25444-82-0

Usage

Uses

Used in Pharmaceutical Industry:
1-Adamantylthiourea is used as an antiviral agent for its inhibitory activity against influenza virus A2 infections in mice. This application is particularly relevant in the development of new treatments for viral infections, as it may help to reduce the severity and spread of such diseases.

InChI:InChI=1/C11H18N2S/c12-10(14)13-11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2,(H3,12,13,14)

Upstream product

• 4240-92-0 S-Thiocarbamoyl-β-mercaptopropionic acid 
• 768-94-5 1-Adamantanamine 
• 768-95-6 1-adamanthanol 
• 17356-08-0 thiourea 
• 4411-26-1 1-adamantylisothiocyanate 
• 333-20-0 potassium thioacyanate 
• 665-66-7 amantadine hydrochloride 

Downstream Products

• 870711-17-4 2-(1-adamantylamino)-5-ethyl-5-methyl-1,3-thiazol-4(5H)-one 

Relevant academic research and scientific papers

2-Amino-1,3-thiazol-4(5H)-ones as potent and selective 11β- hydroxysteroid dehydrogenase type 1 inhibitors: Enzyme-ligand co-crystal structure and demonstration of pharmacodynamic effects in C57Bl/6 mice

11β-Hydroxysteroid dehydrogenase type 1 (11β-HSD1) has attracted considerable attention during the past few years as a potential target for the treatment of diseases associated with metabolic syndrome. In our ongoing work on 11β-HSD1 inhibitors, a series of new 2-amino-1,3-thiazol-4(5H)-ones were explored. By inserting various cycloalkylamines at the 2-position and alkyl groups or spirocycloalkyl groups at the 5-position of the thiazolone, several potent 11β-HSD1 inhibitors were identified. An X-ray cocrystal structure of human 11β-HSD1 with compound 6d (Ki = 28 nM) revealed a large lipophilic pocket accessible by substitution off the 2-position of the thiazolone. To increase potency, analogues were prepared with larger lipophilic groups at this position. One of these compounds, the 3-noradamantyl analogue 8b, was a potent inhibitor of human 11β-HSD1 (Ki = 3 nM) and also inhibited 11β-HSD1 activity in lean C57Bl/6 mice when evaluated in an ex vivo adipose and liver cortisone to cortisol conversion assay.

A convenient method for the preparation of primary and symmetrical N,N'-disubstituted thioureas

A convenient process for the preparation of both primary thioureas 2 and symmetrical N,N'-disubstituted thioureas 6 based on the condensation of amine hydrohalides 5 with potassium thiocyanate has been developed. This approach tolerates sterically bulky primary amine substrates (both chiral and achiral), and the products can usually be isolated by a simple filtration of the reaction mixture. This method is an especially attractive alternative for the synthesis of thioureas when the corresponding isothiocyanates are unavailable, or difficult to prepare. It is also worth noting that a wide variety of amine hydrohalides, which are used in this procedure, are commercially available.

Adamantylation and adamantylalkylation of amides, nitriles, and ureas in trifluoroacetic acid

A new preparative procedure was developed for N-adamantylation of carboxylic acids amides and ureas, and C5-adamantylation of barbituric acid in trifluoroacetic acid medium with tertiary adamantanols and 1-adamantylalkanols. The reaction of 2-adamantanols and secondary 1-adamantylalkanols with nitriles was for the first time used in the preparation of W-(2-adamantyl)-and N-(1-adamantylalkyl)amides.

Adamantylation and adamantylalkylation of amides, nitriles and ureas in trifluoroacetic acid

A new preparative method for N-adamantylation of carboxylic acid amides, ureas and for C5-adamantylation of barbituric acid in trifluoroacetic acid (TFA) is proposed. Tertiary 1-adamantanols and 1-(1-adamantyl)alkanols were used as adamantylating agents. The reaction of 1-(1-adamantyl)alkanols with nitriles in TFA solution was employed for the first time for the preparation of N-[1-(1-adamantyl)alkyl]amides.