Anti-tubercular activity of novel class of spiropyrrolidine tethered indenoquinoxaline heterocyclic hybrids

Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds

“…Ionic liquid chemistry was utilized to prepare 4′-nitrospiro[indeno[1,2- b ]quinoxaline-11,2′-pyrrolidines] 47 by the cycloaddition reaction of nitroalkenes 36 with azomethine ylide (generated from indenoquinoxalinone 45 and L -phenylalanine 46 ) in an ionic liquid [bmim]Br. Some of the synthesized agents revealed antimycobacterial properties ( Mycobacterium tuberculosis H37Rv) with an efficacy comparable to that of ethambutol (reference standard) [ 34 ]. Similarly, spiro compounds 49 were obtained by using L -histidine 48 instead of L -phenylalanine 46 in this reaction.…”

Recent synthetic strategies of spiro-azetidin-2-one, -pyrrolidine, -indol(one) and -pyran derivatives-a review

“…60 The spiro pyrrolidine tethered indenoquinoxaline heterocyclic hybrids 68 were synthesized by heating of b-nitrostyrene (67), o-phenylenediamine (63), ninhydrin (64), and L-phenylalanine (66) with stirring in [bmim]Br medium for 1 h at 100 °C (Scheme 17). 61 Interestingly, the reaction was completely regioselective: the expected regioisomer 69 was not formed (Scheme 17). 61 In vitro activity of these spiroheterocyclic hybrids against Mycobacterium tuberculosis H37Rv, using MABA assay, revealed that the compound with nitro group on the phenyl ring is the most active candidate (1.56 mg mL −1 ) of the series and has an activity similar to that of the standard drug Ethambutol.…”

Salicylic Acid: Synthetic Strategies and Their Biological Activities

“…Shchegolkov et al have synthesised polyfluorinated derivatives of salicylic acid of the type 13 a-d and 14 a-e (Scheme 4). [24] The reaction involved the treatment of penta- [12] 2 Anti-inflammatory Park et al [13] 3 Anti-inflammatory Meshikhes et al [14] 4 Anti-inflammatory Li et al [15] 5 Antipyretic Mamatha et al [16] 6 Antithrombotic Schmidt et al [17] 7 Antineoplastic Li et al [18] 8 Anti-inflammatory Maturana et al [19] 9 Antidiarrheal Svensson et al [20] 10 Antitubercular Arumugam et al [21] ChemistrySelect fluorobenzoic acid 11 a-d with magnesium methoxide and toluene to yield an intermediate 12 a which further reacted with phosphorous pentachloride and hydrogen bromide to obtain tetrafluorosalicylic acid 13 a which on reaction with acetic anhydride and sulfuric acid yielded 2-acetoxy-3,4,5,6tetrafluorobenzoic acid 14 a-e. The synthesised compounds were screened for their permeability, COX-1 inhibitory action (in vitro), acute toxicity, anti-inflammatory and analgesic activities (in vivo).…”