Synthesis of some thiazolyl aminobenzothiazole derivatives as potential antibacterial, antifungal and anthelmintic agents

Amnerkar, Nikhil D.; Bhusari, Kishore P.

doi:10.3109/14756360903555258

Cited by 31 publications

(10 citation statements)

References 20 publications

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“…Among all the congeners of 5-F derivatives of CJM 126 and its isosteric molecule (compounds 17, 18), compound 14 showed higher activity (GI 50 : 0.1nM) in comparison to other compounds (compound [14][15][16][17][18]. Again, among the congeners of hydroxy derivatives of CJM 126, compound 22 had better activity against 3T3 and ANN-1 cell lines as compared to compounds 21 and 23 while compound 20 showed good activity against MCF-7 and WiDr cell lines.…”

Section: Drug Design Strategymentioning

confidence: 97%

“…Benzothiazole (Fig. 1), a heterocyclic compound constitutes an important scaffold of drugs, which can serve as unique and versatile ligand for experimental drug design [8] and have attracted attention because of their varied biological activities that pertain to antitumor [9], antitubercular [10], antimalarial [11], anticonvulsant [12], antidiabetic [13], antimicrobial, antihelmintic [14], analgesic, antiinflammatory [15], diuretic [16] etc. Some of the bis-benzothiazole derivatives exhibit their importance in amyloid-imaging [17], as vulcanization accelerators and also as starting materials for the synthesis of various drugs.…”

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confidence: 99%

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Benzothiazoles: How Relevant in Cancer Drug Design Strategy?

Singh¹,

Singh²

2014

ACAMC

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Heterocyclic compounds, analogs and derivatives have attracted attention due to their diverse biological and pharmacological properties. Benzoheterocycles such as benzothiazoles, benzimidazoles and benzoxazoles are constituents of many bioactive heterocyclic compounds, having wider range of applications. They have been extensively studied for their biological activities, and can serve as unique and versatile scaffolds for drug design. The benzothiazole, in the family of heterocyclic compounds has assumed special significance in synthetic chemistry, pharmaceutical chemistry as well as in clinical applications because of its anti-tumor properties. This review is organized in the following ways. It begins with brief introduction on the chemical diversity of synthetic analogs of benzothiazole. After this, drug design strategy and mechanisms of action through its diverse biological targets in which benzothiazole and its derivatives display their anticancer activity are discussed. It ends with the metabolism pattern of benzothiazole and its analogs. Analysis of the structure-activity relationships (SAR), quantitative structure-activity relationships (QSAR) as well as on docking studies of this family of compounds highlights the potential that may lead to the development of novel anticancer agents. Such relationships will definitely create lot of interest among the researchers to synthesize optimized variety of benzothiazole derivatives and to screen them for their anticancer activity.

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Section: Drug Design Strategymentioning

confidence: 97%

mentioning

confidence: 99%

Benzothiazoles: How Relevant in Cancer Drug Design Strategy?

Singh¹,

Singh²

2014

ACAMC

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“…Indolizines have been reported to exhibit a wide range of biological activities, including anti-mycobacterial 27 and anti-HIV-1 activity. 28,29 Preliminary assessments of the biological activity of indolizine-2-carboxamide derivatives prepared in this study against HIV-1 IN and HIV-1 PR, malaria, trypanosomiasis and tuberculosis were undertaken.…”

Section: Resultsmentioning

confidence: 99%

Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids

Sekgota

Isaacs

Hoppe

et al. 2021

Journal of Chemical Research

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Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by saponification of the corresponding methyl esters produced, in turn, selectively and efficiently, by time-controlled cyclisation of a single Morita–Baylis–Hillman adduct. Various amino and hydrazino compounds with medicinal potential have been used to prepare indolizine-2-carboxamido and hydrazido derivatives.

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“…The 2-aminothiazole scaffold is present in the structure of antiviral [ 4 ], antifungal [ 5 ], antimicrobial [ 6 ], anti-cancerous [ 7 ], and anti-inflammatory compounds [ 8 ]. Recent papers have reported different 2-aminothiazole derivatives as promising agents against kinetoplastids such as Trypanosoma cruzi , Trypanosoma brucei , Leishmania donovani, and Leishmania infantum [ 9 – 11 ].…”

Section: Introductionmentioning

confidence: 99%

4-Phenyl-1,3-thiazole-2-amines as scaffolds for new antileishmanial agents

Rodrigues

Santos

Costa

et al. 2018

J Venom Anim Toxins Incl Trop Dis

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BackgroundThere is still a need for new alternatives in pharmacological therapy for neglected diseases, as the drugs available show high toxicity and parenteral administration. That is the case for the treatment of leishmaniasis, particularly to the cutaneous clinical form of the disease. In this study, we present the synthesis and biological screening of eight 4-phenyl-1,3-thiazol-2-amines assayed against Leishmania amazonensis. Herein we propose that these compounds are good starting points for the search of new antileishmanial drugs by demonstrating some of the structural aspects which could interfere with the observed activity, as well as suggesting potential macromolecular targets.MethodsThe compounds were easily synthesized by the methodology of Hantzsch and Weber, had their purities determined by Gas Chromatography-Mass spectrometry and assayed against the promastigote forms of Leishmania amazonensis as well as against two white cell lines (L929 and THP-1) and the monkey’s kidney Vero cells. PrestoBlue® and MTT viability assays were the methodologies applied to measure the antileishmanial and cytotoxic activities, respectively. A molecular modeling target fishing study was performed aiming to propose potential macromolecular targets which could explain the observed biological behavior.ResultsFour out of the eight compounds tested exhibited important anti-promastigote activity associated with good selectivity indexes when considering Vero cells. For the most promising compound, compound 6, IC50 against promastigotes was 20.78 while SI was 5.69. Compounds 3 (IC50: 46.63 μM; SI: 26.11) and 4 (IC50: 53.12 μM; SI: 4.80) also presented important biological behavior. A target fishing study suggested that S-methyl-5-thioadenosine phosphorylase is a potential target to these compounds, which could be explored to enhance activity and decrease the potential toxic side effects.ConclusionsThis study shows that 4-phenyl-1,3-thiazol-2-amines could be good scaffolds to the development of new antileishmanial agents. The S-methyl-5-thioadenosine phosphorylase could be one of the macromolecular targets involved in the action.Electronic supplementary materialThe online version of this article (10.1186/s40409-018-0163-x) contains supplementary material, which is available to authorized users.

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Synthesis of some thiazolyl aminobenzothiazole derivatives as potential antibacterial, antifungal and anthelmintic agents

Cited by 31 publications

References 20 publications

Benzothiazoles: How Relevant in Cancer Drug Design Strategy?

Benzothiazoles: How Relevant in Cancer Drug Design Strategy?

Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids

4-Phenyl-1,3-thiazole-2-amines as scaffolds for new antileishmanial agents

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