31698-14-3

Basic information

• Product Name: Ancitabine
• Synonyms: 2,2’-anhydroarabinosylcytosine;2,2’-anhydrocytidine;2,2’-cyclocytidine;2,2’-o-cyclocytidine;6h-furo(2’,3’:4,5)oxazolo(3,2-alpha)pyrimidine-2-methanol,2,3,3a,9a-tetrahydro;ancytabine;anhydroarac;anhydrocytidine
• CAS NO: 31698-14-3
• Molecular Formula: C₉H₁₁N₃O₄
• Molecular Weight: 225.2
• Product Categories: Active Pharmaceutical Ingredients
• Mol File: 31698-14-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 269-270 °C (dec.)(lit.)
• Boiling Point: 366.7°C (rough estimate)
• Flash Point: 209.1 °C
• Appearance: /
• Density: 1.3588 (rough estimate)
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: −20°C
• PKA: 12.67±0.40(Predicted)
• CAS DataBase Reference: Ancitabine(CAS DataBase Reference)
• NIST Chemistry Reference: Ancitabine(31698-14-3)
• EPA Substance Registry System: Ancitabine(31698-14-3)

Safety Data

• WGK Germany: 2
• RTECS: LV2615000
• Hazardous Substances Data: 31698-14-3(Hazardous Substances Data)

Usage

Uses

Ancitabine is an antineoplastic. Also, it is an agent demonstrating strong synergistic interaction with irofulven, which possesses antitumor activity against solid tumors.

Definition

ChEBI: An organic heterotricyclic compound resulting from the formal condensation of the oxo group of cytidine to the 2' position with loss of water to give the corresponding cyclic ether. A prodrug, it is metabolised to the antineoplastic agent cytarabine, so is used to maintain a more constant antineoplastic action.

Therapeutic Function

Antineoplastic

InChI:InChI=1/C9H11N3O4/c10-5-1-2-12-8-7(16-9(12)11-5)6(14)4(3-13)15-8/h1-2,4,6-8,10,13-14H,3H2/t4-,6-,7+,8-/m1/s1

Upstream product

• 55628-10-9 2',3'-O-sulfinylcytidine hydrochloride 
• 27963-98-0 O²,N-aminomethanylylidene-β-D-arabinofuranosylamine 
• 58311-73-2 (2-cyano-vinyl)-trimethyl-ammonium; toluene-4-sulfonate 
• 10212-17-6 1-(2-chloro-β-D-2-deoxy-ribofuranosyl)-4-methylsulfanyl-1H-pyrimidin-2-one 
• 10323-20-3 D-Arabinose 
• 74580-91-9 4-Amino-1-((2R,3S,4R,5R)-4-bromo-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one; hydrochloride 
• 65-46-3 CYTIDINE 
• 1070-71-9 propiolonitrile 
• 27963-98-0 2-amino-β-D-arabinofurano[1',2':4,5]-oxazoline 
• 50896-83-8 (3aS)-3c-acetoxy-6-amino-2t-hydroxymethyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidinylium; chloride 

Downstream Products

• 80791-93-1 5-iodo-2'-deoxy-2'-(R)-fluoro-cytidine 
• 10212-20-1 2'-deoxy-2'-fluorocytidine 
• 147-94-4 arabinosyl cytosine 

Relevant articles and documents

Nucleosides. 116. 1-(β-D-Xylofuranosyl)-5-fluorocytosines with a Leaving Group on the 3' Position. Potential Double-Barreled Masked Precursors of Anticancer Nucleosides

Syntheses of five pairs of cytosine and 5-fluorocytosine xylofuranosyl nucleosides in which the 3'-hydroxyl group is replaced by Cl, Br, I, OMs, or OTs are described.Those xylosyl nucleosides with a good leaving group at the 3' position exhibit good inhibitory activity against L5178Y and P815 mouse leukemic cells in vitro at rather low concentrations, and like that of ara-C this cytotoxicity is reversed by 2'-deoxycytidine but not by thymidine.Xylosylcytosines are not active against ara-C resistant lines of L5178Y and P815 cells; however the corresponding 5-fluorocytosine analogues exhibit significant cytotoxicity against these ara-C resistant leukemic cell lines, and this activity is reversed by thymidine but not by deoxycytidine.These data support the "double-barreled" masked precursor hypothesis in that xylosyl-5-fluorocytosines substituted at the 3' position by a good leaving group exhibit activity akin to that of ara-C in the ara-C in the ara-C sensitive lines, while these nucleosides act as 5-fluoropyrimidines in the ara-C resistant lines.

On the reaction of Vilsmeier-Haack reagent with nucleoside: a convenient synthesis of 2,2'-cyclocytidine.

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