%0 Journal Article
%T Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications
%A Khairy A. M. El-Bayouki
%J Organic Chemistry International
%D 2013
%I Hindawi Publishing Corporation
%R 10.1155/2013/210474
%X This review article deals with synthesis and reactions of benzo[1,5]thiazepines and the related derivatives and their applications, biological activity as well as spectroscopic data. Most of the reported data on the methods of synthesis, chemical reactions, and biological activity of these heterocycles published over the last ten years are reviewed in this paper. 1. Introduction 1,5-Benzothiazepines are the most well-known representatives of benzologs of 1,4-thiazepine and one of the three possible benzo-condensed derivatives, namely, 1,4-, 4,1- and 1,5-benzothiazepines. The parent 1,5-benzothiazepine, itself, has not hitherto been described in the literature for its pharmacological properties. However, its 2,4-disubstituted derivatives and many hydrated derivatives have been synthesized. The 1,5-benzothiazepine derivatives are of particular interest for lead discovery because they have been found active against different families of targets. The first molecule of 1,5-benzothiazepine used clinically was diltiazem, followed by clentiazem, for their cardiovascular action. Some of the 1,5-benzothiazepine derivatives were also used clinically for CNS disorders which includes thiazesim and quetiapine fumarate. Moreover, 1,5-benzothiazepine moiety is a privileged class of pharmacophore, as compounds bearing this structural unit possess a broad spectrum of biological activities such as anticonvulsant, Ca+2 channel antagonist, antianginal, anti HIV, squalene synthetase inhibitor, V2 arginine vasopressin receptor antagonist, and HIV-1 reverse transcriptase inhibitor [1¨C3]. The methods for the preparation of 1,5-benzothiazepines can be divided into two major groups, namely, the construction of a seven-membered heteroring from the elements of open chains, and reactions involving ring expansion. 2. Nomenclature and Way of Numbering 1,5-Benzothiazepines are the most well-known representatives of benzologs of 1,4-thiazepine. According to the IUPAC nomenclature, the benzo thiazepine structures IA or IB may be named as ( )-2,3-dihydrobenzo thiazepine or ( )-2,3-dihydro-substituted-benzo thiazepine. Also, the substituted-benzo thiazepines structure IIA or IIB may have the name: 2,3,4,5-tetrahydrobenzo thiazepine or 2,3,4,5-tetrahydro-substituted-benzo thiazepine (see Figure 1). Figure 1 3. Preparation of 1,5-Benzothiazepine System and Its Related Derivatives 3.1. Thiophenol and Its Derivative Approaches 3.1.1. Solid Phase Synthesis: Claisen-Schmidt Condensation of 3-Hydroxyacetophenone with Different Substituted Aldehydes and o-Aminothiophenol The solution phase
%U http://www.hindawi.com/journals/oci/2013/210474/