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Coumarin-derived azolyl ethanols:synthesis,antimicrobial evaluation and preliminary action mechanism

Science China Chemistry 2016年第7期59卷 878-894页

作者： Xin-Mei Peng kannekanti vijaya kumar Guri L.V. Damu Cheng-He Zhou Institute of Bioorganic & Medicinal Chemistry Key Laboratory of Applied chemistry of Chongqing MunicipalitySchool of Chemistry and Chemical EngineeringSouthwest UniversityChongqing 400715China

A series of coumarin-derived azolyl ethanols including imidazolyl,triazolyl,tetrazolyl,benzotriazolyl,thiol-imidazolyl and thiol-triazolyl ones were conveniently synthesized and characterized by IR,~1H NMR,^(13)C NMR and high-resolution mass spectra(HRMS) *** of the prepared compounds showed appropriate logP_(ow) values and effective antibacterial and antifungal ***,compound 14 with bis-triazolyl ethanol group exhibited low minimal inhibitory concentration(MIC)value of 8 μg/mL against MRSA,which was comparable or even superior to reference drugs Norfloxacin(MIC=8μg/mL)and Chloramphenicol(MIC=16μg/mL).It could also effectively inhibit the growth of the tested fungal strains compared to *** binding studies of coumarin 14 with calf thymus DNA were investigated by UV-Vis absorption and fluorescence *** was found that compound 14 could interact with calf thymus DNA by groove binding to form14-DNA complex via both hydrogen bonds and van der Waals force,which might be the factor to exert the powerful antimicrobial activity.

关键词： coumarin imidazole triazole tetrazole antibacterial antifungal calf thymus DNA

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Synthesis of Novel Coumarin-derived Triazole Alcohols as Clinical Fluconazole Analogues

Synthesis of Novel Coumarin-derived Triazole Alcohols as Cli...

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中国化学会全国第十二届有机合成化学学术研讨会

作者： kannekanti,vijaya kumar Zhou,Cheng-He School of Chemistry and Chemical Engineering Southwest University

Coumarin derivatives are very important class of heterocycles distributed in nature exhibiting diverse and functional biological ***,triazole alcohol derivatives are a functional class of aromatic heterocyclic compounds with broad spectrum of biological *** we developed a series of novel coumarin triazole alcohols with crucial medicinal *** synthesized structures were confirmed by H-NMR and MS spectra.

关键词： coumarin triazole antifungal antibacterial DNA

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Synthesis of Novel Coumarin Type of Azoles as Clinical Fluconazole Analogues

Synthesis of Novel Coumarin Type of Azoles as Clinical Fluco...

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中国化学会第九届全国有机化学学术会议

作者： kannekanti vijaya kumar 周成合 Laboratory of Bioorganic ＆ Medicinal Chemistry Key Laboratory of Applied Chemistry of Chongqing MunicipalitySchool of Chemistry and Chemical EngineerinSouthwest University

＜正＞Fluconazole is a well known first-line antifungal drug recommended by World Health Organization and is prevalently used to treat fungal infections with an exceptional therapeutic record including good activity and favorable pharmacokinetic *** derivatives are very important class of heterocycles distributed in nature and exhibit diverse biological *** we have developed novel coumarin type of

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Novel High Active Antibacterial Imidazole-Cu2+-MRSA DNA Ternary Supramolecular Complexes

Novel High Active Antibacterial Imidazole-Cu2+-MRSA DNA Tern...

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全国第十七届大环化学暨第九届超分子化学学术研讨会

作者：张玲 kannekanti vijaya kumar 周成合 School of Chemistry and Chemical Engineering Southwest University Indian Institute of Chemical Technology(IICT)

A series of new imidazole quinolone derivatives were synthesized and exhibited significant activities(MIC=0.0039-64μg/mL).The supramolecular interactions of highly active target compound,MRSA DNA and Cuion were inves... 详细信息

关键词： quinolone imidazole antimicrobial DNA

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Synthesis of Quinolone Benzimidazoles As Topoisomerase Inhibitors

Synthesis of Quinolone Benzimidazoles As Topoisomerase Inhib...

