Licofelone

Base Information

• Chemical Name: Licofelone
• CAS No.: 156897-06-2
• Molecular Formula: C23H22ClNO2
• Molecular Weight: 379.886
• European Community (EC) Number: 694-581-3
• UNII: P5T6BYS22Y
• DSSTox Substance ID: DTXSID40166154
• Nikkaji Number: J592.536C
• Wikipedia: Licofelone
• Wikidata: Q3832015
• NCI Thesaurus Code: C63957
• Pharos Ligand ID: B344SSBLAMSK
• Metabolomics Workbench ID: 144643
• ChEMBL ID: CHEMBL300982
• Mol file: 156897-06-2.mol

Synonyms:(2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetic acid;licofelone;ML 3000;ML-3000

Chemical Property of Licofelone

Chemical Property:

• Appearance/Colour: Yellowish solid
• Vapor Pressure: 1.76E-12mmHg at 25°C
• Melting Point: 162-163 °C
• Refractive Index: 1.626
• Boiling Point: 539.7 °C at 760 mmHg
• PKA: 4.47±0.10(Predicted)
• Flash Point: 280.2 °C
• PSA: 42.23000
• Density: 1.23 g/cm³
• LogP: 5.68490
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Methanol
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 379.1339066
• Heavy Atom Count: 27
• Complexity: 537

Purity/Quality:

Licofelone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2=C(C(=C(N2C1)CC(=O)O)C3=CC=C(C=C3)Cl)C4=CC=CC=C4)C
• Description: Cross-talk between lipoxygenase (LO) and cyclooxygenase (COX) pathways has been observed in human osteoarthritic synovial explants which creates an arachidonic acid shunting phenomenon, stimulating interleukin-1β (IL-1β) synthesis. Licofelone is a dual inhibitor of cyclooxygenase (COX) and lipoxygenase (LO) pathways, that decreases levels of prostaglandin E2, leukotriene B4, and lipoxins and prevents lipopolysaccharide-stimulated IL-1β expression. The IC50 values for inhibition of human thrombocyte COX and human 5-LO are 0.16 μM and 0.23 μM, respectively. Unlike other non-steroidal anti-inflammatory drugs, licofelone causes little or no damage to the gastric mucosa in rabbit parietal cells. This is presumably the result of licofelone’s affects on acid-secretory mechanisms, mediated by the inhibition of 5-LO activity.
• Uses: Dual inhibitor of cyclooxygenase and 5-lipoxygenase. Anti-inflammatory Dual inhibitor of cyclooxygenase and 5-lipoxygenase. Anti-inflammatory.

Technology Process of Licofelone

There total 24 articles about Licofelone 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: 77.0%

ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate (156897-35-7) → licofelone (156897-06-2)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 80 ℃;

DOI:10.1021/jo971480o

Reference yield: 71.0%

methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate (1061179-20-1) → licofelone (156897-06-2)

Guidance literature:

methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate; With sodium hydroxide; water; In ethanol; for 0.5h; Heating / reflux;

With hydrogenchloride; In ethanol; water; Product distribution / selectivity;

Reference yield: 60.0%

[6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester (262426-70-0) → licofelone (156897-06-2)

Guidance literature:

[6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester; With sodium hydroxide; water; In ethanol; for 8h; Heating / reflux;

With hydrogenchloride; In ethanol; water; Product distribution / selectivity;

upstream raw materials:

ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

1-chloro-3-phenyl-2-propyne

2,2-dimethyl-5-phenylpent-4-ynal

2,2-dimethyl-7-phenyl-2,3,5,6-tetrahydro-1H-pyrrolizin-6-one

Downstream raw materials:

4-bromobutyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

8-iodooctyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

12-bromododecyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

2-bromoethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

Refernces

• 1、 Liu, Wukun,Zhou, Jinpei,Bensdorf, Kerstin,Zhang, Huibin,Liu, Haoran,Wang, Yubin,Qian, Hai,Zhang, Yanchun,Wellner, Anja,Rubner, Gerhard,Huang, Wenlong,Guo, Cancheng,Gust, Ronald. "Investigations on cytotoxicity and anti-inflammatory potency of licofelone derivatives". . p. 907 - 913. Retrieved 2011/04/19.
• 2、 -. "A NEW METHOD OF MANUFACTURING 2-(6-(4-CHLOROPHENYL)-2,2-DIMETHYL-7-PHENYL-2,3-DIHYDRO-LH-PYRROLIZINE-5-YL)ACETIC ACID (LICOFELONE)". Page/Page column 15. . Retrieved 2009/06/27.