Synthesis and anti-leishmanial activity of 1-aryl-β-carboline derivatives against Leishmania donovani

Gohil, Vikrantsinh M.; Brahmbhatt, Keyur G.; Loiseau, Philippe M.; Bhutani, K. K.

doi:10.1016/j.bmcl.2012.04.115

Cited by 31 publications

(14 citation statements)

References 16 publications

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“…Several studies has pointed that the interaction with DNA, enzymatic or receptor systems are the most commonly mode of action observed for antitumor compounds of this class. 18) Also, it was demonstrated that the position-1 is a important site for antitumor activity of β-carboline derivatives; appropriate substituent at this position can enhance their antitumor activity. 18) On the other hand, no study on the mechanism of action of benzo [4,5] canthin-6-one derivatives is reported.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Antitumor, Antitrypanosomal and Antileishmanial Activities of Benzo[4,5]canthin-6-ones Bearing the N′-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide Groups at C-2

Silva

Garcia

Rodrigues

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of novel benzo[4,5]canthin-6-ones, bearing the N'-(substituted benzylidene)-carbohydrazide (11a-e) and N-alkylcarboxamide (13a-g) moieties at position-2, were synthesized and screened for their in vitro antitumor activity, against seven human cancer cell lines, and for antitrypanosomal and antileishmanial activities against Trypanosoma cruzi and Leishmania amazonensis. The results indicated that N-methylpiperazyl-6-oxobenzo[4,5]canthine-2-carboxamide (13f) displayed potent antitumor activity with IC(50) values in the range of 1.15-8.46 µM for all cell lines tested. Compounds 13f and 13g bearing an N-methylpiperazylcarboxamide and N-morpholylcarboxamide at C-2, respectively, showed potent activities towards both Trypanosoma cruzi and Leishmania amazonensis parasites, with IC(50) in the range of 0.4 to 16.70 µM.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Antitumor, Antitrypanosomal and Antileishmanial Activities of Benzo[4,5]canthin-6-ones Bearing the N′-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide Groups at C-2

Silva

Garcia

Rodrigues

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…For example selenium dioxide (SeO 2 , 10 equiv) has been used in the presence of an acid for oxidative dehydrogenation of tetrahydro-β-carbolines 49 to afford aromatic β-carbolines 50 ( Scheme 15 ) [ 65 ]. Bhutania et al [ 66 ] has also reported a similar synthesis of 1-aryl-β-carboline derivative 52 starting from 51 ( Scheme 15 ). In this case potassium dichromate (K 2 Cr 2 O 7 ) was used as an oxidant in glacial acetic acid.…”

Section: Reviewmentioning

confidence: 99%

“… Selenium dioxide and potassium dichromate-mediated oxidative dehydrogenation of tetrahydro-β-carbolines [ 65 – 66 ]. …”

Section: Reviewmentioning

confidence: 99%

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

Hati¹,

Holzgrabe²,

Sen³

2017

Beilstein J. Org. Chem.

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Nitrogen heteroarenes form an important class of compounds which can be found in natural products, synthetic drugs, building blocks etc. Among the diverse strategies that were developed for the synthesis of nitrogen heterocycles, oxidative dehydrogenation is extremely effective. This review discusses various oxidative dehydrogenation strategies of C–C and C–N bonds to generate nitrogen heteroarenes from their corresponding heterocyclic substrates. The strategies are categorized under stoichiometric and catalytic usage of reagents that facilitate such transformations. The application of these strategies in the synthesis of nitrogen heteroarene natural products and synthetic drug intermediates are also discussed. We hope this review will arouse sufficient interest among the scientific community to further advance the application of oxidative dehydrogenation in the synthesis of nitrogen heteroarenes.

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“…β-carbolines from various natural and synthetic sources have shown diverse biological activities. A total of 22 compounds were synthesized and tested in vitro against Leishmania donovani, out of which six compounds (4, 5, 10, 11, 19, and 22) showed more activity than the standard miltefosine (IC 50 = 12.07 ± 0.82 lM), with compound 4 being the most potent (IC 50 = 2.16 ± 0.26 lM) [112]. Moreover, a semi-synthetic berberine analogue, 5,6-didehydro-8,8diethyl-13-oxodihydroberberine chloride showed nanomolar level potency against in vitro models of leishmaniasis, malaria, and trypanosomiasis, as well as activity in an in vivo visceral leishmaniasis model [113].…”

Section: Synthetic Drugsmentioning

confidence: 99%

Leishmaniasis: Possible New Strategies for Treatment

Vermelho¹,

Supuran²,

Cardoso³

et al. 2014

Leishmaniasis - Trends in Epidemiology, Diagnosis and Treatment

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Synthesis and anti-leishmanial activity of 1-aryl-β-carboline derivatives against Leishmania donovani

Cited by 31 publications

References 16 publications

Synthesis, Antitumor, Antitrypanosomal and Antileishmanial Activities of Benzo[4,5]canthin-6-ones Bearing the <i>N</i>′-(Substituted benzylidene)-carbohydrazide and <i>N</i>-Alkylcarboxamide Groups at C-2

Synthesis, Antitumor, Antitrypanosomal and Antileishmanial Activities of Benzo[4,5]canthin-6-ones Bearing the <i>N</i>′-(Substituted benzylidene)-carbohydrazide and <i>N</i>-Alkylcarboxamide Groups at C-2

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

Leishmaniasis: Possible New Strategies for Treatment

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