Design and synthesis of benzimidazole-chalcone derivatives as potential anticancer agents

Cheng Ying Hsieh; Pi Wen Ko; Yu Jui Chang; Mohit Kapoor; Yu Chuan Liang; Hsueh Liang Chu; Hui Hsien Lin; Jia Cherng Horng; Ming Hua Hsu

doi:10.3390/molecules24183259

Design and synthesis of benzimidazole-chalcone derivatives as potential anticancer agents

Cheng Ying Hsieh, Pi Wen Ko, Yu Jui Chang, Mohit Kapoor, Yu Chuan Liang, Hsueh Liang Chu, Hui Hsien Lin, Jia Cherng Horng, Ming Hua Hsu

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Numerous reports have shown that conjugated benzimidazole derivatives possess various kinds of biological activities, including anticancer properties. In this report, we designed and synthesized 24 new molecules comprising a benzimidazole ring, arene, and alkyl chain-bearing cyclic moieties. The results showed that the N-substituted benzimidazole derivatives bearing an alkyl chain and a nitrogen-containing 5- or 6-membered ring enhanced the cytotoxic effects on human breast adenocarcinoma (MCF-7) and human ovarian carcinoma (OVCAR-3) cell lines. Among the 24 synthesized compounds, (2E)-1-(1-(3-morpholinopropyl)-1H-benzimidazol-2 -yl)-3-phenyl-2-propen-1-one) (23a) reduced the proliferation of MCF-7 and OVCAR-3 cell lines demonstrating superior outcomes to those of cisplatin.

Original language	English
Article number	3259
Journal	Molecules
Volume	24
Issue number	18
DOIs	https://doi.org/10.3390/molecules24183259
Publication status	Published - 2019 Sep 6

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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@article{5a39b953ef5145118d42cb8a6acc494c,

title = "Design and synthesis of benzimidazole-chalcone derivatives as potential anticancer agents",

abstract = "Numerous reports have shown that conjugated benzimidazole derivatives possess various kinds of biological activities, including anticancer properties. In this report, we designed and synthesized 24 new molecules comprising a benzimidazole ring, arene, and alkyl chain-bearing cyclic moieties. The results showed that the N-substituted benzimidazole derivatives bearing an alkyl chain and a nitrogen-containing 5- or 6-membered ring enhanced the cytotoxic effects on human breast adenocarcinoma (MCF-7) and human ovarian carcinoma (OVCAR-3) cell lines. Among the 24 synthesized compounds, (2E)-1-(1-(3-morpholinopropyl)-1H-benzimidazol-2 -yl)-3-phenyl-2-propen-1-one) (23a) reduced the proliferation of MCF-7 and OVCAR-3 cell lines demonstrating superior outcomes to those of cisplatin.",

author = "Hsieh, {Cheng Ying} and Ko, {Pi Wen} and Chang, {Yu Jui} and Mohit Kapoor and Liang, {Yu Chuan} and Chu, {Hsueh Liang} and Lin, {Hui Hsien} and Horng, {Jia Cherng} and Hsu, {Ming Hua}",

note = "Funding Information: Funding: We thank the National Tsing Hua University and Ministry of Science and Technology of the Republic of China for financial support, also thanks the Laboratory Animal Core Facility which is funded by Agriculture Biotechnology Research Center (ABRC) at Academia Sinica for technical support in cytotoxic, cell morphology and flow cytometry experiments. The authors also thank Ms. Miranda Loney for manuscript editing. This work was supported by the Ministry of Science and Technology (MOST 104-2119-M-007-017)(MOST 106-2113-M -018-008)(MOST 107-2113-M-018-008)(MOST 108-2113-M-018-009).",

year = "2019",

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doi = "10.3390/molecules24183259",

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T1 - Design and synthesis of benzimidazole-chalcone derivatives as potential anticancer agents

AU - Hsieh, Cheng Ying

AU - Ko, Pi Wen

AU - Chang, Yu Jui

AU - Kapoor, Mohit

AU - Liang, Yu Chuan

AU - Chu, Hsueh Liang

AU - Lin, Hui Hsien

AU - Horng, Jia Cherng

AU - Hsu, Ming Hua

N1 - Funding Information: Funding: We thank the National Tsing Hua University and Ministry of Science and Technology of the Republic of China for financial support, also thanks the Laboratory Animal Core Facility which is funded by Agriculture Biotechnology Research Center (ABRC) at Academia Sinica for technical support in cytotoxic, cell morphology and flow cytometry experiments. The authors also thank Ms. Miranda Loney for manuscript editing. This work was supported by the Ministry of Science and Technology (MOST 104-2119-M-007-017)(MOST 106-2113-M -018-008)(MOST 107-2113-M-018-008)(MOST 108-2113-M-018-009).

PY - 2019/9/6

Y1 - 2019/9/6

N2 - Numerous reports have shown that conjugated benzimidazole derivatives possess various kinds of biological activities, including anticancer properties. In this report, we designed and synthesized 24 new molecules comprising a benzimidazole ring, arene, and alkyl chain-bearing cyclic moieties. The results showed that the N-substituted benzimidazole derivatives bearing an alkyl chain and a nitrogen-containing 5- or 6-membered ring enhanced the cytotoxic effects on human breast adenocarcinoma (MCF-7) and human ovarian carcinoma (OVCAR-3) cell lines. Among the 24 synthesized compounds, (2E)-1-(1-(3-morpholinopropyl)-1H-benzimidazol-2 -yl)-3-phenyl-2-propen-1-one) (23a) reduced the proliferation of MCF-7 and OVCAR-3 cell lines demonstrating superior outcomes to those of cisplatin.

AB - Numerous reports have shown that conjugated benzimidazole derivatives possess various kinds of biological activities, including anticancer properties. In this report, we designed and synthesized 24 new molecules comprising a benzimidazole ring, arene, and alkyl chain-bearing cyclic moieties. The results showed that the N-substituted benzimidazole derivatives bearing an alkyl chain and a nitrogen-containing 5- or 6-membered ring enhanced the cytotoxic effects on human breast adenocarcinoma (MCF-7) and human ovarian carcinoma (OVCAR-3) cell lines. Among the 24 synthesized compounds, (2E)-1-(1-(3-morpholinopropyl)-1H-benzimidazol-2 -yl)-3-phenyl-2-propen-1-one) (23a) reduced the proliferation of MCF-7 and OVCAR-3 cell lines demonstrating superior outcomes to those of cisplatin.

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