Synthesis and antimicrobial activity of β-lactam–bile acid conjugates linked via triazole

Vatmurge, Namdev S.; Hazra, Banasri; Pore, Vandana S.; Shirazi, Fazal; Chavan, Pradnya S.; Deshpande, Mukund V.

doi:10.1016/j.bmcl.2008.01.102

Cited by 175 publications

(102 citation statements)

References 33 publications

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“…[104] Most of the compounds exhibited significant antifungal and moderate antibacterial activity against all the tested strains. One of the compounds showed very good antifungal activity with an MIC value of 16 mg mL À1 against C. albicans and 8 mg mL À1 against B. poitrasii.…”

Section: Antifungal and Antibacterialsmentioning

confidence: 95%

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

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1,143

508

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The copper(I)-catalyzed 1,2,3-triazole-forming reaction between azides and terminal alkynes has become the gold standard of click chemistry due to its reliability, specificity, and biocompatibility. Applications of click chemistry are increasingly found in all aspects of drug discovery; they range from lead finding through combinatorial chemistry and target-templated in vitro chemistry, to proteomics and DNA research by using bioconjugation reactions. The triazole products are more than just passive linkers; they readily associate with biological targets, through hydrogen-bonding and dipole interactions. The present review will focus mainly on the recent literature for applications of this reaction in the field of medicinal chemistry, in particular on use of the 1,2,3-triazole moiety as pharmacophore.

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Section: Antifungal and Antibacterialsmentioning

confidence: 95%

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

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1,143

508

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“…As an important type of nitrogen-containing aromatic heterocyclic compounds, 1,2,3-triazole was regarded as the bioisosteric replacement of itsbioisoster 1,2,4-triazole, amide, or even other nitrogen-containingaromatic heterocycles [21,22]. 1,2,3-Triazole was stable to metabolic degradation and capable of forming hydrogen bonds, which could favor binding to biomolecular targets and improve solubility [23]. The team of Ifuku prepared new chitosan derivatives containing triazolyl moieties at the C 6 position of glucosamine units by coupling between azide and propargyl groups of chitosan via a 1,3-dipolar cycloaddition [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of water soluble chitosan derivatives with halogeno-1,2,3-triazole and their antifungal activity

Tan

Zhang

et al. 2016

International Journal of Biological Macromolecules

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a b s t r a c tChitosan is an abundant and renewable polysaccharide, which exhibits attractive bioactivities and natural properties. Improvement such as chemical modification of chitosan is often performed prior to further utilization. Three novel water soluble chitosan derivatives containing 1,2,3-triazole with or without halogen was designed and synthesized. Their antifungal activity against three kinds of phytopathogens was estimated by hyphal measurement in vitro. The inhibitory property and water solubility of the synthesized chitosan derivatives exhibited a remarkable improvement over chitosan. It is hypothesized that thiazolyl groups enable the synthesized chitosan to possess obviously better antifungal activity. Moreover, CTCTS and BTCTS, which have halogens at the periphery of polymers, inhibited the growth of tested phytopathogens more effectively with inhibitory indices of 81-93% at 1.0 mg/mL. The halogens could have a synergistic effect with triazole as they exhibited antifungal activity and electron-withdrawing capacity, which improve the antifungal activity of chitosan derivatives.

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“…19) 1,2,3-Triazole is not produced in nature although this moiety and its derivatives are a significant category of nitrogen-containing aromatic heterocyclic compounds, and have been considered because of their various biological properties such as antibacterial, antifungal, anti-human immunodeficiency virus (HIV), antitubercular, anticancer, anti-inflammatory and analgesic, anticonvulsant, antiparasitic, antidiabetic, antihistaminic and antihypertensive activities. [20][21][22] Triazole derivatives have increasingly been used as clinical remedies or candidates for the treatment of various types of diseases with powerful pharmacological activities, less side effects, fewer multidrug resistances, high bioavailability, good pharmacokinetic properties and drug targeting, diversity of drug administration and better curative effects. These evidences can be realized broad potential of triazolebased compounds as medicinal agents.…”

mentioning

confidence: 99%