Synthesis and characterization of novel bioactive azo compounds fused with benzothiazole and their versatile biological applications

Prakash, S.; Somiya, Govindharaj; Elavarasan, N.; Subashini, K.; Kanaga, Selvaraj; Dandapani, Ramamurthy; Magudeeswaran, Sivanandam; Kumaradhas, Poomani; Thirunavukkarasu, Chinnasamy; Sujatha, Venugopal

doi:10.1016/j.molstruc.2020.129016

Cited by 74 publications

(38 citation statements)

References 42 publications

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“…A series of conjugates with three biological active pharmacophores of naphthalimide, benzothiazole, and indole substituted with different aliphatic and aromatic amines (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) has been synthesized in moderate to good yields. Compounds 7-22 were tested for their cytotoxicity against A549 (lung), MCF7 (breast), and HeLa (cervix) human cancer cells that showed cytotoxicity in the range of IC 50 values of 0.14-8.59 mM, indicated that compounds showed excellent activity towards these cancer cell lines.…”

Section: Discussionmentioning

confidence: 99%

“…9,10 Another heterocyclic moiety, benzothiazole-based compounds, were also reported to show extensive activities towards various biological agents [11][12][13] in which this moiety exhibited excellent anticancer activity. [14][15][16] Previously, various hybrids of benzimidazole and naphthalimide moieties, 17 combined without any linker, have been synthesized and were evaluated for their anticancer activities. These hybrids revealed more activity than hybrids of benzimidazole and imidazo[1,2-a]pyrazine, 18,19 or naphthalimide and phenanthroimidazole.…”

Section: Introductionmentioning

confidence: 99%

“…thiazol-2-yl)-1H-indol-5-yl)-2substituted-1H-benzo[de]isoquinoline-1,3(2H)-dione(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22). For the synthesis of 6-(1-allyl-3-(benzo[d]thiazol-2-yl)-1H-indol-5-yl)-2-substituted-1H-benzo[de]isoquinoline-1,3(2H)-dione(8- 22), respective amine was treated with 6-(1-allyl-3-(benzo[d] …”

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confidence: 99%

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Synthesis and photobiological applications of naphthalimide–benzothiazole conjugates: cytotoxicity and topoisomerase IIα inhibition

et al. 2022

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and photobiological applications of naphthalimide–benzothiazole conjugates: cytotoxicity and topoisomerase IIα inhibition

et al. 2022

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“…The versatile biological applications such as antibacterial, antioxidant, anti-tumor and EGFR protein were assessed. The obtained data were compared with the respective standard drugs and suggested that few of the designed drugs ( 5d – e ) were potentially active against free radicals, pathogenic bacterial strains and showed interactions with EFGR protein due to the presence of phenolic ring fused with benzothiazole through diazo group that led to the increase in electron density and more potency [ 50 ] ( Figure 5 ).…”

Section: Pharmacological Properties Of Phenol Derivativesmentioning

confidence: 99%

Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

et al. 2021

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Synthetic heterocyclic compounds have incredible potential against different diseases; pyridines, phenolic compounds and the derivatives of azo moiety have shown excellent antimicrobial, antiviral, antidiabetic, anti-melanogenic, anti-ulcer, anticancer, anti-mycobacterial, anti-inflammatory, DNA binding and chemosensing activities. In the present review, the above-mentioned activities of the nitrogen-containing heterocyclic compounds (pyridines), hydroxyl (phenols) and azo derivatives are discussed with reference to the minimum inhibitory concentration and structure–activity relationship, which clearly indicate that the presence of nitrogen in the phenyl ring; in addition, the hydroxyl substituent and the incorporation of a diazo group is crucial for the improved efficacies of the compounds in probing different diseases. The comparison was made with the reported drugs and new synthetic derivatives that showed recent therapeutic perspectives made in the last five years.

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“…It was also concluded that the polar functionalities like –OH around the heterocyclic rings of triazene compounds enhanced the inhibition potential against glucosidase and amylase 24 . The azo fused with synthetic phenolic molecules such as butylated hydroxyanisole, phlorogucinal, 2,4-di-tert-butylphenol and 2,6-di-tert-butylphenol were proved to be remarkable antibacterial, antioxidant and antitumor agents 25 . Similarly, a series of new phenol ether derivatives were found to be excellent proteasome inhibitors 26 .…”

Section: Introductionmentioning

confidence: 99%

Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies

Tahir

Shahzad

Tabassum

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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In the present study, a series of azo derivatives (TR-1 to TR-9) have been synthesised via the diazo-coupling approach between substituted aromatic amines with phenol or naphthol derivatives. The compounds were evaluated for their therapeutic applications against alpha-glucosidase (anti-diabetic) and pathogenic bacterial strains E. coli (gram-negative), S. aureus (gram-positive), S. aureus (gram-positive) drug-resistant strain, P. aeruginosa (gram-negative), P. aeruginosa (gram-negative) drug-resistant strain and P. vulgaris (gram-negative). The IC 50 (mg/mL) of TR-1 was found to be most effective (15.70 ± 1.3 mg/mL) compared to the reference drug acarbose (21.59 ± 1.5 mg/mL), hence, it was further selected for the kinetic studies in order to illustrate the mechanism of inhibition. The enzyme inhibitory kinetics and mode of binding for the most active inhibitor (TR-1) was performed which showed that the compound is a noncompetitive inhibitor and effectively inhibits the target enzyme by binding to its binuclear active site reversibly.

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Synthesis and characterization of novel bioactive azo compounds fused with benzothiazole and their versatile biological applications

Cited by 74 publications

References 42 publications

Synthesis and photobiological applications of naphthalimide–benzothiazole conjugates: cytotoxicity and topoisomerase IIα inhibition

Synthesis and photobiological applications of naphthalimide–benzothiazole conjugates: cytotoxicity and topoisomerase IIα inhibition

Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies

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