Synthesis and antimycobacterial activity of isoniazid derivatives from renewable fatty acids

Rodrigues, Marieli Oliveira; Cantos, Jéssica Borges; D'Oca, Carolina da Ros Montes; Soares, Karina Lotz; Coelho, Tatiane S.; Piovesan, Luciana A.; Russowsky, Dennis; Silva, Pedro Eduardo Almeida da; D’Oca, Marcelo Gonçalves Montes

doi:10.1016/j.bmc.2013.09.034

Cited by 50 publications

(17 citation statements)

References 15 publications

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“…Previously, we reported the synthesis of new fatty acid isoniazid (INH-fatty acids) and demonstrated that the fatty acid chain is of fundamental importance to biological activity, most likely facilitating the permeability of INH-fatty acids in bacterial cells, suggesting that the increased lipophilicity of isoniazid plays an important role in its antimycobacterial activity. 36 Among the tested derivatives, INH derived from palmitic acid could represent a prototype of a new anti-TB drug because it exhibited good MIC values against all the studied strains.…”

Section: Methodsmentioning

confidence: 99%

“…The ricinoleic acid (cis-C18:1,12-OH) was obtained from castor oil or via castor oil biodiesel hydrolysis. 36 The other reagents were purchased from Aldrich Chemical Co. and used without further purification. All organic solvents used for the synthesis were of analytical grade.…”

Section: Experimental Apparatus and Chemistrymentioning

confidence: 99%

“…These results suggested that the Please do not adjust margins Please do not adjust margins hybrids DHPMs derived respectively from palmitic and oleic acids represent promising candidates for the treatment of glioma. In a continuation of our studies aimed at devising the synthesis of new compounds from renewable resources [35][36][37][38][39] and the development of greener approaches for the synthesis of hybrid compounds, we report here a convenient synthesis of new hybrids of fatty acids polyhydroquinolines (PHQ-fatty acids). In addition, this work investigated for the first time the synthesis of 30 new PHQ-fatty acids 12-17a-e 2-substituted from palmitic (C16:0), stearic (C18:0), oleic (cis-C18:1), linoleic (cis, cis-C18:2) and ricinoleic (cis-C18:1, 12-OH) acids.…”

Section: Introductionmentioning

confidence: 99%

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Multicomponent synthesis of novel hybrid PHQ-fatty acids

et al. 2015

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Multicomponent reactions as methods for green synthesis are important pathways for obtaining of pharmacological compounds. In this work, an efficient synthesis of new fatty Hantzsch derivative compounds using a four-component reaction is described. We demonstrate for the first time a fatty acid polyhydroquinoline (hybrid PHQ-fatty acids) synthesis from renewable resources containing C16 and C18 saturated and unsaturated fatty chains, including the ricinoleic acid (12-hydroxy-9-cis-octadecenoic acid), the major constituent of castor oil. The experimental results demonstrate that the best value for charging the sulfamic acid was 20 mol% and that thirty new hybrids PHQ-fatty acids were synthesised in good yields.

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Section: Methodsmentioning

confidence: 99%

Section: Experimental Apparatus and Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Multicomponent synthesis of novel hybrid PHQ-fatty acids

et al. 2015

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“…Due to the fact that the cell wall of mycobacteria contains lipophilic substances, more lipophilic substances are likely to penetrate more easily into the cell. It has been reported that the modulation of ClogP values often contributes better antitubercular activity for some compounds [13]. As shown in Table 1, the ClogP values of building blocks 1, 3 and 5 revealed moderate potency (16, 32, and 16 μg/mL against M. phlei, respectively) as well as general lipophilicity.…”

Section: Antibacterial Activitymentioning

confidence: 96%

Synthesis and antimycobacterial evaluation of natural oridonin and its enmein-type derivatives

Pei

et al. 2014

Fitoterapia

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“…Figure 7b): in the structure of the conventional proto anti-TB drug both saturated and unsaturated fatty acid chains has been incorporated resulting in improvement in antimicrobial activity with appreciable MIC values. Compound, produced from palmitic acid, could a turning point for the new antibiotic era is being reported [65].…”

Section: -Nitrothiazolylthiosemicarbazones (Figure 6a)mentioning

confidence: 99%

Tuberculosis: Still a Way to go ahead for a Lead- A Review

Bose

Harit

Halder

2017

JAPLR

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Although decades of worship bring a light of new chemical classes and moieties for the treatment of tuberculosis and still running to enlighten more possible ways to withstand and draw a full stop to the condition, the standard reports of tuberculosis enlisting cases are still on the increment side rather to declining state. Since 90s the regimen of anti-TB drugs is well established but now it is under red alters concern as the drugs are resistant to the causative bacilli, M. tuberculosis, endangering mostly the developing countries and disease prone areas of the world. With the motivation of new drug approved for the disease, the moieties in the pipe line for the consideration of being a successful drug, the review also concerns about possible new classes for lead optimization process along with repurposed drugs trial.

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Synthesis and antimycobacterial activity of isoniazid derivatives from renewable fatty acids

Cited by 50 publications

References 15 publications

Multicomponent synthesis of novel hybrid PHQ-fatty acids

Multicomponent synthesis of novel hybrid PHQ-fatty acids

Synthesis and antimycobacterial evaluation of natural oridonin and its enmein-type derivatives

Tuberculosis: Still a Way to go ahead for a Lead- A Review

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