6742-07-0

Basic information

• Product Name: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-4-aminopyrimidin-2(1H)-one
• Synonyms: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-4-aminopyrimidin-2(1H)-one;4-Amino-1-(2-O,3-O,5-O-triacetyl-β-D-arabinofuranosyl)-2(1H)-pyrimidinone;NSC-93150;1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine;2',3',5'-tri-O-acetyl-arabinofuranosyl-cytidine;AraC 2',3',5'-tri-O-acetyl ester
• CAS NO: 6742-07-0
• Molecular Formula: C₁₅H₁₉N₃O₈
• Molecular Weight: 369.32666
• Mol File: 6742-07-0.mol

Chemical Properties

• Boiling Point: 499.47°C (rough estimate)
• Flash Point: 260.6°C
• Appearance: /
• Density: 1.2870 (rough estimate)
• Vapor Pressure: 2.04E-10mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• CAS DataBase Reference: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-4-aminopyrimidin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-4-aminopyrimidin-2(1H)-one(6742-07-0)
• EPA Substance Registry System: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-4-aminopyrimidin-2(1H)-one(6742-07-0)

Safety Data

• Hazardous Substances Data: 6742-07-0(Hazardous Substances Data)

Usage

Safety Profile

intraperitoneal route. When heatedto decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C15H19N3O8/c1-7(19)23-6-10-12(24-8(2)20)13(25-9(3)21)14(26-10)18-5-4-11(16)17-15(18)22/h4-5,10,12-14H,6H2,1-3H3,(H2,16,17,22)

Upstream product

• 82855-62-7 4-(1,2,4-triazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)pyrimidine-2(1H)one 
• 25130-27-2 2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl-4-thiouridine 
• 69-74-9 cytarabine hydrochloride 
• 3736-77-4 2,2'-Anhydrouridine 
• 3083-77-0 araU 
• 58-96-8 uridine 
• 14057-18-2 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil 
• 880633-88-5 tri-O-acetyl-N4-(1-(5-nitrothien-2-yl)ethyl)oxycarbonyl-1-β-D-arabinofuranosylcytosine 

Downstream Products

• 147-94-4 arabinosyl cytosine 

Relevant articles and documents

BIOREDUCTIVELY-ACTIVATED PRODRUGS

The present invention relates to a compound of formula (1), or a pharmaceutically acceptable salt thereof, Formula: (1); wherein: R1 is a substituted aryl or heteroaryl group bearing at least one nitro or azido group or is an optionally substituted benzoquinone, optionally substituted naphthoquinone or optionally substituted fused heterocycloquinone; R2 is H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted heterocycloalkyl, aryl or heteroaryl; and R3 is selected such that R3NH2 represents a cytotoxic nucleoside analogue or an ester or phosphate ester prodrug of a cytotoxic nucleoside analogue, with the proviso that if R1 is an aryl group then R2 is not H.

Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane

A general and convenient method for the synthesis of several pyrimidine and purine nucleosides by selective oxidation of thionucleosides with dimethyldioxirane is reported. Thioketo moieties in the C-4 position of the pyrimidine ring, and in the C-6, and C-8 positions of the purine ring are the domain of oxidative nucleophilic substitution. Thioketo moieties in the C-2 position of both purine and pyrimidine rings are the domain of desulfurization or formation of disulfides.

Acetylenic nucleosides. 4. 1-β-D-arabinofuranosyl-5-ethynylcytosine. Improved synthesis and evaluation of biochemical and antiviral properties

5-Ethynyl-1-β-D-arabinofuranosylcytosine (EAC) was prepared from 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine by iodination followed by coupling with (trimethylsilyl)acetylene and deblocking. At 50 μM, EAC was found to inhibit the in vitro replication of herpes simplex virus type 1 and type 2 by >99%. EAC also showed activity against a strain of HSV-1 resistant to (E)-5-(2-bromovinyl)-2'-deoxyuridine which has an alteration of the virus-induced thymidine kinase (TK).. At 100 μM, EAC did not inhibit the in vitro growth of leukemia L1210 and HeLa cells. EAC was resistant to the action of dCR-CR deaminase, its rate of deamination being approximately 2% that of dCR. The compound was a poor substitute for dCR kinase, but it was phosphorylated by HSV-1- and HSV-2-induced TKs at 50% and 30%, respectively, the rate of thymidine.

4-(1,2,4-Triazol-1-yl)- and 4-(3-Nitro-1,2,4-triazol-1-yl)-1-(β-D-2,3,5-tri-O-acetylarabinofuranosyl)pyrimidin-2(1H)-ones. Valuable Intermediates in the Synthesis of Derivatives of 1-(β-D-Arabinofuranosyl)cytosine (Ara-C)

Treatment of the acetylated derivative (3b), which was prepared from uridine in 86 percent overall yield, with tri(1H-1,2,4-triazol-1-yl)phosphine oxide gave compound (6a) in high yield, and with 3-nitro-1,2,4-triazole and diphenyl phosphorochloridate it gave compound (6b) in high yield.When the former product (6a) was allowed to react with ammonia, methylamine, dimethylamine, and morpholine at room temperature, and the products further deacetylated if necessary, ara-C (1; R1=R2=H) and its corresponding 4-N-alkyl derivatives (1; R1=H, R2=Me), (1: R1=R2=Me), and 1,R2= -(CH2)2O(CH2)2-> were obtained in very high yields. 4-N-Phenyl-ara-C (1; R1=H, R2=Ph) was obtained in high yield when compound (6a) or (6b) was heated with aniline in pyridine solution and the products then deacetylated.The nitro-compound (6b) was converted into the ara-C derivative (1; R1=H, R2=CH2CO2Me), and the sulphide (7) was obtained following the deacetylation of the products of the reaction between the 1,2,4-triazolyl derivative (6a), toluene-p-thiol, and triethylamine.