Bio-Potent (5-Chloro-2-Thienyl)-3-(Substituted Phenyl) Bicyclo[2.2.1]Heptane-2-yl Methanone Derivatives

Abstract

A series of (5-chloro-2-thienyl)(3-(substituted phenyl) bicyclo[2.2.1]hept-5-en-2-yl)methanones have been synthesized by fly-ash catalyzed [4+2] cycloaddition Diels-Alder reaction of cyclopentadiene and 5-chloro-2-thienyl chalcones under cooling conditions. The yields of the methanones are more than 60%. The synthesized (5-chloro-2-thienyl)(3-(substituted phenyl) bicyclo[2.2.1]hept-5-en-2-yl)methanones are characterized by their physical constants and spectral data. The antimicrobial, antioxidant and insect antifeedant activities of synthesized methanones have been studied using their respective bacterial, fungal strains, DPPH radical scavenging activity and Dethler's leaf-discs bioassay method.

Green approach using water mediated Diels-Alder reaction for the synthesis of some 2-(4-bromo-1-naphthyl)-3-(aryl) bicyclo[2.2.1]hept-5-ene methanones and evaluation of their antimicrobial and antioxidant activities

“…The diphenyl picryl hydrazyl (DPPH) radical scavenging activity technique [35] was used for the measurement of the antioxidant activity of all prepared methanones. About 20 ml of sodium acetate buffer solution was prepared by dissolving 1.64 g of sodium acetate in 15 ml of water and 150 µl of acetic acid, and the final volume was adjusted to 20 ml of water.…”

“…The synthesized ketones were characterized by their analytical data, physical constants (Table 1), and spectroscopic data, as follows. Based on earlier reports [1,3,4,9,[21][22][23][24][25] -1-yl)((1S,2S,3S,4R)-3-(3-bromophenyl) Bromonaphthalen-1-yl)((1S,2S,3S,4R)-3-(4-chlorophenyl) Bromonaphthalen-1-yl)((1S,2S,3S,4R)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-en-2-yl) Bromonaphthalen-1-yl)((1S,2S,3S,4R)-3-(4-nitrophenyl) …”

“…The antioxidant activities of synthesized (4-bromo-1-naphthyl)-(3-(substituted phenyl)bicycle [2.2.1]hept-5-en-2-yl)methanones were measured using the diphenyl picryl hydrazyl (DPPH) radical scavenging method [35]. The observed antioxidant activities of methanones are presented in Table 4.…”

“…The water mediated environmentally benign hetero Diels-Alder [4+2] cycloaddition reaction was 700 times faster than in nonaqueous phase [3]. Numerous catalysts were employed to perform this Diels-Alder reaction, such as specific and chiral Lewis acids [3,15], chiral bases [16], chiral amines [5,6], non-natural α-amino acids [17], bimodal catalysts [18], hydrogen bonding interactions [1], chiral silver phosphates [4], Ti(IV) compounds [19], alkaline salts [20], lithium perchlorate [10], pyridyl-modified RNA [11], fly-ash [21][22][23][24][25], carbocations [13], Cu(II) compounds [2], organo-tungstates with ionicliquids [26], ribozymes [27], low melting carbohydrates [28], and metal-free non-covalent compounds [29]. Fard et al have studied the solvent effect and performed DFT analysis of acid catalyzed Diels-Alder cycloaddition reaction of 2,5-dimethyl furan and maleic anhydride [30].…”

“…These ketones possess important biological potential such as antimicrobial, antioxidant, insect antifeedant [35][36][37], cytotoxic [38], cardiotonic, antiarrhythmic, and antishock activities [39], and as fragrance ingredients [40] and anticonvulsants [41]. Recently, Thirunarayanan prepared some bicyclic methanones through a water-mediated Diels-Alder reaction catalyzed by fly-ash:H 2 O catalyst and studied the antimicrobial, antioxidant, and insect antifeedant activities [35][36][37]. The literature review reveals that there is no information available about the water-mediated fly-ash catalyzed Diels-Alder[4+2] cycloaddition reaction for the synthesis of titled compounds.…”