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180300-43-0,MFCD00942308
Catalog No.:AA0021T2

180300-43-0 | Cytidine, 3'-c-ethynyl-

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1mg
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5mg
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10mg
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25mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0021T2
Chemical Name:
Cytidine, 3'-c-ethynyl-
CAS Number:
180300-43-0
Molecular Formula:
C11H13N3O5
Molecular Weight:
267.2380
MDL Number:
MFCD00942308
SMILES:
Nc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@]([C@H]1O)(O)C#C)CO
Properties
Computed Properties
 
Complexity:
508  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
3  
XLogP3:
-2.7  

Downstream Synthesis Route

[1]Synthesis,2002,p.2387-2392

Literature

Title: Cytotoxicity of new duplex drugs linking 3'-C-ethynylcytidine and 5-fluor-2'-deoxyuridine against human melanoma cells.

Journal: International journal of cancer 20121101

Title: A phase I study to determine the safety and pharmacokinetics of intravenous administration of TAS-106 once per week for three consecutive weeks every 28 days in patients with solid tumors.

Journal: Anticancer research 20120501

Title: Phase I and pharmacokinetic study of 3'-C-ethynylcytidine (TAS-106), an inhibitor of RNA polymerase I, II and III,in patients with advanced solid malignancies.

Journal: Investigational new drugs 20120201

Title: Cytostatic activity of the duplex drug linking 2'-deoxy-5-fluorouridine (5FdU) with 3'-C-ethynylcytidine (ECyd) against gastric adenocarcinoma cell lines.

Journal: Investigational new drugs 20111201

Title: ATP chemosensitivity testing of new antitumor duplex drugs linking 3`-C-ethynylycytidine (ECyd) and 2´-deoxy-5-fluorouridine (5-FdU) in comparison to standard cytostatica and combinations thereof.

Journal: Investigational new drugs 20110601

Title: Cellular pharmacology of multi- and duplex drugs consisting of ethynylcytidine and 5-fluoro-2'-deoxyuridine.

Journal: Investigational new drugs 20110401

Title: Acceptance of oral chemotherapy in breast cancer patients - a survey study.

Journal: BMC cancer 20110101

Title: RNA polymerase III transcription in cancer: the BRF2 connection.

Journal: Molecular cancer 20110101

Title: A nucleoside anticancer drug, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine (TAS106), sensitizes cells to radiation by suppressing BRCA2 expression.

Journal: Molecular cancer 20110101

Title: Cytotoxicity and antileukaemic activity of new duplexes linking 3-C-ethynylcytidine and 5-fluorodeoxyuridine.

Journal: Anticancer research 20101201

Title: Association of RNase L with a Ras GTPase-activating-like protein IQGAP1 in mediating the apoptosis of a human cancer cell-line.

Journal: The FEBS journal 20101101

Title: An RNA-directed nucleoside anti-metabolite, 1-(3-C-ethynyl-beta-d-ribo-pentofuranosyl)cytosine (ECyd), elicits antitumor effect via TP53-induced Glycolysis and Apoptosis Regulator (TIGAR) downregulation.

Journal: Biochemical pharmacology 20100615

Title: Synthesis and in vitro activities of new anticancer duplex drugs linking 2'-deoxy-5-fluorouridine (5-FdU) with 3'-C-ethynylcytidine (ECyd) via a phosphodiester bonding.

Journal: Bioorganic & medicinal chemistry 20091001

Title: PK-PD modeling of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine and the enhanced antitumor effect of its phospholipid derivatives in long-circulating liposomes.

Journal: International journal of pharmaceutics 20090730

Title: Antiviral and cytotoxic activities of aminoarylazo compounds and aryltriazene derivatives.

Journal: Bioorganic & medicinal chemistry 20090701

Title: 1-(3-C-Ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106), a novel potent inhibitor of RNA polymerase, potentiates the cytotoxicity of CDDP in human cancer cells both in vitro and in vivo.

Journal: International journal of oncology 20090501

Title: Role of RNase L in apoptosis induced by 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine.

Journal: Cancer chemotherapy and pharmacology 20090401

Title: Molecular mechanisms of apoptosis induced by 3'-ethynylcytidine.

Journal: Nucleic acids symposium series (2004) 20090101

Title: Inhibition of HIF-1alpha by the anticancer drug TAS106 enhances X-ray-induced apoptosis in vitro and in vivo.

Journal: British journal of cancer 20081104

Title: Cytotoxic nucleoside analogues: different strategies to improve their clinical efficacy.

Journal: Current medicinal chemistry 20080101

Title: In vitro activity and mechanism of action of a duplex and multidrug of ethynylcytidine and 5-fluorodeoxyuridine.

Journal: Nucleic acids symposium series (2004) 20080101

Title: Cellular localization and functional characterization of the equilibrative nucleoside transporters of antitumor nucleosides.

