Effective Synthesis of 1,5-Disubstituted 2,1-Benzisothiazol-3(1<i>H</i>)-ones

Diabetes mellitus is a chronic metabolic disorder in which the pancreas secretes insulin but the body cells do not recognize it. As a result, carbohydrate metabolism causes hyperglycemia, which may be fatal for various organs. This disease is increasing day by day and it is prevalent among people of all ages, including young adults and children. Acarbose and miglitol are famous alpha-glucosidase inhibitors but they complicate patients with the problems of flatulence, pain, bloating, diarrhea, and loss of appetite. To overcome these challenges, it is crucial to discover new anti-diabetic drugs with minimal side effects. For this purpose, benzotriazinone sulfonamides were synthesized and their structures were characterized by FT-IR, 1H-NMR and 13C-NMR spectroscopy. In vitro alpha-glucosidase inhibition studies of all synthesized hybrids were conducted using the spectrophotometric method. The synthesized compounds revealed moderate-to-good inhibition activity; in particular, nitro derivatives 12e and 12f were found to be the most effective inhibitors against this enzyme, with IC50 values of 32.37 ± 0.15 µM and 37.75 ± 0.11 µM. In silico studies, including molecular docking as well as DFT analysis, also strengthened the experimental findings. Both leading compounds 12e and 12f showed strong hydrogen bonding interactions within the enzyme cavity. DFT studies also reinforced the strong binding interactions of these derivatives with biological molecules due to their lowest chemical hardness values and lowest orbital energy gap values.

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“…m.p. 220 °C) [ 44 ]. FT-IR (v-cm −1 ): 1355 (NO 2 ), 1578 (NO 2 ), 1680 (C=O), 1738 (C=O), 3198 (N-H).…”

Section: Experiments Workmentioning

confidence: 99%

Experimental and Computational Analysis of Newly Synthesized Benzotriazinone Sulfonamides as Alpha-Glucosidase Inhibitors

et al. 2022

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“…Melting points of the compounds were determined by using a digital melting point apparatus and are uncorrected. 2-Aminobenzamide derivatives were prepared according to reported procedures. − …”

Section: Experimental Sectionmentioning

confidence: 99%

A Serendipitous Synthesis of 11a-Hydroxy-11,11a-dihydrobenzo[e]indeno[2,1-b][1,4]diazepine-10,12-dione Derivatives by Condensation of 2-Aminobenzamides with Ninhydrin in Water

et al. 2016

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Ninhydrin undergoes an unprecedented condensation reaction with various 2-aminobenzamide derivatives in boiling water to afford 11a-hydroxy-11,11a-dihydrobenzo[e]indeno[2,1-b][1,4]diazepine-10,12-dione derivatives. These hitherto unreported products are easily isolated in high yield by a simple filtration step. An interesting "ortho effect" was observed in the condensation reaction of ninhydrin with 2-amino-N-phenylbenzamide derivatives having an ortho- substituent in the N-phenyl moiety wherein the corresponding expected 3'-phenyl-1'H-spiro[indene-2,2'-quinazoline]-1,3,4'(3'H)-triones were obtained.

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ChemInform Abstract: Effective Synthesis of 1,5‐Disubstituted 2,1‐Benzisothiazol‐3(1H)‐ones.

et al. 2012

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Effective Synthesis of 1,5-Disubstituted 2,1-Benzisothiazol-3(1H)-ones. -An improved procedure is used for the preparation of 1,5-disubstituted benzoisothiazoles, e.g. (VI). The free amino group at the 5-position is suitable for further derivatization. -(KHARUL*, R. K.; PRAJAPATI, P. N.; THORAVE, A. A.; SHAH, H. A.; DHAR, A.; JOSHI, D. A.; JAIN, M. R.; PATEL, P. R.; PANCHOLI, S. S.; Synth. Commun. 41 (2011) 22, 3265-3279, http://dx.

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Effective Synthesis of 1,5-Disubstituted 2,1-Benzisothiazol-3(1H)-ones

Cited by 6 publications

References 5 publications

Experimental and Computational Analysis of Newly Synthesized Benzotriazinone Sulfonamides as Alpha-Glucosidase Inhibitors

Experimental and Computational Analysis of Newly Synthesized Benzotriazinone Sulfonamides as Alpha-Glucosidase Inhibitors

A Serendipitous Synthesis of 11a-Hydroxy-11,11a-dihydrobenzo[e]indeno[2,1-b][1,4]diazepine-10,12-dione Derivatives by Condensation of 2-Aminobenzamides with Ninhydrin in Water

ChemInform Abstract: Effective Synthesis of 1,5‐Disubstituted 2,1‐Benzisothiazol‐3(1H)‐ones.

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