146464-94-0

Basic information

• Product Name: 10-propargyl-10-deazaaminopterin diethyl ester
• Synonyms: 10-propargyl-10-deazaaminopterin diethyl ester
• CAS NO: 146464-94-0
• Molecular Weight: 533.587
• Mol File: 146464-94-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 10-propargyl-10-deazaaminopterin diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 10-propargyl-10-deazaaminopterin diethyl ester(146464-94-0)
• EPA Substance Registry System: 10-propargyl-10-deazaaminopterin diethyl ester(146464-94-0)

Safety Data

• Hazardous Substances Data: 146464-94-0(Hazardous Substances Data)

Upstream product

• 52787-14-1 methyl 4-(2-methoxy-2-oxoethyl)benzoate 
• 1445586-44-6 potassium 10-propargyl-4-deoxy-4-amino-10-deazapteroate 
• 1118-89-4 diethyl-L-glutamate hydrochloride 
• 146464-91-7 methyl-4-(2-((2,4-diaminopteridin-6-yl)methyl)-1-methoxy-1-oxopent-4-yn-2-yl)benzoate 
• 146464-92-8 4-(2-carboxy-1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl)benzoic acid 
• 146464-93-9 4-(1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl)benzoic acid 
• 146464-90-6 α-propargylhomoterephthalic acid dimethyl ester 

Downstream Products

• 146464-95-1 pralatrexate 

Relevant articles and documents

Synthesis and antitumor activity of 10-propargyl-10-deazaaminopterin

Successive alkylation of dimethyl homoterephthalate with propargyl bromide and 2,4-diamino-6-(bromomethyl)pteridine followed by ester saponification at room temperature afforded 2,4-diamino-4-deoxy-10-carboxy-10-propargyl-10- deazapteroic acid. The 10-COOH was readily decarboxylated by heating in DMSO at a temperature of only 120 °C to yield the diamino-10-propargyl-10- deazapteroic acid intermediate. Coupling with diethyl L-glutamate and ester hydrolysis gave the title compound. The 10-propargyl analogue was about 5 times more potent than MTX as an inhibitor of growth in L1210 cells, but was only one-third as potent as an inhibitor of DHFR from L1210. The analogue was transported inward very effectively in L1210 cells showing a 10-fold advantage over MTX. At a dose of 36 mg/kg the 10-propargyl compound caused shrinkage of the E0771 solid murine mammary tumor to only 1% of untreated controls.

PROCESSES AND INTERMEDIATES FOR PREPARING PRALATREXATE

Processes for preparing and purifying Pralatrexate are described in the present application, as well as intermediates in these processes, and salts and solid state forms of the Pralatrexate intermediates.