5-[Substituted]-1, 3, 4-thiadiazol-2-amines: Synthesis, Spectral Characterization, and Evaluation of their DNA interactions

Abstract

The presence of heterocyclic moiety in diverse compounds, strongly indicative of the desired effect on physiological activity, and it reflects on efforts to find useful synthetic drugs. In this connection, here reporting the synthesis and characterization of 5-[substituted]-1, 3, 4thiadiazol-2-amines (1-7). All the prepared compounds were characterized by spectroscopic methods viz. 1 H-NMR, 13 C{ 1 H}-NMR, FT-IR, and LC-MS. The results of the DNA binding interactions using absorption and fluorescence spectroscopy reveal that the compounds are avid binders to DNA. A DNA cleavage study with pUC18 DNA using gel electrophoresis indicates the compounds are able to cleave DNA in presence of oxidant H2O2.

Synthesis and antimicrobial activity of new 1,2,4‐triazole, 1,3,4‐oxadiazole, 1,3,4‐thiadiazole, thiopyrane, thiazolidinone, and azepine derivatives

“…All compounds were tested in vitro to microbial activity (bacteria and fungi) and all the results were offered in Tables 1 and 2 μmol cm −3 of 14a-c (1-5), 13 (2-6), 12a-c (4-8), and 11a-c (6-10) when compared with the positive control, nystatin (MIC 2-5 μmol mL −1 ). Some of the compounds showed moderate antifungal activity when compared with nystatin (MIC 2-5 μmol mL −1 ): 10a-c (8-12), 9a-c (10-15), 8a-c (13)(14)(15)(16)(17), and 5a-c (15)(16)(17)(18)(19). The tested fungi were Candida albicans, Curvularia lunata, Alternaria alternata, and Aspergillus niger.…”

“…[ 7 ] Also, 1,3,4‐oxadiazoles have been famous for 80 years, thus it have important biological activities such as antispasmolytic and hypotensive, [ 8 ] anticonvulsant, [ 9 ] antimicrobial, [ 10 ] anti‐inflammatory and analgesic, [ 11 ] anticancer, [ 12 ] antiproliferative, [ 13 ] anti‐allergic, [ 14 ] and hypoglycemic. [ 15 ] Moreover, the interaction of 1,3,4‐oxadiazole or 1,3,4‐thiadiazole derivatives with CT‐DNA was investigated by different spectroscopic methods, [ 16,17 ] hence can benefit in understanding the binding mechanism of heterocyclic molecules and the design of new effective molecules. Also, the interaction of DNA with 1,3,4‐oxadiazoles or 1,3,4‐thiadiazoles lead to the formation of antiproliferative cells, anticancer and antitumor agents through many scientific studies, [ 18–20 ] thus these compounds have the ability to the binding to DNA which makes researchers use these compounds to develop many drugs in the future.…”

H2O2:HCl Catalyzed Synthesis of 5-(3-Substituted-Thiophene) Pyrimidine Derivatives and Evaluation for Their Pharmacological Effects

“…A solution of CT-DNA in 50 mM Tris-HCl/50 mM NaCl buffer solution was prepared at pH 6.9-7.01. In buffer solution, the ratio of absorption values of CT-DNA at 260 and 280 nm is 1.8-1.9, indicates that DNA was free of proteins [32]. Then a concentrated stock solution of DNA was prepared in 50 mM Tris HCl/50 mM NaCl in double distilled water at pH 6.9-7.01 and the concentration of CT-DNA was determined per nucleotide by taking the absorption coefficient (6600 dm 3 mol -1 cm -1 ) at 260 nm [33].…”

Crystal structure and Hirshfeld surface analysis of 5-(5-phenyl-1,2-oxazol-3-yl)-1,3,4-thiadiazol-2-amine

“…The synthesis and structure of the compound has not published before. There are many approaches for building a thiadiazole heterocycle based on the use of carboxylic acids (Bhinge et al, 2015;Nayak et al, 2014), carbonyl chlorides (Sun et al, 2001;Kudelko et al, 2020), aldehydes (Shivakumara et al, 2019;Wang et al, 2019), etc. We chose here a method based on the transformation of carbonitriles (as shown in the scheme) as the shortest and most convenient way to achieve this purpose (Sakthivel et al, 2016;Abdelhamid et al, 2011).…”