Cilostamide

Base Information

• Chemical Name: Cilostamide
• CAS No.: 68550-75-4
• Molecular Formula: C20H26N2O3
• Molecular Weight: 342.438
• UNII: 45S5605Q18
• DSSTox Substance ID: DTXSID3045140
• Nikkaji Number: J18.750J
• Wikipedia: Cilostamide
• Wikidata: Q15634085
• NCI Thesaurus Code: C76315
• Pharos Ligand ID: NMLVHY3HHZW1
• ChEMBL ID: CHEMBL34431
• Mol file: 68550-75-4.mol

Synonyms:cilostamide;N-cyclohexyl-N-methyl-4-(1,2-dihydro- 2-oxo-6-quinolyloxy)butyramide;OPC-3689

Chemical Property of Cilostamide

Chemical Property:

• Vapor Pressure: 4.29E-14mmHg at 25°C
• Melting Point: 186～188℃
• Refractive Index: 1.585
• Boiling Point: 594.3 °C at 760 mmHg
• PKA: 11.12±0.70(Predicted)
• Flash Point: 313.2 °C
• Density: 1.18 g/cm³
• Storage Temp.: 0-6°C
• Solubility.: Soluble in DMSO (up to 30 mg/ml).
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 342.19434270
• Heavy Atom Count: 25
• Complexity: 499

Purity/Quality:

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

Cilostamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C1CCCCC1)C(=O)CCCOC2=CC3=C(C=C2)NC(=O)C=C3
• Description: Cilostamide (68550-75-4) is a selective inhibitor of phosphodiesterase-3 (PDE3). Displays limited selectivity for PDE3A versus PDE3B (IC50 = 27 and 50 nM).1,2 Blocks PKB/Akt signaling pathway downstream via inhibition of Akt-activated PDE3B.3 Cilostamide reverses the effect of leptin on food intake and body weight.4
• Uses: Serotonin receptor ligand Cilostamide (OPC 3689) is a specific phosphodiesterase 3 (PDE3) inhibitor.

Technology Process of Cilostamide

There total 16 articles about Cilostamide 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: 80.0%

N-methylcyclohexylamine (100-60-7) + 4-(2-oxo-1,2-dihydro-quinolin-6-yloxy)-butyric acid (58899-33-5) → cilostamide (68550-75-4)

Guidance literature:

4-(2-oxo-1,2-dihydro-quinolin-6-yloxy)-butyric acid; With 1,8-diazabicyclo[5.4.0]undec-7-ene; isobutyl chloroformate; In chloroform; at 20 ℃; Cooling with ice;

N-methylcyclohexylamine; In chloroform; at 20 ℃; for 3h;

DOI:10.1515/HC.2008.14.3.183

Reference yield:

methyl bromoacetate + N-methylcyclohexylamine (100-60-7) + 4-(2-oxo-1,2-dihydro-quinolin-6-yloxy)-butyric acid (58899-33-5) → cilostamide (68550-75-4)

Guidance literature:

With pyridine; In tetrahydrofuran;

Reference yield:

(E)-3-{2-Amino-5-[3-(cyclohexyl-methyl-carbamoyl)-propoxy]-phenyl}-acrylic acid (105763-72-2) → cilostamide (68550-75-4)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; toluene; for 48h; Yield given; Heating;

DOI:10.1021/jm00385a011

upstream raw materials:

N-methylcyclohexylamine

4-(2-oxo-1,2-dihydro-quinolin-6-yloxy)-butyric acid

(E)-3-{2-Amino-5-[3-(cyclohexyl-methyl-carbamoyl)-propoxy]-phenyl}-acrylic acid

2-nitro-5-hydroxybenzaldehyde

Downstream raw materials:

N-cyclohexyl-N-methyl-4-(1,2-dihydro-1-methyl-2-oxo-6-quinolyloxy)butyramide

6-[3-(N-cyclohexyl-N-methylaminothiocarbonyl)propoxy]carbostyril

4-(1-Benzyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-N-cyclohexyl-N-methyl-butyramide

Refernces

• 1、 Jones,Venuti,Alvarez,Bruno,Berks,Prince. "Inhibitors of cyclic AMP phosphodiesterase. 1. Analogues of cilostamide and anagrelide". . p. 295 - 303. Retrieved 2007/10/02.
• 2、 Nishi,Tabusa,Tanaka,Ueda,Shimizu,Kanbe,Kimura,Nakagawa. "Studies on 2-oxoquinoline derivatives as blood platelet aggregation inhibitors. III. N-cyclohexyl-N-(2-hydroxyethyl)-4-(1,2-dihydro-2-oxo-6-quinolyloxy) butyramide and related compounds". . p. 852 - 860. Retrieved 2007/10/02.