180300-43-0

Basic information

• Product Name: 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine
• Synonyms: 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine;ETHYNYCYTIDINE;ECyd;TAS 106;Ethynylcytidine;4-Amino-1-((2R,3R,4S,5R)-4-ethynyl-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;cytidine, 3'-c-ethynyl-;Ethynylcytidine (TAS-106)
• CAS NO: 180300-43-0
• Molecular Formula: C₁₁H₁₃N₃O₅
• Molecular Weight: 267.23802
• Product Categories: Nucleosides
• Mol File: 180300-43-0.mol

Chemical Properties

• Melting Point: 233-235 °C
• Boiling Point: 536.4°Cat760mmHg
• Flash Point: 278.2°C
• Appearance: /
• Density: 1.61g/cm³
• PKA: 11.54±0.70(Predicted)
• CAS DataBase Reference: 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine(180300-43-0)
• EPA Substance Registry System: 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine(180300-43-0)

Safety Data

• Hazardous Substances Data: 180300-43-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine is used as an anticancer agent for its potent synergistic growth-inhibitory effect when combined with cisplatin. This combination targets Vaults dysfunction, leading to enhanced therapeutic outcomes in cancer treatment.
Used in Cancer Research:
In the field of cancer research, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine serves as a valuable tool for studying the mechanisms of RNA polymerase inhibition and its implications in cancer cell growth and proliferation. This knowledge can contribute to the development of new therapeutic strategies and drug candidates.

Upstream product

• 848644-37-1 1,2,3,5-tetra-O-acetyl-3-C-ethynyl-D-ribo-pentofuranose 
• 72409-15-5 N⁴-benzoyl-5'-O-(4-monomethoxytrityl)cytidine 
• 182825-16-7 methyl 2,3,5-tri-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose 
• 182825-17-8 1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl-D-ribofuranose 
• 72409-30-4 N⁴-benzoyl-2'-O-(tert-butyldimethylsilyl)-5'-O-(4-monomethoxytrityl)cytidine 
• 501014-32-0 N⁴-benzoyl-2'-O-(tert-butyldimethylsilyl)-3'-keto-5'-O-(4-monomethoxytrityl)cytidine 
• 501014-34-2 N⁴-benzoyl-2'-O-(tert-butyldimethylsilyl)-3'-C-(trimethylsilylethynyl)cytidine 
• 501014-33-1 N⁴-benzoyl-2'-O-(tert-butyldimethylsilyl)-3'-ketocytidine 
• 65-46-3 CYTIDINE 
• 13089-48-0 N₄-benzoylcytidine 
• 35810-59-4 (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 
• 155470-63-6 3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose 
• 97694-32-1 1,2-O-isopropylidene-3-C-ethynyl-α-D-allofuranose 
• 97694-33-2 3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 

Downstream Products

• 616239-79-3 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-(3-nitrobenzylidene)-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine 
• 616239-80-6 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-(4-aminobenzylidene)-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine 
• 616239-78-2 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-(4-nitrobenzylidene)-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine 
• 616239-81-7 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-(3-aminobenzylidene)-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine 
• 616239-76-0 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-isopropylidene-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine 
• 616239-77-1 4-N-benzoyl-1-[3-C-ethynyl-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine 
• 616239-62-4 1-[3-C-ethynyl-2,3-O-(4-nitrobenzylidene)-β-D-ribo-pentofuranosyl]cytosine 
• 616239-63-5 1-[3-C-ethynyl-2,3-O-(3-nitrobenzylidene)-β-D-ribo-pentofuranosyl]cytosine 
• 616239-68-0 1-[3-C-ethynyl-5-O-[1-isopropoxy-1-(4-nitrophenyl)methyl]-β-D-ribo-pentofuranosyl]cytosine 
• 616239-67-9 1-[3-C-ethynyl-5-O-[1-ethoxy-1-(4-nitrophenyl)methyl]-β-D-ribo-pentofuranosyl]cytosine 
• 616239-66-8 1-[3-C-ethynyl-5-O-[1-methoxy-1-(4-nitrophenyl)methyl]-β-D-ribo-pentofuranosyl]cytosine 

Relevant articles and documents

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

A series of nucleobase-modified analogs of the anticancer compounds 3′-C-ethynyluridine (EUrd) and 3′-C-ethynylcytidine (ECyd) were designed to overcome the strict substrate specificity of the activating uridine-cytidine kinase. EUrd, ECyd and target nucleosides were obtained using a short convergent synthetic route utilizing diacetone-α-d-glucose as starting material. 5-Iodo-substituted EUrd was the most potent inhibitor among the novel nucleobase-modified analogs in in vitro assays against human adenocarcinoma breast and prostate cancer cells with IC50 values down to 35 nM.

