Efficient click chemistry towards novel 1H-1,2,3-triazole-tethered 4H-chromene−d-glucose conjugates: Design, synthesis and evaluation of in vitro antibacterial, MRSA and antifungal activities

Thành, Nguyễn Đình; Hai, Do Son; Bich, Vu Thi; Hien, Pham Thi Thu; Duyen, Nguyen Thi Ky; Thị, Nguyễn; Dd, Do; Toan, Vu Ngoc; Van, Hoàng Thi Kim; Dang, Le Hai; Toan, Duong Ngoc; Vân, Trần Thị Thanh

doi:10.1016/j.ejmech.2019.01.060

Cited by 69 publications

(27 citation statements)

References 43 publications

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“…Molecules 72f, 72g, 72h , and 72i showed the highest potency toward S. epidermidis (MIC ranges of 3.12, 6.25, 1.56, and 3.12 μM, separately). On the other hand, the aforementioned triazoles showed similar inhibitory activity to ciprofloxacin but less than vancomycin, except for 72f, 72d, 72e (MICs 1.56 μM) (Thanh et al, 2019 ).…”

Section: Biological Activities Of 2h/4h-chromenesmentioning

confidence: 99%

“…The SAR features of a series of 1H-1,2,3-triazole containing tethered 4H-chromene-D-glucose conjugates by the alteration of the group at R position were reported with in-vitro potency against the microorganisms such as B. subtilis, S. aureus , and S. epidermidis ( Figure 9A ). The SAR result revealed the following significant point, such as ( 1 ) substitution with an electron-withdrawing group at the position of R in benzene increased the potency against the Gram-positive such as B. subtilis except for a nitro group; ( 2 ) substitution with an electron-donating group at the R position, such as alkyl (isopropyl, methyl) and dimethylamino group, reduced the microbial potency toward Gram-positive/negative bacteria; and ( 3 ) increasing the number of methoxy groups at the R position resulted in decreased Gram-negative antibacterial activity and increased Gram-positive antibacterial activity (Thanh et al, 2019 ).…”

Section: Structure-activity Relationship (Sar) Of 2h/4h-chromenesmentioning

confidence: 99%

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2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2020

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2H/4H-chromene (2H/4H-ch) is an important class of heterocyclic compounds with versatile biological profiles, a simple structure, and mild adverse effects. Researchers discovered several routes for the synthesis of a variety of 2H/4H-ch analogs that exhibited unusual activities by multiple mechanisms. The direct assessment of activities with the parent 2H/4H-ch derivative enables an orderly analysis of the structure-activity relationship (SAR) among the series. Additionally, 2H/4H-ch have numerous exciting biological activities, such as anticancer, anticonvulsant, antimicrobial, anticholinesterase, antituberculosis, and antidiabetic activities. This review is consequently an endeavor to highlight the diverse synthetic strategies, synthetic mechanism, various biological profiles, and SARs regarding the bioactive heterocycle, 2H/4H-ch. The presented scaffold work compiled in this article will be helpful to the scientific community for designing and developing potent leads of 2H/4H-ch analogs for their promising biological activities.

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Section: Biological Activities Of 2h/4h-chromenesmentioning

confidence: 99%

Section: Structure-activity Relationship (Sar) Of 2h/4h-chromenesmentioning

confidence: 99%

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2020

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“…Thanh et al [50] designed a hybrid structure of chromene and triazole by applying click chemistry approach for the synthesis of 1H-1,2,3-triazole-tethered 4H-chromene-D-glucose analogs (25) using Cu@MOF-5 (2 mol%) as a catalyst to afford 80-97.8% yields. The copper supported over metal organic frame work was found better catalyst in comparison to conventional catalysts viz.…”

