60084-10-8

Basic information

• Product Name: Tiazofurine
• Synonyms: Tiazofurine;tiazofurin;NSC-286193;NSC-286-193;Riboxamide;TCAR;2-.beta.-D-Ribofuranosyl-4-thiazolecarboxamide;Aids014479
• CAS NO: 60084-10-8
• Molecular Formula: C₉H₁₂N₂O₅S
• Molecular Weight: 260.269
• Product Categories: Carbohydrates & Derivatives;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 60084-10-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 145-146°
• Boiling Point: 641.3°C at 760 mmHg
• Flash Point: 341.6°C
• Appearance: /
• Density: 1.4797 (rough estimate)
• Vapor Pressure: 2.53E-17mmHg at 25°C
• Refractive Index: 1.6800 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
• Stability: Very Very Hygroscopic
• CAS DataBase Reference: Tiazofurine(CAS DataBase Reference)
• NIST Chemistry Reference: Tiazofurine(60084-10-8)
• EPA Substance Registry System: Tiazofurine(60084-10-8)

Safety Data

• Hazardous Substances Data: 60084-10-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 60084-10-8 differently. You can refer to the following data:
1. Tiazofurin has antitumor activity and is a potential therapeutic agent in the treatment of cancer. Tiazofurin acts as an inhibitor of Inosine-5'-monophosphate (IMP) dehydrogenase.
2. Tiazofurin has antitumor activity and is a potential therapeutic agent in the treatment of cancer. Tiazofurin acts as an inhibitor of Inosine-5''-monophosphate (IMP) dehydrogenase.

Definition

ChEBI: A C-glycosyl compound that is 1,3-thiazole-4-carboxamide in which the hydrogen at position 2 has been replaced by a beta-D-ribofuranosyl group. It is metabolised to thiazole-4-carboxamide adenine dinucle tide (TAD), a selective inhibitor of inosine monophosphate dehydrogenase (IMP dehydrogenase).

Brand name

Tiazofurine is INN.

InChI:InChI=1/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5-,6-,7-/m1/s1

Upstream product

• 129452-78-4 benzyl 3-methyl-2-<2-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)thiazol-4-ylcarbonylamino>but-2-enoate 
• 129470-60-6 benzyl 3-methyl-2-<(1R,5R)-3-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-7-oxo-4-thia-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>but-2-enoate 
• 129452-81-9 (1R,5R)-3-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-thia-2,6-diazabicyclo<3.2.0>hept-2-en-7-one 
• 95936-48-4 ethyl 5-amino-2-(β-D-ribofuranosyl)thiazole-4-carboxylate 
• 95936-45-1 methyl 2,5-anhydroallonothioate 
• 62404-62-0 β-D-ribofuranosyl-1-carboximidic acid methyl ester 
• 57944-10-2 2,5-anhydro-3,4,6-tri-O-benzoyl-D-allonthioamide 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 218145-21-2 ethyl 2-(5'-O-benzoyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)thiazoline-4-carboxylate 
• 218145-22-3 ethyl 2-(5'-O-benzoyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)thiazole-4-carboxylate 
• 29868-36-8 5-O-benzoyl-2,3-di-O-isopropylidene-β-D-ribofuranosyl-1-carbonitrile 
• 477881-06-4 methyl 1'-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)thiazoline-4'-carboxylate 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 5517-60-2 methyl 3'-O-benzoyl-2,3-O-isopropylidene-β-D-apiofuranoside 

Downstream Products

• 60084-11-9 2-(2',3'-O-isopropylidene-β-D-ribofuranosyl)thiazole-4-carboxamide 
• 896420-04-5 2-(5-O-benzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)thiazole-4-carboxamide 
• 83285-83-0 Tiazofurin adenine dinucleotide 
• 92952-38-0 2-[(2R,3R,4R,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-thiazole-4-carboxylic acid amide 
• 92952-39-1 Acetic acid (2R,3S,4R,5R)-5-(4-carbamoyl-thiazol-2-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester 
• 92982-23-5 Trifluoro-methanesulfonic acid (2R,3R,4S,5R)-5-(4-carbamoyl-thiazol-2-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester 
• 92952-40-4 2-(β-D-xylofuranosyl)thiazole-4-carboxamide 
• 92952-33-5 ara-tiazofurin 

Relevant articles and documents

Synthesis of 4-Substituted 5-Amino-2-(β-D-ribofuranosyl)thiazoles and 4-Substituted 5-Amino-2-(β-D-ribofuranosyl)selenazoles and Their Respective Conversion into 2-(β-D-Ribofuranosyl)thiazolopyrimidines and 2-(β-D-Ribofuranosyl)selenazolopyrimidines. A New Synthesis ...

A novel ring closure has been devised to produce fully substituted thiazoles and selenazoles from the condensation of thio- and selenoates with various 2-aminoacetonitrile derivatives.The syntheses of methyl 2,5-anhydroallonothioate (3) and methyl 2,5-anhydroallonoselenoate (4) from methyl 2,5-anhydroallonimidate are described.The condensations of these carboxylates with the appropriate 2-aminoacetonitrile derivatives to give the corresponding 5-amino-2-(β-D-ribofuranosyl)thiazole and -selenazole nucleosides bearing the carboxamide (10 and 13) ethyl carboxylate (11 and 14), and cyano (12) functions at the four positions are reported.Further manipulation of these functionalized thiazoles and selenazoles yielded the corresponding thiazolo- and selenazolopyrimidine nucleosides (20, 21, and 22), as well as a thiazolotriazine nucleoside (23).New syntheses of tiazofurin (1) and selenazofurin (2) via the reductive dediazotization products of ethyl 5-amino-2-(β-D-ribofuranosyl)thiazole-4-carboxylate (11) and ethyl 5-amino-2-(β-D-ribofuranosyl)selenazole-4-carboxylate (14) are also reported.

A concise route to tiazofurin

Successful oxidation of a key thiazoline intermediate allows an efficient synthesis of tiazofurin in four steps from commercially available 1′-acetoxy-2′,3′,5′-tri-O-benzoyl-β-D- ribofuranose.

A new synthetic methodology for tiazofurin

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