5737-79-1

Basic information

• Product Name: methyl 2′-amino-[1,1′-biphenyl]-4-carboxylate
• Synonyms: methyl 2′-amino-[1,1′-biphenyl]-4-carboxylate
• CAS NO: 5737-79-1
• Molecular Weight: 227.263
• Mol File: 5737-79-1.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: methyl 2′-amino-[1,1′-biphenyl]-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2′-amino-[1,1′-biphenyl]-4-carboxylate(5737-79-1)
• EPA Substance Registry System: methyl 2′-amino-[1,1′-biphenyl]-4-carboxylate(5737-79-1)

Safety Data

• Hazardous Substances Data: 5737-79-1(Hazardous Substances Data)

Upstream product

• 5737-78-0 methyl 2'-nitro-[1,1'-biphenyl]-4-carboxylate 
• 86-00-0 2-nitrobiphenyl 
• 3215-92-7 2'-nitrobiphenyl-4-carboxylic acid 
• 5730-96-1 4-acetyl-2'-nitrobiphenyl 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 92-92-2 biphenyl-4-carboxylic acid 
• 586-76-5 4-Bromobenzoic acid 
• 98-80-6 phenylboronic acid 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 615-43-0 2-iodophenylamine 
• 577-19-5 2-nitrophenyl bromide 
• 615-36-1 2-bromoaniline 

Downstream Products

• 5730-77-8 methyl 2'-amino-[1,1'-biphenyl]-4-carboxylate 
• 26000-33-9 methyl 9H-carbazole-2-carboxylate 
• 99585-18-9 9H-carbazole-2-carboxaldehyde 
• 873056-45-2 2-amino-4'-hydroxymethylbiphenyl 
• 2523-36-6 methyl 9H-fluorene-2-carboxylate 
• 857646-08-3 methyl 2'-({(2S)-5-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]pentanoyl}amino)-4-biphenylylcarboxylate 

Relevant articles and documents

Regioselective nitration of a biphenyl derivative to derive a fluorescent chloride sensor

Methyl 2′-aminobiphenyl-4-carboxylate, an optical chloride sensor has been synthesized via Suzuki-Miyaura cross-coupling followed by regioselective nitration. In general biphenyl systems are prone to undergo poly nitration whenever they are subjected to nitration via different nitrating agents. But in this present work, a highly selective nitration in the 2′ position of methyl biphenyl-4-carboxylate was achieved using 70% HNO3 and acetic anhydride to derive 3. Upon reduction, 3 produces 4 which shows bright blue emission in different organic solvents. In presence of chloride ion the blue emission of the sensor changes to enhanced bright green emission. The chloride sensing has also been explored using other spectroscopic techniques such as 1H NMR, UV–vis spectroscopy, and theoretical study.

Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids

A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.

Design, synthesis, and evaluation of N-phenyl-4-(2-phenylsulfonamido)-benzamides as microtubule-targeting agents in drug-resistant cancer cells, displaying HDAC inhibitory response

Microtubule-targeting agents (MTA) have enjoyed significant clinical success for decades. However, several mechanisms may cause inactivation of such drugs, leading to acquired resistance in patients treated with them. Therefore, drugs containing a stilbene-like skeleton and possessing dual inhibitory activity may provide a new and differentiated treatment for patients to overcome challenging acquired resistance. A new compound (16c) displays promising anticancer activity with GI50 of 22 ± 2 and 12 ± 0.1 nM in vincristine-resistant nasopharyngeal (KB-Vin) cancer cells and etoposide-resistant nasopharyngeal (KB-7D) cancer cells and is better than vincristine, etoposide, ABT-751, and MS-275. A mechanistic study revealed that 16c interferes with the cell cycle distribution and induces cell cycle arrest at the G2/M phase and severe mitotic spindle defects followed by apoptosis. In addition, it produces much more significant cytotoxicity than vincristine and etoposide in the corresponding resistant cells, indicating that it may be a promising candidate to overcome drug resistance in cancer cells. Compound 16c also displays inhibitory activity against HDAC 1 and HDAC 2 with IC50 values of 1.07 μM, and 1.47 μM, respectively. These findings may lead to a new type of structural motif for future development of drugs that could overcome acquired resistance to MTAs.