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中国化学会全国第十二届有机合成化学学术研讨会

作者： Zhang,Ling kannekanti,vijaya kumar Zhou,Cheng-He Laboratory of Bioorganic & Medicinal Chemistry Key Laboratory of Applied Chemistry of Chongqing MunicipalitySchool of Chemistry and Chemical EngineeringSouthwest University

Synthesis of topoisomerases inhibitors has earned considerable interest in medicinal chemistry as they are able to catalyze changes in DNA topology and are clinically validated targets for antibacterial drug *** and quinolones were revealed to important kind of important topoisomerase *** development of quinolone benzimidazole derivatives as novel antibacterial agents may be served as a good strategy to exploit new anti-infective agents with better activity and less bacterial *** we developed a series of novel fluoroquinolone-based benzimidazoles with various types of linkers including-CH-,-CH-CH-,-CH-NH- and shiffbase(-C=N-) ones,as well as the spacers with different lengths of aliphatic *** target compounds were obtained in yields of 49.3-87.6%via multistep *** new compounds were confirmed by NMR,MS and IR *** results indicated that target compound gave good topoisomerase inhibitory activities(MIC = 19 μM) with low *** properties in biologically relevant conditions including antibiofilm and bacterial membrane permeabilization activity were *** preliminary antimicrobial mechanism by evaluating the interaction of the prepared highly active compound with DNA was also investigated.

关键词： quinolone benzimidazole DNA topoisomerase antibacterial

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Novel Imidazo[2,1-b]benzothiazole Benzimidazoles: Synthesis,and Supramolecular Interaction with Calf Thymus DNA

Novel Imidazo[2,1-b]benzothiazole Benzimidazoles: Synthesis,...

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全国第十八届大环化学暨第十届超分子化学学术讨论会

作者： Swetha Kameswari Maddili kannekanti vijaya kumar 周成合 School of Chemistry and Chemical Engineering Southwest University

＜正＞A stipulating requirement is increasing for potent antimicrobial agents that can deal with the infectious diseases caused by destructive bacteria and *** studies disclosed that benzimidazoles have substantial ability to restrict the growth of bacterial and fungal ***,we have intended to alter imidazo[2,1-b]benzothiazole moiety by incorporating benzimidazole nucleus which has ended up in a

关键词： imidazo[2,1-b] benzothiazole benzimidazole bacterial fungal

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A Unique C-N Breakage of Sulfonylated Cyclic Amines by Azole Ring to Access Novel Antimicrobial Sulfonamide Azoles

A Unique C-N Breakage of Sulfonylated Cyclic Amines by Azole...

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中国化学会全国第十二届有机合成化学学术研讨会

作者： Zhang,Hui-Zhen kannekanti,vijaya kumar Zhou,Cheng-He Shandong Provincial Engineering Technology Research Center for Lunan Chinese Herbal Medicine Linyi University School of Chemistry and Chemical Engineering Southwest University

Sulfonamides are extensively employed as artificial antifolic agents for the prevention and cure of bacterial infections in human biological systems and a large amount of their heterocyclic derivatives such as pyrimidines has been developed and *** has been continuously attracting an increasing interest towards heterocyclic azole derivatives of sulfonamides,especially their highly efficient synthesis towards bioactive sulfonamide derivatives with heterocyclic *** a unique ring-opening reaction of C-N breakage of sulfonylated cyclic amine by azole ring to access novel antimicrobial sulfonamide azoles was *** single-crystals of the prepared compounds were cultured and determined by X-ray analysis in order to confirm this *** important influential factors including temperature,solvent and reaction time for this unique reaction were also *** the newly prepared compounds were screened for their antimicrobial activities.

关键词： sulfonamide C-N breaking imidazole triazole

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Coumarin-derived Metronidazoles:Design,Synthesis,Activity and Supramolecular Interaction with DNA

Coumarin-derived Metronidazoles:Design,Synthesis,Activity an...

