2002-04-2Relevant articles and documents
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 Anti-bacterial Agents
Do, tuoi thi Hong,Dong, Nguyen Hanh,Vo, Duy Duc,pham, Em canh,truong, tuyen Ngoc
, p. 558 - 573 (2022/03/09)
Objective: The objective of the present study was to prepare the 5-substituted 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole derivatives and evaluate their potential anticancer, antibac-terial and antifungal activities. Methods: Twenty-seven derivatives were synthesized by iodine-mediated cyclization of semicarba-zones or thiosemicarbazones obtained from condensation of semicarbazide or thiosemicarbazide and aldehydes. The structures were confirmed by1H-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 faecal-is, MSSA and MRSA with MIC value ranging between 4 to 64 μg/mL. Compound (2g) showed anti-fungal 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 compara-ble 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 have also been reported.
Aryl or heteroaryl substituted thiadiazole compound and antibacterial application thereof
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Paragraph 0095-0097; 0194-0195, (2021/01/30)
The invention belongs to the technical field of medicines, and particularly relates to an aryl or heteroaryl substituted thiadiazole compound, a preparation method and application thereof as an antibacterial drug. The compound is represented by formula (1
Method for preparing 2-amino-5-substituted-1,3,4-thiadiazole
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Paragraph 0045-0051, (2020/02/14)
The invention relates to a method for preparing 2-amino-5-substituted-1,3,4-thiadiazole, The method comprises: adding choline chloride and urea into a reaction container according to a formula ratio,and stirring at 80 DEG C to obtain a colorless transparent solution, ie., a eutectic solvent DES; cooling to a room temperature, adding carboxylic acid and thiosemicarbazide according to a formula ratio, slowly heating, reacting at 80 DEG C, and carrying out TLC monitoring until the reaction is finished; cooling the reaction mixed liquid to a room temperature, adding ammonia water into the mixed liquid under ice bath cooling to adjust the pH value to 8-9, precipitating the solid, carrying out suction filtration, washing the filter cake with ice water, and drying to obtain the 2-amino-5-substituted-1,3,4-thiadiazole; and recovering the filtrate to obtain the eutectic solvent capable of being repeatedly used. According to the invention, the method has characteristics of simple operation, simple post-treatment, short reaction time, high efficiency, catalyst recycling, environmental protection, cost reducing and no requirement of organic solvents, and is a method for efficiently synthesizing 2-amino-5-substituted-1,3,4-thiadiazole.