1281816-34-9

Upstream product

• 1003-85-6 5.5-dimethyl-1,3,2-dioxathiane-2-oxide 
• 103804-80-4 3,3-dimethyl-4-hydroxy butyronitrile 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 79-04-9 chloroacetyl chloride 
• 133111-56-5 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine 
• 116673-94-0 4-chloro-3,3-dimethylbutyronitrile 
• 116673-95-1 5-benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole 
• 536-38-9 4-chlorobenzoylmethyl bromide 

Downstream Products

• 1281816-52-1 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 2-methylbenzoate 
• 1281816-58-7 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 2-(4-chlorophenyl)acetate 
• 1281816-57-6 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 2-phenylacetate 
• 1281816-35-0 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl formate 
• 1281816-56-5 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 2,4-dichlorobenzoate 
• 1281816-36-1 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl acetate 
• 1281816-37-2 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl propionate 
• 1281816-43-0 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 4-methylbenzoate 
• 1281816-41-8 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 4-methoxybenzoate 
• 1281816-50-9 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 2-methoxybenzoate 
• 1281816-54-3 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 2-hydroxybenzoate 
• 1281816-39-4 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 4-chlorobenzoate 
• 1281816-45-2 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 3-chlorobenzoate 
• 1281816-48-5 2-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-2-oxoethyl 2-chlorobenzoate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of licofelone derivatives as anticancer and anti-inflammatory agents

Two C5-substituted licofelone derivatives were developed and investigated for cytotoxicity against mammary (MCF-7 and MDA-MB 231) as well as colon carcinoma (HT-29) cancer cells. Both compounds were at least 2-fold more active than 5-fluorouracil (5-FU) and licofelone against mammary carcinoma cells. At HT-29 cells, they were less active, but nevertheless distinctly as active as 5-FU and still 2-fold more active than licofelone. However, variation of the C5- carboxylic group results in an occasionally remarkable decrease of anti-inflammatory potency in in vitro and in vivo.

Investigations on cytotoxicity and anti-inflammatory potency of licofelone derivatives

A series of C5-substituted licofelone ([2,2-dimethyl-6-(4-chlorophenyl)-7- phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid) derivatives were developed by a parallel synthesis approach and investigated for cytotoxicity against MCF-7 and MDA-MB-231 cells as well as for anti-inflammatory potency in vitro and in vivo. Dependent on the C5-substituent, the compounds showed high selectivity for MCF-7 cells. Especially 2-oxoethyl benzoate derivatives were inactive at the MDA-MB-231 cell line and as active as 5-FU at MCF-7 cells. C5-acetyl (8a), -2-oxoethyl formiate (8e), -2-oxoethyl acetate (8f) and -2-oxoethyl propionate (8g) derivatives showed growth inhibition at both cell lines, comparable with cisplatin. Modifications significantly reduced the inhibitory potency at COX-1 and COX-2 in vitro and in the xylene-induced ear swelling assay in mice. Only compound 8a was equipotent to licofelone, ibuprofen and celecoxibe in vivo.