Monastrol

Base Information

• Chemical Name: Monastrol
• CAS No.: 329689-23-8
• Molecular Formula: C14H16 N2 O3 S
• 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: 329689-23-8.mol

Synonyms:monastrol

Chemical Property of Monastrol

Chemical Property:

• Vapor Pressure: 2.13E-08mmHg at 25°C
• Melting Point: 190-193℃ (ethanol )
• Refractive Index: 1.648
• Boiling Point: 441.3°C at 760 mmHg
• PKA: 9.63±0.10(Predicted)
• Flash Point: 220.7°C
• PSA: 109.72000
• Density: 1.34±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 1.92380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated)
• 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:

99% ^*data from raw suppliers

Monastrol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=S)NC1C2=CC(=CC=C2)O)C
• Uses: Monastrol is a small molecule that inhibits mitotic kinesin Eg5 and arrests cells in mitosis with monopolar spindles (1, 2).Monastrol is an anticancer agent against MCF-7 tumor cells (3).

Technology Process of Monastrol

There total 5 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: 92.0%

ammonium thiocyanate (1147550-11-5) + ethyl acetoacetate (141-97-9) + meta-hydroxybenzaldehyde (100-83-4) → monastrol (329689-23-8,254753-54-3,268739-54-4)

Guidance literature:

In isopropyl alcohol; for 2h; Reflux;

DOI:10.2174/1570178617999201006200102

Reference yield: 90.0%

thiouronium hydrogensulfate (37622-16-5) + ethyl acetoacetate (141-97-9) + meta-hydroxybenzaldehyde (100-83-4) → monastrol (329689-23-8,254753-54-3,268739-54-4)

Guidance literature:

With thiourea; at 65 ℃; for 3h;

DOI:10.3987/COM-04-10312

upstream raw materials:

ethyl acetoacetate

meta-hydroxybenzaldehyde

thiourea

thiouronium hydrogensulfate

Downstream raw materials:

C₁₆H₁₆N₂O₄S

Refernces

• 1、 Razavian Mofrad, Raheleh,Kabirifard, Hassan,Tajbakhsh, Mahmood,Firouzzadeh Pasha, Ghasem. "Amine-functionalized nano-NaY zeolite for the synthesis of N-acetyl pyrazoles and dihydropyrimidines". . . Retrieved 2021/08/23.
• 2、 Potdar, Santoshkumar M.,Deshmukh, Aishwarya R.,Waghmode, Krishnakant T.. "New Strategy for Synthesis of Anticancer Active Piperastrol, Enastron Using Ammonium Sulfocyanate". . p. 924 - 927. Retrieved 2022/03/01.