137465-07-7

Basic information

• Product Name: 5,10-ethano-5,10-dideazaaminopterin
• Synonyms: 5,10-ethano-5,10-dideazaaminopterin
• CAS NO: 137465-07-7
• Molecular Formula: C₂₃H₂₄N₆O₅
• Molecular Weight: 464.47386
• Mol File: 137465-07-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.475g/cm³
• Refractive Index: 1.712
• CAS DataBase Reference: 5,10-ethano-5,10-dideazaaminopterin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10-ethano-5,10-dideazaaminopterin(137465-07-7)
• EPA Substance Registry System: 5,10-ethano-5,10-dideazaaminopterin(137465-07-7)

Safety Data

• Hazardous Substances Data: 137465-07-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H24N6O5/c24-19-18-15-6-5-13(9-14(15)10-26-20(18)29-23(25)28-19)11-1-3-12(4-2-11)21(32)27-16(22(33)34)7-8-17(30)31/h1-4,10,13,16H,5-9H2,(H,27,32)(H,30,31)(H,33,34)(H4,24,25,26,28,29)/t13?,16-/m0/s1

Upstream product

• 137465-02-2 methyl 4-amino-4-deoxy-5,10-ethano-7-hydroxy-5,10-dideazapteroate 
• 137465-03-3 4-(1,3-Diamino-5,6,7,8,9,10-hexahydro-pyrimido[4,5-c]isoquinolin-8-yl)-benzoic acid methyl ester 
• 137465-00-0 4-(4-carbomethoxyphenyl)-2,4-dicarbomethoxycyclohexanone 
• 137465-05-5 pteroic acid 
• 137464-95-0 4-(4'-cyanophenyl)-4-hydroxycyclohexanone ethylene ketal 
• 137464-98-3 4-(4-oxocyclohexyl)benzoic acid methyl ester 
• 137465-01-1 4-(4-oxocyclohexyl)benzoic acid 
• 52787-14-1 methyl 4-(2-methoxy-2-oxoethyl)benzoate 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 137465-06-6 5,10-ethano-5,10-dideazaaminopterin diethyl ester 
• 1118-89-4 diethyl-L-glutamate hydrochloride 
• 137464-99-4 2-carbomethoxy-4-(4'-carbomethoxyphenyl)cyclohexanone 
• 137464-97-2 4-(4'-carbomethoxyphenyl)-4-hydroxycyclohexanone ethylene ketal 
• 137464-96-1 4-(4'-carboxyphenyl)-4-hydroxycyclohexanone ethylene ketal 

Relevant articles and documents

Synthesis and antifolate properties of 5,10-ethano-5,10-dideazaaminopterin

2-Carbomethoxy-4-(p-carbomethoxyphenyl)cyclohexanone was prepared in a four-step process and thermally condensed with 2,4,6-triaminopyrimidine to afford methyl 2,4-diamino-4-deoxy-7-hydroxy-5,10-ethano-5,10-dideazapteroate. Reduction of the 7-oxo function with borane gave the 7,8-dihydro pterin which was subsequently oxidized to the fully aromatic pteroate ester with dicyanodichlorobenzoquinone. Saponification of the benzoate ester, coupling with diethyl glutamate and final ester hydrolysis afforded the title compound. This novel deazaaminopterin analogue was approximately as potent as methotrexate in vitro in terms of DHFR and L1210 cell growth inhibition. There are indications of diastereomeric differences in the enzyme inhibition measurements. A significant transport advantage over MTX for influx into L1210 cells was observed. The compound was active against the E 0771 murine mammary solid tumor, but further investigation with individual diastereomers is required to define the ED50.