95539-27-8

Basic information

• Product Name: Benzenepropanoic acid, a-[(aminothioxomethyl)hydrazono]-2-nitro-, (Z)-
• CAS NO: 95539-27-8
• Molecular Formula: C10H10N4O4S
• Molecular Weight: 282.28
• Mol File: 95539-27-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenepropanoic acid, a-[(aminothioxomethyl)hydrazono]-2-nitro-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, a-[(aminothioxomethyl)hydrazono]-2-nitro-, (Z)-(95539-27-8)
• EPA Substance Registry System: Benzenepropanoic acid, a-[(aminothioxomethyl)hydrazono]-2-nitro-, (Z)-(95539-27-8)

Safety Data

• Hazardous Substances Data: 95539-27-8(Hazardous Substances Data)

Upstream product

• 5461-32-5 o-nitrophenylpyruvic acid 
• 79-19-6 thiosemicarbazide 

Downstream Products

• 901787-88-0 2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 
• 901787-86-8 2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 
• 1601469-01-5 4-(2-(2-(1-carboxy-2-(2-nitrophenyl)ethylidene)hydrazinyl)thiazol-4-yl)benzoic acid 
• 1601469-00-4 4-(2-(2-(1-carboxy-2-(2-nitrophenyl)ethylidene)hydrazinyl)thiazol-4-yl)benzoic acid 
• 1601469-14-0 2-(2-(4-(4-bromophenyl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 
• 1601469-13-9 2-(2-(4-(4-bromophenyl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 
• 1601469-11-7 2-(2-(4-(4-azidophenyl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 
• 1601469-09-3 2-(2-(4-(naphthalen-2-yl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 
• 1601469-08-2 2-(2-(4-([1,1'-biphenyl]-4-yl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 
• 901788-03-2 3-(2-nitrophenyl)-2-(2-(4-(4-(pyrrolidin-1-yl)phenyl)thiazol-2-yl)hydrazono)propanoic acid 
• 1601469-05-9 2-(2-(4-(4-morpholinophenyl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 
• 1601469-04-8 2-(2-(4-(4-morpholinophenyl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 
• 1601469-03-7 2-(2-(4-(4-Aminophenyl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 
• 1601469-02-6 2-(2-(4-(4-aminophenyl)thiazol-2-yl)hydrazono)-3-(2-nitrophenyl)propanoic acid 

Relevant articles and documents

Structure-activity relationship study of 4EGI-1, small molecule eIF4E/eIF4G protein-protein interaction inhibitors

Abstract Protein-protein interactions are critical for regulating the activity of translation initiation factors and multitude of other cellular process, and form the largest block of untapped albeit most challenging targets for drug development. 4EGI-1, (E/Z)-2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl) hydrazono)-3-(2-nitrophenyl)propanoic acid, is a hit compound discovered in a screening campaign of small molecule libraries as an inhibitor of translation initiation factors eIF4E and eIF4G protein-protein interaction; it inhibits translation initiation in vitro and in vivo. A series of 4EGI-1-derived thiazol-2-yl hydrazones have been designed and synthesized in order to delineate the structural latitude and improve its binding affinity to eIF4E, and increase its potency in inhibiting the eIF4E/eIF4G interaction. Probing a wide range of substituents on both phenyl rings comprising the 3-phenylpropionic acid and 4-phenylthiazolidine moieties in the context of both E- and Z-isomers of 4EGI-1 led to analogs with enhanced binding affinity and translation initiation inhibitory activities.

SYNTHESIS OF 1,2,4-TRIAZINO- AND IMIDAZOQUINOLINE DERIVATIVES

o-Nitrophenylpyruvic acid thiosemicarbazone (I) has been cyclized to 2-thio-5-(o-nitrobenzyl)-6-azauracil (II) which has been transformed in 5-quinolin-3-one (VI).Compound VI is transformed in acid medium to 1-amino-1,2-dihydroimidazoquinolin-2-one (VIII) via the tautomer VII, and in boiling acetic acid it gives the acetylamino derivative IX.The N-amino derivative VIII reacts with carbonyl compounds to give the corresponding hydrazones X-XII, and its nitrosation gives 1,2-dihydroimidazoquinolin-2-one (XIII).