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全国第十七届大环化学暨第九届超分子化学学术研讨会

作者： kannekanti vijaya kumar Maddili Swetha Kameswari 周成合 School of Chemistry and Chemical Engineering Southwest University Indian Institute of Chemical Technology(IICT)

＜正＞Novel coumarin metronidazoles as antimicrobial agents were synthesized and their synthesized compounds were confirmed by NMR and MS *** new compounds exhibited strong antimicrobial activities against four Gram-p... 详细信息

关键词： Coumarin Metronidazole Antimicrobial

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A Facile Synthesis of Coumarin-quinolone Hybrids as Potential Novel Antimicrobial Agents

A Facile Synthesis of Coumarin-quinolone Hybrids as Potentia...

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中国化学会全国第十二届有机合成化学学术研讨会

作者： Peng,Xin-Mei kannekanti,vijaya kumar Srinivasa,Rao Avula Zhou,Cheng-He School of Chemistry and Chemical Engineering Southwest University

Quinolones containing 3-carboxylic benzopyridone skeletons are an important kind of synthetic antibacterial agents as they are generally well tolerated with good treatment effectiveness,broad antibacterial spectrum and favorable pharmacokinetic *** the first quinolone drug was discovered in 1960 s,the related structural modifications based on 3-carboxylic benzopyridone skeletons have become an extremely attractive topic in antibacterial field,and much effort has been focusing on this *** represent an important type of aromatic oxygen heterocyclic compounds with typical 1,2-benzopyrone framework and possess large π-conjugated system,desirable electronic,charge-transport properties,as well as easily structural modification of coumarin ring by various functional *** structural features result in widely potential applications of coumarin compounds in the fields of bromatology（food additives and perfumes）,material and supramolecular chemistry（dyes,luminescence materials,chemical sensors and fluorescent probes,etc.） as well as pharmacochemistry（agrochemical and medicinal agents）.Numerous efforts,including the separation and purification of naturally occurring coumarins from a variety of plants as well as artificial synthesis of coumarin compounds with novel structures and properties have been *** the importance of quinolones and coumarins,herein we reported a facile synthetic approach of the coumarin-quinolone hybrids as potential novel antimicrobial agents.

关键词： amination coumarin quinolone

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Novel benzimidazole derived naphthalimide triazoles: synthesis, antimicrobial activity and interactions with calf thymus DNA

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Science China Chemistry 2015年第3期58卷 483-494页

作者： Yun-Lei Luo Kishore Baathulaa vijaya kumar kannekanti Cheng-He Zhou Gui-Xin Cai Key Laboratory of Applied Chemistry of Chongqing Municipality Institute of Bioorganic & Medicinal Chemistry School of Chemistry and Chemical Engineering Southwest University Department of Chemistry Kakatiya University Indian Institute of Chemical Technology

A novel series of benzimidazole derived naphthalimide triazoles and some corresponding triazoliums have been successfully synthesized and characterized by 1H NMR, 13 C NMR, 1H-1H COSY, IR and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution. 2-Chlorobenzyl triazolium 8g and compound 9b with octyl group exhibited the best antibacterial activities among all the tested compounds, especially against S. aureus with inhibitory concentration of 2 μg/mL which was equipotent potency to Norfloxacin(MIC=2 μg/mL) and more active than Chloromycin(MIC=7 μg/mL). Triazoliums 8g and 8f bearing 3-fluorobenzyl moiety displayed the best antifungal activities(MIC=2-19 μg/mL) against all the tested fungal strains without being toxic to PC12 cell line within concentration of 128 μg/m L. Further investigations by fluorescence and UV-Vis spectroscopic methods revealed that the compound 8g could effectively intercalate into calf thymus DNA to form the 8g-DNA complex which could block DNA replication, exerting powerful antimicrobial activities.

关键词： naphthalimide benzimidazole triazole antibacterial antifungal calf thymus DNA

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