122594-35-8

Basic information

• Product Name: 9-methyl-10-deazaminopterin
• Synonyms: 9-methyl-10-deazaminopterin
• CAS NO: 122594-35-8
• Molecular Formula: C₂₁H₂₃N₇O₅
• Molecular Weight: 453.45122
• Mol File: 122594-35-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.473g/cm³
• Refractive Index: 1.699
• CAS DataBase Reference: 9-methyl-10-deazaminopterin(CAS DataBase Reference)
• NIST Chemistry Reference: 9-methyl-10-deazaminopterin(122594-35-8)
• EPA Substance Registry System: 9-methyl-10-deazaminopterin(122594-35-8)

Safety Data

• Hazardous Substances Data: 122594-35-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H23N7O5/c1-10(14-9-24-18-16(25-14)17(22)27-21(23)28-18)8-11-2-4-12(5-3-11)19(31)26-13(20(32)33)6-7-15(29)30/h2-5,9-10,13H,6-8H2,1H3,(H,26,31)(H,29,30)(H,32,33)(H4,22,23,24,27,28)/t10?,13-/m0/s1

Upstream product

• 122594-29-0 methyl 4-amino-4-deoxy-9-methyl-10-deazapteroate 
• 122594-31-4 4-amino-4-deoxy-9-methyl-10-deazapteroic acid 
• 122594-12-1 benzyl 2-methyl-3-hydroxy-p-carbomethoxyhydrocinnamate 
• 122594-15-4 benzyl 2-methyl-p-carbomethoxycinnamate 
• 122594-22-3 1-azido-3-methyl-4-(p-carbomethoxyphenyl)-2-butanone 
• 122594-20-1 1-chloro-3-methyl-4-(p-carbomethoxyphenyl)-2-butanone 
• 122594-17-6 2-methyl-p-carbomethoxyhydrocinnamic acid 
• 122594-19-8 4-(2-Chlorocarbonyl-propyl)-benzoic acid methyl ester 
• 122594-33-6 9-methyl-10-deazaminopterin diethyl ester 

Relevant articles and documents

Synthesis and antifolate properties of 9-alkyl-10-deazaminopterins

Reformatski condensation of benzyl 2-bromopropionate with 4-carbomethoxybenzaldehyde, followed by dehydration afforded benzyl 2-methyl-p-carbomethoxycinnamate (4a). Hydrogenation over a Pd catalyst gave the hydrocinnamic acid 5a. Conversion to the chloromethyl (6a) and azidomethyl ketone (7a) was followed by hydrogenation to the aminomethyl ketone (8a). Direct N-alkylation by 2,4-diamino-5-nitro-6-chloropyrimidine followed by reductive ring closure in Zn-HOAc and subsequent saponification of the benzoate ester yielded 4-amino-4-deoxy-9-methyl-10-deazapteroic acid (11a). Coupling with diethyl L-glutamate and saponification afforded 9-methyl-10-deazaminopterin (13a). The 9-ethyl analogue (13b) was similarly prepared from benzyl 2-bromobutyrate. The 9-methyl analogue (13a) was 21 times more potent than MTX as an inhibitor of cell growth in L1210 cells. The reason for this enhanced cytotoxicity in L1210 is unclear, since enzyme inhibition and transport parameters were similar to those of MTX. In human Manca leukemia cells growth inhibition was not dramatic and paralleled MTX.