ethyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• ChemBase编号: 155116
• 分子式: C14H16N2O3S
• 平均质量: 292.35344
• 单一同位素质量: 292.08816338
• SMILES: CCOC(=O)C1=C(NC(=S)NC1c1cccc(c1)O)C
• Canonical SMILES: CCOC(=O)C1=C(C)NC(=S)NC1c1cccc(c1)O
• InChI: InChI=1S/C14H16N2O3S/c1-3-19-13(18)11-8(2)15-14(20)16-12(11)9-5-4-6-10(17)7-9/h4-7,12,17H,3H2,1-2H3,(H2,15,16,20)
• InChIKey: LOBCDGHHHHGHFA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ethyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• IUPAC传统名: monastrol; ethyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 别名: 4-(3-Hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-4H-pyrimidin-5-carboxylic Acid Ethyl Ester; Monastrol; 6-Methyl-4-(3-hydroxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate; Monastrol

登记号

• CAS号: 254753-54-3; 254753-54-3
• MDL号: MFCD00813077
• PubChem SID: 24897267; 162249254
• PubChem CID: 2987927

理论计算性质

• Acid pKa: 9.374903
• 质子受体: 2
• 质子供体: 3
• LogD (pH = 5.5): 1.8265492
• LogD (pH = 7.4): 1.8220707
• Log P: 1.8266066
• 摩尔折射率: 81.4057 cm^3
• 极化性: 31.166754 Å^3
• 极化表面积: 70.59 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; DMSO: >5 mg/mL; Ethanol; Ethyl Acetate
• 外观: White Solid; white to off-white solid
• 熔点: 184-186°C; 185-185.9 °C(lit.)

安全信息

• 保存条件: -20°C Freezer; protect from light
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 生物活性机理: Selective inhibitor of mitotic kinesin Eg5

产品相关信息

• 纯度: ≥98% (HPLC)
• 应用领域: Antineoplastic agent
• Empirical Formula (Hill Notation): C14H16N2O3S

详细说明

Sigma Aldrich - M8515

包装
Packaged under inert gas.
Biochem/physiol Actions
Monastrol is a potent, cell-permeant inhibitor of mitosis. Monastrol arrested cells are characterized by monopolar spindles. This phenotype is induced through specific disruption of mitotic molecular motor kinesin Eg5 with IC50 at 14 μM. No effect on other motor proteins and tubulin.

Toronto Research Chemicals - M505750

A cell-permeablesmall molecule inhibitor of the mitotic kinesin, Eg5, arrests cells in mitosis with monoastral spindles.

参考文献

• Mayer, T.U., et al.: Science, 286, 971 (1999)
• Kappe, C.O., et al.: Tetrahedron, 56, 1859 (2000)
• Mayeret al (1999) Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. Science 286 971.