Synthesis of 4-Methyl-1,2,3-thiadiazole Derivatives via Ugi Reaction and Their Biological Activities†

2010 ◽  
Vol 58 (5) ◽  
pp. 2755-2762 ◽  
Author(s):  
Xiang Zuo ◽  
Na Mi ◽  
Zhijin Fan ◽  
Qingxiang Zheng ◽  
Haike Zhang ◽  
...  
Keyword(s):  
Biological Activities ◽  
Ugi Reaction ◽  
Thiadiazole Derivatives

Synthesis and characterization of a new series of thiadiazole derivatives as potential anticancer agents

2020 ◽  
Vol 26 (1) ◽  
pp. 6-13 ◽  
Author(s):  
Ulviye Acar Çevik ◽  
Derya Osmaniye ◽  
Serkan Levent ◽  
Begüm Nurpelin Sağlik ◽  
Betül Kaya Çavuşoğlu ◽  
...  
Keyword(s):  
Anticancer Agents ◽  
Biological Activities ◽  
Cancer Cell Line ◽  
Chemotherapeutic Agents ◽  
Anticancer Activities ◽  
Normal Tissues ◽  
H Nmr ◽  
Wide Range ◽  
Thiadiazole Derivatives ◽  
Low Efficiency

AbstractCancer is one of the most common causes of death in the world. Despite the importance of combating cancer in healthcare systems and research centers, toxicity in normal tissues and the low efficiency of anticancer drugs are major problems in chemotherapy. Nowadays the aim of many medical research projects is to discover new safer and more effective anticancer agents. 1,3,4-Thiadiazole compounds are important fragments in medicinal chemistry because of their wide range of biological activities, including anticancer activities. The aim of this study was to determine the capacity of newly synthesized 1,3,4-thiadiazole compounds as chemotherapeutic agents. The structures of the obtained compounds were elucidated using 1H-NMR, 13C-NMR and mass spectrometry. Although the thiadiazole derivatives did not prove to be significantly cytotoxic to the tumour tissue cultures, compound 4i showed activity against the C6 rat brain cancer cell line (IC50 0.097 mM) at the tested concentrations.

Synthesis of a Series of Novel 2-Amino-5-Substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole Derivatives as Potential Anticancer, Antifungal and Antibacterial Agents

2021 ◽  
Vol 17 ◽  
Author(s):  
Em Canh Pham ◽  
Tuyen Ngoc Truong ◽  
Nguyen Hanh Dong ◽  
Duy Duc Vo ◽  
Tuoi Thi Hong Do
Keyword(s):  
Cell Line ◽  
Biological Activities ◽  
Chemical Properties ◽  
Diffusion Method ◽  
Anticancer Activities ◽  
Molecular Docking Study ◽  
Antifungal Activities ◽  
Antibacterial And Antifungal Activities ◽  
Thiadiazole Derivatives ◽  
Antibacterial And Antifungal

Background: Many compounds containing a five-membered heterocyclic ring display exceptional chemical properties and versatile biological activities. Objective: The objective of the present study was the desire to prepare the 5-substituted 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole derivatives and evaluate their potential anticancer, antibacterial and antifungal activities. Methods: Twenty-seven derivatives were synthesized by iodine-mediated cyclization of semicarbazones or thiosemicarbazones obtained from condensation of semicarbazide or thiosemicarbazide and aldehydes. The structures were confirmed by 1H-NMR, 13C-NMR and MS spectra. The antibacterial and antifungal activities were evaluated by diffusion method and the anticancer activities were evaluated by MTT assay. Results: Twenty-seven derivatives have been synthesized in moderate to good yields. A number of derivatives exhibited potential antibacterial, antifungal and anticancer activities. Conclusion: Compounds (1b, 1e and 1g) showed antibacterial activity against Streptococcus faecalis, MSSA and MRSA with MIC ranging between 4 to 64 µg/mL. Compound (2g) showed antifungal activity against Candida albicans (8 µg/mL) and Aspergillus niger (64 µg/mL). Compound (1o) exhibited high cytotoxic activity against HepG2 cell line (IC50 value 8.6 µM), which is comparable to the activity of paclitaxel, and is non-toxic on LLC-PK1 normal cell line. The structure activity relationship and molecular docking study of the synthesized compounds are also reported.

