Rearrangement of 1,6-bis(3,4-dimethoxyphenyl)hexane-1,6-dione (8) gave two isomeric products having cyclopentene moiety. Starting from the major product (3,4-dimethoxyphenyl)[2-(3,4-dimethoxyphenyl)cyclopent-1-en-1-yl]methanone (11), eight new compounds (16-23) were obtained by the reactions such as reduction (by catalytic hydrogenation and NaBH4 ), nitration, 1,4-addition, bromination, and esterification reactions. Carbonic anhydrases (CA, E.C.4.2.1.1) are ubiquitous metalloenzymes present in almost all living organism that catalyze a simple reaction, the conversion of carbon dioxide (CO2 ) and water (H2 O) to bicarbonate ion (HCO3 (-) ) and a proton (H(+) ). CA isoenzymes I and II (hCA I and II) inhibition effects of synthesized eleven new and four known compounds (8-13 and 15-23) were investigated. Inhibition studies of the hCA I and II with 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene derivatives revealed that they possess effective inhibitory potency. Cytosolic hCA I and II isoenzymes were potently inhibited by new synthesized 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene derivatives with Ki s in the range of 313.16-1537.00 nm against hCA I and in the range of 228.31-1927.31 nm against hCA II, respectively.
The reaction of 1,2,3-trimethoxybenzene with adipoyl
chloride in
the presence of AlCl3 gave two isomeric cyclopentene derivatives,
1,6-bis(2,3,4-trimethoxyphenyl)hexane-1,6-dione, and two demethylation
products of aryl methyl ethers. The cyclopentene derivatives including
unconjugated or conjugated enones are products formed in a cascade
reaction resulting from first the Friedel–Crafts acylation
reaction and then aldol condensation. All compounds were optimized
by density functional theory calculated using two functional levels,
B3LYP and M06-2X, with the 6-311+G(d,p) basis set. The structural
properties were established, natural bond orbital analysis of donor–acceptor
interactions was carried out, and charges on the atoms and quantum
chemical reactivity identifiers were determined to compare the strength
of the intramolecular hydrogen bonds formed and their stabilities.
To compare the experimental 1H and 13C NMR chemical
shifts with the calculated values, NMR chemical shift calculations
were carried out using the gauge-invariant atomic orbital method.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.