691846-63-6

Basic information

• Product Name: 2-METHYL-BIPHENYL-4,4'-DICARBOXYLIC ACID 4-AMIDE 4'-([4-METHOXY-3-(4-METHYL-PIPERAZIN-1-YL)-PHENYL]-AMIDE)
• Synonyms: [1,1'-BIPHENYL]-4,4'-DICARBOXAMIDE, N4'-[4-METHOXY-3-(4-METHYL-1-PIPERAZINYL)PHENYL]-2-METHYL-;2-METHYL-BIPHENYL-4,4'-DICARBOXYLIC ACID 4-AMIDE 4'-([4-METHOXY-3-(4-METHYL-PIPERAZIN-1-YL)-PHENYL]-AMIDE);GMC3-15
• CAS NO: 691846-63-6
• Molecular Formula: C27H30N4O3
• Molecular Weight: 458.559
• Mol File: 691846-63-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-METHYL-BIPHENYL-4,4'-DICARBOXYLIC ACID 4-AMIDE 4'-([4-METHOXY-3-(4-METHYL-PIPERAZIN-1-YL)-PHENYL]-AMIDE)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-BIPHENYL-4,4'-DICARBOXYLIC ACID 4-AMIDE 4'-([4-METHOXY-3-(4-METHYL-PIPERAZIN-1-YL)-PHENYL]-AMIDE)(691846-63-6)
• EPA Substance Registry System: 2-METHYL-BIPHENYL-4,4'-DICARBOXYLIC ACID 4-AMIDE 4'-([4-METHOXY-3-(4-METHYL-PIPERAZIN-1-YL)-PHENYL]-AMIDE)(691846-63-6)

Safety Data

• Hazardous Substances Data: 691846-63-6(Hazardous Substances Data)

Upstream product

• 148546-79-6 4-Bromo-N-[4-methoxy-3-(4-methyl-piperazin-1-yl)-phenyl]-benzamide 
• 148672-39-3 3-(4'-bromo-3'-methylphenyl)-5-methyl-1,2,4-oxadiazole 
• 148547-21-1 [4-({[4-(methyloxy)-3-(4-methyl-1-piperazinyl)phenyl]amino}carbonyl)phenyl]boronic acid 

Relevant articles and documents

New selective and potent 5-HT(1B/1D) antagonists: Chemistry and pharmacological evaluation of N-piperazinylphenyl biphenylcarboxamides and biphenylsulfonamides

A series of new analogues of N-[4-methoxy-3-(4-methylpiperazin-1- yl)phenyl] 2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide (1; GR127935) as potent and selective 5-HT(1B/1D) antagonists were synthesized and evaluated pharmacologically. Their receptor binding profiles were comparable to that of 1. The 1,3,4-oxadiazole isomer 2 and the 4'- aminocarbonyl and 4'-amidinyl analogues (9 and 10) of 1 had higher affinities at the rat 5-HT(1B) receptor (IC50 = 0.93, 1.3, and 0.5 nM, respectively) and calf 5-HT(1D) receptor (IC50 = 37, 10, and 3 nM, respectively) than did 1 (1.6 and 52 nM for rat 5-HT(1B) and calf 5-HT(1D) receptors, respectively). In the functional in vitro testing of 5-HT(1B/1D) antagonistic properties, 2, 9, 10, 11b (Odemethylated derivative of 2), 13a (O-methylsulfonyl analogue of 2), and 16 (which differs from 2 with a sulfonamide linker) showed more pronounced effects in the K+-induced 5-HT release in the cortex of guinea pig than did 1 and 3 (SB224289). Compounds 2, 9, and 10 were equally potent as 1 in rabbit saphenous vein model (pA2 > 9). A biochemical study of 2 with in vivo microdialysis in the rat brain showed that it is capable of augmenting citalopram (a selective serotonin reuptake inhibitor, SSRI) induced 5-HT release in rat ventral hippocampus, while preventing the decrease in acetylcholine release elicited by citalopram administration. The molecular structure of 2 was determined by single-crystal X-ray analysis. The log P and log D values of these compounds were calculated. This study contributes to the SAR study of N-piperazinylphenyl biphenylcarboxamides as selective and potent 5-HT(1B/1D) antagonists.