Cytidine, 2'-deoxy-5-fluoro-

Base Information

• Chemical Name: Cytidine, 2'-deoxy-5-fluoro-
• CAS No.: 10356-76-0
• Molecular Formula: C₉H₁₂FN₃O₄
• Molecular Weight: 245.21
• Hs Code.: 2934999090
• NSC Number: 48006
• DSSTox Substance ID: DTXSID50860075
• ChEMBL ID: CHEMBL110020
• Mol file: 10356-76-0.mol

Synonyms:MLS002702854;4-amino-5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;5-Flurodeoxycytidine;5-fluor-deoxycytidine;4-amino-1-(2-deoxypentofuranosyl)-5-fluoropyrimidin-2(1h)-one;Cytidine, 2'-deoxy-5-fluoro-;CHEMBL110020;SCHEMBL16212282;SCHEMBL24141674;DTXSID50860075;NSC48006;AKOS040759236;SB17172;SMR001566676;FT-0600855;WLN: T6N CNJ DZ EF F- BT5OTJ EO1

Chemical Property of Cytidine, 2'-deoxy-5-fluoro-

Chemical Property:

• Appearance/Colour: Fine white powder
• Melting Point: 196 °C
• Refractive Index: 70 ° (C=1, H2O)
• Boiling Point: 464.966 °C at 760 mmHg
• PKA: 14.03±0.60(Predicted)
• Flash Point: 235.003 °C
• PSA: 110.60000
• Density: 1.829 g/cm³
• LogP: -0.81350
• Storage Temp.: room temp
• Solubility.: DMSO: >20mg/mL
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 245.08118403
• Heavy Atom Count: 17
• Complexity: 398

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Fluoro-2''-deoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=NC2=O)N)F)CO)O
• Description: 5-Fluoro-2-Deoxycytidine is an antimetabolite consisting of a fluorinated pyrimidine analog with potential antineoplastic activity. As a prodrug, 5-fluoro-2-deoxycytidine is converted by intracellular deaminases to the cytotoxic agent 5-Fluorouracil (5-FU). 5-FU is subsequently metabolized to active metabolites including 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). FdUMP binds to and inhibits thymidylate synthase, thereby reducing the production of thymidine monophosphate, which leads to depletion of thymidine triphosphate. This inhibits DNA synthesis and cell division. FUTP competes with uridine triphosphate for incorporation into the RNA strand thus leading to an inhibition of RNA and protein synthesis. Other fluorouracil metabolites also get incorporated into both DNA and RNA, thereby further hampering cellular growth.
• Uses: 5-Fluoro-2''-deoxycytidine is a mechanism-based DNMT inhibitor. 5-fluoro-2'-deoxycytidine has been used in trials studying the treatment of Neoplasms, Lung Neoplasms, Breast Neoplasms, Head and Neck Neoplasms, and Urinary Bladder Neoplasms, among others.
• Clinical Use: A DNA methyltransferase inhibitor currently in clinical trials for breast cancer and other solid tumors. Like 5’-Azacytidine and decitabine, 2’-Deoxy-5-fluorocytidine is a pyrimidine analog that integrates into chromatin to inhibit DNA methylation. It blocks proliferation in colon cancer-derived HCT116 cells by activating DNA response pathways. It inhibits various strains of pathogenic avian influenza viruses in vitro and in vivo.

Technology Process of Cytidine, 2'-deoxy-5-fluoro-

There total 15 articles about Cytidine, 2'-deoxy-5-fluoro- 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: 67.0%

1-(3,5-di-O-benzoyl-2-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-p-toluoylcytosine (92574-68-0) → 5-fluoro-2'-deoxycytidine (10356-76-0)

Guidance literature:

With ammonia; In methanol; at 40 ℃; for 15h;

DOI:10.1248/cpb.32.1441

Reference yield: 60.0%

acetyl hypofluorite (78948-09-1) + deoxycytidine (951-77-9) → (5R,6R)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-imino-tetrahydro-pyrimidin-2-one (119003-16-6,119067-95-7) + (5S,6S)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-imino-tetrahydro-pyrimidin-2-one (119003-16-6,119067-95-7) + Acetic acid (S)-5,5-difluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-imino-2-oxo-hexahydro-pyrimidin-4-yl ester (119003-17-7) + 5-Fluor-2'-deoxy-cytidin (10356-76-0)

Guidance literature:

In acetic acid; Yield given. Further byproducts given;

DOI:10.1039/P19880002547

Reference yield: 60.0%

acetyl hypofluorite (78948-09-1) + deoxycytidine (951-77-9) → (5R,6R)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-imino-tetrahydro-pyrimidin-2-one (119003-16-6,119067-95-7) + (5S,6S)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-imino-tetrahydro-pyrimidin-2-one (119003-16-6,119067-95-7) + Acetic acid (R)-5,5-difluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-imino-2-oxo-hexahydro-pyrimidin-4-yl ester (119003-18-8) + 5-Fluor-2'-deoxy-cytidin (10356-76-0)

Guidance literature:

In acetic acid; Yield given. Further byproducts given;

DOI:10.1039/P19880002547

upstream raw materials:

acetyl hypofluorite

deoxycytidine

1-(3,5-di-O-benzoyl-2-deoxy-β-D-ribofuranosyl)-5-fluoro-N₄-p-toluoylcytosine

5-fluoro-4-(1,2,4-triazol-1-yl)-1-(3,5-di-O-acetyl-2-deoxy-β-D-ribofuranosyl)-pyrimidine-2(1H)-one

Downstream raw materials:

5-fluoro-5'-(dimethoxytrityl)-2'-deoxycytid-3'-yl 2-cyanoethyl N,N-diisopropylphosphoramidite

5-fluoro-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine

Refernces

• 1、 Visser, Gerard W. M.,Herder, Renella E.,Noordhuis, Paul,Zwaagstra, Oene,Herscheid, Jacobus D. M.,Kanter, Frans J. J. de. "Reaction of Acetyl Hypofluorite with Pyrimidines. Part 3. Synthesis, Stereochemistry, and Properties of 5-Fluoro-5,6-dihydropyrimidine Nucleosides". . p. 2547 - 2554. Retrieved 2007/10/02.
• 2、 -. "2,2'-Anhydro-β-D-arabinofuranosyl-5-fluorocytosine". . . Retrieved 2008/06/13.