300852-09-9

Basic information

• Product Name: N-(4-(dimethylamino)phenyl)-2-phenylquinoline-4-carboxamide
• Synonyms: N-(4-(dimethylamino)phenyl)-2-phenylquinoline-4-carboxamide
• CAS NO: 300852-09-9
• Molecular Weight: 367.45
• Mol File: 300852-09-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-(4-(dimethylamino)phenyl)-2-phenylquinoline-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-(dimethylamino)phenyl)-2-phenylquinoline-4-carboxamide(300852-09-9)
• EPA Substance Registry System: N-(4-(dimethylamino)phenyl)-2-phenylquinoline-4-carboxamide(300852-09-9)

Safety Data

• Hazardous Substances Data: 300852-09-9(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 
• 91-56-5 indole-2,3-dione 
• 59661-86-8 2-phenylquinoline-4-carbonyl chloride 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 132-60-5 cinchophen 

Downstream Products

• 1351929-53-7 N-(4-(methylamino)phenyl)-2-phenylquinoline-4-carboxamide 

Relevant articles and documents

SMALL MOLECULE ENTEROVIRUS INHIBITORS AND USES THEREOF

This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quinoline (or similar) structure which function as antagonists of androgen receptor activity, and their use as therapeutics for the treatment of cancer (e.g., castration-resistant prostate cancer) and other conditions characterized with androgen receptor activity and/or androgen receptor expression.

Comparative study of the affinity and metabolism of type i and type II binding quinoline carboxamide analogues by cytochrome P450 3A4

Compounds that coordinate to the heme-iron of cytochrome P450 (CYP) enzymes are assumed to increase metabolic stability. However, recently we observed that the type II binding quinoline carboxamide (QCA) compounds were metabolically less stable. To test if the higher intrinsic clearance of type II binding compounds relative to type I binding compounds is general for other metabolic transformations, we synthesized a library of QCA compounds that could undergo N-dealkylation, O-dealkylation, benzylic hydroxylation, and aromatic hydroxylation. The results demonstrated that type II binding QCA analogues were metabolically less stable (2- to 12-fold) at subsaturating concentration compared to type I binding counterparts for all the transformations. When the rates of different metabolic transformations between type I and type II binding compounds were compared, they were found to be in the order of N-demethylation > benzylic hydroxylation> O-demethylation > aromatic hydroxylation. Finally, for the QCA analogues with aza-heteroaromatic rings, we did not detect metabolism in aza-aromatic rings (pyridine, pyrazine, pyrimidine), indicating that electronegativity of the nitrogen can change regioselectivity in CYP metabolism.