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60084-10-8, Tiazofurine, CAS:60084-10-8

60084-10-8, Tiazofurine,
CAS:60084-10-8
C9H12N2O5S / 260.27
MFCD00866494

Tiazofurine, 噻唑呋林

Tiazofurin is a novel anticancer agent that inhibits the activity of various enzymes, including dehydrogenase and acetyl-CoA carboxylase. Tiazofurin shows significant cytotoxicity against human leukemia cells in vitro. It also has an anti-infectious effect on hl-60 cells and k562 cells, which are carcinoma cell lines. Tiazofurin has been shown to have a higher inhibitory effect on dextran sulfate than on basic protein in vitro, suggesting that it may be more effective as an anticancer compound against cancerous tumors with high levels of glycolipids.

Tiazofurin is a synthetic nucleoside analogue with antineoplastic activity. Tiazofurin (TR) is anabolized intracellularly to an analogue of NAD, tiazole-4-carboxamide adenine dinucleotide (TAD), a potent inhibitor of IMP dehydrogenase (IMPDH); IMPDH is the rate-limiting enzyme for de novo purine synthesis. Inhibition of IMPDH results in reduced levels of guanylates, resulting in the inhibition tumor cell growth in vitro and in vivo. (NCI04)

Tiazofurine is a C-glycosyl compound that is 1,3-thiazole-4-carboxamide in which the hydrogen at position 2 has been replaced by a beta-D-ribofuranosyl group.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 dinucleotide (TAD), a selective inhibitor of inosine monophosphate dehydrogenase (IMP dehydrogenase). It has a role as an EC 1.1.1.205 (IMP dehydrogenase) inhibitor, a prodrug and an antineoplastic agent. It is a C-glycosyl compound, a member of 1,3-thiazoles and a monocarboxylic acid amide. It derives from a beta-D-ribose.

Tiazofurine has potential clinical use in cancer treatment as it is a potential inhibitor of Inosine- 5’-monophosphate (IMP) dehydrogenase.

Title: Tiazofurin

CAS Registry Number: 60084-10-8

CAS Name: 2b-D-Ribofuranosyl-4-thiazolecarboxamide

Additional Names: riboxamide; TCAR

Manufacturers' Codes: CI-909; NSC-286193

Trademarks: Tiazole (ICN)

Molecular Formula: C9H12N2O5S

Molecular Weight: 260.27

Percent Composition: C 41.53%, H 4.65%, N 10.76%, O 30.74%, S 12.32%

Literature References: Nucleoside analog that inhibits inosine monophosphate dehydrogenase (IMPDH). Prepn: M. Fuertes et al., J. Org. Chem. 41, 4074 (1976); and antiviral activity: P. C. Srivastava et al., J. Med. Chem. 20, 256 (1977). Structure-activity study: G. Gebeyehu et al., ibid. 28, 99 (1985). HPLC determn in plasma: R. W. Klecker, Jr., J. M. Collins, J. Chromatogr. 307, 361 (1984). Clinical pharmacokinetics: D. Raghavan et al., Cancer Chemother. Pharmacol. 16, 160 (1986). Clinical evaluation in leukemia: G. Tricot et al, Int. J. Cell Cloning 8, 161 (1990). Series of articles on pharmacology and clinical experience: Anticancer Res. 16, 3307-3354 (1996).

Properties: Crystals from ethanol-ethyl acetate, mp 145-146°. [a]D25 -9° (c = 0.5 in ethanol). uv max in ethanol: 215, 237 nm (e 9450, 7625).

Melting point: mp 145-146°

Optical Rotation: [a]D25 -9° (c = 0.5 in ethanol)

Absorption maximum: uv max in ethanol: 215, 237 nm (e 9450, 7625)

Therap-Cat: Antineoplastic.

Keywords: Antineoplastic; Antimetabolites; Purine Analogs; IMPDH Inhibitor.

CAS Number60084-10-8
Product NameTiazofurin
IUPAC Name2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide
Molecular FormulaC9H12N2O5S
Molecular Weight260.27 g/mol
InChIInChI=1S/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
InChI KeyFVRDYQYEVDDKCR-DBRKOABJSA-N
SMILESC1=C(N=C(S1)C2C(C(C(O2)CO)O)O)C(=O)N
SolubilitySoluble in DMSO, not in water
Synonyms2-beta-D-ribofuranosylthiazole-4-carboxamide, 2-ribofuranosylthiazole-4-carboxamide, NSC 286193, riboxamide, tiazofurin, tiazofurin, (alpha-D)-isomer, Tiazole
Canonical SMILESC1=C(N=C(S1)C2C(C(C(O2)CO)O)O)C(=O)N
Isomeric SMILESC1=C(N=C(S1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
CAS No: 60084-10-8 Synonyms: 2-b-D-Ribofuranosyl-4-thiazolecarboxamideCI 909NSC 286-193 MDL No: MFCD00866494 Chemical Formula: C9H12N2O5S Molecular Weight: 260.27
References: 1. Streeter, D.G. et al., Biochem. Biophys. Res. Comm., 115, 544 (1983)2. Boritzki, T. et al., Biochem. Pharmacol., 34, 1109 (1985)3. Malek, K. et al., Leuk. Res., 28, 1125 (2004)


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