Study the pharmacological potential of 1,2,4-thiadiazine 1,1-dioxides: A minireview

Abstract

Study of the pharmacological activity of new heterocyclic scaffolds becomes a passion of many medicinal chemists around the world. 1,2,4-thiadiazine 1,1-dioxide derivatives are one of the heterocyclic derivatives that haveattracted researchers' attention since the early 1940's. In spite of this, however, the study of the pharmacological activities of this nucleus remains scant and needs to shed lighter on it. Therefore, in this review, the authors in this review collected all the families that included this nucleus whose biological activities were studied for the period between 1993 and 2020 in order to get an idea of the effectiveness of these compounds and highlighted the most effective ones. In addition, knowing the pharmacological aspects that had not been studied previously to focus more on them in the future by interested researchers.

Efficient Synthesis of Fused Heterocycles Incorporating Pyrazole/Thiadiazine or Pyrazole/Thiadiazepine Fragments Using N‐Chlorosulfonyltrihaloacetimidoyl Chlorides

“…Yield 235 mg (33 %), yellow solid (acetone-benzene, 1 : 1). mp 181-182 ο C. 1 H-NMR (DMSO-d 6 , 400 MHz) δ 9.50 (br, 1H), 8.46 (br, 1H), 7.82 (s, 1H), 3.77 (s, 3H), 2.41 (s, 3H). 13 Typical procedure for the synthesis of compounds 15 a,b.…”

“…Recent reviews have summarized the advances in the biological applications of heterocyclic compounds containing 1,2,4-thiadiazine dioxides. [1,2] Pyrazole derivatives have demonstrated remarkable biological activities, including anti-inflammatory, analgesic, antimicrobial, and anticancer properties. [3,4] Similarly, thiadiazines have exhibited diverse pharmacological profiles, such as antimicrobial, antitumor, antiviral, and anticonvulsant activities.…”

“…[3,4] Similarly, thiadiazines have exhibited diverse pharmacological profiles, such as antimicrobial, antitumor, antiviral, and anticonvulsant activities. [1,2,[5][6][7][8] However, the available data on the thiadiazepine analogs of the well-known pharmacophore diazepine motif are currently limited. Considering the distinct bioactivities associated with these fragments, their combination in condensed heterocycles holds great potential for the synthesis of bioactive molecules.…”

“…Dimethyl-3-(trichloromethyl)-4,5-dihydropyrazolo[3,4e][1,2,4]thiadiazine-1,1-dioxide 5 a.The title compound was prepared from 1,3-dimethyl-1H-pyrazol-5-amine 4 a (0.83 g, 7.5 mmol), N-chlorosulfonyltrichloroacetimidoyl chloride 1 a (2.1 g, 7.5 mmol), N,N-diisopropylethylamine (6.5 mL, 37.5 mmol). Yield 1.19 g (50 %), colorless crystals, mp 257-258 °C (CH 3 CN) 1. H-NMR (DMSO-d 6 , 300 MHz) δ 8.31 (br, NH + H 2 O), 3.68 (s, 3H), 2.27 (s, 3H) 13.…”

“…1 H-NMR (DMSO-d 6 , 400 MHz) δ 3.91 (s, 3H), 2.36 (s, 3H) 13. C-NMR (DMSO-d 6 , 100 MHz) δ 150, 136.3, 123.5, 122.1, 91.7, 38, 11.8.…”