26526-57-8

Usage

InChI:InChI=1/C12H17N3S/c13-11-15-14-10(16-11)12-4-7-1-8(5-12)3-9(2-7)6-12/h7-9H,1-6H2,(H2,13,15)

Upstream product

• 17846-15-0 adamantane-1-carbohydrazide 
• 828-51-3 1-Adamantanecarboxylic acid 
• 79-19-6 thiosemicarbazide 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 139158-45-5 1-(1-adamantylcarbonyl)-4-benzylthiosemicarbazide 
• 40536-84-3 2-(adamantane-1-carbonyl)hydrazine-1-carbothioamide 

Downstream Products

• 1257344-22-1 C₁₉H₂₂N₄S₂ 
• 1257344-24-3 C₁₉H₂₁ClN₄S₂ 
• 1257344-23-2 C₁₉H₂₁FN₄S₂ 

Relevant academic research and scientific papers

5-Adamantan thiadiazole-based thiazolidinones as antimicrobial agents. Design, synthesis, molecular docking and evaluation

In continuation of our efforts to develop new compounds with antimicrobial properties we describe design, synthesis, molecular docking study and evaluation of antimicrobial activity of seventeen novel 2-{[5-(adamantan-1-yl)-1,3,4-thiadiazol-2-yl]-imino}-5-arylidene-1,3-thiazolidin-4-ones. All compounds showed antibacterial activity against eight Gram positive and Gram negative bacterial species. Twelve out of seventeen compounds were more potent than streptomycin and all compounds exhibited higher potency than ampicillin. Compounds were also tested against three resistant bacterial strains: MRSA, P. aeruginosa and E. coli. The best antibacterial potential against ATCC and resistant strains was observed for compound 8 (2-{[5-(adamantan-1-yl)-1,3,4-thiadiazol-2-yl]-imino}-5-(4-nitrobenzylidene)-1,3thiazolidin-4-one). The most sensitive bacterium appeared to be S. typhimirium, followed by B. cereus while L. monocitogenes and M. flavus were the most resistant. Compounds were also tested for their antifungal activity against eight fungal species. All compounds exhibited antifungal activity better than the reference drugs bifonazole and ketokonazole (3-115 times). It was found that compound 8 appeared again to be the most potent. Molecular docking studies on E. coli MurB, MurA as well as C. albicans CYP 51 and dihydrofolate reductase were used for the prediction of mechanism of antibacterial and antifungal activities confirming the experimental results.

Novel tdp1 inhibitors based on adamantane connected with monoterpene moieties via heterocyclic fragments

Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is a promising target for anticancer therapy due to its ability to counter the effects topoisomerase 1 (Top1) poison, such as topotecan, thus, decreasing their efficacy. Compounds containing adamantane and monoterpenoid residues connected via 1,2,4-triazole or 1,3,4-thiadiazole linkers were synthesized and tested against Tdp1. All the derivatives exhibited inhibition at low micromolar or nanomolar concentrations with the most potent inhibitors having IC50 values in the 0.35–0.57 μM range. The cytotoxicity was determined in the HeLa, HCT-116 and SW837 cancer cell lines; moderate CC50 (μM) values were seen from the mid-teens to no effect at 100 μM. Furthermore, citral derivative 20c, α-pinene-derived compounds 20f, 20g and 25c, and the citronellic acid derivative 25b were found to have a sensitizing effect in conjunction with topotecan in the HeLa cervical cancer and colon adenocarcinoma HCT-116 cell lines. The ligands are predicted to bind in the catalytic pocket of Tdp1 and have favorable physicochemical properties for further development as a potential adjunct therapy with Top1 poisons.

Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies

A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole am

Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives

New 1-adamanyl-1,3,4-thiadiazole derivatives namely, 5-(1-adamantyl)-1,3,4- thiadiazoline-2-thione 3, 5-(1-adamantyl)-3-(benzyl- or 4-substituted benzyl)-1,3,4-thiadiazoline-2-thione 4a-d, 5-(1-adamantyl)-3-(4-substituted-1- piperazinylmethyl)-1,3,4-thiadiazoline-2-thiones 5a-c, 2-[5-(1-adamantyl)-2- thioxo-1,3,4-thiadiazolin-3-yl]acetic acid 7, (±)-2-[5-(1-adamantyl)-2- thioxo-1,3,4-thiadiazolin-3-yl]propionic acid 9, 3-[5-(1-adamantyl)-2-thioxo-1, 3,4-thiadiazolin-3-yl]propionic acid 11, N-[5-(1-adamantyl)-1,3,4-thiadiazol-2- yl]-N′-arylthioureas 15a-c and 5-(1-adamantyl)-1,3,4-thiadiazoline-2-one 16, were synthesized and tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 7, 9, 15b and 15c displayed marked activity against the tested Gram-positive bacteria, while compound 3 was highly active against the tested Gram-negative bacteria. Compounds 4b, 7 and 15c were weakly or moderately active against C. albicans. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenan-induced paw oedema method in rats. The propionic acid derivative 9 produced good dose-dependent anti-inflammatory activity.

Adamantane Derivatives IV: Unexpected Debenzylation on Ring Closure of 1-(1-Adamantylcarbonyl)-4-benzylthiosemicarbazide with Sulphuric Acid

Cyclization of 1-(1-adamantylcarbonyl)-4-substituted thiosemicarbazides 2a-e with sulphuric acid at ambient temperature or by heating with phosphorus oxychloride yielded the corresponding 2-(1-adamantyl)-5-amino-1,3,4-thiadiazoles 3a-e.Cyclization of 1-(1-adamantylcarbonyl)-4-benzylthiosemicarbazide 2f with sulphuric acid gave the debenzylated product 2-(1-adamantyl)-5-amino-1,3,4-thiadiazole 4.On the other hand, cyclization of 2f using phosphorus oxychloride yielded 2-(1-adamantyl)-5-benzylamino-1,3,4-thiadiazole 3f. - Keywords: Adamantanes; Debenzylation; 1,3,4-Thiadiazoles.