2-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-Yl)Thiazole-4-Carboxamide 2-((2R,3R,4S,5R)-3,4-二羟基-5-(羟甲基)四氢呋喃-2-基)噻唑-4-甲酰胺
CAS 60084-10-8 MFCD00866494
化学结构图
SMILES: NC(=O)c1csc([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)n1
化学属性
| Mol. Formula | C9H12N2O5S |
|---|---|
| Mol. Weight | 260.27 |
| Appearance | Solid powder |
| Solubility | Soluble in DMSO, not in water |
别名和识别编码
| Chemical Name | 2-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-Yl)Thiazole-4-Carboxamide |
|---|---|
| CAS Number | 60084-10-8 |
| Synonym | 2-?-D-Ribofuranosyl-4-thiazolecarboxamide 2-?-D-Ribofuranosylthiazole-4-carboxamide 2-beta-D-Ribofuranosyl-4-thiazolecarboxamide 2-beta-D-Ribofuranosylthiazole-4-carboxamide CI 909 NSC 286-193 NSC 286193 NSC-286193 Riboxamide TCAR Tiazofurin Tiazofurin; Riboxamide; TCAR. Tiazofurine |
| Beilstein Registry Number | 1084555 |
| Formula | C9H12N2O5S |
| IUPAC Name | 2-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)thiazole-4-carboxamide |
| InChIKey | FVRDYQYEVDDKCR-DBRKOABJSA-N |
| InChI | InChI=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 |
| Canonical SMILES | O=C(C1=CSC([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=N1)N |
| Chemical Name Translation | 2-((2R,3R,4S,5R)-3,4-二羟基-5-(羟甲基)四氢呋喃-2-基)噻唑-4-甲酰胺 |
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分类
- Carbohydrates & Derivatives
- Inhibitors
- Pharmaceuticals
- Intermediates & Fine Chemicals
- Sulfur & Selenium Compounds
产品应用
- 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.
相关文献及参考
- Streeter, D.G. et al.: Biochem. Biophys. Res. Comm., 115, 544 (1983); Boritzki, T. et al.: Biochem. Pharmacol., 34, 1109 (1985); Malek, K. et al.: Leuk. Res., 28, 1125 (2004);
安全信息
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human DOSE/DURATION : 1135 mg/kg/15D-I TOXIC EFFECTS : Behavioral - headache Musculoskeletal - other changes REFERENCE : CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 45,5169,1985
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 3400 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Blood - other changes REFERENCE : NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB83-156901
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1684 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human DOSE/DURATION : 892 mg/kg/10D-I TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold REFERENCE : CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 45,5169,1985
TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED
TYPE OF TEST : DNA inhibition TEST SYSTEM : Rodent - mouse Lymphocyte DOSE/DURATION : 10 umol/L REFERENCE : CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 45,5512,1985
TYPE OF TEST : DNA inhibition TEST SYSTEM : Rodent - mouse Leukocyte DOSE/DURATION : 10 umol/L REFERENCE : BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 34,1109,1985
TYPE OF TEST : Mutation test systems - not otherwise specified TEST SYSTEM : Rodent - mouse Lymphocyte DOSE/DURATION : 20 umol/L REFERENCE : CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 45,5512,1985
TYPE OF TEST : Mutation test systems - not otherwise specified TEST SYSTEM : Rodent - mouse Leukocyte DOSE/DURATION : 10 umol/L REFERENCE : BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 34,1109,1985
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE : 3425 mg/kg SEX/DURATION : male 1 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - testes, epididymis, sperm duct REFERENCE : NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB83-156901
