Nocodazole

Base Information

• Chemical Name: Nocodazole
• CAS No.: 31430-18-9
• Molecular Formula: C14H11N3O3S
• Molecular Weight: 301.326
• Hs Code.: 29349990
• European Community (EC) Number: 250-626-5
• NSC Number: 759882,238159
• UN Number: 2811
• UNII: SH1WY3R615
• DSSTox Substance ID: DTXSID9031800
• Nikkaji Number: J20.370J
• Wikipedia: Nocodazole
• Wikidata: Q2506092
• NCI Thesaurus Code: C75228
• Pharos Ligand ID: SSBYCCFNFL61
• Metabolomics Workbench ID: 151453
• ChEMBL ID: CHEMBL9514
• Mol file: 31430-18-9.mol

Synonyms:Nocodazole;NSC 238159;NSC-238159;NSC238159;Oncodazole;R 17934;R-17934;R17934

Chemical Property of Nocodazole

Chemical Property:

• Appearance/Colour: Amber powder
• Melting Point: 300 °C (dec.)
• Refractive Index: 1.731
• PKA: 10.67±0.10(Predicted)
• PSA: 112.32000
• Density: 1.491 g/cm³
• LogP: 3.10670
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 10 mg/mL, soluble
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 301.05211239
• Heavy Atom Count: 21
• Complexity: 420
• Transport DOT Label: Poison

Purity/Quality:

98%,99%, ^*data from raw suppliers

Nocodazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, C, F
• Hazard Codes: T,C,F,Xn
• Statements: 61-40-36/37/38-34-11-68-63
• Safety Statements: 53-45-36/37/39-26-16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=CS3
• Description: Nocodazole reversibly binds tubulin and alters tubulin-associated GTP hydrolysis as well as microtubule dynamics. While nocodazole is used to study many aspects on microtubule function, it is most commonly used to synchronize cell cycling in culture. Typically, nanomolar concentrations of nocodazole reduce both microtubule elongation and shortening velocities, resulting in arrest of cycling in a G2/M phase. Nocodazole is also used to induce the formation of Golgi ministacks in eukaryotic cells.
• Uses: Antineoplastic;Microtubule poison A potent Tubulin production inhibitor and anti-neoplastic agent Nocodazole has been shown to enhance CRISPR genome editing efficiency. To see other small molecule CRISPR enhancers, visit sigma.com/CRISPR-enhancers. A synthetic chemotherapeutic agent with antineoplastic, antifungal and anthelmintic activities. Microtubule inhibitor; inhibits mitosis

Technology Process of Nocodazole

There total 2 articles about Nocodazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(R)-((S)-2-Amino-propionylamino)-[2-methoxycarbonylamino-5-(thiophene-2-carbonyl)-benzoimidazol-1-yl]-acetic acid (127590-63-0,127590-65-2) → nocodazole (31430-18-9) + [1-((2R,5S)-5-Methyl-3,6-dioxo-piperazin-2-yl)-5-(thiophene-2-carbonyl)-1H-benzoimidazol-2-yl]-carbamic acid methyl ester (127590-67-4)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 25 - 60 ℃;

DOI:10.1016/0223-5234(89)90079-2

Reference yield:

→ nocodazole (31430-18-9)

Guidance literature:

entspr. o-Phenylendiamin, H2NC(NH)SMe, ClCO2Me;

Reference yield:

nocodazole (31430-18-9) + N-carboxybenzoxy-L-alanyl-D,L-2-acetoxyglycine benzyl ester (89625-84-3) → ((S)-2-Benzyloxycarbonylamino-propionylamino)-[2-methoxycarbonylamino-6-(thiophene-2-carbonyl)-benzoimidazol-1-yl]-acetic acid benzyl ester (127590-60-7,127590-62-9) + ((S)-2-Benzyloxycarbonylamino-propionylamino)-[2-methoxycarbonylamino-5-(thiophene-2-carbonyl)-benzoimidazol-1-yl]-acetic acid benzyl ester (127590-59-4,127590-61-8)

Guidance literature:

With toluene-4-sulfonic acid; triethylamine; In N,N-dimethyl-formamide; at 25 ℃; for 24h; Title compound not separated from byproducts;

DOI:10.1016/0223-5234(89)90079-2

upstream raw materials:

(R)-((S)-2-Amino-propionylamino)-[2-methoxycarbonylamino-5-(thiophene-2-carbonyl)-benzoimidazol-1-yl]-acetic acid

Downstream raw materials:

((S)-2-Benzyloxycarbonylamino-propionylamino)-[2-methoxycarbonylamino-6-(thiophene-2-carbonyl)-benzoimidazol-1-yl]-acetic acid benzyl ester

((S)-2-Benzyloxycarbonylamino-propionylamino)-[2-methoxycarbonylamino-5-(thiophene-2-carbonyl)-benzoimidazol-1-yl]-acetic acid benzyl ester

Refernces

• 1、 Raeymackers,Van Gelder,Roevens,Janssen. "Synthesis and anthelminthic acitivity of alkyl-(5-acyl-1-benzimidazol-2-yl) carbamates". . p. 586 - 594. Retrieved 2007/10/05.