38334-91-7

Basic information

• Product Name: Benzamide, N-(aminothioxomethyl)-4-methyl-
• CAS NO: 38334-91-7
• Molecular Formula: C9H10N2OS
• Molecular Weight: 194.257
• Mol File: 38334-91-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzamide, N-(aminothioxomethyl)-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-(aminothioxomethyl)-4-methyl-(38334-91-7)
• EPA Substance Registry System: Benzamide, N-(aminothioxomethyl)-4-methyl-(38334-91-7)

Safety Data

• Hazardous Substances Data: 38334-91-7(Hazardous Substances Data)

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 99-94-5 p-Toluic acid 
• 17356-08-0 thiourea 
• 333-20-0 potassium thioacyanate 
• 16794-68-6 4-methylbenzoyl isothiocyanate 
• 4570-41-6 1,3-benzoxazol-2-amine 
• 106-43-4 para-chlorotoluene 

Downstream Products

• 1450899-60-1 ethyl (Z)-2-(2-(4-methylbenzamido)thiazol-4-yl)pent-2-enoate 
• 1450899-76-9 ethyl (E)-2-(2-(4-methylbenzamido)thiazol-4-yl)pent-2-enoate 
• 75150-34-4 N-{[1-(4-Chloro-phenyl)-thioureido]-imino-methyl}-4-methyl-benzamide; hydrochloride 
• 75127-75-2 N-[Imino-(1-p-tolyl-thioureido)-methyl]-4-methyl-benzamide; hydrochloride 
• 75127-74-1 N-[Imino-(1-phenyl-thioureido)-methyl]-4-methyl-benzamide; hydrochloride 
• 28918-73-2 N-(4,6-dioxo-5,6-dihydro-4H-[1,3]thiazin-2-yl)-4-methyl-benzamide 

Relevant articles and documents

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.