Section: Metal Nano-particle Based Triazole Synthesismentioning

confidence: 99%

Role of Click Chemistry in Organic Synthesis

Sethiya¹,

Sahiba²,

Agarwal³

2021

Current Topics in Chirality - From Chemistry to Biology

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Click chemistry involves highly efficient organic reactions of two or more highly functionalized chemical entities under eco-benign conditions for the synthesis of different heterocycles. Several organic reactions such as nucleophilic ring-opening reactions, cyclo-additions, nucleophilic addition reactions, thiol-ene reactions, Diels Alder reactions, etc. are included in click reactions. These reactions have very important features i.e. high functional group tolerance, formation of a single product, high atom economy, high yielding, no need for column purification, etc. It also possesses several applications in drug discovery, supramolecular chemistry, material science, nanotechnology, etc. Being highly significant and valuable, we have elaborated on several aspects of click reactions in organic synthesis in this chapter. Recent advancements in the field of organic synthesis using click chemistry approach have been deliberated by citing last five years articles.

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“…Compostos heterocíclicos aromáticos contendo átomos de nitrogênios, se destacam no campo da química medicinal pelo seu amplo potencial biológico, incluindo efeito antiviral (Garcıá et al, 2003;Sun et al, 2020), antibacteriano (Gonzaga et al, 2013), antifúngico (Thanh et al, 2019) e antiparasitário (Tahghighi et al, 2012). Além disso, derivados azólicos, especialmente o 1,2,3triazol pode ser facilmente sintetizado com baixo custo, através da reação click chemistry, reações que podem ser catalisadas por iodeto de cobre entre alcinos e azidas, com formação de um grupamento 1,2,3-triazólico (Tale et al, 2015).…”

Section: Introductionunclassified

ESTUDO IN SILICO DO POTENCIAL DE FÁRMACOS AZÓLICOS SOBRE SARS-CoV-2: UMA ABORDAGEM QUÍMICA-MEDICINAL

Silva

Silva²,

Holanda³

2020

Rev. Interfaces

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A doença do Novo Coronavírus 2019 (COVID-19) é causada pelo agente etiológico SARS-CoV-2 e até o momento, não existem medicamentos antivirais com eficácia comprovada contra o vírus. Neste cenário, a Organização Mundial de Saúde adotou estratégias de reposicionamentos de medicamentos para a busca de um tratamento contra a COVID-19. Dessa forma, medicamentos antifúngicos contendo grupos derivados de azóis chamam atenção da comunidade científica pelo seu potencial farmacológico já estabelecido. Fármacos como fluconazol, voriconazol e itraconazol apresentam um grupo triazol e o cetoconazol um grupamento imidazol em suas estruras químicas, comumente relacionados ao efeito biológico. A análise in silico é o primeiro passo para investigar a possibilidade de reposicionamento de fármacos já utilizados na prática clínica, além disso essa técnica permite a triagem de moléculas a fim de buscar o melhores compostos e com potencial terapêutico. Dessa forma, o presente trabalho teve por objetivo analisar o perfil farmacocinético, físico-químico e toxicológico in silico, bem como o estudo da interação destes compostos sobre alvos proteicos do SARS-CoV-2. As análises mostraram que somente os compostos cetoconazol e itraconazol violaram a regra de Lipinski. A análise de ancoragem molecular revelou que o fluconazol e voriconazol apresentaram valores favoráveis de energia livre para a interação com a protease principal do SARS-CoV-2 e proteína do nucleocapsídeo. Em conjunto, esses resultados apontam para o potencial de estruturas formasdas por grupos triazólicos como candidatos a terapia contra o novo coronavírus.

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Efficient click chemistry towards novel 1H-1,2,3-triazole-tethered 4H-chromene−d-glucose conjugates: Design, synthesis and evaluation of in vitro antibacterial, MRSA and antifungal activities

Cited by 69 publications

References 43 publications

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

Role of Click Chemistry in Organic Synthesis

ESTUDO IN SILICO DO POTENCIAL DE FÁRMACOS AZÓLICOS SOBRE SARS-CoV-2: UMA ABORDAGEM QUÍMICA-MEDICINAL

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