Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents

Dawood, Kamal M.; Eldebss, Taha M. A.; Elzahabi, Heba S. A.; Yousef, Mahmoud H Ayesh Haj; Metz, Peter

doi:10.1016/j.ejmech.2013.10.042

Cited by 123 publications

(60 citation statements)

References 37 publications

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“…Thiazole and thiadiazole derivatives are known to exhibit various biological activities, such as anti-allergy [4], antihypertensive [5], anti-in-flammatory [6][7], anti-schizophrenia [8], antifungal [9], antibacterial [10], antimicrobial [11][12][13], analgesic [14], anti-HIV [15], anticonvulsant [16], antidepressant [17], and anti-cancer [18][19][20][21] properties. Other uses of heterocyclic compounds containing nitrogen and sulfur include manufacturing biocides, dyes [22][23][24], and plant-growth regulators [25].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

Şahin

Tahtacı

2014

Maced. J. Chem. Chem. Eng.

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Thiosemicarbazone derivatives 3a-e were synthesized by the reaction of various aldehydes 1a-e with 4-methyl thiosemicarbazide 2 in 78% to 90% yield. Then, the thiazole moieties of the target materials 5a-e were obtained in high yields (71-93%) using the Hantzsch reaction utilizing thiosemicarbazone derivatives 3a-e with ethyl-2-chloroacetoacetic ester. The substituted nitrile derivatives 7a-e were obtained in moderate to high yield (58-84%) from the reaction of compounds 5a-e with chloroacetonitrile by the nucleophilic aliphatic substitution reaction in the presence of anhydrous potassium carbonate. Finally, substituted 2-amino-1,3,4-thiadiazole compounds 9a-e were obtained in moderate to good yields (51-62%) from the reaction of thiosemicarbazide with substituted nitrile derivatives 7a-e. As a result, compounds that all share a high disposition for biological activities were obtained. The structures of the newly synthesized compounds were confirmed by IR, 1 H NMR, 13 C NMR, elemental analysis, and mass spectrometric techniques.Keywords: thiosemicarbazone; 1,3-thiazole; 2-amino-1,3,4-thiadiazole; Hantzsch reaction СИНТЕЗА И КАРАКТЕРИЗАЦИЈА НА НОВИ ДЕРИВАТИ НА 1,3-ТИАЗОЛ И 2-АМИНО-1,3,4-ТИАДИАЗОЛТиосемикарбазонските деривати 3a-e беа синтетизирани при реакција на разни алдехиди 1a-e со 4-метилтиосемикарбазид 2 со принос од 78 до 90%. Тиазолските прстени на целните соединенија 5a-e беа добиени со висок принос од 71-93% со реакцијата на Hantzsch со примена на тиосемикарбазонските деривати 3a-e и етил-2-хлороацетооцетен естер. Супституираните нитрилни деривати 7a-e беа добиени со умерен до висок принос при реакција на соединенијата 5a-e со хлороацетонитрил при нуклеофилна алифатична супституција во присуство на безводен калиумкарбонат. Конечно, супституираните 2-амино-1,3,4-тиодиазолните соединенија 9a-e беа добиени со умерен до добар принос (51-62%) при реакција на тиосемикарбазид со супституирани нитрилни деривати 7a-e. Сите овие добиени соединенија покажуваат висока биолошка активност. Структурите на новосинтетизираните соединенија беа потврдени по пат на IR, 1 H NMR, 13 C NMR, елементарна анализа и масеноспектрометриски техники.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

Şahin

Tahtacı

2014

Maced. J. Chem. Chem. Eng.

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“…Most of the synthe-sized compounds were tested for anticancer activity against human hepatocellular carcinoma HepG2, human breast cancer MCF-7 and human lung cancer A549. 119 …”

Section: N-(4-(pyrazol-4-yl)thiazol-2-yl)-n'-phenylthiourea Derivativmentioning

confidence: 99%

Recent Developments and Biological Activities of 2-Aminothiazole Derivatives

Khalifa

2018

ACSi

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Aminothiazole nuclei and their various derivatives have been long used as precursors for the synthesis of biologically active molecules. As a typical heterocyclic amine, 2-aminothiazole is a cornerstone for the synthesis of many compounds, including sulfur drugs, biocides, fungicides, various types of dyes for synthetic fibers and chemical reaction accelerators and as intermediates in the synthesis of antibiotics, where a large number of 2-aminothiazoles have been substituted with different groups for various pharmaceutical purposes, besides their activity as corrosion inhibitors for mild steel protection as well. The synthetic utility of 2-amino-4-substituted-thiazoles, their reactions and biological activities have been surveyed and are presented in this review.

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“…Numerous studies demonstrated that thiadiazole scaffold shows anticancer activity against various tumor cell lines [8][9][10]. Various reports suggested that various substituted thiadiazole derivatives exhibited significant anticancer activity against MCF-7 cell lines [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and <i>in vitro</i> evaluation of novel isatinincorporated thiadiazole hybrids as potential anti-breast cancer agents

Kumar¹,

Sharma²,

Singh³

et al. 2017

Trop. J. Pharm Res

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Purpose: To synthesis and characterize some novel isatin-incorporated thiadiazoles and screen them for anti-breast cancer activity in human breast adenocarcinoma cells (MCF-7). Method: A series of isatin incorporated Schiff bases of thiadiazoles (3a-3l) was synthesized by reaction of substituted thiadiazoles (1a-1d) with isatin (2a) and N-alkyl substituted isatin (2b-2c) and characterized by elemental analysis, IR, 1H NMR, 13C NMR and LCMS. The newly synthesized compounds were screened for their in-vitro cytotoxicity against MCF-7 cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric and Sulforhodamine B (SRB) methods.Results: Compounds 3a, 3c, 3d, 3g and 3j showed anticancer activity in both 3, showed most potent cytotoxic activity against MCF-7 cell lines. Conclusion:The novel isatin incorporated thiadiazoles synthesized and characterized in this study possess anti-cancer activities in human breast adenocarcinoma cells . This can possibly lead to emergence of new anti-breast cancer agents.

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Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents

Cited by 123 publications

References 37 publications

Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

Recent Developments and Biological Activities of 2-Aminothiazole Derivatives

Synthesis and <i>in vitro</i> evaluation of novel isatinincorporated thiadiazole hybrids as potential anti-breast cancer agents

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