Monastrol

Base Information

• Chemical Name: Monastrol
• CAS No.: 254753-54-3
• Molecular Formula: C₁₄H₁₆N₂O₃S
• Molecular Weight: 292.359
• NSC Number: 716782
• DSSTox Substance ID: DTXSID10388124,DTXSID501317756
• Nikkaji Number: J1.229.496D
• Wikipedia: Monastrol
• Wikidata: Q6898425
• Pharos Ligand ID: S7LS593LZTM7
• ChEMBL ID: CHEMBL236789
• Mol file: 254753-54-3.mol

Synonyms:monastrol

Chemical Property of Monastrol

Chemical Property:

• Vapor Pressure: 2.13E-08mmHg at 25°C
• Melting Point: 185-185.9 °C(lit.)
• Boiling Point: 441.3°Cat760mmHg
• PKA: 9.63±0.10(Predicted)
• Flash Point: 220.7°C
• PSA: 102.68000
• Density: 1.34g/cm³
• LogP: 2.40570
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 100 mg/mL
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 292.08816355
• Heavy Atom Count: 20
• Complexity: 436

Purity/Quality:

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

Monastrol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=S)NC1C2=CC(=CC=C2)O)C
• Description: Monastrol (254753-54-3) is a potent, cell-permeable, small molecule inhibitor of mitosis. Monastrol-arrested cells are characterized by monopolar spindles.1?Does not affect other motor proteins or tubulin. Specifically inhibits the mitotic molecular motor kinesin Eg5, a motor protein required for spindle formation (IC50?= 14 μM).2?Mimics the effect of amyloid β on long term potentiation in a cellular model of learning and memory.3?Enhances regeneration of adult axons.4
• Uses: Inhibitor of mammalian cell mitosis. Monastrol has been used:to treat MDA-MB-231 cells as a non-microtubule-targeting agentas a antineoplastic agent, to treat mouse myeloma cell line SP 2/0, to induce apoptosis and to elucidate the role of metabotropic glutamate receptor 3 (Grm3) in apoptosisas an inhibitor of pteridine reductase in GFP-transfected promastigotes infected macrophages for flow cytometer-based growth inhibition assay and to evaluate anti-leishmanial activity of Leishmania donovani hamster model in vivo A cell-permeablesmall molecule inhibitor of the mitotic kinesin, Eg5, arrests cells in mitosis with monoastral spindles

Technology Process of Monastrol

There total 32 articles about Monastrol 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: 99.0%

ethyl acetoacetate (141-97-9) + meta-hydroxybenzaldehyde (100-83-4) + thiourea (17356-08-0) → monastrol (329689-23-8,254753-54-3,268739-54-4)

Guidance literature:

Wells-Dawson heteropolyacid catalyst; at 80 ℃; for 1.5h;

DOI:10.1080/00397910701572332

Reference yield: 98.0%

C18H22N2O4S (1243989-70-9) → (S)-monastrol (254753-54-3,268739-54-4)

Guidance literature:

With water; In dichloromethane; at 40 ℃; for 49h; pH=7; optical yield given as %ee; enantioselective reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1016/j.bmcl.2010.05.063

Reference yield: 95.0%

(R)-3-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-carbonyl)-4-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (482655-64-1) → (-)-4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (254753-54-3,268739-54-4)

Guidance literature:

With sodium ethanolate; In ethanol; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(02)01269-8

upstream raw materials:

ethyl acetoacetate

meta-hydroxybenzaldehyde

thiourea

thiouronium hydrogensulfate

Downstream raw materials:

C₁₉H₂₂N₂O₆S

Refernces

• 1、 Chen, Xiao-Hua,Xu, Xiao-Ying,Liu, Hua,Cun, Lin-Feng,Gong, Liu-Zhu. "Highly enantioselective organocatalytic Biginelli reaction". . p. 14802 - 14803. Retrieved 2006.
• 2、 Khaskel, Anamika,Gogoi, Prasanta,Barman, Pranjit,Bandyopadhyay, Biman. "Grindstone chemistry: A highly efficient and green method for synthesis of 3,4-dihydropyrimidin-2-(1H)-ones by l-tyrosine as an organocatalyst: A combined experimental and DFT study". . p. 35559 - 35567. Retrieved 2014.
• 3、 Durai Ananda Kumar, T.,Satyanarayana, K.,Subrahmanyam, C. V. S.,Swathi, N.. "Application of design of experiments (Doe) approach for the optimization of phase-transfer catalyzed biginelli dihydropyrimidinone (dhpm) synthesis". . p. 520 - 531. Retrieved 2021/07/25.
• 4、 Braga, Taniris Cafiero,De Jesus, Itamar Couto Guedes,Soares, Kathleen Viveiros,Guatimosim, Silvia,Da Silva Neto, Leonardo,Da-Silva, Cristiane Jovelina,Modolo, Luzia Valentina,Menezes Filho, José Evaldo Rodrigues,Rhana, Paula,Cruz, Jader Santos,De Fátima, ?ngelo. "A novel H2S releasing-monastrol hybrid (MADTOH) inhibits L-type calcium channels". . p. 671 - 678. Retrieved 2021/01/25.