Synthesis and Antileishmanial Activity of Indoloquinones Containing a Fused Benzothiazole Ring

Tapia, Ricardo A.; Prieto, Yolanda; Pautet, F.; Domard, M.; Sarciron, Marie‐Elisabeth; Walchshofer, Nadia; Fillion, H.

doi:10.1002/1099-0690(200212)2002:23<4005::aid-ejoc4005>3.0.co;2-l

Cited by 30 publications

(14 citation statements)

References 6 publications

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“…Some heterocyclic quinones have been reported to be active in vitro against virulent strains of Leishmania sp. (Tournaire et al, 1996;Valderrama et al, 1999;Tapia et al, 2003a;Tapia et al, 2002b;Tapia et al, 2003b), it is why we have explored the antileishmanial activity of various quinonic compounds. We have performed in vitro tests in order to identify three-dimensional structural similarities between these compounds that may explain their potency against L. donovani, or L. major or both strains.…”

Section: Molecular Modeling Studymentioning

confidence: 99%

Antileishmanial activity of polycyclic derivatives

et al. 2005

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Summary :33 polycyclic derivatives have been studied and tested on Leishmania donovani and L. major promastigotes. Their antileishmanial activity was assessed in vitro and an assay of their cytotoxicity was realized on human myelomonocytic cell line. The reference molecules used in the assays were amphotericin B and pentamidine. Among the compounds tested, 29 possess an antileishmanial activity; 25 of those were more active against L. donovani than amphotericin B, and nine were as effective as amphotericin B against L. major. Many synthesized derivatives were more active against L.donovani than against L. major. The cytotoxicity studies have shown that among the thirty-three derivatives tested, 12 molecules have an IC 50 towards THP-1 cells about equal than that reference drugs, the 21 other derivatives are much less toxic. A 3D QSAR study was undertaken and has permitted to predict activity against L. donovani and L. major and to highlight critical area to optimize activity against the two species. Résumé

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Section: Molecular Modeling Studymentioning

confidence: 99%

Antileishmanial activity of polycyclic derivatives

et al. 2005

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“…The most common and classical method was reported as direct method that involved condensation of an ortho-amino thiophenol with a substituted aromatic aldehyde, carboxylic acid, acyl chloride or nitrile to synthesize C-2 substituted benzothiazoles, but it was found that this method is not appropriate for majority of substituted C-2 aryl benzothiazoles because the main difficulty encountered in synthesis of the readily oxidisable 2-amino thiophenols bearing substituent groups. For above said reason some other methods were reported and extensively used in the laboratories that based on the use of the potassium ferricyanide radical cyclization of thiobenzanilides 10 . This method was named as Jacobsen cyclization and popularized because it produced only one product.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Activity of Novel Hydroxy Substituted Benzothiazole Derivatives Against Streptococcus Pyogenes

Gupta¹

2018

Int. Res. J. Pharm.

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Synthesis and screening of benzothiazole derivatives have great importance in heterocyclic chemistry because of its potent and significant biological activities against Streptococcus (S) pyogenes especially hydroxy substitution at benzothiazole. Hydroxy-substituted benzothiazole derivatives were synthesized by reaction of 4-amino-2-chlorophenol with potassium thiocyanate under temperature control and presence of bromine in glacial acetic acid and ammonia. Hydroxy-substituted nitrobenzamides then synthesized by condensation of 2-amino-4-chlorobenzothiazol-5-ol with 2(3or4)nitrobenzoylchloride acid in presence of dry pyridine and acetone. Finally, newly synthesized derivatives (A-01 to A-09) were synthesized through replacing of chlorine of nitrobenzamide by reaction with 2-nitroaniline, 3-nitroaniline, and 4-nitroaniline in presence of DMF. Analytical characterization was performed by TLC, melting point, IR and NMR spectra. Antibacterial activity was performed against S. pyogenes by cup plate method (diffusion technique) using procaine penicillin as standard. Compound A-03, A-04 and A-08 showed potent antibacterial activity against S. pyogenes at both concentrations 50µg/ml and 100µg/ml as compared to standard while the rest of compounds showed moderate to negligible activity when further assessed to determine MIC by broth dilution method.

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“…Since then, significant research has been carried out taking benzothiazole as the basic moiety. From the literature survey, it has been found that extensive work has been reported on 2-substituted benzothiazole derivatives in the past and evaluated for different activities, such as, antibacterial,[ 1 ] antiproliferative activity,[ 2 ] antiviral,[ 3 ] antitumor,[ 4 ] antifungal,[ 5 ] anti-inflammatory,[ 6 ] antioxidative and radioprotective,[ 7 ] antidiabetic,[ 8 ] antihelmintic,[ 9 ] antileishmanial,[ 10 ] anticonvulsant,[ 11 ] antimycobacterial,[ 12 ] neuroprotective,[ 13 ] and antipsychotic. [ 14 ] There are a number of pharmaceuticals and nutraceutical drugs available in the market containing benzothiazole moiety, reported to have different clinical uses.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Biological Evaluation of certain 6-methyl-2(3H)-benzo-1, 3-thiazolyl-1'-ethylidene-2-(o, p- Substituted Acetophenones) Hydrazine Analogs

Alang¹,

Kaur²,

Kaur³

et al. 2010

Journal of Young Pharmacists

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In the present study, five new derivatives (GG4 to GG8) of benzothiazoles were synthesized and evaluated against Staphylococcus aureus (MTCC 737), Pseudomonas aeruginosa (MTCC 424), Escherichia coli (MTCC 1687), and yeast-like fungi Candida tropicalis. p-Toluidine on treatment with ammonium thiocynate formed 2-benzothiazolamines (II), which on reaction with hydrazine hydrate formed a hydrazino derivative (III). Compounds GG4 to GG8 were synthesized by reacting the hydrazine derivative with different acetophenones. All the synthesized compounds were identified by IR and 1H-NMR, and antimicrobial activity was performed on the synthesized compounds. Presence of NO2, Br, OCH3, and Cl groups to the substituted benzothiazole enhanced the antibacterial and antifungal activities.

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Synthesis and Antileishmanial Activity of Indoloquinones Containing a Fused Benzothiazole Ring

Cited by 30 publications

References 6 publications

Antileishmanial activity of polycyclic derivatives

Antileishmanial activity of polycyclic derivatives

Antibacterial Activity of Novel Hydroxy Substituted Benzothiazole Derivatives Against Streptococcus Pyogenes

Synthesis, Characterization, and Biological Evaluation of certain 6-methyl-2(3H)-benzo-1, 3-thiazolyl-1'-ethylidene-2-(o, p- Substituted Acetophenones) Hydrazine Analogs

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