Stereochemical calculations on substituted benzene and benzene-like compounds

Semi-empirical calculations have been done on hexaphenyl benzene, triphenyl benzene ands-triphenyl triazine free molecules and the results are compared with X-ray crystal structure studies. The conformation of isolated molecule differs from that found in crystals. The agreement improves when packing forces are also included in the minimum energy calculations. Contribution No. 419, from the Department of Crystallography and Biophysics, University of Madras, Guindy, Madras 600025.     

Synthesis of Some Novel 1,2-Disubstituted Benzimidazole-5-carboxylates via One-Pot Method Using Sodium Dithionite and Its Effect on N-Debenzylation

A series a novel of 1,2-disubstituted benzimidazole-5-carboxylates were prepared by the one-pot nitroreductive cyclization route using sodium dithionite, and its effect on N-debenzylation has been described. Different ethyl 4-(alkyl/arylamino)-3-nitrobenzoates were reacted with various aromatic/heteroaromatic aldehydes in dimethyl sulfoxide to yield the target benzimidazoles in good yield and purity. Wide varieties of aldehydes used for the cyclization were found to be susceptible under the reaction conditions. This method afforded the products within a very short reaction time and isolation was an easy workup procedure. Debenzylation resulting in the cleavage of the N-benzyl group was observed under experimental conditions with sodium dithionite without the aid of any cocatalyst and the presence of ethanol increased the extent of debenzylation.     

Antidiabetic,Antiglycation, and Antioxidant Activities of Ethanolic Seed Extract of Passiflora edulis and Piceatannol In Vitro

The objective of this work was to investigate the antidiabetic, antiglycation, and antioxidant potentials of ethanolic extract of seeds of Brazilian Passiflora edulis fruits (PESE), a major by-product of the juice industry, and piceatannol (PIC), one of the main phytochemicals of PESE. PESE, PIC, and acarbose (ACB) exhibited IC₅₀ for alpha-amylase, 32.1 ± 2.7, 85.4 ± 0.7, and 0.4 ± 0.1 µg/mL, respectively, and IC₅₀ for alpha-glucosidase, 76.2 ± 1.9, 20.4 ± 7.6, and 252 ± 4.5 µg/mL, respectively. The IC₅₀ of PESE, PIC, and sitagliptin (STG) for dipeptidyl-peptidase-4 (DPP-4) was 71.1 ± 2.6, 1137 ± 120, and 0.005 ± 0.001 µg/mL, respectively. PESE and PIC inhibited the formation of advanced glycation end-products (AGE) with IC₅₀ of 366 ± 1.9 and 360 ± 9.1 µg/mL for the initial stage and 51.5 ± 1.4 and 67.4 ± 4.6 µg/mL for the intermediate stage of glycation, respectively. Additionally, PESE and PIC inhibited the formation of β-amyloid fibrils in vitro up to 100%. IC₅₀ values for 1,1-diphenyl-2-picrylhydrazyl radical (DPPH^•) scavenging activity of PESE and PIC were 20.4 ± 2.1, and 6.3 ± 1.3 µg/mL, respectively. IC₅₀ values for scavenging hypochlorous acid (HOCl) were similar in PESE, PIC, and quercetin (QCT) with values of 1.7 ± 0.3, 1.2 ± 0.5, and 1.9 ± 0.3 µg/mL, respectively. PESE had no cytotoxicity to the human normal bronchial epithelial (BEAS-2B), and alpha mouse liver (AML-12) cells up to 100 and 50 µg/mL, respectively. However, 10 µg/mL of the extract was cytotoxic to non-malignant breast epithelial cells (MCF-10A). PESE and PIC were found to be capable of protecting cultured human cells from the oxidative stress caused by the carcinogen NNKOAc at 100 µM. The in vitro evidence of the inhibition of alpha-amylase, alpha-glucosidase, and DPP-4 enzymes as well as antioxidant and antiglycation activities, warrants further investigation of the antidiabetic potential of P. edulis seeds and PIC.