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
• Article Data: 7

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

Description

1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine, also known as Ethynylcytidine, is a novel nucleoside antimetabolite and an RNA polymerase inhibitor. It is characterized by the presence of an ethynyl group attached to the cytosine base, which contributes to its unique properties and potential applications.

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

• 182825-17-8 1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl-D-ribofuranose 
• 182825-16-7 methyl 2,3,5-tri-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose 
• 72409-30-4 N⁴-benzoyl-2'-O-(tert-butyldimethylsilyl)-5'-O-(4-monomethoxytrityl)cytidine 
• 72409-15-5 N⁴-benzoyl-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 
• 861444-58-8 Acetic acid (3aR,5R,6R,6aR)-5-acetoxymethyl-6-ethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

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.

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