Structural Activity Relationship and Importance of Benzothiazole Derivatives in Medicinal Chemistry: A Comprehensive Review

Abstract

: Benzothiazole (1, 3-benzothiazole) is one of the heterocyclic compounds, which is a weak base having varied biological activities. The unique methine center present in the thiazole ring makes benzothiazole as the most important heterocyclic compound. It is a common and integral structure of many natural and synthetic bioactive molecules. Benzothiazole derivatives show a variety of activities, with less toxic effects and their derivatives showed enhanced activities, which has proven Benzothiazole scaffold as one of the important moieties in medicinal chemistry. Benzothiazole ring containing compounds possess various pharmacological activities such as anti-viral, anti-microbial, antiallergic, anti-diabetic, anti-tumor, anti-inflammatory, anthelmitic and anti-cancer, which makes benzothiazole a rapidly developing and interesting compound in the medicinal chemistry. This review briefly explains the importance, common methods of synthesis of the benzothiazole scaffold and also explains the popular benzothiazole molecules which have applications in various fields of chemistry. A review has been carried out based on various pharmacological activities containing benzothiazole moieties and rationalize the activities based on the structural variations. Literature on benzothiazole derivatives reveals that substitution on the C-2 carbon atom and C-6 are the reasons for a variety of biological activities.

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

“…Thus the numerous medicinal aspects of this scaffold have encouraged medicinal chemists to design and synthesize a significant number of therapeutic agents. [168][169][170][171][172][173] In this regard, Shi et al, 174 in 2012 synthesized various benzothiazole-2-thiol congeners by incorporating heterocyclic scaffolds namely, pyridine, pyrimidine, and thiazole. In addition, they demonstrated their effects on a panel of human tumor cell lines.…”

Solid‐Supported Materials‐Based Synthesis of 2‐Substituted Benzothiazoles: Recent Developments and Sanguine Future

“…The catalytic system was applied efficiently for the synthesis of various aliphatic, aromatic and heteroaromatic substituted benzothiazoles (19) in high to excellent yields. In the mechanism, ionogel mediated activation of ketone (108) facilitated the nucleophilic attack of (18) followed by intramolecular cyclization resulted in (111). The Me-group of (111) was oxidized to aldehyde (112) followed by the release of formaldehyde resulting in the formation of (19).…”

“…Owing to the huge pharmacological significance associated with benzothiazole motif, several review articles were written on their synthetic methodologies and therapeutic potential [90–181] . We searched across various Web Engines such as SciFinder, Google Scholar, ScienceDirect and Pubmed with the keywords solid‐supported/Heterogeneous synthesis of benzothiazoles.…”

“…There were numerous review articles published in the literature encompassing the synthetic methodologies and pharmacological potential of benzothiazole scaffolds. Keri et al., [90] Choudhary et al., [91] Ali and Siddiqui, [92] Hisamoddin et al., [93] Jena, [94] Srivastava et al., [95] Gagoria et al., [96] Kamal et al., [97] Gjorgjieva et al., [98] Singh and Singh, [99] Pathak et al., [100] Sharma et al., [101] Rouf and Tanyeli, [102] Sompalle and Roopan, [103] Raju et al., [104] Tariq et al., [105] Abrol et al., [106] Irfan et al., [107] Temiz et al., [108] Wu et al., [109] Bhutani et al., [110] Bhat et al., [111] Sharma et al., [112] Bainsal et al., [113] Gupta et al., [114] Elamin et al., [115] Rana et al., [116] Firdaus et al., [117] Ammazzalorso et al., [118] Mohammad et al., [119] Satyadev et al., [120] Sumit et al., [121] Rouf et al., [102] Agarwal et al., [122] Kumar et al., [123] Asiri et al., [124] Amir et al., [125] Malik et al., [126] Agarwal et al., [127] and Azam et al [128] . published review articles on the developments of benzothiazole‐based scaffolds of pharmacological importance.…”

“…published review articles on the developments of benzothiazole‐based scaffolds of pharmacological importance. Khokra et al., [129] Liu et al., [130] Gandhi et al., [131] Mene and Kale, [132] Bhoi et al., [133] Henary et al., [134] Malik et al., [135] Mathur, [136] Gupta and Rawat, [137] Shaista and Amrita, [138] Dadmal et al., [139] Gao et al., [140] Prajapati et al., [141] Kai et al., [142] Achaiah et al., [143] Bhat and Belagali, [111] Midhula et al., [144] Nangare et al., [145] Banerjee et al., [146] Jiang et al., [147] Ning et al., [148] Weekes and Westwell, [149] Li and Wang, [150] Yadav et al., [151] Ulrich, [152] Li et al., [153] Jaiswal et al., [154] Pandey and Pal, [155] Zhu et al., [156] Cheng et al., [157] and Zhilitskaya et al [158] . published reviews focusing on the protocols employed for the synthesis of benzothiazole derivatives.…”