Synthesis of diarylidenecyclohexanone derivatives as potential anti-inflammatory leads against COX-2/mPGES1 and 5-LOX

Abstract

This study establishes the diarylidenecyclohexanones as good anti-inflammatory pharmacophores with selective high potency against PGE2 and 5-LOX without toxicity towards healthy human cells.

Structure–Property Relationships of Dibenzylidenecyclohexanones

“…Yield: 82%, mp: 178–180 °C (cf. ref ( 26 ): 183–184 °C). 1 H NMR (δ, ppm, J /Hz): 1.81 (m, 2 H, C(4)H 2 ), 2.53 (s, 6 H, 2 MeS), 2.95 (m, 4 H, C(3)H 2 , C(5)H 2 ), 7.33 (d, 4 H, 2 H(3′), 2 H(5′), J = 8.4), 7.49 (d, 4 H, 2 H(2′), 2 H(6′), J = 8.4), 7.66 (s, 2 H, 2 C H Ar).…”

Semisynthesis of ursolic acid‐2‐(2‐thienylidene)‐oxadiazole hybrid molecule and an evaluation of its COX inhibition property

“…It has been reported that Claisen‐Schmidt condensation of 3‐oxo‐UA with various aldehydes led to the synthesis of 2‐arylidene derivatives, which showed increased α‐glucosidase inhibitory activity . Very recently, it has been reported that di(2‐thienylidene) cyclohexanones exhibited increased anti‐inflammatory activity via COX and LOX inhibition pathways . Inspired by the above literature reports and due to our continued interest in the synthesis and screening of OA and UA derivatives, we have done the synthesis and evaluation of a novel UA hybrid molecule as discussed below.…”

Tandem Hydroamination/Cyclization Access to N-2(5H)-Furanone Derivatives for COX-2 Inhibitor

“…Introduction of a one-carbon spacer group between the central pyrrole ring and the cycloalkyl or aryl substituent offers more flexibility, resulting in more potent COX-2 inhibitors. , In contrast, the COX inhibitory activity and selectivity of compounds 1r – 1v decreased. It is indicated that the 2-substituent introduced methyl, and methoxy in the pyrrole ring might affect the combination with COX-1 to COX-2 due to steric hindrance. , …”