219739-90-9

Basic information

• Product Name: 2-Propenoic acid, 3-(dimethylamino)-2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (2Z)-
• CAS NO: 219739-90-9
• Molecular Formula: C14H18N2O4
• Molecular Weight: 278.308
• Mol File: 219739-90-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(dimethylamino)-2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (2Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(dimethylamino)-2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (2Z)-(219739-90-9)
• EPA Substance Registry System: 2-Propenoic acid, 3-(dimethylamino)-2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (2Z)-(219739-90-9)

Safety Data

• Hazardous Substances Data: 219739-90-9(Hazardous Substances Data)

Upstream product

• 1212-53-9 methyl N-benzyloxycarbonylglycinate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 5815-08-7 tert-Butoxybis(dimethylamino)methane 

Downstream Products

• 915118-11-5 benzyl-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl carbamate 
• 223718-30-7 3-(benzyloxycarbonyl)amino-7-hydroxy-8-methyl-2H-1-benzopyran-2-one 
• 223718-54-5 3-(benzyloxycarbonyl)amino-5,6-dihydro-2H-pyrano<3,2-c>pyridine-2,5-dione 
• 223718-61-4 6-(benzyloxycarbonyl)amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-7H-pyrano<2,3-d>pyrimidin-7-one 
• 865234-58-8 C₁₂H₁₃NO₅ 
• 1038399-84-6 2,3-diethyl 1-methyl (1E,3E)-1-[(benzyloxycarbonyl)amino]-4-(dimethylamino)buta-1,3-diene-1,2,3-tricarboxylate 
• 1038399-83-5 trimethyl (1E,3E)-1-[(benzyloxycarbonyl)amino]-4-(dimethylamino)buta-1,3-diene-1,2,3-tricarboxylate 

Relevant articles and documents

Syntheses of 5-amino-2-phenyl-4(3H)-pyrimidinone derivertives starting with glycine

N-Cbz derivative of 5-amino-2-phenyl-4(3H)-pyrimidinone was prepared from sodium salt of methyl hydroxymethylene glycinate and benzamidine hydrochloride in good yield. However, the reaction with N-substituted benzamidine did not proceed to give the desired pyrimidinone. In contrast, the reaction of 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone readily prepared from hippuric acid and N-substituted benzamidine proceeded nicely to give 5-(benzoylamino)-6-oxo-2- phenyl-1(6H)-pyrimidineacetic acid in high yield.

Development of novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines

(Chemical Equation Presented) Recent studies have shown that the DNA gyrase inhibitor, novobiocin, binds to a previously unrecognized ATP-binding site located at the C-terminus of Hsp90 and induces degradation of Hsp90-dependent client proteins at ～700 μM. As a result of these studies, several analogues of the coumarin family of antibiotics have been reported and shown to exhibit increased Hsp90 inhibitory activity; however, the monomeric species lacked the ability to manifest anti-proliferative activity against cancer cell lines at concentrations tested. In an effort to develop more efficacious compounds that produce growth inhibitory activity against cancer cell lines, structure - activity relationships were investigated surrounding the prenylated benzamide side chain of the natural product. Results obtained from these studies have produced the first novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines.