138386-58-0

Basic information

• Product Name: 2-Propenoic acid, 3-[2-[(triphenylphosphoranylidene)amino]phenyl]-, methyl ester, (E)-
• CAS NO: 138386-58-0
• Molecular Formula: C28H24NO2P
• Molecular Weight: 437.478
• Mol File: 138386-58-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-[2-[(triphenylphosphoranylidene)amino]phenyl]-, methyl ester, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-[2-[(triphenylphosphoranylidene)amino]phenyl]-, methyl ester, (E)-(138386-58-0)
• EPA Substance Registry System: 2-Propenoic acid, 3-[2-[(triphenylphosphoranylidene)amino]phenyl]-, methyl ester, (E)-(138386-58-0)

Safety Data

• Hazardous Substances Data: 138386-58-0(Hazardous Substances Data)

Upstream product

• 88939-75-7 methyl (2E)-3-(2-aminophenyl)propenoate 
• 603-35-0 triphenylphosphine 
• 88939-75-7 methyl β-(o-aminophenyl)acrylate 
• 612-41-9 2-nitrocinnamic acid 
• 39228-29-0 methyl 2-nitrocinnamate 

Downstream Products

• 839672-50-3 methyl 3-[2-((4-biphenyl)iminomethyleneamino)phenyl]acrylate 
• 928006-45-5 KYS₀₅₀₇₉ 
• 955009-86-6 3-biphenyl-4-yl-2-[(5-N,N-dibenzylaminopentyl)-N'-methylamino]-4-methoxycarbonylmethyl-3,4-dihydroquinazoline 
• 955011-81-1 KYS₀₅₀₈₉ 
• 1076689-75-2 2-[N-(5-aminopentyl)-N-methylamino]-3-(4-biphenylyl)-4-methoxycarbonylmethyl-3,4-dihydroquinazoline 
• 1076689-73-0 4-(N-benzylacetamino)-3-(4-biphenylyl)-2-[N-(5-aminopentyl)-N-methylamino]-3,4-dihydroquinazoline 
• 139210-07-4 (E)-3-(2-p-Tolyliminomethyleneamino-phenyl)-acrylic acid methyl ester 
• 139210-07-4 (E)-3-(2-p-Tolyliminomethyleneamino-phenyl)-acrylic acid methyl ester 
• 139210-05-2 methyl 3-[2-(phenyliminomethyleneamino)phenyl]acrylate 
• 139210-05-2 (E)-3-(2-Phenyliminomethyleneamino-phenyl)-acrylic acid methyl ester 
• 144752-27-2 (E)-3-[2-((E)-Styryliminomethyleneamino)-phenyl]-acrylic acid methyl ester 
• 139210-15-4 (E)-3-[2-((E)-Styryliminomethyleneamino)-phenyl]-acrylic acid methyl ester 
• 139210-19-8 (E)-3-[2-(Thiophen-2-yliminomethyleneamino)-phenyl]-acrylic acid methyl ester 
• 139210-17-6 (E)-3-[2-(Furan-2-yliminomethyleneamino)-phenyl]-acrylic acid methyl ester 

Relevant articles and documents

Antitumor activity of 3,4-dihydroquinazoline dihydrochloride in A549 xenograft nude mice

In the previous article we have reported that 3,4-dihydroquinazoline 1 is a potent and selective T-type calcium channel blocker that exhibited strong anti-cancer activity in vitro. Compound 1·2HCl was further in vivo evaluated against A549 xenograft in BALB/c nude mice, which exhibited 49% tumor-weight inhibition through intravenous administration of 2 mg/kg of body weight and was more potent than doxorubicin. Moreover, compound 1·2HCl has an oral bioavailability of 98% with LD50 values of 693 mg/kg (po route) and 40.0 mg/kg (iv route) of body weight. In addition, its efficient scale-up synthetic method was developed.

3,4-DIHYDROQUINAZOLINE DERIVATIVES

The present invention relates to 3,4-dihydroquinazoline derivatives, a process of preparing them and a pharmaceutical composition including them. The 3,4-dihydroquinazoline derivatives of the present invention have excellent T-type calcium channel blocking effect and anti-cancer activity.

Discovery of potent T-type calcium channel blocker

The intensive SAR study of 3,4-dihydroquinazoline series led to the most potent compound 10 (KYS05090: IC50 = 41 ± 1 nM) against T-type calcium channel and its potency is nearly comparable to that of Kurtoxin. As a small organic molecule, this compound showed the highest blocking activity reported to date.