2415-10-3

Upstream product

• 4141-08-6 2-Amino-N-methylbenzamid 
• 101329-35-5 3-methyl-2-mercapto-2-thioxo-2,3-dihydro-1H-2λ⁵-benzo[1,3,2]diazaphosphinine-4-thione pyridinium salt 

Downstream Products

• 917495-62-6 2-(4-methylbenzoylamino)-N-methylthiobenzamide 
• 917495-63-7 2-(4-chlorobenzoylamino)-N-methylthiobenzamide 
• 917495-64-8 2-(4-nitrobenzoylamino)-N-methylthiobenzamide 
• 25478-30-2 2-(4-methoxyphenyl)-3-methylquinazoline-4-thione 
• 49699-40-3 2-phenyl-3-methylquinazoline-4(3H)-thione 
• 90418-01-2 3-methyl-3H-quinazoline-4-thione 
• 917495-65-9 2-(3-nitrobenzoylamino)-N-methylthiobenzamide 

Relevant academic research and scientific papers

Cyclization of 2-benzoylamino-N-methyl-thiobenzamides to 3-methyl-2-phenylquinazolin-4-thiones

Acylation of 2-amino-N-methyl-thiobenzamide with substituted benzoyl chlorides has been used to synthesize the corresponding 2-benzoylamino-N- methylthiobenzamides. Subsequent sodium methoxide-catalyzed ring closure gives the corresponding 3-methyl-2-phen

Synthesis of substituted 2-benzoylaminothiobenzamides and their ring closure to substituted 2-phenylquinazoline-4-thiones

Acylation of 2-aminothiobenzamide or 2-methylaminothiobenzamide with substituted benzoyl chlorides has been used to synthesise the corresponding 2-benzoyl-aminothiobenzamides whose subsequent sodium methoxide-catalysed ring closure gives the corresponding quinazoline-4-thiones. These compounds were characterised by means of their 1H- and 13C-NMR spectra. The preferred tautomeric form of selected compounds has been discussed on the basis of their 13C-NMR, IR and Raman spectra. It has been found that in the given medium 1-methyl-quinazoline-4-thiones undergo a replacement of the sulphur substituent by oxygen giving 1-methyl-quinazoline-4-ones. In strong acid media, 2-benzoylaminothiobenzamide is cyclised through its sulphur atom to give 2-phenylbenzo[d-1,3]thiazin-4-one.

Synthesis and pharmacological activity of triazole derivatives inhibiting eosinophilia

In order to develop novel antiasthmatic agents based on a new mechanism of action, a series of 3-substituted 5-amino-1- [(methylamino)(thiocarbonyl)]-1H-1,2,4-triazole derivatives were synthesized and evaluated in a model in which eosinophilia was induced in the airway through intravenous (iv) injection of Sephadex particles on days 0, 2, and 5. After screening of several hundred derivatives, we finally identified the highly potent eosinophilia inhibitor 5-amino-3-(4-chlorophenyl)-1- [(methylamino)(thiocarbonyl)]-1H-triazole (23c, GCC-AP0341), which had ID50 values of 0.3 and 0.07 mg/kg when administered orally (os) and intraperitoneally (ip), respectively. This compound showed complete inhibition of the hypersensitivity induced by ascaris inhalation at an ip dose of 1 mg/kg as well as low toxicity, with an LD50 value of >2.0 g/kg in mice. Extensive study of its mechanism of action revealed that 23c inhibited eosinophil survival induced by interleukin-5 (IL-5), but had little or no effect on leukotriene D4 (LTD4) or platelet-activating factor (PAF)- induced responses. Taken together, these results suggest 23c as a novel candidate for the treatment of chronic asthma. Further studies are now underway.