176683-46-8

Basic information

• Product Name: Phosphoric acid 2,3-bis-octadecyloxy-propyl ester 2-chloro-phenyl ester (2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS NO: 176683-46-8
• Molecular Weight: 1251.2
• Mol File: 176683-46-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Phosphoric acid 2,3-bis-octadecyloxy-propyl ester 2-chloro-phenyl ester (2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid 2,3-bis-octadecyloxy-propyl ester 2-chloro-phenyl ester (2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester(176683-46-8)
• EPA Substance Registry System: Phosphoric acid 2,3-bis-octadecyloxy-propyl ester 2-chloro-phenyl ester (2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester(176683-46-8)

Safety Data

• Hazardous Substances Data: 176683-46-8(Hazardous Substances Data)

Upstream product

• 55726-45-9 N⁴-Palmitoyl-1-β-D-arabinofuranosylcytosin 
• 176683-44-6 Phosphoric acid 2,3-bis-octadecyloxy-propyl ester 2-chloro-phenyl ester 
• 4672-45-1 2-chlorophenylphosphoryl dichloride 
• 96969-38-9 1,2-Dioctadecyl-3-benzyl-sn-glycerin 
• 6076-38-6 2,3-bis(octadecyloxy)propan-1-ol 

Relevant articles and documents

Synthesis of liposomal phospholipid-(N4-palmitoyl-1-β-D-arabinofuranosylcytosine) conjugates and evaluation of their cytostatic activity against L1210 murine leukemia

N4-Palmitoyl-araC, a prodrug of the cytostatic compound 1-β-D-arabinofuranosylcytosine (araC), was linked by means of the triester method to the phospholipids (2-chlorophenyl) (1,2-di-O-palmitoylglyceryl) phosphate, (2-chlorophenyl) (1,2-di-O-octadecylglyceryl) phosphate and (2-chlorophenyl) (1-O-octadecyl-2-O-palmitoylglyceryl) phosphate. In the first step of these gram-scale syntheses phospholipid-(N4-palmitoyl-araC) conjugates were obtained the linkage of which was accomplished via a triester group. In the second step the final condensates were obtained through transformation of the triester into a diester linkage by removal of the 2-chlorophenyl group. The cytostatic activity of these compounds which form stable liposomal preparations together with matrix lipids was evaluated according to the L1210 mouse leukemia model. The conjugates containing a triester linkage were shown to be ineffective, whereas those with a diester linkage display a significantly higher antitumor activity as compared to N4-palmitoyl-araC and araC. With the diester 6a-8a 80-100% of the treated animals were cured at a total dose of 200 μmol/kg, whereas with araC given at a fourfould higher concentration none of the treated mice survived. VCH Verlagsgesellschaft mbH, 1996.