The novel scaffold 1,2,4-benzothiadiazine-1,1-dioxide: a review
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Medicinal Chemistry Research https://doi.org/10.1007/s00044-020-02644-y
REVIEW ARTICLE
The novel scaffold 1,2,4-benzothiadiazine-1,1-dioxide: a review Sumit Chhabra1 Kamal Shah ●
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Received: 19 June 2020 / Accepted: 29 September 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract The aim of this review is an attempt to highlight the progress in the chemistry and to present an outline of various pharmacological activities of 1,2,4-benzothiadiazine-1,1-dioxide ring. The biological activities of 1,2,4-benzothiadiazine1,1-dioxide, for example, antimicrobial, antiviral, antihypertensive, antidiabetic, anticancer, KATP channel activators, and AMPA receptor modulators etc., are reported. Many functional groups attached to the ring are responsible for the activity of 1,2,4-benzothiadiazine-1,1-dioxide like a halo, the group at 7 and 8 positions of the ring gave active compounds. Meanwhile, other functional groups like alkyl, aryl, alkylamino, benzyl, keto, etc. at different position of 1,2,4-benzothiadiazine-1,1dioxide ring are responsible for the activity. The review aims are to collect literature work stated by scholars on 1,2,4benzothiadiazine-1,1-dioxide for their different therapeutic activities and report the current efforts made on this ring. Keywords Heterocycles 1,2,4-Benzothiadiazine-1,1-dioxide Antimicrobial Antidiabetic Antitumor agents Antiviral activity ●
Abbreviations HIV Human Immunodeficiency Virus AMPAr Ionotropic α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor KATP ATP-sensitive potassium channel channel E. coli Escherichia coli M. tuber- Mycobacterium tuberculosis culosis μg Micro Gram MIC Minimum inhibitory concentration mL Milliliter
Introduction Apart from the various tautomeric forms, there are four kinds of parent thiadiazine structures, having molecular formula C3H4N2S, in which the sulfur atom is adjacent to at least one ring nitrogen atom (structures I–IV) (Fig. 1). To name a particular tautomer, the “extra” hydrogen requires
* Kamal Shah [email protected] 1
Institute of Pharmaceutical Research, GLA University, Mathura, UP 281406, India
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designation. Thus, using chemical abstracts nomenclature, the structure I is named as 6H-1,2,3-thiadiazine and structures V, VI, and VII (Fig. 1) are named as 2H-1,2,4-thiadiazine, 4H-1,2,4-thiadiazine, and 2H-1,2,6-thiadiazine, respectively. If the sulfur atom exhibits a valency other than 2, then the valency is indicated by including the small Greek letter λ after the numeral that specifies the ring sulfur atom, followed by a superscript numeral to show the valency of the sulfur atom. For instance, structure VIII (Fig. 1) is named 3H-1λ4, 2,6-thiadiazine. These four thiadiazine systems can give rise to benzo derivatives, i.e., structures IX–XII (Fig. 1); examples of all four types are known [1]. During the period covered by this review, a greater variety of applications has appeared. The main area of interest is in the search for antihypertensives. However, with
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