38334-93-9

Upstream product

• 64037-15-6 5-methylbenzo[d]oxazol-2-amine 
• 28115-86-8 3-methylbenzoyl isothiocyanate 
• 99-04-7 m-Toluic acid 
• 17356-08-0 thiourea 
• 1711-06-4 3-Methylbenzoyl chloride 
• 4570-41-6 1,3-benzoxazol-2-amine 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship studies of n-monosubstituted aroylthioureas as urease inhibitors

Background: Thiourea is a classical urease inhibitor which is usually used as a positive control, and many N,N'-disubstituted thioureas have been determined as urease inhibitors. However, due to steric hindrance, N,N'-disubstituted thiourea motif could not bind urease as thiourea. On the contrary, N-monosubstituted thiourea with a tiny thiourea motif could theoretically bind into the active pocket as thiourea. Objective: A series of N-monosubstituted aroylthioureas were designed and synthesized for evaluation as urease inhibitors. Methods: Urease inhibition was determined by the indophenol method and IC50 values were calculated using computerized linear regression analysis of quantal log dose-probit functions. The kinetic parameters were estimated via surface plasmon resonance (SPR) and by nonlinear regression analysis based on the mixed type inhibition model derived from Michaelis-Menten kinetics. Results: Compounds b2, b11, and b19 reversibly inhibited urease with a mixed mechanism, and showed excellent potency against both cell-free urease and urease in the intact cell, with IC50 values being 90-to 450-fold and 5-to 50-fold lower than the positive control acetohydroxamic acid, respectively. The most potent compound b11 showed an IC50 value of 0.060 ± 0.004μM against cell-free urease, which bound to urea binding site with a very low KD value (0.420±0.003nM) and a very long residence time (6.7 min). Compound b11 was also demonstrated to have very low cytotoxicity to mammalian cells. Conclusion: The results revealed that N-monosubstituted aroylthioureas bound to the active site of urease as expected, and represent a new class of urease inhibitors for the development of potential therapeutics against infections caused by urease-containing pathogens.

A facile synthesis of substituted N-benzoylthiourea

One pot reaction of benzoyl isothiocyanate and Tris(hydroxymethyl)aminomethane (Tris) at room temperature with polyethylene glycol-400 (PEG-400) as solid-liquid phase-transfer catalyst produced substituted N-benzoylthioureas with high yield. A reasonable pathway for their formation has been suggested.

One Pot Synthesis of 4-Arylbenzoxazolo-s-triazine-2-thiones

The reaction of 2-aminobenzoxazoles (1a-b) with aroyl isothiocyanates in acetone gave 4-arylbenzoxazolo-s-triazine-2-thiones (3a-g), aroylthioureas (5a-e) and 2-benzoxazolones (6a-b).A reasonable pathway for the formation of 3, 5 and 6 from 1 has been suggested.