methyl N-[6-(thiophene-2-carbonyl)-1H-1,3-benzodiazol-2-yl]carbamate

• ChemBase编号: 5936
• 分子式: C14H11N3O3S
• 平均质量: 301.32044
• 单一同位素质量: 301.05211223
• SMILES: O=C(OC)Nc1[nH]c2cc(ccc2n1)C(=O)c1cccs1
• Canonical SMILES: COC(=O)Nc1nc2c([nH]1)cc(cc2)C(=O)c1cccs1
• InChI: InChI=1S/C14H11N3O3S/c1-20-14(19)17-13-15-9-5-4-8(7-10(9)16-13)12(18)11-3-2-6-21-11/h2-7H,1H3,(H2,15,16,17,19)
• InChIKey: KYRVNWMVYQXFEU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: methyl N-[6-(thiophene-2-carbonyl)-1H-1,3-benzodiazol-2-yl]carbamate; methyl N-[5-(thiophene-2-carbonyl)-1H-1,3-benzodiazol-2-yl]carbamate
• IUPAC传统名: nocodazol; methyl N-[5-(thiophene-2-carbonyl)-3H-1,3-benzodiazol-2-yl]carbamate; nocodazole; methyl N-[5-(thiophene-2-carbonyl)-1H-1,3-benzodiazol-2-yl]carbamate
• 别名: Methyl [5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl]carbamate; Nocodazole; N-[6-(2-Thienylcarbonyl)-1H-benzimidazol-2-yl]carbamic Acid Methyl Ester; N-[5-(2-Thenoyl)-2-benzimidazolyl]carbamic Acid Methyl Ester; NSC 238159; Methyl-(5-[2-thienylcarbonyl]-1H-benzimidazol-2yl)carbamate; nocodazole; Nocodazole; R 17934; Methyl N-(5-thenoyl-2-benzimidazolyl)carbamate; Oncodazole; [5-(2-Thienylcarbonyl)-1H-benzimidazol-2-yl]-carbamic acid methyl ester; METHYL [5-(2-THIENYL-CARBONYL)-1H-BENZ-IMIDAZOLE-2-YL]-CARBAMATE; methyl (5-(2-thienylcarbonyl)-1h-benzimidazol-2-yl)carbamate

登记号

• CAS号: 31430-18-9
• EC号: 250-626-5
• MDL号: MFCD00005588
• Beilstein号: 1085978
• PubChem SID: 99444784; 24886650; 24278535; 160969361
• PubChem CID: 4122
• CHEMBL: 9514
• 维基百科标题: Nocodazole

理论计算性质

JChem

• Acid pKa: 9.114124
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 3.1699927
• LogD (pH = 7.4): 3.1656659
• Log P: 3.1729898
• 摩尔折射率: 78.3938 cm^3
• 极化性: 30.559483 Å^3
• 极化表面积: 84.08 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.84
• LOG S: -4.21
• 溶解度: 1.85e-02 g/l

分子性质

理化性质

• 溶解度: approximately 10 mg/mL in DMSO; DMSO; DMSO: soluble10 mg/mL (may require heating); H2O: insoluble
• 外观: Light Tan to Brown Solid; white powder; White with faint yellow cast powder
• 熔点: >280°C (dec.); 256°C; 300 °C (dec.)

安全信息

• 保存条件: -20°C Freezer; 2-8°C
• RTECS编号: DD6521000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 63-68
• 安全公开号: 36/37
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H341-H361d
• GHS警示性声明: P281
• 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

• 作用靶点: Microtubule Associated
• 相关基因信息: human ... TUBB(203068)

产品相关信息

• 纯度: ≥98.0% (HPLC); ≥99% (TLC); 98%
• 级别: purum
• 成盐信息: Free Base
• 产品质量级别: PREMIUM
• Empirical Formula (Hill Notation): C14H11N3O3S

详细说明

MP Biomedicals - 02152405

Purity: 98%
A synthetic microtubule inhibitor shown to induce the disappearance of microtubules from neoplastic cells in vivo and mammalian cells in culture.

DrugBank - DB08313

Drug information: experimental

Sigma Aldrich - 74151

Other Notes
Inhibitor of tubulin polymerization1,2,3

Sigma Aldrich - M1404

Biochem/physiol Actions
Antimitotic agent that disrupts microtubules by binding to β?tubulin and preventing formation of one of the two interchain disulfide linkages, thus inhibiting microtubule dynamics, disruption of mitotic spindle function, and fragmentation of the Golgi complex. Arrests the cell cycle at G2/M phase. Prevents phosphorylation of the T cell antigen receptor and inhibits its activity. Stimulates the intrinsic GTPase activity of tubulin. Activates the JNK/SAPK signaling pathway and induces apoptosis in several normal and tumor cell lines.

Toronto Research Chemicals - M330350

A synthetic chemotherapeutic agent with antineoplastic, antifungal and anthelmintic activities. Microtubule inhibitor; inhibits mitosis.

参考文献

• Lacey., E., et al.: Biochem. Pharmacol., 34, 1073 (1985)
• Lacey., E., et al.: Biochem. Pharmacol., 34, 3603 (1985)
• Massa, S., et al.: J. Het. Chem., 27, 1131 (1985)
• Rennison et al.: J. Cell. Sci. , 102, 239 (1985)
• Vasquez et al. Mol. Biol. Cell, 8, 973