Design, synthesis and antitumor activity of C3/C3 bis-fluoroquonolones cross-linked with [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazole

Hu, Guoqiang; Yang, Yong; Yi, Lei; Wang, Guoqiang; Duan, Nannan; Wen, Xin; Tieyao, Cao; Xie, Songqiang; Huang, Wenlong

doi:10.1016/j.apsb.2011.07.001

Cited by 19 publications

(13 citation statements)

References 7 publications

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“…The compounds were evaluated against L1210 (lymphocytic leukemia), CHO (Chinese hamster ovary) and HL60 (human leukemia) cell lines in the MTT assay. Some of the compounds exhibited good cytotoxicity against cell lines, with IC 50 values of 1.5 µM (L1210), 0.12 µM (HL60) and 3.4 µM (CHO) for compounds with methyl substituent 104 (Figure 54) [61]. Continuing research on fluoroquinolone derivatives, Hu and co-workers (2011) reported synthesis and anticancer activity in a series of new compounds with 1,3,4-thiadiazole rings.…”

Section: -83mentioning

confidence: 95%

Section: 134-thiadiazole Condensed With Other Heterocyclic Ringsmentioning

confidence: 99%

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

2020

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Section: -83mentioning

confidence: 95%

Section: 134-thiadiazole Condensed With Other Heterocyclic Ringsmentioning

confidence: 99%

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

2020

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“…19 Structures of the 27 sophoridinic acid/ester and sophoridinol derivatives and their antiproliferative activities were depicted in Table 1. SAR analysis was first focused on the substituents at the 12-nitrogen atom. Since trimethoxyphenyl group (Figure 1) is crucial for the anticancer activity in many natural medicines against cancer such as colchicine and podophyllotoxin, this group was introduced into the nitrogen atom at position 12 to create N-trimethoxybenzyl sophoridinic ester/acid (5a and 6a) and sophoridinol (7a).…”

mentioning

confidence: 99%

“…All the desired compounds were evaluated for their cytotoxic activities in human HepG2 hepatoma cell lines using MTT assay with Taxol as the positive control. 19 Structures of the 27 sophoridinic acid/ester and sophoridinol derivatives and their antiproliferative activities were depicted in Table 1.…”

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confidence: 99%

Synthesis and Biological Evaluation of Sophoridinol Derivatives as a Novel Family of Potential Anticancer Agents

Zhang

et al. 2014

ACS Med. Chem. Lett.

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New N-substituted sophoridinic acid/ester and sophoridinol derivatives were synthesized and evaluated for their cytotoxic activity in human HepG2 hepatoma cells from the lead sophoridine (1). Among the newly synthesized compounds, sophoridinol 7i displayed a potential antiproliferative activity with an IC 50 of 3.1 μM. Importantly, it exerted an almost equipotent effect against both wild MCF-7 and adriamycin (AMD)-resistant MCF-7 (MCF-7/AMD) breast carcinoma cell lines. Its mode of action was to arrest the cell cycle at the G0/G1 phase, consistent with that of the parent 1. In addition, compound 7i also showed a reasonable ClogP value and favorable pharmacokinetic property with an area under the concentration−time curve (AUC) of 10.3 μM·h in rats, indicating an ideal druggable characteristic. We consider sophoridinol derivatives to be a novel family of promising antitumor agents with an advantage of inhibiting drug-resistant cancer cells.

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“…The human cancer cell lines (HeLa and HepG2) and the human normal ones (HL7702 and HUVEC) were chosen to evaluate the antitumor activity and cell toxicity of target compounds in vitro by the MTT assay [ 21 , 22 , 23 , 24 ]. HeLa, HepG2, and HUVEC cells were cultured in a Dulbecco’s modified Eagle’s medium (DMEM) supplemented with 10% fetal bovine serum, and HL7702 cells were cultured in a DMEM supplemented with 10% fetal bovine serum.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Biological Activity of a Novel Series of Benzo[4,5]imidazo[2,1-b]thiazole Derivatives as Potential Epidermal Growth Factor Receptor Inhibitors

Deng

Tan

et al. 2019

Molecules

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Based on the analysis of epidermal growth factor receptor (EGFR) complexes with gefitinib with molecular docking, the scaffold-hopping strategy, combination of the active substructures, and structural optimization of EGFR inhibitors, a novel series of benzo[4,5]imidazo[2,1-b]thiazole derivatives was designed, synthesized, and evaluated for antitumor activity in human cancer cell lines and cellular toxicity against human normal cell lines using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay and EGFR inhibitory activities in vitro. Some target compounds such as 2-(benzo[4,5]imidazo[2,1-b]thiazol-3-yl)-N-(2-hydroxyphenyl)acetamide (D04) and 2-(benzo[4,5]imidazo[2,1-b]thiazol-3-yl)-N-(naphthalen-1-yl)acetamide (D08) have shown significant antitumor activity against the EGFR high-expressed human cell line HeLa. All the target compounds showed hardly any antitumor activity against the EGFR low-expressed human cell line HepG2, and nearly no cellular toxicity against the human normal cell lines HL7702 and human umbilical vein endothelial cell lines (HUVEC). The inhibitory activities against EGFR kinase in vitro of the three target compounds were greatly consistent with the anti-proliferative activities. The preliminary structure–activity relationships of the target compounds were summarized. Conclusively, the novel benzo[4,5]imidazo[2,1-b]thiazole derivatives as novel potential EGFR inhibitors may be used as the potential lead compounds for the development of antitumor agents.

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Design, synthesis and antitumor activity of C3/C3 bis-fluoroquonolones cross-linked with [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazole

Cited by 19 publications

References 7 publications

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

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

Synthesis and Biological Evaluation of Sophoridinol Derivatives as a Novel Family of Potential Anticancer Agents

Synthesis, Characterization, and Biological Activity of a Novel Series of Benzo[4,5]imidazo[2,1-b]thiazole Derivatives as Potential Epidermal Growth Factor Receptor Inhibitors

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