scholarly journals Biological activities of imidazo[2,1-b][1,3,4]thiadiazole derivatives: A review

2016 ◽  
Vol 20 ◽  
pp. S463-S475 ◽  
Author(s):  
Bhoomendra A. Bhongade ◽  
Sirajunisa Talath ◽  
Ravikiran A. Gadad ◽  
Andanappa K. Gadad
Keyword(s):  
Biological Activities ◽  
Thiadiazole Derivatives

scholarly journals Studies on the Selective Toxicity. VIII. : Biological Activities of 1, 2, 4-Thiadiazole Derivatives

1968 ◽  
Vol 88 (11) ◽  
pp. 1437-1449 ◽  
Author(s):  
TERUHISA NOGUCHI ◽  
YOSHINOBU HASHIMOTO ◽  
TOSHIRO MORI ◽  
SABURO KANO ◽  
KOOSHIN MIYAZAKI
Keyword(s):  
Biological Activities ◽  
Selective Toxicity ◽  
Thiadiazole Derivatives

ChemInform Abstract: Synthesis, Biological Activities and Chemistry of Thiadiazole Derivatives and Schiff Bases

ChemInform ◽  
2013 ◽  
Vol 44 (16) ◽  
pp. no-no
Author(s):  
Sunny Jalhan ◽  
Anil Jindal ◽  
Avneet Gupta ◽  
Hemraj Hemraj
Keyword(s):  
Schiff Bases ◽  
Biological Activities ◽  
Thiadiazole Derivatives

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

2014 ◽  
Vol 33 (2) ◽  
pp. 189 ◽  
Author(s):  
Mustafa Er ◽  
Ayşe Şahin ◽  
Hakan Tahtacı
Keyword(s):  
Biological Activities ◽  
High Yield ◽  
Synthesis And Characterization ◽  
Hantzsch Reaction ◽  
H Nmr ◽  
Thiadiazole Derivatives ◽  
High Yields ◽  
Mass Spectrometric Techniques ◽  
C Nmr

<p>Thiosemicarbazone derivatives <strong>3a–e</strong> were synthesized by the reaction of various aldehydes<strong> 1a–e</strong> with 4-methyl thiosemicarbazide <strong>2</strong> in 78% to 90% yield. Then, the thiazole moieties of the target materials <strong>5a–e</strong> were obtained in high yields (71–93%) using the Hantzsch reaction utilizing thiosemicarbazone derivatives <strong>3a–e</strong> with ethyl-2-chloroacetoacetic ester. The substituted nitrile derivatives <strong>7a–e</strong> were obtained in moderate to high yield (58–84%) from the reaction of compounds <strong>5a–e</strong> with chloroacetonitrile by the nucleophilic aliphatic substitution reaction in the presence of anhydrous potassium carbonate. Finally, substituted 2-amino-1,3,4-thiadiazole compounds <strong>9a–e</strong> were obtained in moderate to good yields (51–62%) from the reaction of thiosemicarbazide with substituted nitrile derivatives <strong>7a–e</strong>. 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, <sup>1</sup>H NMR, <sup>13</sup>C NMR, elemental analysis, and mass spectrometric techniques.</p>

scholarly journals Synthesis and Biological Activities of Some New 3,6-Disubstituted 1,2,4-Triazolo[3,4-b]1,3,4-thiadiazole Derivatives

2012 ◽  
Vol 33 (12) ◽  
pp. 3943-3949 ◽  
Author(s):  
Muhammad Rafiq ◽  
Muhammad Saleem ◽  
Muhammad Hanif ◽  
Muhammad Rizwan Maqsood ◽  
Nasim Hasan Rama ◽  
...  
Keyword(s):  
Biological Activities ◽  
Thiadiazole Derivatives

scholarly journals Thiadiazole derivatives as anticancer agents

2020 ◽  
Vol 72 (5) ◽  
pp. 1079-1100 ◽  
Author(s):  
Monika Szeliga
Keyword(s):  
Anticancer Agents ◽  
Biological Activities ◽  
Cellular Membrane ◽  
Biological Targets ◽  
Cancer Pathogenesis ◽  
Thiadiazole Ring ◽  
Substantial Progress ◽  
Thiadiazole Derivatives

Abstract 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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