389602-70-4

Basic information

• Product Name: AKOS BAR-2003
• Synonyms: AKOS BAR-2003;4'-METHYL-BIPHENYL-4-METHANAMINE;OTAVA-BB 1179126;(4'-methyl-[1,1'-biphenyl]-4-yl)methanamine
• CAS NO: 389602-70-4
• Molecular Formula: C₁₄H₁₅N
• Molecular Weight: 197.279
• Mol File: 389602-70-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: AKOS BAR-2003(CAS DataBase Reference)
• NIST Chemistry Reference: AKOS BAR-2003(389602-70-4)
• EPA Substance Registry System: AKOS BAR-2003(389602-70-4)

Safety Data

• Hazardous Substances Data: 389602-70-4(Hazardous Substances Data)

Upstream product

• 5720-05-8 4-methylphenylboronic acid 
• 104-86-9 4-chlorobenzylamine 
• 50670-50-3 p-(p-tolyl)benzonitrile 
• 623-03-0 4-Cyanochlorobenzene 

Downstream Products

• 486436-30-0 N-(4'-methylbiphenyl-4-yl)methyl-4-[1-oxo-7-(4-trifluoromethylphenyl)-1,3-dihydro-isoindol-2-yl]-1-methyl-pyrrole-2-carboxylic acid amide 
• 1334717-24-6 6-chloro-2-ethyl-N-{(4′-methyl-[1,1′-biphenyl]-4-yl)methyl}-imidazo[1,2-a]pyridine-3-carboxamide 
• 1334717-36-0 7-chloro-2-ethyl-N-{(4′-methyl-[1,1′-biphenyl]-4-yl)methyl}-imidazo[1,2-a]pyridine-3-carboxamide 
• 1383484-23-8 C₂₀H₁₉NOS 
• 486436-24-2 N-(4'-methylbiphenyl-4-yl)methyl-4-[2-(pyrrolidin-1-yl)phenyl-carbonylamino]-1-methyl-pyrrole-2-carboxylic acid amide 
• 486435-72-7 N-(4'-methylbiphenyl-4-yl)methyl-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)-1-ethyl-pyrrole-2-carboxylic acid amide 
• 486435-63-6 N-(4'-Methylbiphenyl-4-yl)methyl-4-(4'-methyl biphenyl-2-carbonyl-amino)-1-methyl-pyrrole-2-carboxylic acid amide 
• 486435-61-4 N-(4'-methylbiphenyl-4-yl)methyl-4-(4'-fluorobiphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid amide 
• 486435-01-2 N-(4'-methylbiphenyl-4-yl)methyl-4-(biphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid amide 
• 486434-70-2 N-(4'-methylbiphenyl-4-yl)methyl-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)-1-methyl-imidazol-2-carboxylic acid amide 
• 486434-64-4 N-(4'-methylbiphenyl-4-yl)methyl-5-(4'-trifluoromethylbiphenyl-2-carbonylamino)-nicotinic acid amide 
• 486434-97-3 N-(4'-Methylbiphenyl-4-yl)methyl-4-(4'-trifluormethylbiphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid amide 
• 486436-47-9 N-(4'-methylbiphenyl-4-yl)methyl-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)-1-isopropyl-pyrrole-2-carboxylic acid amide 

Relevant articles and documents

Solvent-controlled synthesis of bulky and polar-bulky galactonoamidines

The goal of this study was the design and synthesis of bulky and polar-bulky galactonoamidines that have a potential to interact with both catalytic amino acids in the active site of human α-galactosidase. While a library of more than 25 compounds was previously synthesized following established protocols, the coupling of the selected amines with activated perbenzylated galactothionolactam yielded only small amounts for some of the perbenzylated targets. A computational approach disclosed relative energy differences of selected adducts and suggested a solvent change that then allowed a successful synthesis of the precursor compounds in 20–75%. Subsequent attempts to globally deprotect perbenzylated galactonoamidines by Pd catalyzed hydrogenation resulted in unwanted Pd coordination, incomplete debenzylation reactions, partial compound hydrolysis, and even complete decomposition. A lengthy protocol was elaborated to purify the targeted carbohydrate derivatives after modified debenzylation conditions.

Lead optimization of a novel series of imidazo[1,2-a]pyridine amides leading to a clinical candidate (Q203) as a multi- and extensively-drug- resistant anti-tuberculosis agent

A critical unmet clinical need to combat the global tuberculosis epidemic is the development of potent agents capable of reducing the time of multi-drug-resistant (MDR) and extensively-drug-resistant (XDR) tuberculosis therapy. In this paper, we report on the optimization of imidazo[1,2-a]pyridine amide (IPA) lead compound 1, which led to the design and synthesis of Q203 (50). We found that the amide linker with IPA core is very important for activity against Mycobacterium tuberculosis H37Rv. Linearity and lipophilicity of the amine part in the IPA series play a critical role in improving in vitro and in vivo efficacy and pharmacokinetic profile. The optimized IPAs 49 and 50 showed not only excellent oral bioavailability (80.2% and 90.7%, respectively) with high exposure of the area under curve (AUC) but also displayed significant colony-forming unit (CFU) reduction (1.52 and 3.13 log10 reduction at 10 mg/kg dosing level, respectively) in mouse lung.