Synthesis and Antitumor Activities of Disulfide Derivatives Containing 1,3,4-Thiadiazole Moiety

李莎,; 荆芬,; 付小云,; 赵继军,; 王学锋,; 李宝林,; 刘玉明,; 陈宝泉,

doi:10.6023/cjoc201505027

Cited by 6 publications

(7 citation statements)

References 13 publications

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“… 1,3,4-thiadiazole derivatives recently identified as possessing cytotoxic activity against MCF-7 cancer cell lines [ 10 , 12 , 14 , 17 , 18 , 19 , 21 , 22 , 23 , 25 , 26 , 28 ]. …”

Section: Figures Scheme and Tablesmentioning

confidence: 99%

“…Some of them have been shown to have promising anticancer activity, exceeding the reference drugs in tests. Many studies have demonstrated the activity of compounds from this group against breast cancer cell lines ( Figure 1 ) [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ]. Therefore, we assumed that the search for cytotoxic compounds in the group of simple 2,5-disubstituted 1,3,4-thiadiazole derivatives is a promising direction of research.…”

Section: Introductionmentioning

confidence: 99%

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New 1,3,4-Thiadiazole Derivatives with Anticancer Activity

et al. 2022

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We designed and synthesized the 1,3,4-thiadiazole derivatives differing in the structure of the substituents in C2 and C5 positions. The cytotoxic activity of the obtained compounds was then determined in biological studies using MCF-7 and MDA-MB-231 breast cancer cells and normal cell line (fibroblasts). The results showed that in both breast cancer cell lines, the strongest anti-proliferative activity was exerted by 2-(2-trifluorometylophenylamino)-5-(3-methoxyphenyl)-1,3,4-thiadiazole. The IC50 values of this compound against MCF-7 and MDA-MB-231 breast cancer cells were 49.6 µM and 53.4 µM, respectively. Importantly, all new compounds had weaker cytotoxic activity on normal cell line than on breast cancer cell lines. In silico studies demonstrated a possible multitarget mode of action for the synthesized compounds. The most likely mechanism of action for the new compounds is connected with the activities of Caspase 3 and Caspase 8 and activation of BAX proteins.

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“… 1,3,4-thiadiazole derivatives recently identified as possessing cytotoxic activity against MCF-7 cancer cell lines [ 10 , 12 , 14 , 17 , 18 , 19 , 21 , 22 , 23 , 25 , 26 , 28 ]. …”

Section: Figures Scheme and Tablesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New 1,3,4-Thiadiazole Derivatives with Anticancer Activity

et al. 2022

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“…The compounds have shown better antiproliferative activity then 5-fluorouracil used as reference drug. 4-Chlorobenzyl-(2-amino-1,3,4-thiadiazol-5-yl)disulfide ( 43 ) ( Figure 22 ) compounds have shown significant inhibition of proliferation activities against breast and lung cancer with IC 50 = 1.78 μmol/L and IC 50 = 4.04 μmol/L, respectively [ 32 ].…”

Section: Derivatives Of 25-disubstituted-134-thiadiazolementioning

confidence: 99%

Cytotoxic Properties of 1,3,4-Thiadiazole Derivatives—A Review

2020

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“…近年来, 随着对该类化合物研究的不断深入, 发现含 1,3,4-噻二唑结构的化合物对癌细胞表现出较强的抑制作用 [7～11] . 李莎等 [12] 将 1,3, (9a)和化合物 5a 在相同条件下进行反应, 3 h 后分离得到了化合物 8a (Eq. 1), 由此推出的反应机理如 Scheme 3 所示.…”

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Synthesis and Biological Activities of 1,3,4-Thiadiazole Triazene Compound

张明千¹,

刘斌凯²,

雷强³

et al. 2019

Chin. J. Org. Chem.

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Using the splicing principle of combining the pharmacological group triazene with 1,3,4-thiadiazole, 15 unreported 1,3,4-thiadiazole triazene derivatives were synthesized. The structures of the compounds were determined by nucleated magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). By using the typical triazene drug dacarbazine (DTIC) and drug 5-fluorouracil (5-FU) as a reference, the activity detections of human esop-hageal cancer cells (EC109), human gastric cancer cells (MGC803), and human prostate cancer cells (PC-3) were carried out. The results showed that some compounds inhibited human gastric cancer cells (MGC803) more strongly than dacarbazine (DTIC), and the IC 50 values of compounds 2- 3,4-thiadiazole (8f), and 2-(3,4-dichloroanilino)-5-[4-(3,3-dimethyltriazol-1-yl) phenyl]-1,3,4-thiadiazole (8l) were lower than those of 5-fluorouracil with 5.3, 6.5 and 6.3 μmol/L, respectively. Some compounds inhibited human prostate cancer cells (PC-3) more strongly than dacarbazine (DTIC), and the IC 50 value of 8l is lower than that of 5-fluorouracil with 13.5 μmol/L. Keywords triazene; 1,3,4-thiadiazole; human esophageal cancer cells; human gastric cancer cells; human prostate cancer cells 三氮烯类化合物是指一类含有 N＝N-N 结构的化合物, 又称重氮氨基化合物. 作为多电子中心, 可以和 Lewis 酸作用发生 Stille 偶联反应 [1] , 环合成特殊杂环 [2] .

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Synthesis and Antitumor Activities of Disulfide Derivatives Containing 1,3,4-Thiadiazole Moiety

Cited by 6 publications

References 13 publications

New 1,3,4-Thiadiazole Derivatives with Anticancer Activity

New 1,3,4-Thiadiazole Derivatives with Anticancer Activity

Cytotoxic Properties of 1,3,4-Thiadiazole Derivatives—A Review

Synthesis and Biological Activities of 1,3,4-Thiadiazole Triazene Compound

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