Synthesis and biological evaluation of D-ring fused 1,2,3-thiadiazole dehydroepiandrosterone derivatives as antitumor agents

Cui, Hai-Wei; Peng, Shihong; Gu, Xiang-Zhong; Huang, Chung‐Ju; He, Yonghong; Gao, Wei; Lv, Fang; Wang, Jinhua; Wang, Yan; Xie, Jia; Liu, Mingyao; Yi, Zhengfang; Qiu, Wen‐Wei

doi:10.1016/j.ejmech.2016.01.058

Cited by 29 publications

(28 citation statements)

References 44 publications

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“…The in vivo anticancer effect of 65 when evaluated in T47D tumor-bearing mice displayed no toxicity thereby making it a candidate of interest for further development in cancer therapy. 97 Subsequently, in 2016 Charitos et al, 98 designed, synthesized, and evaluated new disubstituted triazolo-thiadiazole derivatives for their potential cytotoxic action. Herein, two pharmacologically harmonious molecules, that is, triazole and thiadiazole were combined in a single framework by employing molecular hybridization as the prominent approach.…”

Section: Thiadiazolementioning

confidence: 99%

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Laxmikeshav

Kumari

Shankaraiah

2021

Medicinal Research Reviews

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This review article proposes a comprehensive report of the design strategies engaged in the development of various sulfur-bearing cytotoxic agents. The outcomes of various studies depict that the sulfur heterocyclic framework is a fundamental structure in diverse synthetic analogs representing a myriad scope of therapeutic activities. A number of five-, six-and seven-membered sulfur-containing heterocyclic scaffolds, such as thiazoles, thiadiazoles, thiazolidinediones, thiophenes, thiopyrans, benzothiazoles, benzothiophenes, thienopyrimidines, simple and modified phenothiazines, and thiazepines have been discussed. The subsequent studies of the derivatives unveiled their cytotoxic effects through multiple mechanisms (viz. inhibition of tyrosine kinases, topoisomerase I and II, tubulin, COX, DNA synthesis, and PI3K/Akt and Raf/MEK/ERK signaling pathways), and several others. Thus, our concise illustration explains the design strategy and anticancer potential of these five-and six-membered sulfur-containing heterocyclic molecules along with a brief outline on seven-membered sulfur heterocycles. The thorough assessment of antiproliferative activities with the reference drug allows a proficient assessment of the structure-activity relationships (SARs) of the diversely synthesized molecules of the series.

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Section: Thiadiazolementioning

confidence: 99%

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Laxmikeshav

Kumari

Shankaraiah

2021

Medicinal Research Reviews

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“…Decreased viability of human cervical carcinoma HeLa and osteosarcoma U2OS cells [7] Decreased proliferation of colon adenocarcinoma HCT-116 cells; induction of apoptosis [8] d-ring fused 1,2,3-thiadiazole dehydroepiandrosterone (DHEA) derivatives Unknown Decreased proliferation, ability to form colonies and migrate of human breast cancer T47D cells; induction of apoptosis [9] Reduced tumor growth and metastatic ability in T47D xenografts [10] Pyrazole oxime derivatives bearing 1,2,3-thiadiazole…”

Section: Hsp90mentioning

confidence: 99%

“…Clearly further studies are required to elucidate whether the deregulation of EphA2 and EphB3 contributes to the anticancer activity of compound 25 or not. Of note, compound 25 significantly inhibited tumor growth and metastatic ability in T47D xenografts [ 10 ].…”

Section: Derivatives Of 123-thiadiazolementioning

confidence: 99%

Thiadiazole derivatives as anticancer agents

Szeliga

2020

Pharmacol. Rep

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In spite of substantial progress made toward understanding cancer pathogenesis, this disease remains one of the leading causes of mortality. Thus, there is an urgent need to develop novel, more effective anticancer therapeutics. Thiadiazole ring is a versatile scaffold widely studied in medicinal chemistry. Mesoionic character of this ring allows thiadiazole-containing compounds to cross cellular membrane and interact strongly with biological targets. Consequently, these compounds exert a broad spectrum of biological activities. This review presents the current state of knowledge on thiadiazole derivatives that demonstrate in vitro and/or in vivo efficacy across the cancer models with an emphasis on targets of action. The influence of the substituent on the compounds’ activity is depicted. Furthermore, the results from clinical trials assessing thiadiazole-containing drugs in cancer patients are summarized.

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“…The reaction was 9.28, 27.43, 30.75, 50.69, 55.38, 65.71, 72.84, 97.16, 119.59, 119.68, 126.55, 128.79, 130.86, 131.64, 145.81, 146.33, 149.53, 150.47, 152.99, 157.26, 172.91, 173.10 The in vivo antitumor studies were performed following the method described previously with minor modifications (Cao et al, 2016;Cui et al, 2016;Li et al, 2017;Wang, Huang, Sun, & Pan, 2015). Then 60 μL of propionic anhydride was added dropwise.…”

Section: Synthesis Of Pcptmentioning

confidence: 99%

“…These data revealed that the concentration of the active metabolite HCPT was much higher than that of PCPT in vivo. As shown in Figure 7, the concentration of PCPT 9.28, 27.43, 30.75, 50.69, 55.38, 65.71, 72.84, 97.16, 119.59, 119.68, 126.55, 128.79, 130.86, 131.64, 145.81, 146.33, 149.53, 150.47, 152.99, 157.26, 172.91, 173.10 The in vivo antitumor studies were performed following the method described previously with minor modifications (Cao et al, 2016;Cui et al, 2016;Li et al, 2017;Wang, Huang, Sun, & Pan, 2015). C57BL/6 J mice (20 ± 2 g) obtained from the Laboratory Animal Mice were divided into four groups (n = 6) randomly on the next day after implantation.…”

Section: Pharmacokinetic Studymentioning

confidence: 99%

Synthesis, antitumor activity and pharmacokinetic study of 10‐propionyloxy camptothecin in rats

Zheng

Shao

Fan

et al. 2018

Biomedical Chromatography

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In the present study, a 10-position modified of camptothecin, 10-propionyloxy camptothecin (PCPT) was esterified from 10-hydroxcamptothecin (HCPT), which could metabolize to HCPT in vivo. PCPT displayed a relatively stronger antitumor activity in vitro and in vivo. Thereafter a simple, sensitive and rapid HPLC method coupled with a fluorescence detector was developed and validated for the assay of PCPT and its active metabolite HCPT in rat plasma. The method was validated for accuracy, precision, linearity, selectivity and recovery. The validated method was successfully applied to the pharmacokinetic study of PCPT in rats after intravenous administration. The results showed that PCPT could be mainly converted to HCPT in plasma with the AUC value of 3.69 ± 4.44 and 311.16 ± 188.81 ng h/mL for PCPT and HCPT, respectively.

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Synthesis and biological evaluation of D-ring fused 1,2,3-thiadiazole dehydroepiandrosterone derivatives as antitumor agents

Cited by 29 publications

References 44 publications

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Thiadiazole derivatives as anticancer agents

Synthesis, antitumor activity and pharmacokinetic study of 10‐propionyloxy camptothecin in rats

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