N-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide

Base Information

• Chemical Name: N-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide
• CAS No.: 72926-24-0
• Molecular Formula: C13H15N3O2S
• Molecular Weight: 277.347
• Hs Code.: 2934999090
• European Community (EC) Number: 663-070-7
• UNII: ZA4OIM722G
• DSSTox Substance ID: DTXSID40972156
• Wikidata: Q27166285
• Pharos Ligand ID: 6K4K2XNR23Z3
• ChEMBL ID: CHEMBL1413473
• Mol file: 72926-24-0.mol

Synonyms:K 858;K-858;K858 cpd

Chemical Property of N-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide

Chemical Property:

• Melting Point: 216-217 °C(Solv: ethanol (64-17-5))
• PKA: 8.61±0.40(Predicted)
• PSA: 90.56000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 2.07550
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 277.08849790
• Heavy Atom Count: 19
• Complexity: 418

Purity/Quality:

97% ^*data from raw suppliers

K 858 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1=NN(C(S1)(C)C2=CC=CC=C2)C(=O)C
• Description: K858 (72926-24-0) is a selective mitotic kinesin Eg5 inhibitor (IC50 = 1.3 μM) which acts in an ATP-noncompetitive manner.1,2?It is at least 150-fold more selective for Eg5 than other members of the kinesin superfamily. K-858 blocks centrosome separation, activates the spindle checkpoint and induces mitotic arrest accompanied by the formation of monopolar spindles. Displays no effect on microtubule polymerization. Selectively displays antiproliferative effects via induction of mitotic cell death in cancer cells over nontransformed cells.1
• Uses: K 858 is a selective ATP-uncompetitive mitotic kinesin Eg5 inhibitor.

Technology Process of N-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide

There total 2 articles about N-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide 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: 86.0%

acetic anhydride (108-24-7) + [(1-aza-2-phenylprop-1-enyl)amino]aminomethane-1-thione (132121-93-8) → (±)-N-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide (72926-24-0)

Guidance literature:

for 2h; Reflux;

DOI:10.1016/j.ejmech.2018.07.006

Reference yield: 73.0%

acetophenonethiosemicarbazone (2302-93-4) + acetic anhydride (108-24-7) → (±)-N-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide (72926-24-0)

Guidance literature:

at 100 ℃; for 1h;

DOI:10.1021/jo01296a025

Reference yield: 78.0%

(±)-N-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide (72926-24-0) → 4-acetyl-2-acetylamino-5-methyl-5-phenyl-Δ2-1,3,4-thiadiazoline 1-oxide

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; Ambient temperature;

DOI:10.1039/c39820000901

upstream raw materials:

acetophenonethiosemicarbazone

acetic anhydride

[(1-aza-2-phenylprop-1-enyl)amino]aminomethane-1-thione

Downstream raw materials:

1-(5-amino-2-methyl-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-ethan-1-one