Synthesis, reactions and biological activity of 3-arylidene-5-(4-methylphenyl)-2(3H)-furanones?

Abstract

3-Arylidene-5-(4-methylphenyl)-2(3H)-furanones 2a-m were prepared from 3-(4-methyl-benzoyl)propanoic acid 1 and several aromatic aldehydes. Some of the selected furanones were reacted with ammonia gas and benzylamine to give corresponding 3-arylidene-1,3-dihydro-5-(4-methylphenyl)-2H-pyrrol-2-ones 3a-h and 3-arylidene-1-benzyl-1,3-dihydro-5-(4-methylphenyl)-2H--pyrrol-2-ones 4a-f, respectively, which were characterized on the basis of IR, 1 H-NMR, mass spectral data and elemental analysis results. These compounds were tested for their anti-inflammatory and antibacterial activities. The compounds, which showed significant anti-inflammatory activity, were further screened for their analgesic and ulcerogenic activities. Three new compounds (2e, 2h and 4d), out of twenty-seven showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. The antibacterial activity is expressed as the corresponding MIC values.

Pyridazinones and pyrrolones as promising Scaffolds in Medicinal Chemistry

“…Pyrrolone considered as an important nucleus with variable biological activities including antibacterial [72], antiinflamatory [72], analgesic, antimycobacterial [73], antidepressant [74], antiviral [75] and antitumor activities [76]. (Figure 17)…”

“…A series of pyrrol-2-one was prepared by A. Husain et al, [72], the anti-inflammatory activity results showed that compound 81 has comparable activity to declofenac. S. Khokra et al, [77] synthesized a series of quinolinylpyrrolone derivatives and tested as anti-inflammatory agents using carrageenan induced paw edema.…”

“…A. Husain et al, [72] introduced a series of pyrrole-2-one derivatives, the pyrrole-2-one 90 showed significant activity against S. aureus with MIC (6.5 µg/mL) and good activity against E.coli with MIC (15 µg/mL. A novel 2(3H) pyrrolone derivatives were synthesized by A. Ahmad et al, [81] and evaluated as antibacterial agents.…”

Utility of novel 2-furanones in synthesis of other heterocyclic compounds having anti-inflammatory activity with dual COX2/LOX inhibition

“…These heterocycles acquired an obvious medicinal interest as antimicrobial [22][23][24] , antiviral [25][26][27] , antimycobacterial 28,29 , and anti-cancer agents [30][31][32] . Literature is enriched with different 2-furanones subjected to ring opening to form 2-pyrrolone, pyridazinone, and oxadiazole derivatives, all have high activity as anti-inflammatory 24,[33][34][35][36][37][38][39][40][41] . As shown in Figure 1, 2-furanone derivatives Ia-c were reported to exhibit comparable anti-inflammatory activity to that of diclofenac 33,35,36 , while 2-pyrrolone derivatives II, IIIa-b, and IV were reported to have comparable anti-inflammatory activity to that of indomethacin, ibuprofen, and diclofenac, respectively 24,[34][35][36] .…”

Synthesis of Heterocyclic and Non-heterocyclic Compounds Derived from Novel 2-Furanones and Evaluation of their Anti-viral Activity

“…2-Furanones; well-known heterocyclic derivatives; had attracted a great attention during the last decade due to facile ring opening and conversion to other heterocycles; pyrrolones, pyridazinones, pyrazoles and oxadizoles. These heterocycles acquired an obvious medicinal interest as antimicrobial [6][7][8] , anti-inflammatory [8][9][10][11][12][13][14][15][16] , antimycobacterial 18,19 and anti-cancer agents [20][21][22] Literature is also enriched with furanone derivatives and other heterocyclic and non-heterocyclic compounds derived from them having antiviral activities [23][24][25] , as shown in Figure 1; 2-furanone derivative A showed remarkable activity comparable to that of zanamivir 23 , and furanone derivative B which is reported as potent anti-adenoviral agent. 26 pyridazinone D were reported to have promising antiviral activities against anti-avian influenza virus H5N1 virus.…”