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

• ChemBase ID: 5936
• Molecular Formular: C14H11N3O3S
• Molecular Mass: 301.32044
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: 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
• Synonyms: 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

Database IDs

• CAS Number: 31430-18-9
• EC Number: 250-626-5
• MDL Number: MFCD00005588
• Beilstein Number: 1085978
• PubChem SID: 24886650; 24278535; 160969361; 99444784
• PubChem CID: 4122
• CHEMBL: 9514
• Wikipedia Title: Nocodazole

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.114124
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.1699927
• LogD (pH = 7.4): 3.1656659
• Log P: 3.1729898
• Molar Refractivity: 78.3938 cm^3
• Polarizability: 30.559483 Å^3
• Polar Surface Area: 84.08 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.84
• LOG S: -4.21
• Solubility (Water): 1.85e-02 g/l

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• RTECS: DD6521000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-68
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H341-H361d
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Microtubule Associated
• Gene Information: human ... TUBB(203068)

Product Information

• Purity: ≥98.0% (HPLC); ≥99% (TLC); 98%
• Grade: purum
• Salt Data: Free Base
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C14H11N3O3S

DETAILS

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.

REFERENCES

• 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