us to access the desired product in a reduced time reaction compared to the thermal heating and a slightly better yield (48% compared to 45%). The new imidazolone derivatives were evaluated for their anticancer activity in vitro against MCF-7, MDA-MB-231 and HepG2 cell lines. The results showed good cytotoxic effects for some of these derivatives on both MCF-7 and HepG2 cell lines in the range of 5.7–11.3 µM. Among the synthesized derivatives, 2ab and 2b showed the strongest activity with IC50 values of 7 and 5.7 µM (MCF-7) and 6.2 and 8.6 µM (HepG2), respectively. The cytotoxic activities of these derivatives were moderate compared to those of doxorubicin. However, this product showed higher toxicity in vivo on the development of zebrafish embryos than the synthesized imidazolones. These derivatives at high concentrations exhibited some morphological abnormalities on the embryos. Herein we describe the synthesis of five new 2-aryl and 2-alkylimidazolone derivatives via an effective one-pot synthetic strategy assisted by microwave irradiations which allowed us to access the desired product in a reduced time reaction compared to the thermal heating and a slightly better yield (48% compared to 45%). The new imidazolone derivatives were evaluated for their anticancer activity in vitro against MCF-7, MDA-MB-231 and HepG2 cell lines. The results showed good cytotoxic effects for some of these derivatives on both MCF-7 and HepG2 cell lines in the range of 5.7–11.3 µM. Among the synthesized derivatives, 2ab and 2b showed the strongest activity with IC 50 values of 7 and 5.7 µM (MCF-7) and 6.2 and 8.6 µM (HepG2), respectively. The cytotoxic activities of these derivatives were moderate compared to those of doxorubicin. However, this product showed higher toxicity in vivo on the development of zebrafish embryos than the synthesized imidazolones. These derivatives at high concentrations exhibited some morphological abnormalities on the embryos. |
| Author | Hamade, Aline Bou Zeid, Samar Carreaux, Francois Eid, Samar Najjar, Fadia |
| Author_xml | – sequence: 1 givenname: Samar surname: Bou Zeid fullname: Bou Zeid, Samar organization: Departments of Biology, Chemistry and Biochemistry, Laboratoire D’Innovation Thérapeutique, Faculty of Sciences II, Lebanese University, Université de Rennes 1, CNRS, ISCR, UMR 6226 – sequence: 2 givenname: Aline surname: Hamade fullname: Hamade, Aline organization: Departments of Biology, Chemistry and Biochemistry, Laboratoire D’Innovation Thérapeutique, Faculty of Sciences II, Lebanese University – sequence: 3 givenname: Fadia surname: Najjar fullname: Najjar, Fadia email: fnajjar@ul.edu.lb organization: Departments of Biology, Chemistry and Biochemistry, Laboratoire D’Innovation Thérapeutique, Faculty of Sciences II, Lebanese University – sequence: 4 givenname: Francois surname: Carreaux fullname: Carreaux, Francois email: francois.carreaux@univ-rennes1.fr organization: Université de Rennes 1, CNRS, ISCR, UMR 6226 – sequence: 5 givenname: Samar orcidid: 0000-0002-0128-8670 surname: Eid fullname: Eid, Samar email: s.eid@ul.edu.lb organization: Departments of Biology, Chemistry and Biochemistry, Laboratoire D’Innovation Thérapeutique, Faculty of Sciences II, Lebanese University |
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| Cites_doi | 10.1158/0008-5472.CAN-14-2443 10.7150/jca.18457 10.1016/j.jtbi.2014.02.025 10.1007/s10562-007-9285-4 10.1002/cam4.2006 10.1007/s11030-009-9138-8 10.1021/acs.joc.6b01262 10.1007/s00044-014-0954-8 10.1159/000086183 10.1002/jhet.766 10.1016/j.bioorg.2020.103729 10.3389/fgene.2014.00189 10.1016/j.bioorg.2019.103102 10.1248/cpb.c13-00340 10.3791/57567 10.3109/08923970903296136 10.3322/caac.21412 10.1021/np200906s 10.1007/128_060 10.1016/j.yjmcc.2012.03.006 10.3322/caac.21492 10.1021/jm200274d 10.1021/jm301034u 10.1039/C8NP00092A 10.4161/15384101.2014.950126 10.1016/j.bmc.2016.05.016 10.1002/ejoc.200400591 10.1080/00397919508015462 10.1016/j.ejmech.2013.01.035 10.1002/adsc.201800844 10.1016/j.cclet.2013.05.009 10.1007/s00268-006-0616-1 10.3233/BME-130885 10.1007/s00044-016-1566-2 10.4172/2161-0444.1000156 10.1021/jo01059a098 10.1021/np50091a016 10.1016/j.ejmech.2009.10.009 10.1016/j.cbpc.2010.08.008 10.1002/cpet.19 10.1021/jm00074a014 10.1007/978-1-59745-285-4_13 |
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| Copyright | Institute of Chemistry, Slovak Academy of Sciences 2021 Institute of Chemistry, Slovak Academy of Sciences 2021. Distributed under a Creative Commons Attribution 4.0 International License |
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| Keywords | One-pot synthesis Zebrafish embryos Imidazolone derivatives Microwave irradiations Anticancer activity |
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| SubjectTerms | Abnormalities Anticancer properties Aromatic compounds Biochemistry Biocompatibility Biotechnology Cancer Chemical Sciences Chemistry Chemistry and Materials Science Chemistry/Food Science Cytotoxicity Doxorubicin Embryos Industrial Chemistry/Chemical Engineering Materials Science Medicinal Chemistry Original Paper Synthesis Toxicity Zebrafish |
| Title | Microwave-assisted synthesis of new 2-aryl and 2-alkylimidazolones and evaluation of their in vitro anticancer activity and their in vivo toxicity on zebrafish embryos |
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