Search

Suzuki coupling reaction is one of the useful methods for carbon‐carbon bond formation. In the present study, the aforementioned method is used to expand an aryl appendage on the indolenine nucleus of diastereomeric syn‐ and anti‐6‐bromo‐4a‐isopropyl‐2‐methyl‐2,3,4,4a‐tetrahydro‐1H‐carbazole analogs. Therefore, two sets of new diastereomeric Suzuki‐coupled products (16 compounds) were prepared. For this, diastereomeric syn‐ and anti‐6‐bromo‐4a‐isopropyl‐2‐methyl‐2,3,4,4a‐tetrahydro‐1H‐carbazole analogs were treated with arylboronic acids in the presence of palladium catalyst under thermal catalysis. Structures of synthesized compounds were inferred using spectroscopic studies. DFT‐based quantum chemical calculations were used to decipher structural attributes and stability of diastereomeric bromo‐2,3,4,4a‐tetrahydro‐1H‐carbazoles and their Suzuki‐coupled products, which revealed chair conformation for methylcyclohexane ring of syn‐compound while twist‐boat conformation for diastereomeric anti‐compound. syn‐Compound was found more stable than its anti‐isomer based on DFT‐calculations. Also, results demonstrated agreement between experimental and theoretical chemical shift values in NMR spectra with some deviations. Thus, structural elucidation based on computational advances in combination with the spectroscopic method can provide a powerful method for studying and comparing the structural attributes of diastereomeric compounds. [ABSTRACT FROM AUTHOR]

α‐Glucosidase inhibition is one of the key targets for controlling diabetes. In consideration of that, new L‐valinol derived fluorinated sultam triazoles were synthesized as α‐glucosidase inhibitors, and their activities were further compared with the precursor molecules (sulfonamides, sultams, and N‐propargyl sultams). Primarily, all the synthesized sultam triazoles and precursor compounds (sulfonamides, sultams, and N‐propargyl sultams) were evaluated for different biological activities, including cytotoxicity, anti‐inflammatory, and α‐glucosidase inhibitory activities. Results revealed that only sultam triazoles exhibited inhibition against α‐glucosidase enzyme (IC50 values: 173 to 194 μM) using acarbose (IC50: 875.85 ± 2.03 μM) as the standard drug. These sultam triazoles were prepared after few steps, starting from enantiopure L‐valinol, which differ electronically (due to the position of fluorine atom and different positions on aromatic ring). Structures of all the compounds were evaluated using different spectroscopic techniques. Kinetics of active compounds were also investigated to find their mode of inhibition. [ABSTRACT FROM AUTHOR]

The carbazoles are synthesized from L-menthone and substituted phenyl hydrazines in acetic acid and show promising inhibitory activities against acetyl- and butyrylcholinesterase. [ABSTRACT FROM AUTHOR]