Home Other Building Blocks Cytidine, 3'-c-ethynyl-

Cytidine, 3'-c-ethynyl-

CAS No.:
180300-43-0
Catalog Number:
AG0021VU
Molecular Formula:
C11H13N3O5
Molecular Weight:
267.2380
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
99%
1 week
United States
$251
- +
10mg
99%
1 week
United States
$390
- +
25mg
99%
1 week
United States
$807
- +
Product Description
Catalog Number:
AG0021VU
Chemical Name:
Cytidine, 3'-c-ethynyl-
CAS Number:
180300-43-0
Molecular Formula:
C11H13N3O5
Molecular Weight:
267.2380
MDL Number:
MFCD00942308
IUPAC Name:
4-amino-1-[(2R,3R,4S,5R)-4-ethynyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
InChI:
InChI=1S/C11H13N3O5/c1-2-11(18)6(5-15)19-9(8(11)16)14-4-3-7(12)13-10(14)17/h1,3-4,6,8-9,15-16,18H,5H2,(H2,12,13,17)/t6-,8+,9-,11-/m1/s1
InChI Key:
JFIWEPHGRUDAJN-DYUFWOLASA-N
SMILES:
Nc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@]([C@H]1O)(O)C#C)CO
UNII:
Y3O05I09ZK
Properties
Complexity:
508  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
267.086g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
267.241g/mol
Monoisotopic Mass:
267.086g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
129A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.7  
Literature
Title Journal
Cytotoxicity of new duplex drugs linking 3'-C-ethynylcytidine and 5-fluor-2'-deoxyuridine against human melanoma cells. International journal of cancer 20121101
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. Anticancer research 20120501
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. Investigational new drugs 20120201
Cytostatic activity of the duplex drug linking 2'-deoxy-5-fluorouridine (5FdU) with 3'-C-ethynylcytidine (ECyd) against gastric adenocarcinoma cell lines. Investigational new drugs 20111201
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. Investigational new drugs 20110601
Cellular pharmacology of multi- and duplex drugs consisting of ethynylcytidine and 5-fluoro-2'-deoxyuridine. Investigational new drugs 20110401
Acceptance of oral chemotherapy in breast cancer patients - a survey study. BMC cancer 20110101
RNA polymerase III transcription in cancer: the BRF2 connection. Molecular cancer 20110101
A nucleoside anticancer drug, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine (TAS106), sensitizes cells to radiation by suppressing BRCA2 expression. Molecular cancer 20110101
Cytotoxicity and antileukaemic activity of new duplexes linking 3-C-ethynylcytidine and 5-fluorodeoxyuridine. Anticancer research 20101201
Association of RNase L with a Ras GTPase-activating-like protein IQGAP1 in mediating the apoptosis of a human cancer cell-line. The FEBS journal 20101101
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. Biochemical pharmacology 20100615
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. Bioorganic & medicinal chemistry 20091001
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. International journal of pharmaceutics 20090730
Antiviral and cytotoxic activities of aminoarylazo compounds and aryltriazene derivatives. Bioorganic & medicinal chemistry 20090701
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. International journal of oncology 20090501
Role of RNase L in apoptosis induced by 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine. Cancer chemotherapy and pharmacology 20090401
Molecular mechanisms of apoptosis induced by 3'-ethynylcytidine. Nucleic acids symposium series (2004) 20090101
Inhibition of HIF-1alpha by the anticancer drug TAS106 enhances X-ray-induced apoptosis in vitro and in vivo. British journal of cancer 20081104
Cytotoxic nucleoside analogues: different strategies to improve their clinical efficacy. Current medicinal chemistry 20080101
In vitro activity and mechanism of action of a duplex and multidrug of ethynylcytidine and 5-fluorodeoxyuridine. Nucleic acids symposium series (2004) 20080101
Cellular localization and functional characterization of the equilibrative nucleoside transporters of antitumor nucleosides. Cancer science 20071001
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. Oncology reports 20070601
Treatment combining X-irradiation and a ribonucleoside anticancer drug, TAS106, effectively suppresses the growth of tumor cells transplanted in mice. International journal of radiation oncology, biology, physics 20070501
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. Nucleic acids symposium series (2004) 20070101
An apoptotic pathway of 3'-Ethynylcytidine(ECyd) involving the inhibition of RNA synthesis mediated by RNase L. Nucleic acids symposium series (2004) 20060101
X irradiation induces the proapoptotic state independent of the loss of clonogenic ability in Chinese hamster V79 cells. Radiation research 20050701
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. Cancer science 20050501
Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd). Bioorganic & medicinal chemistry 20050401
Synthesis and biological evaluation of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd). Bioorganic & medicinal chemistry 20050215
Synthesis and biological evaluation of conformationally restricted and nucleobase-modified analogs of the anticancer compound 3'-C-ethynylcytidine (ECyd). Nucleosides, nucleotides & nucleic acids 20050101
A novel anticancer ribonucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine, enhances radiation-induced cell death in tumor cells. Radiation research 20041201
A crucial role of uridine/cytidine kinase 2 in antitumor activity of 3'-ethynyl nucleosides. Drug metabolism and disposition: the biological fate of chemicals 20041001
New nucleoside analogs in the treatment of solid tumors. Acta poloniae pharmaceutica 20040101
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. Bioorganic & medicinal chemistry 20030529
Determination of 3'-C-ethynylcytidine in human plasma and urine by liquid chromatographic-electrospray ionization tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis 20030205
Sensitivity of human cancer cells to the new anticancer ribo-nucleoside TAS-106 is correlated with expression of uridine-cytidine kinase 2. Japanese journal of cancer research : Gann 20020701
Cellular and biochemical mechanisms of the resistance of human cancer cells to a new anticancer ribo-nucleoside, TAS-106. Japanese journal of cancer research : Gann 20020401
Analysis of single nucleotide polymorphisms in uridine/cytidine kinase gene encoding metabolic enzyme of 3'-ethynylcytidine. Nucleic acids research. Supplement (2001) 20020101
Anticancer mechanisms of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl) cytosine (ECyd, TAS-106). Nucleic acids research. Supplement (2001) 20020101
Cloning and expression of uridine/cytidine kinase cDNA from human fibrosarcoma cells. International journal of molecular medicine 20010901
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. Chemistry (Weinheim an der Bergstrasse, Germany) 20010601
Improvement in precision of the liquid chromatographic-electrospray ionization tandem mass spectrometric analysis of 3'-C-ethynylcytidine in rat plasma. Journal of chromatography. B, Biomedical sciences and applications 20010415
Antitumor activity and pharmacokinetics of TAS-106, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine. Japanese journal of cancer research : Gann 20010301
1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106)1: antitumor effect and mechanism of action. Nucleosides, nucleotides & nucleic acids 20010101
Anticancer molecular mechanism of 3'-ethynylcytidine (ECyd). Nucleic acids research. Supplement (2001) 20010101
Properties