130378-89-1

Basic information

• Product Name: 3-deazacyclopentenylcytosine
• Synonyms: 3-deazacyclopentenylcytosine
• CAS NO: 130378-89-1
• Molecular Formula: C11H13NO5
• Molecular Weight: 239.22462
• Mol File: 130378-89-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 475°Cat760mmHg
• Flash Point: 241.1°C
• Appearance: /
• Density: 1.687g/cm³
• Vapor Pressure: 5.1E-11mmHg at 25°C
• Refractive Index: 1.748
• CAS DataBase Reference: 3-deazacyclopentenylcytosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-deazacyclopentenylcytosine(130378-89-1)
• EPA Substance Registry System: 3-deazacyclopentenylcytosine(130378-89-1)

Safety Data

• Hazardous Substances Data: 130378-89-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13NO5/c13-5-6-3-8(11(17)10(6)16)12-2-1-7(14)4-9(12)15/h1-4,8,10-11,13,15-17H,5H2/t8-,10-,11+/m1/s1

Upstream product

• 89291-77-0 (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol methanesulfonate 
• 53937-02-3 4-(benzyloxy)pyridin-2(1H)-one 
• 130378-92-6 (1'R,4'R,5'S)-1-<3-<(benzyloxy)methyl>-4,5-(isopropylidenedioxy)-2-cyclopenten-1-yl>-4-(benzyloxy)-2-pyridone 

Relevant articles and documents

Synthesis of two cyclopentenyl-3-deazapyrimidine carbocyclic nucleosides related to cytidine and uridine

The cytosine analogue of neplanocin A, cyclopentenylcytosine (CPE-C, 3), has significant antitumor and antiviral activity commensurate with the drug's ability to produce a significant depletion of cytidine triphosphate (CTP) levels that result from the potent inhibition of cytidine triphosphate synthetase. Another important antitumor agent, previously identified as a potent inhibitor of the same enzyme, is 3-deazauridine (2). The synthesis of the cyclopentenyl nucleosides 3-deaza-CPE-C (5) and 3-deaza-CPE-U (6) was undertaken in order to investigate the effects of a modified 3-deaza pyrimidine aglycon moiety on the biological activity of the parent CPE-C. These compounds were synthesized via an S(N)2 displacement reaction on cyclopenten-1-ol methanesulfonate (10) by the sodium salt of the corresponding aglycon. In each case, separation and characterization of the corresponding N- and O-alkylated products was necessary before final removal of the blocking groups. The target compounds were devoid of in vitro antiviral activity against the HSV-1 and human influenza viruses. Although 3-deaza-CPE-C was nontoxic to L1210 cells in culture, 3-deaza-CPE-U displayed significant cytotoxicity against murine L1210 leukemia in vitro.