Facile synthesis of novel benzotriazole derivatives and their antibacterial activities (original) (raw)
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Medicinal Chemistry Research, 2010
Ten novel benzotriazole compounds were synthesized. Their chemical structures were confirmed by 1 H NMR, IR, and elemental analyses, coupled with three selected single-crystal structures (compounds A2, B3, and B5). Their antimycotic and antitumor activities were also investigated. The title compounds showed some antitumor activities, especially in the case of A3 and A4, which showed the most potent activity of propagation inhibition in liver and galactophore cancer cells.
International Journal of Pharmacy and Pharmaceutical Sciences
Benzotriazole derivatives have shown several pharmacological activities, which are antimicrobial activity, anti-inflammatory, analgesic activity, anticancer. On the basis of our observation the present research work was carried out to synthesize substituted benzotriazole derivatives containing pyrazilidin-3,5dione moieties. The various benzotriazole derivatives were prepared by diazotisation using substituted benzene 1, 2 diamine with glacial acetic acid (1A-1I) the various benzotriazole derivatives were treated with ethyl chloroacetate and anhydrous potassium carbonate to yield its ethyl 1 H benzotriazole-1-yl acetate (2A-2I). The formed acetate is converted into hydrazide (3A-3I) by reacting with various substituted hydrazines. Finally the resulted hydrazides were condensed with diethyl propanedioate to yield some new 1, 2, 3, benzotriazole derivative containing pyrazolidine 3, 5 dione moieties. The entire synthesized compounds were characterized by IR, 1H-NMR, Mass spectroscopy and elemental analysis. Purity of the compounds was checked by using TLC and elemental analysis. The antimicrobial activity of the synthesized compounds was evaluated by cup plate diffusion method. These compounds had a considerable anti-bacterial activity against S. aureus, B. subtilis, E. coli, Proteus vulgaris compared to Ciprofloxacin, Amoxicillin respectively. Similarly compounds had considerable antifungal activity against A. niger, C. albicans compared to Ketoconazole, Clotrimazole respectively.
Synthesis and antimicrobial evolution of some new benzotriazole substituted 1,3,4-thiadiazoles
World Scientific News, 2018
A series of novel benzotriazole-substituted 1,3,4-thiadiazole-2(3H)-thione derivatives was synthesized by cyclization of Schiff base. The structures were recognized on the foundation of spectral tools and their purity by elemental analysis. All the compounds were preliminary evaluated for their in vitro antimicrobial activities against five bacterial strains viz [Staphylococcus aureus (MRSA; ATCC 43300), Klebsiella pneumoniae (ATCC 700603), Escherichia coli (ATCC 25922), Acinetobacter baumannii (ATCC 19606), Pseudomonas aeruginosa (ATCC 27853)] and two fungi Strains viz. [Candida albicans (ATCC 90028), Cryptococcus neoformans (ATCC 208821)]. Several compounds exhibited remarkable antimicrobial activity, out of 15 compounds, three compounds viz. 5a, 5g and 5i showed promising antifungal activities with no signs of human cells cytotoxic [HEK293: Human Embryonic Kidney cells (ATCC CRL-1573)] and haemolytic activity [Whole blood (ARCBS 5400 00150)].
https://www.ijrrjournal.com/IJRR\_Vol.8\_Issue.5\_May2021/IJRR-Abstract046.html, 2021
Benzotriazole (BTA) is a nitrogen containing heterocyclic derivative containing three nitrogen atoms at 1 st , 2 nd and 3 rd positions with chemical formula C 6 H 5 N 3. Benzotriazole and its derivatives have great significance in medicinal chemistry and these derivatives were used by several chemists for therapeutic conditions because it possessing a wide spectrum of pharmacological activities including anti bacterial, anti fungal, anti viral, anti inflammatory, anti hyperglycemic, anti hypertensive, anti cancer and analgesic activity. In this review, different synthetic methods for the preparation of benzotriazole, importance of benzotriazole derivatives in biomedical research, highlighting its biological behavior, versatile activities and Structure Activity Relationship (SAR) studies are described. This review will help the researchers to understand the structure activity relationships and improvise the concepts in their research field.
SYNTHESIS AND SIGNIFICATION OF BENZOTRIAZOLE ANALOGS IN DIFFERENT PHARMACEUTICAL DRUG
European Journal of Biomedical AND Pharmaceutical sciences, 2016
Benzotriazole being a hetrocylic compound find for their different bioactive structure. Literature indicates that compounds having Benzotriazole nucleus have wide range of therapeutic uses that include antifungal, anticonvulsant, anti-inflammatory, antidiabetic, analgesic, Anti-HIV, ant tubercular, antioxidant, antidepressant, miscellaneous & antitumor activity. The purpose of this review is give an overview of different property of Benzotriazole and some of its application in synthesis of pharmacologically active drug.
