Antimycobacterial activity of natural products and synthetic agents: Pyrrolodiquinolines and vermelhotin as anti-tubercular leads against clinical multidrug resistant isolates of Mycobacterium tuberculosis

Ganihigama, Dakshina U.; Sureram, Sanya; Sangher, Sasithorn; Hongmanee, Poonpilas; Aree, Thammarat; Mahidol, Chulabhorn; Ruchirawat, Somsak; Kittakoop, Prasat

doi:10.1016/j.ejmech.2014.10.026

Cited by 75 publications

(45 citation statements)

References 43 publications

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“…[10] Cycloaddition of an itrile oxide and alkyne is also widely used in click chemistry,particularly for nucleic acids and materials chemistry, [11] and such acycloaddition is strictly performed either under basic conditions or using metal catalysts.Organic reactions in water can not only be considered green chemistry (abundance in nature and environmentally friendly solvent), but also have the advantage of being run in biological systems (e.g., click reactions, bioconjugation, and bioorthogonal chemistry). As part of our research program directed at green chemistry approaches for the synthesis of bioactive molecules, [12] we report herein the synthesis of isoxazolines,1 ,2,4-oxadiazoles,a nd isoxazoles in aqueous solutions.S ince the reactions in water have both environmental and economic advantages,e fforts to generate the nitrile oxide in water have been made for the synthesis of isoxazolines and isoxazoles. [13] Herein we show that nitrile oxides can be generated from oxime halides in catalyst-free aqueous solutions,and that the cycloaddition of nitrile oxide with alkenes and alkynes occurs under acidic conditions, rather than under the conventional basic conditions ( Figure 1).…”

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confidence: 99%

Water‐Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4‐Oxadiazoles

et al. 2016

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Conventional methods generate nitrile oxides from oxime halides in organic solvents under basic conditions. However, the present work revealed that water-assisted generation of nitrile oxides proceeds under mild acidic conditions (pH 4-5). Cycloadditions of nitrile oxides with alkynes and alkenes easily occurred in water without using catalysts, thus yielding isoxazoles and isoxazolines, respectively, with excellent stereoselectivity toward five- and six-membered cyclic alkenes. A double stereoselective cycloaddition of two units of a nitrile oxide with cyclohexene was also achieved, thus yielding 1,2,4-oxadiazole derivatives having a unique hybrid isoxazoline-oxadiazole skeleton. Enantiomerically pure isoxazolines were prepared from monoterpenes with a ring strain. In one case, the isoxazoline with a butterfly-like structure was simply prepared, and it might be used as a ligand in asymmetric catalysis.

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confidence: 99%

Water‐Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4‐Oxadiazoles

et al. 2016

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“…As the treatment of multidrug‐resistant tuberculosis (MDR‐TB) is still problematic, a the use of natural compounds as templates in drug design remains a challenging task . A few natural products have been previously found to exhibit potent antimycobacterial activity against isolates of MDR‐TB; however, they exhibit cytotoxic activity toward normal cell lines …”

Section: Introductionmentioning

confidence: 99%

Synthetic piperine amide analogs with antimycobacterial activity

et al. 2017

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Piperine amide analogs are synthesized by replacement of the piperidine moiety with different types of cyclic amines, including adamantyl and monoterpene-derived fragments. The compounds are screened for activity against Mycobacterium tuberculosis H37Rv. The most potent compounds are the 1-adamantyl and the monoterpene-derived hybrids, which combine nanomolar antimycobacterial activity with low cytotoxicity against human cells. The presence of quaternary carbon atom as main structural requirement for anti-TB activity is pointed out by a QSAR study. The most promising compound is the (+)-isopinocampheylamine-derived amide which is characterized with selectivity index of 1387.8.

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“…Various benzoxazocines, coumarins, chromenes, and pyrrolodiquinoline derivatives were tested for their anti‐TB activities by Ganihigama et al . The 5‐methylpyrrolo[1,2‐a:3,4‐c′]diquinolin‐5‐ium iodide 3a and its derivative 3b were found to be most active against 59 clinical MDR‐TB isolates (resistant to INH, RIF, and/or EMB, SM, and ofloxacin) with MIC values ranging from 0.3 to 6.2 μg/mL.…”

Section: Quinoline‐based Derivativesmentioning

confidence: 99%

Quinoline Derivatives with Potential Activity Against Multidrug‐resistant Tuberculosis

Zhou

et al. 2018

Journal of Heterocyclic Chem

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Tuberculosis (TB), which affects primarily the lungs (pulmonary TB) apart from other vital organs, is a life‐threatening chronic deadliest infectious disease caused by members of Mycobacterium tuberculosis (MTB) complex and mainly by MTB itself. The emergence of MTB new virulent forms that are resistant to some or all first‐line and second‐line anti‐TB agents, including multidrug‐resistant (MDR), extensively drug‐resistant, and totally drug‐resistant strains has further aggravated the spread of this disease and was increased up to an alarming level in the recent decades. More than ever, it is imperative to develop novel, high effective, and fast acting anti‐TB drugs to prevent the spread of TB, particularly in its hard‐to‐kill MDR‐TB, extensively drug‐resistant‐TB, and totally drug‐resistant‐TB strains. In recent years, numerous compounds have been synthesized for this purpose, but only a handful of compounds have entered human trials after the discovery of rifampicin, reflecting the inherent difficulties of developing new anti‐TB agents. Despite of bedaquiline and delamanid have received approval from many countries for treatment of MDR‐TB infected patients, both drugs are associated with serious side effects and are only recommended for those MDR‐TB patients without other treatment options. All these aforementioned facts make it an urgent need to develop novel drugs. Quinoline‐based derivatives including quinolones ex biological activities, and some of them displayed excellent in vitro and in vivo activities against MDR‐TB. This review outlines the recent developments of quinoline‐based derivatives with potential activity against MDR‐TB as well as the structure–activity relationship.

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Antimycobacterial activity of natural products and synthetic agents: Pyrrolodiquinolines and vermelhotin as anti-tubercular leads against clinical multidrug resistant isolates of Mycobacterium tuberculosis

Cited by 75 publications

References 43 publications

Water‐Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4‐Oxadiazoles

Water‐Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4‐Oxadiazoles

Synthetic piperine amide analogs with antimycobacterial activity

Quinoline Derivatives with Potential Activity Against Multidrug‐resistant Tuberculosis

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