Recent progress in the drug development of coumarin derivatives as potent antituberculosis agents

Keri, Rangappa S.; Sasidhar, B. S.; Nagaraja, Bhari Mallanna; Santos, M. Amélia

doi:10.1016/j.ejmech.2015.06.017

Cited by 212 publications

(74 citation statements)

References 94 publications

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“…They are colorless and crystalline phytochemicals belonging to the family of benzopyrones (Jain and Joshi 2012;Rohini and Srikumar 2014), consisting of fused benzene and α-pyrone rings (Jain and Joshi 2012;Venugopala et al 2013;Rohini and Srikumar 2014). The numbering of coumarin starts from the ring oxygen, i.e., oxygen receives position-1 and goes round anti-clockwise along with the ring (Keri et al 2015). Coumarins can be classified into four categories: simple coumarin, furanocoumarin, pyranocoumarin, and coumarin with substituent on the pyrone ring (Jain and Joshi 2012;Lin et al 2013b;Venugopala et al 2013;Rohini and Srikumar 2014), as shown in Table 1.…”

Section: Coumarins: Classifications and Propertiesmentioning

confidence: 99%

Fungi as a source of natural coumarins production

Costa

Tavares

Oliveira

2016

Appl Microbiol Biotechnol

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Natural coumarins and derivatives are compounds that occur naturally in several organisms (plant, bacteria, and fungi) consisting of fused benzene and α-pyrone rings. These compounds show high technological potential applications in agrochemical, food, pharmaceuticals, and cosmetics industries. Therefore, the need for bulk production of coumarins and the advancement of the chemical and pharmaceutical industries led to the development of synthetic coumarin. However, biotransformation process, synthetic bioengineering, metabolic engineering, and bioinformatics have proven effective in the production of natural products. Today, these biological systems are recognized as green chemistry innovation and business strategy. This review article aims to report the potential of fungi for synthesis of coumarin. These microorganisms are described as a source of natural products capable of synthesizing many bioactive metabolites. The features, classification, properties, and industrial applications of natural coumarins as well as new molecules obtained by basidiomycetes and ascomycetes fungi are reported in order to explore a topic not yet discussed in the scientific literature.

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Section: Coumarins: Classifications and Propertiesmentioning

confidence: 99%

Fungi as a source of natural coumarins production

Costa

Tavares

Oliveira

2016

Appl Microbiol Biotechnol

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“…Decoding of the genome of Mycobacterium tuberculosis and searching for the genes responsible for production of drug resistance are very interesting [7]. The search of completely new biologically active substances of various chemical classes that can effectively inhibit the growth of Mycobacterium tuberculosis at all stages of development do not lose its relevance [8][9][10][11].…”

Section: синтез та протитуберкульозна активність 1-бензил-4-гідрокси-mentioning

confidence: 99%

The synthesis and the antitubercular activity of 1-benzyl-4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxamides

Davydenko

2015

J. org. pharm. chem.

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“…A large variety of coumarin derivatives have been isolated from natural products and an array of pharmacological activities have been described for these, as well as related synthetic coumarins [2,3]. The ability of the coumarin moiety to form several possible interactions with a particular binding site (including hydrogen bonds, electrostatic, π-π and hydrophobic interactions) likely stabilize target binding and contribute to the versatile pharmacological profile of coumarin derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…The ability of the coumarin moiety to form several possible interactions with a particular binding site (including hydrogen bonds, electrostatic, π-π and hydrophobic interactions) likely stabilize target binding and contribute to the versatile pharmacological profile of coumarin derivatives. Both the type and placement of functional groups on the coumarin scaffold determine the specific activity of the given derivative [2][3][4]. Antibacterial and more specifically, antimycobacterial activity are amongst the pharmacological effects that have been described for a range of structurally diverse coumarin derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…central nervous system acting, anticoagulant and anti-cancer agents) often overlap with that for potent antimicrobial activity [3,22]. A number of review papers describe the importance of coumarin compounds in the field of neurodegenerative disorders where they have shown inhibitory properties towards monoamine oxidases, cholinesterases, β-and γ-secretase and other targets involved in the progression of neurodegenerative disorders [23][24][25].…”

Section: Introductionmentioning

confidence: 99%

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Versatility of 7-Substituted Coumarin Molecules as Antimycobacterial Agents, Neuronal Enzyme Inhibitors and Neuroprotective Agents

Kapp

Visser

Sampson

et al. 2017

Preprint

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An in vitro medium-throughput screen using M. tuberculosis H37Rv was employed to screen an in-house library of structurally diverse compounds for antimycobacterial activity. From this initial screen, eleven 7-substituted coumarin derivatives with confirmed monoamine oxidase-B and cholinesterase inhibitory activities, demonstrated growth inhibition of more than 50% at a 50 µM concentration. This prompted further exploration of all the 7-substituted coumarins in our library, nineteen in total, as potential antimycobacterial agents. Four derivatives showed promising antimycobacterial activity with MIC99 values of 8.31 -29.70 µM and 44.15 -57.17 µM on M. tuberculosis H37Rv in independent assays using Gaste-Fe and 7H9 + OADC media, respectively. These compounds were found to bind to albumin which may explain the variations in MIC between the two assays. Preliminary antimycobacterial evaluation of moxifloxacin resistant M. tuberculosis show that these compounds are able to maintain their activity in fluoroquinolone resistant mycobacteria. Analysis of structure activity relationships for antimycobacterial versus neuronal enzyme inhibitory activity indicate that structural modification on position 4 and/or 7 of the coumarin scaffold may be utilized to improve selectivity towards either inhibition of neuronal enzymes or antimycobacterial effect. Cytotoxicity evaluations of the compounds indicate moderate cytotoxicity with slight selectivity towards mycobacteria. Further neuroprotective assays on SH-SY5Y human neuroblastoma cells indicate significant neuroprotection for selected compounds irrespective of their neuronal enzyme inhibitory properties. These coumarin molecules are thus interesting lead compounds that may provide insight into the design of new antimicrobacterial and/or neuroprotective agents.

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Recent progress in the drug development of coumarin derivatives as potent antituberculosis agents

Cited by 212 publications

References 94 publications

Fungi as a source of natural coumarins production

Fungi as a source of natural coumarins production

The synthesis and the antitubercular activity of 1-benzyl-4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxamides

Versatility of 7-Substituted Coumarin Molecules as Antimycobacterial Agents, Neuronal Enzyme Inhibitors and Neuroprotective Agents

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