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

60084-10-8
SMILES: NC(=O)c1csc([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)n1

化学属性

Mol. FormulaC9H12N2O5S
Mol. Weight260.27
Appearance Solid powder
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical Name2-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-Yl)Thiazole-4-Carboxamide
CAS Number60084-10-8
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 Number1084555
FormulaC9H12N2O5S
IUPAC Name2-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)thiazole-4-carboxamide
InChIKeyFVRDYQYEVDDKCR-DBRKOABJSA-N
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
Canonical SMILESO=C(C1=CSC([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=N1)N
Chemical Name Translation2-((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

RTECSXJ3600000 
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

Storage condition Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

系列性分类

  1. Medical Research Areas
  2. Metabolism
  3. Dehydrogenase

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