Journal: Cancer science 20071001

Title: Mechanism of action of a new antitumor ribonucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106), differs from that of 5-fluorouracil.

Journal: Oncology reports 20070601

Title: Treatment combining X-irradiation and a ribonucleoside anticancer drug, TAS106, effectively suppresses the growth of tumor cells transplanted in mice.

Journal: International journal of radiation oncology, biology, physics 20070501

Title: A novel apoptotic pathway of 3'-Ethynylcytidine(ECyd) involving the inhibition of RNA synthesis--the possibility of RNase L activated pathway as a target of ECyd.

Journal: Nucleic acids symposium series (2004) 20070101

Title: An apoptotic pathway of 3'-Ethynylcytidine(ECyd) involving the inhibition of RNA synthesis mediated by RNase L.

Journal: Nucleic acids symposium series (2004) 20060101

Title: X irradiation induces the proapoptotic state independent of the loss of clonogenic ability in Chinese hamster V79 cells.

Journal: Radiation research 20050701

Title: Possible antitumor activity of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106) against an established gemcitabine (dFdCyd)-resistant human pancreatic cancer cell line.

Journal: Cancer science 20050501

Title: Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd).

Journal: Bioorganic & medicinal chemistry 20050401

Title: Synthesis and biological evaluation of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd).

Journal: Bioorganic & medicinal chemistry 20050215

Title: Synthesis and biological evaluation of conformationally restricted and nucleobase-modified analogs of the anticancer compound 3'-C-ethynylcytidine (ECyd).

Journal: Nucleosides, nucleotides & nucleic acids 20050101

Title: A novel anticancer ribonucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine, enhances radiation-induced cell death in tumor cells.

Journal: Radiation research 20041201

Title: A crucial role of uridine/cytidine kinase 2 in antitumor activity of 3'-ethynyl nucleosides.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20041001

Title: New nucleoside analogs in the treatment of solid tumors.

Journal: Acta poloniae pharmaceutica 20040101

Title: Synthesis of the cyclic and acyclic acetal derivatives of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine, a potent antitumor nucleoside. Design of prodrugs to be selectively activated in tumor tissues via the bio-reduction-hydrolysis mechanism.

Journal: Bioorganic & medicinal chemistry 20030529

Title: Determination of 3'-C-ethynylcytidine in human plasma and urine by liquid chromatographic-electrospray ionization tandem mass spectrometry.

Journal: Journal of pharmaceutical and biomedical analysis 20030205

Title: Sensitivity of human cancer cells to the new anticancer ribo-nucleoside TAS-106 is correlated with expression of uridine-cytidine kinase 2.

Journal: Japanese journal of cancer research : Gann 20020701

Title: Cellular and biochemical mechanisms of the resistance of human cancer cells to a new anticancer ribo-nucleoside, TAS-106.

Journal: Japanese journal of cancer research : Gann 20020401

Title: Analysis of single nucleotide polymorphisms in uridine/cytidine kinase gene encoding metabolic enzyme of 3'-ethynylcytidine.

Journal: Nucleic acids research. Supplement (2001) 20020101

Title: Anticancer mechanisms of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl) cytosine (ECyd, TAS-106).

Journal: Nucleic acids research. Supplement (2001) 20020101

Title: Cloning and expression of uridine/cytidine kinase cDNA from human fibrosarcoma cells.

Journal: International journal of molecular medicine 20010901

Title: An efficient method for the preparation of 1'alpha-branched-chain sugar pyrimidine ribonucleosides from uridine: the first conversion of a natural nucleoside into 1'-substituted ribonucleosides.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20010601

Title: Improvement in precision of the liquid chromatographic-electrospray ionization tandem mass spectrometric analysis of 3'-C-ethynylcytidine in rat plasma.

Journal: Journal of chromatography. B, Biomedical sciences and applications 20010415

Title: Antitumor activity and pharmacokinetics of TAS-106, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine.

Journal: Japanese journal of cancer research : Gann 20010301

Title: 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106)1: antitumor effect and mechanism of action.

Journal: Nucleosides, nucleotides & nucleic acids 20010101

Title: Anticancer molecular mechanism of 3'-ethynylcytidine (ECyd).

Journal: Nucleic acids research. Supplement (2001) 20010101

Title: Shimamoto Y, et al. Antitumor activity and pharmacokinetics of TAS-106, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine. Jpn J Cancer Res. 2001 Mar;92(3):343-51.

Title: Abdelrahim M, et al. TAS-106: preclinical, clinical and beyond. Oncology. 2013;85(6):356-363.

Title: Hammond-Thelin LA, et al. Phase I and pharmacokinetic study of 3'-C-ethynylcytidine (TAS-106), an inhibitor of RNA polymerase I, II and III,in patients with advanced solid malignancies. Invest New Drugs. 2012;30(1):316-326.

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