Facile synthesis, structural evaluation, antimicrobial activity and synergistic effects of novel imidazo[1,2- a ]pyridine based organoselenium compounds

Kumar, Sanjeev; Sharma, Nidhi; Maurya, Indresh Kumar; Bhasin, Aman; Wangoo, Nishima; Brandão, Paula; Félix, Vı́tor; Bhasin, K. K.; Sharma, Rohit K.

doi:10.1016/j.ejmech.2016.07.076

Cited by 93 publications

(28 citation statements)

References 51 publications

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“…The antimicrobial activity of synthesized compounds ( 1a-1g ) ranged from 250 μM to 15.67 μM and results have been summarized in Tables 1 and 2 . The activities and efficacies of the compounds were compared with kanamycin, a routinely used standard antibiotic, and amphotericin B, a well-established antifungal drug [ 56 – 58 ]. Interestingly, the compounds 1b and 1f have been found to be the most potent antimicrobial agents among all tested compounds.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, DFT, docking studies and ADME prediction of some new coumarinyl linked pyrazolylthiazoles: Potential standalone or adjuvant antimicrobial agents

et al. 2018

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The control of antimicrobial resistance (AMR) seems to have come to a dead end. The major consequences of the use and abuse of antibacterial drugs are the development of resistant strains due to genetic mutability of both pathogenic and nonpathogenic microorganisms. We, herein, report the synthesis, characterization and biological activities of coumarin-thiazole-pyrazole (CTP) molecular hybrids with an effort to explore and overcome the increasing antimicrobial resistance. The compounds were characterized by analyzing their IR, Mass, 1H and13C NMR spectral data and elemental analysis. The in vitro antimicrobial activity of the synthesized compounds was investigated against various pathogenic strains; the results obtained were further explained with the help of DFT and molecular orbital calculations. Compound 1b and 1f displayed good antimicrobial activity and synergistic effects when used with kanamycin and amphotericin B. Furthermore, in vitro cytotoxicity of compounds 1b and 1f were studied against HeLa cells (cervical cancer cell) and Hek-293 cells. The results of molecular docking study were used to better rationalize the action and prediction of the binding modes of these compounds.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, DFT, docking studies and ADME prediction of some new coumarinyl linked pyrazolylthiazoles: Potential standalone or adjuvant antimicrobial agents

et al. 2018

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“…例如 , Sharma 课题组发现, 以氯乙酸为底物与 2-氨基吡啶 1 反应, 经历亲核取代和分子内环化得到中间体 2-氯咪唑并 [1,2-a]吡啶 11. 该中间体可转化为用于分子自组装的氮稠环化合物 12 和 14 [46] , 且后二者均可进一步将卤素硒化得到具有抗菌活性的咪唑并[1,2-a]吡啶化合物 13 和 15 [45,47] (Scheme 7). 除了酮、醛、羧酸外, 一些二羰基化合物也与 2-氨基吡啶构建稠杂环 [48][49] , 其中另一个羰基可以是酯羰基 [50] .…”

Section: 以醛为原料unclassified

Application of 2-Aminopyridines in the Synthesis of Five- and Six-Membered Azaheterocycles

Chen¹,

Chen²,

Wu³

et al. 2021

Chinese Journal of Organic Chemistry

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2-Aminopyridine is a significant synthetic synthon, with unique dual nucleophilic structure. It can react with ketones, aldehydes, acids, multifunctional esters, halogenated aromatics and other compounds to synthesize five-and six-member azaheterocycles. In recent years, the cyclization reactions based on 2-aminopyridines have been under the spotlight. According to the different types of substrates, the research progress on the synthesis of imidazo[1,2-a]pyridines and pyrido[1,2-a]pyrimidines based on 2-aminopyridines in the past 5 years is reviewed, and its applications in organic synthesis methodology, drug synthesis and fluorescent probes are summarized. Furthermore, the development trend of green cyclization and its application based on 2-aminopyridines in the future are prospected. Keywords 2-aminopyridine; imidazo[1,2-a]pyridine; pyrido[1,2-a]pyrimidine; azaheterocycle; C-N bond formation; retrosynthetic analysis 吡啶环上氮原子具有较强的吸电子效应, 且吡啶 α 位基团具有特殊的作用, 使吡啶 α 位的衍生物作为合成子或中间体在有机合成、药物合成中日益引人瞩目 [1][2][3] . 其中, 2-氨基吡啶作为最典型的一种, 因其独特的双亲核结构特点为人们所重视 [4] , 特别是基于吡啶环上的氮与氨基的成环反应倍受关注 [5][6][7] .

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“…In recent years, the development of new sustainable methodologies has gained the attention of the scientific community, leading to the application of environmentally benign synthetic procedures. [11] Organochalcogen compounds are gaining increasing interest in the area of synthesis, mainly because of their impressive potential application in the biological sciences, [12] as anticancer, [13][14][15][16] anti-Alzheimer, [17][18][19][20] antimicrobial, [21][22][23] antiviral, [24][25][26] anti-inflammatory, [27][28][29] anti-diabetic, [30][31][32] and antidepressant agents, [33][34][35] among other uses. [36][37][38] They also play a significant role in modern organic synthesis and materials science.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Electrochemical Chalcogen (S/Se)‐Functionalization of Organic Molecules

et al. 2019

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Achieving advances in the development of clean and efficient synthetic routes has become an important aim in research. In recent years, the search for new sustainable methodologies, notably environmentally benign synthetic procedures, has gained the attention of the scientific community. Electrosynthesis is a tool that has been extensively studied due to its potential application in chemical transformations and it adheres to the principles of green chemistry. Organochalogen compounds form an important class of molecules, since many of them have properties that can be applied in medicine and materials science. Thus, herein we provide a comprehensive and updated overview covering recent advances in the electrochemical C(sp2)−H bond chalcogenation of activated arenes and heterocycles as well as electrochemical chalcogenation through oxidative cross‐coupling reactions and chalcogen‐functionalization of alkenes/alkynes. The scope, limitations, and mechanisms are described and discussed, detailing the fundamental aspects and benefits of electrochemistry for the chalcogenation of organic compounds. The content of this Minireview demonstrates that it is possible to provide new synthetic routes and to improve the existing methodologies, to obtain processes more in line with current environmental protection aims. The reader will also find a discussion on the fundamental aspects and benefits of applying electrosynthesis to the assembly and operation of an electrolytic cell.

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Facile synthesis, structural evaluation, antimicrobial activity and synergistic effects of novel imidazo[1,2- a ]pyridine based organoselenium compounds

Cited by 93 publications

References 51 publications

Design, synthesis, DFT, docking studies and ADME prediction of some new coumarinyl linked pyrazolylthiazoles: Potential standalone or adjuvant antimicrobial agents

Design, synthesis, DFT, docking studies and ADME prediction of some new coumarinyl linked pyrazolylthiazoles: Potential standalone or adjuvant antimicrobial agents

Application of 2-Aminopyridines in the Synthesis of Five- and Six-Membered Azaheterocycles

Recent Advances in Electrochemical Chalcogen (S/Se)‐Functionalization of Organic Molecules

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