Synthesis and biological evaluation of conformationally restricted and nucleobase-modified analogs of the anticancer compound 3′-C- ethynylcytidine (ECYD)

A series of conformationally restricted and nucleobase-modified analogs of the anticancer compound 3′-C-ethynylcytidine (ECyd) and its uracil analog (EUrd) have been synthesized. While none of the conformationally restricted analogs displayed anticancer a

Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction

A practical synthetic route to the antitumor nucleoside, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine (ECyd, 1) from 1,2-O-isopropylidene-D-xylofuranose (3) has been developed. Since most of the compounds were obtained as crystals, the target ECyd was prepared without any chromatographic purification in 31% overall yield from compound 3. The isobutyryloxy group was found to be an effective leaving group at the anomeric position of the 3-β-C-ethynyl glycosyl donors in the key Vorbru?ggen glycosylation reaction. Using a similar procedure without chromatographic purification, the uracil congener EUrd [1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)uracil (2), which also has a potent antitumor effect, was synthesized from 3 in 39% overall yield.

A new laboratory scale synthesis for the anticancer drug 3′-C-ethynylcytidine

A new synthetic route for the preparation of larger quantities of the anticancer nucleoside analogue 3′-C-ethynylcytidine is described. Starting from cytidine which was orthogonally protected in three steps, the ketonucleoside analogue as the key intermediate was obtained through oxidation of the unprotected 3′-hydroxy group. Stereoselective addition of the trimethylsilyl-protected acetylide residue at the 3′-carbonyl group followed by a complete deprotection afforded 3′-C-ethynylcytidine in an overall yield of 24% in seven steps.

D-pentofuranose derivatives and process for preparing the same

The present invention relates to D-pentofuranose derivatives represented by the following formulas (1) through (4): STR1 (wherein A represents a chlorobenzoyl group; R1 represents a hydrogen atom, an aliphatic lower acyl group, a substituted or

3'-substituted nucleoside derivatives

The invention relates to a 3'-substituted nucleoside derivative represented by the following general formula (1): STR1 wherein B means a nucleic acid base which may have a substituent, Z represents a lower alkynyl or lower alkenyl group which may be subst

Nucleosides and nucleotides. 158. 1-(3-C-ethynyl-β-D-ribo- pentofuranosyl)-cytosine, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)uracil, and their nucleobase analogues as new potential multifunctional antitumor nucleosides with a broad spectrum of activity

We previously designed 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)uracil (EUrd) as a potential multifunctional antitumor nucleoside antimetabolite. It showed a potent and broad spectrum of antitumor activity against various human tumor cells in vitro and in vivo. To determine the structure-activity relationship, various nucleobase analogues of EUrd, such as 5-fluorouracil, thymine, cytosine, 5-fluorocytosine, adenine, and guanine derivatives, were synthesized by condensation of 1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl- α-β-D-ribo-pentofuranose (6) and the corresponding pertrimethylsilylated nucleobases in the presence of SnCl4 or TMSOTf as a Lewis acid in CH3CN followed by debenzoylation. The in vitro tumor cell growth inhibitory activity of these 3'-C-ethynyl nucleosides against mouse leukemia L1210 and human nasopharyngeal KB cells showed that 1-(3-C-ethynyl-β-D-ribo- pentofuranosyl)cytosine (ECyd) and EUrd were the most potent inhibitors in the series, with IC50 values for L1210 cells of 0.016 and 0.13 μM and for KB cells of 0.028 and 0.029 μM, respectively. 5-Fluorocytosine, 5- fluorouracil, and adenine nucleosides showed much lower activity, with IC50 values of 0.42.5 μM, while thymine and guanine nucleosides did not exhibit any activity up to 300 μM. We next evaluated the tumor cell growth inhibitory activity of ECyd and EUrd against 36 human tumor cell lines in vitro and found that they were highly effective against these cell lines with IC50 values in the nanomolar to micromolar range. These nucleosides have a similar inhibitory spectrum. The in vivo antitumor activities of ECyd and EUrd were compared to that of 5-fluorouracil against 11 human tumor xenografts including three stomach, three colon, two pancreas, one renal, one breast, and one bile duct cancers. ECyd and EUrd showed a potent tumor inhibition ratio (73-92% inhibition relative to the control) in 9 of 11 and 8 of 11 human tumors, respectively, when administered intravenously for 10 consecutive days at doses of 0.25 and 2.0 mg/kg, respectively, while 5- fluorouracil showed potent inhibitory activity against only one tumor. Such excellent antitumor activity suggests that ECyd and EUrd are worth evaluating further for use in the treatment of human cancers.