Unknown

Dataset Information

0

Design, synthesis, and biological evaluation of 1,9-diheteroarylnona-1,3,6,8-tetraen-5-ones as a new class of anti-prostate cancer agents.


ABSTRACT: In search of more effective chemotherapeutics for the treatment of castration-resistant prostate cancer and inspired by curcumin analogues, twenty five (1E,3E,6E,8E)-1,9-diarylnona-1,3,6,8-tetraen-5-ones bearing two identical terminal heteroaromatic rings have been successfully synthesized through Wittig reaction followed by Horner-Wadsworth-Emmons reaction. Twenty-three of them are new compounds. The WST-1 cell proliferation assay was employed to assess their anti-proliferative effects toward both androgen-sensitive and androgen-insensitive human prostate cancer cell lines. Eighteen out of twenty-five synthesized compounds possess significantly improved potency as compared with curcumin. The optimal compound, 78, is 14- to 23-fold more potent than curcumin in inhibiting prostate cancer cell proliferation. It can be concluded from our data that 1,9-diarylnona-1,3,6,8-tetraen-5-one can serve as a new potential scaffold for the development of anti-prostate cancer agents and that pyridine-4-yls and quinolin-4-yl act as optimal heteroaromatic rings for the enhanced potency of this scaffold. Two of the most potent compounds, 68 and 75, effectively suppress PC-3 cell proliferation by activating cell apoptosis and by arresting cell cycle in the G0/G1 phase.

SUBMITTER: Zhang X 

PROVIDER: S-EPMC5014612 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

altmetric image

Publications

Design, synthesis, and biological evaluation of 1,9-diheteroarylnona-1,3,6,8-tetraen-5-ones as a new class of anti-prostate cancer agents.

Zhang Xiaojie X   Wang Rubing R   Perez German Ruiz GR   Chen Guanglin G   Zhang Qiang Q   Zheng Shilong S   Wang Guangdi G   Chen Qiao-Hong QH  

Bioorganic & medicinal chemistry 20160806 19


In search of more effective chemotherapeutics for the treatment of castration-resistant prostate cancer and inspired by curcumin analogues, twenty five (1E,3E,6E,8E)-1,9-diarylnona-1,3,6,8-tetraen-5-ones bearing two identical terminal heteroaromatic rings have been successfully synthesized through Wittig reaction followed by Horner-Wadsworth-Emmons reaction. Twenty-three of them are new compounds. The WST-1 cell proliferation assay was employed to assess their anti-proliferative effects toward b  ...[more]

Similar Datasets

| S-EPMC6010103 | biostudies-literature
| S-EPMC4987241 | biostudies-literature
| S-EPMC9656436 | biostudies-literature
| S-EPMC7497412 | biostudies-literature
| S-EPMC2597393 | biostudies-literature
| S-EPMC6072516 | biostudies-literature
| S-EPMC5822041 | biostudies-literature
| S-EPMC5521218 | biostudies-literature
| S-EPMC6152717 | biostudies-literature
| S-EPMC6891324 | biostudies-literature