Chinese Journal of Organic Chemistry >
Synthesis of Diethyl 2,5-Diaminothiophene-3,4-dicarboxylate Derivatives and Antitumor Activity Study
Received date: 2022-10-30
Revised date: 2023-01-08
Online published: 2023-02-07
Supported by
National Key R&D Program of China(2020YFE0205600)
Based on the sulfur heterocyclic compound thiophene, thirty diethyl 2,5-diaminothiophene-3,4-dicarboxylate derivatives were designed and synthesized. The structures of all compounds were confirmed by 1H NMR, 13C NMR and HRMS, and antiproliferative activities of the target compounds against four human cancer cell lines (HeLa, HT-29, A549 and HepG2) were evaluated by methyl thiazolyl tetrazolium (MTT) in vitro. The results showed that some compounds exhibited good anticancer activity. Especially, diethyl 2-(4-(trifluoromethoxy)benzamido-5-(5-nitrothiophen-2-yl)methylene-aminothiophene- 3,4-dicarboxylate (C25) possessed the best activity, whose IC50 values were (0.35±0.07) and (0.66±0.09) μmol/L against HT-29 and A549, respectively; diethyl 2-(3-(trifluoromethyl)benzamido-5-(5nitrothiophen-2-yl)methyleneaminothiophene- 3,4-dicarboxylate (C29) also possessed the best activity, whose IC50 values were (0.47±0.03) and (0.41±0.04) μmol/L against HT-29 and HepG2, respectively, better than positive control drug doxorubicin (DOX) (IC50 values were (1.15±0.03), (0.86±0.07) and (0.86±0.02) μmol/L against HT-29, A549, and HepG2, respectively).
Weishu Zhang , Lifei Nie , Khurshed Bozorov , Haji Akber Aisa , Jiangyu Zhao . Synthesis of Diethyl 2,5-Diaminothiophene-3,4-dicarboxylate Derivatives and Antitumor Activity Study[J]. Chinese Journal of Organic Chemistry, 2023 , 43(7) : 2543 -2552 . DOI: 10.6023/cjoc202210040
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