669065-21-8

Basic information

• Product Name: Ethanethioic acid, [(4-chlorophenyl)amino]oxo-, hydrazide
• CAS NO: 669065-21-8
• Molecular Formula: C8H8ClN3OS
• Molecular Weight: 229.69
• Mol File: 669065-21-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Ethanethioic acid, [(4-chlorophenyl)amino]oxo-, hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanethioic acid, [(4-chlorophenyl)amino]oxo-, hydrazide(669065-21-8)
• EPA Substance Registry System: Ethanethioic acid, [(4-chlorophenyl)amino]oxo-, hydrazide(669065-21-8)

Safety Data

• Hazardous Substances Data: 669065-21-8(Hazardous Substances Data)

Upstream product

• 3289-75-6 2-chloro-N-(4-chlorophenyl)acetamide 
• 220897-82-5 N-(4-chloro-phenyl)-2-morpholin-4-yl-2-thioxo-acetamide 

Downstream Products

• 1621311-42-9 3β-acetoxy-17-chloro-16-{2-[2-(4-chlorophenylamino)-2-oxo-1-thioxoethyl]hydrazonomethyl}formylandrosta-5,16-diene 
• 890406-19-6 N-(4-chloro-phenyl)-2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-2-thioxo-acetamide 

Relevant articles and documents

Novel steroidal 1,3,4-thiadiazines: Synthesis and biological evaluation in androgen receptor-positive prostate cancer 22Rv1 cells

A flexible approach to previously unknown spirofused and linked 1,3,4-thiadiazine derivatives of steroids with selective control of heterocyclization patterns is disclosed. (N-Arylcarbamoyl)spiroandrostene-17,6′ [1,3,4]thiadiazines and (N-arylcarbamoyl)17-[1′,3′,4′]thiadiazine-substituted androstenes, novel types of heterosteroids, were prepared from 16β,17β-epoxypregnenolone and 21-bromopregna-5,16-dien-20-one in good to high yields by the treatment with oxamic acid thiohydrazides. The synthesized compounds were screened for antiproliferative activity against the human androgen receptor-positive prostate cancer cell line 22Rv1. Most of (N-arylcarbamoyl)17-[1′,3′,4′]thiadiazine-substituted androstenes exhibit better antiproliferative potency (IC50 = 2.1–6.6 μM) than the antiandrogen bicalutamide. Compounds 7d with IC50 = 3.0 μM and 7j with IC50 = 2.1 μM proved to be the most active in the series under study. Lead synthesized compound 7j downregulates AR expression and activity in 22Rv1 cells. NF-κB activity is also blocked in 7j-treated 22Rv1 cells. Apoptosis is considered as a possible mechanism of 7j-induced cell death.

Novel free fatty acid receptor 1 (GPR40) agonists based on 1,3,4-thiadiazole-2-carboxamide scaffold

Free fatty acid receptor 1 (FFA1), previously known as GPR40 is a G protein-coupled receptor and a new target for treatment of type 2 diabetes. Two series of FFA1 agonists utilizing a 1,3,4-thiadiazole-2-caboxamide scaffold were synthetized. Both series offered significant improvement of the potency compared to the previously described 1,3,4-thiadiazole-based FFA1 agonists and high selectivity for FFA1. Molecular docking predicts new aromatic interactions with the receptor that improve agonist potency. The most potent compounds from both series were profiled for in vitro ADME properties (plasma and metabolic stability, Log D, plasma protein binding, hERG binding and CYP inhibition). One series suffered very rapid degradation in plasma and in presence of mouse liver microsomes. However, the other series delivered a lead compound that displayed a reasonable ADME profile together with the improved FFA1 potency.

Synthesis of oxamic acids thiohydrazides and carbamoyl-1,3,4-thiadiazoles

A convenient preparation method was developed for oxamic acids thiohydrazides by reaction of α-chloroacetamides with a preliminary prepared solution of elemental sulfur and hydrazines. A series of carbamoyl-1,3,4-thiadiazole derivatives was obtained.