Cyclopentenyl cytosine

Base Information

• Chemical Name: Cyclopentenyl cytosine
• CAS No.: 90597-22-1
• Molecular Formula: C10H13N3O4
• Molecular Weight: 239.231
• NSC Number: 375575
• UNII: 69MO0NDN8K
• DSSTox Substance ID: DTXSID70238212
• Nikkaji Number: J362.075A
• Wikidata: Q27264364
• NCI Thesaurus Code: C1359
• ChEMBL ID: CHEMBL63647
• Mol file: 90597-22-1.mol

Synonyms:1-(4-hydroxymethyl-2,3-dihydroxy-4-cyclopenten-1-yl)cytosine;1-cCyd;4-amino-1-(4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl)-2(1H)-pyrimidinone;cCyd;CPE-c;CPE-cytosine;cyclopentenyl cytosine;cyclopentenyl cytosine, (1R-(1alpha,4beta,5alpha))-isomer;cyclopentenylcytosine;NSC 375575;NSC-375575

Chemical Property of Cyclopentenyl cytosine

Chemical Property:

• Vapor Pressure: 1.82E-12mmHg at 25°C
• Boiling Point: 508.4oC at 760 mmHg
• Flash Point: 261.3oC
• PSA: 121.60000
• Density: 1.73g/cm3
• LogP: -1.39810
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 239.09060590
• Heavy Atom Count: 17
• Complexity: 429

Purity/Quality:

99% ^*data from raw suppliers

Cyclopentenylcytosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)N=C1N)C2C=C(C(C2O)O)CO
• Isomeric SMILES: C1=CN(C(=O)N=C1N)[C@@H]2C=C([C@H]([C@H]2O)O)CO
• Uses: Cyclopentenylcytosine induces senescence in breast cancer cells through nucleolar stress response and activation of p53. It also has antitumor activity.

Technology Process of Cyclopentenyl cytosine

There total 25 articles about Cyclopentenyl cytosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

4-amino-1-<(1R,2S,3R)-2,3-isopropylidenedioxy-4-methoxymethyloxymethyl-4-cyclopenten-1-yl>-2(1H)-pyrimidinone (99238-74-1) → cyclopentenyl cytosine (90597-22-1)

Guidance literature:

In hydrogenchloride; methanol; at 30 - 35 ℃; for 16h;

DOI:10.1016/S0008-6215(00)90890-5

Reference yield: 73.0%

1-((1R,4R,5S)-4,5-Dihydroxy-3-hydroxymethyl-cyclopent-2-enyl)-4-methylsulfanyl-1H-pyrimidin-2-one (92642-67-6) → cyclopentenyl cytosine (90597-22-1)

Guidance literature:

With ammonia; In methanol; at 80 ℃; for 48h;

DOI:10.1021/jm00378a002

Reference yield: 62.0%

(1R,4R,5S)-1-<3-<(benzyloxy)methyl>-4,5-(isopropylidenedioxy)-2-cyclopentenyl>cytosine (105522-19-8) → cyclopentenyl cytosine (90597-22-1)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 ℃; for 2.5h;

DOI:10.1021/jm00117a004

upstream raw materials:

1-((1R,4R,5S)-4,5-Dihydroxy-3-hydroxymethyl-cyclopent-2-enyl)-4-methylsulfanyl-1H-pyrimidin-2-one

4-amino-1-<(1R,2S,3R)-2,3-isopropylidenedioxy-4-methoxymethyloxymethyl-4-cyclopenten-1-yl>-2(1H)-pyrimidinone

(1R,4R,5S)-1-<3-<(benzyloxy)methyl>-4,5-(isopropylidenedioxy)-2-cyclopentenyl>cytosine

(1'R,2'S,3'R)-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]cytosine

Refernces

• 1、 Marquez, Victor E.,Lim, Mu-Ill,Treanor, Susan P.,Plowman, Jacqueline,Priest, Matthew A.,et al.. "Cyclopentenylcytosine. A Carbocyclic Nucleoside with Antitumor and Antiviral Properties". . p. 1687 - 1694. Retrieved 2007/10/02.
• 2、 Lim, Mu-Ill,Moyer, James D.,Cysyk, Richard L.,Marquez, Victor E.. "Cyclopentenyluridine and Cyclopentenylcytidine Analogues as Inhibitors of Uridine-Cytidine Kinase". . p. 1536 - 1538. Retrieved 2007/10/02.