2010
Benzothiazole are important group of compounds repo rt d to have various biological activities and hence the present study was undertaken in order to synthesize same new compounds built upon this nucleus with the hope to enhance the biol ogical properties of newly designed compounds. In the present work 2-substituted benzot hiazole (a) was prepared from p-tolnidine via cyclization reaction then N-2-benzothiazolyl th iourea was synthesized by reacting (a) with ammonium thiocyanate. Then its semicarbazide deriva tive was formed reacting with hydrazine hydrate in ethylene glycol which was reacted with v arious acetophenons to form respective derivatives. Chemical structure of product and thei r purity was ascertained by TLC, MP and various spectral methods as FTIR and NMR. The inhib tion of microorganism under standard condition was determined to demonstrate antimicrobi al activity of derivatives using gram positive and gram negative bacteria such as St phylococcus aureus, Pseudomonas....
Design, synthesis and determination of antifungal activity of 5(6)-substituted benzotriazoles
European Journal of Medicinal Chemistry, 2010
In an effort to find inhibitors that are effective against both Candida and Aspergillus spp., a series of 5(6)-(un)substituted benzotriazole analogs, represented by compounds 3a-3h and 3b 0 -3f 0 , were prepared using a crystalline oxirane intermediate 1 previously synthesized in our laboratory. All the compounds were evaluated for inhibitory activity against various species of Candida and Aspergillus. Compounds 3b 0 (5,6-dimethylbenzotriazol-2-yl derivative), 3d (5-chlorobenzotriazol-1-yl derivative) and 3e 0 (6-methylbenzotriazol-1-yl derivative) exhibited potent antifungal activity, with the MICs for Candida spp. and Aspergillus niger, ranging from 1.6 mg/mL to 25 mg/mL and 12.5 mg/mL to 25 mg/mL, respectively. The present work describes the design, synthesis, regioisomer characterization (through COSY and NOESY 2D-NMR spectroscopy and single molecule X-ray crystallography), antifungal evaluation, molecular docking, and structure-activity relationships of the various 5(6)-(un)substituted benzotriazole analogs.
ChemInform, 2010
In an effort to find inhibitors that are effective against both Candida and Aspergillus spp., a series of 5(6)-(un)substituted benzotriazole analogs, represented by compounds 3a-3h and 3b 0 -3f 0 , were prepared using a crystalline oxirane intermediate 1 previously synthesized in our laboratory. All the compounds were evaluated for inhibitory activity against various species of Candida and Aspergillus. Compounds 3b 0 (5,6-dimethylbenzotriazol-2-yl derivative), 3d (5-chlorobenzotriazol-1-yl derivative) and 3e 0 (6-methylbenzotriazol-1-yl derivative) exhibited potent antifungal activity, with the MICs for Candida spp. and Aspergillus niger, ranging from 1.6 mg/mL to 25 mg/mL and 12.5 mg/mL to 25 mg/mL, respectively. The present work describes the design, synthesis, regioisomer characterization (through COSY and NOESY 2D-NMR spectroscopy and single molecule X-ray crystallography), antifungal evaluation, molecular docking, and structure-activity relationships of the various 5(6)-(un)substituted benzotriazole analogs.
Many of the classical synthetic methodologies have broad scope but generate copious amounts of waste. The chemical and pharmaceutical industries have been subjected to increasing pressure to minimize or, preferably, eliminate this waste. In the present study a series of some newer 1,2,3–benzotriazole derivatives were synthesized under ultrasonicated and solvent–free conditions. Newer “1–(1H–benzo[d][1,2,3]triazole–1–carbonyl) derivatives” (5A – 5P) were synthesized from “1H–benzo[d][1,2,3]triazole” (1) by optimizing the reaction conditions. The resulting products were isolated and characterized by spectral studies. The anti bacterial activities of these compounds were screened in vitro against different strains of bacteria i.e. Gram negative organism (Pseudonomous aureginosa, MTCC – 1035) and Gram positive organisms (Bacillus cereus, MTCC – 430, Bacillus subtilis, MTCC – 441, Staphylococcus aureus, MTCC – 737, Staphylococcus epidermidis, MTCC – 3086) by paper disc diffusion method. Some of the synthesized compounds showed significant activity against various bacteria.