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Synthesis and in vitro evaluation of 2-(((2-ether)amino)methylene)-dimedone derivatives as potential antimicrobial agents.
Microb Pathog. 2018 Jan; 114:431-435.MP

Abstract

The study was designed with an aim to synthesize a series of 2-(((2-ether)amino)methylene)-dimedone derivatives and evaluate the synthesized compounds for antimicrobial activity. Compound library was synthesized by reaction with alkyl, alkenyl, alkynyl and alicyclic bromo-compounds. Characterization of the synthesized compounds was performed by 1H NMR, 13C NMR and mass spectral techniques. The compounds were evaluated for their antibacterial activity against Gram-positive (Staphylococcus aureus, Bacillus subtilis, Clostridium sporogenes) and Gram-negative bacteria (Pseudomonas aeruginosa, Escherichia coli). The activity of these compounds was also evaluated against fungi (Aspergillus fumigatus, Penicillium chrysogenum, Fusarium oxysporum, Candida albicans) and molds (A. niger and A. oryzae). Broth microdilution method and CLSI guidelines with minor modification were used for the determination of anti-bacterial and antifungal activity, respectively. Although four compounds (4i, 4j, 4k and 4l) showed good antibacterial activity but compound 4k was found to be most active chemotype in the series. Compound 4k was found to be active against S. aureus, B. cereus and B. subtilis bacterial strains at one dilution lower compared to the control ciprofloxacin. Antibacterial activity of compound 4k was comparable to ciprofloxacin against S. pyogenes and M. luteus. The compound 4d, 4e and 4s showed good antifungal and antimold activity compared to other chemotypes. However, in comparison to fluconazole both the compounds showed lower activity. The results merit the antimicrobial promise of the 2-(((2-ether)amino)methylene)-dimedone analogs.

Authors+Show Affiliations

Laboratory of Organic Synthesis, Department of Chemistry, Govt. Degree College for Women Baramulla, Jammu & Kashmir 193101, India. Electronic address: loneali33@gmail.com.Department of Biochemistry, University of Kashmir, Srinagar, Jammu & Kashmir 190006, India. Electronic address: rathermuzafar52@yahoo.com.Department of Chemistry, Faculty of Science, SHUATS Allahabad, Uttar Pradesh 211007, India.Academy of Scientific and Innovative Research (AcSIR), New Delhi 110012, India.Department of Biochemistry, Faculty of Medicine, Jawaharlal Nehru Medical College, Aligarh Muslim University, UP 190006, India.Department of Chemistry, Faculty of Science, SHUATS Allahabad, Uttar Pradesh 211007, India.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29233781

Citation

Lone, Ali Mohd, et al. "Synthesis and in Vitro Evaluation of 2-(((2-ether)amino)methylene)-dimedone Derivatives as Potential Antimicrobial Agents." Microbial Pathogenesis, vol. 114, 2018, pp. 431-435.
Lone AM, Rather MA, Bhat MA, et al. Synthesis and in vitro evaluation of 2-(((2-ether)amino)methylene)-dimedone derivatives as potential antimicrobial agents. Microb Pathog. 2018;114:431-435.
Lone, A. M., Rather, M. A., Bhat, M. A., Bhat, Z. S., Tantry, I. Q., & Prakash, P. (2018). Synthesis and in vitro evaluation of 2-(((2-ether)amino)methylene)-dimedone derivatives as potential antimicrobial agents. Microbial Pathogenesis, 114, 431-435. https://doi.org/10.1016/j.micpath.2017.12.022
Lone AM, et al. Synthesis and in Vitro Evaluation of 2-(((2-ether)amino)methylene)-dimedone Derivatives as Potential Antimicrobial Agents. Microb Pathog. 2018;114:431-435. PubMed PMID: 29233781.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and in vitro evaluation of 2-(((2-ether)amino)methylene)-dimedone derivatives as potential antimicrobial agents. AU - Lone,Ali Mohd, AU - Rather,Muzafar Ahmad, AU - Bhat,Muneer Ahmad, AU - Bhat,Zubair Shanib, AU - Tantry,Irfan Qadir, AU - Prakash,Poonam, Y1 - 2017/12/09/ PY - 2017/09/01/received PY - 2017/12/06/revised PY - 2017/12/08/accepted PY - 2017/12/14/pubmed PY - 2018/8/14/medline PY - 2017/12/14/entrez KW - Anti-Microbial KW - Aspergillosis KW - Condensation KW - Diones KW - Formylation SP - 431 EP - 435 JF - Microbial pathogenesis JO - Microb. Pathog. VL - 114 N2 - The study was designed with an aim to synthesize a series of 2-(((2-ether)amino)methylene)-dimedone derivatives and evaluate the synthesized compounds for antimicrobial activity. Compound library was synthesized by reaction with alkyl, alkenyl, alkynyl and alicyclic bromo-compounds. Characterization of the synthesized compounds was performed by 1H NMR, 13C NMR and mass spectral techniques. The compounds were evaluated for their antibacterial activity against Gram-positive (Staphylococcus aureus, Bacillus subtilis, Clostridium sporogenes) and Gram-negative bacteria (Pseudomonas aeruginosa, Escherichia coli). The activity of these compounds was also evaluated against fungi (Aspergillus fumigatus, Penicillium chrysogenum, Fusarium oxysporum, Candida albicans) and molds (A. niger and A. oryzae). Broth microdilution method and CLSI guidelines with minor modification were used for the determination of anti-bacterial and antifungal activity, respectively. Although four compounds (4i, 4j, 4k and 4l) showed good antibacterial activity but compound 4k was found to be most active chemotype in the series. Compound 4k was found to be active against S. aureus, B. cereus and B. subtilis bacterial strains at one dilution lower compared to the control ciprofloxacin. Antibacterial activity of compound 4k was comparable to ciprofloxacin against S. pyogenes and M. luteus. The compound 4d, 4e and 4s showed good antifungal and antimold activity compared to other chemotypes. However, in comparison to fluconazole both the compounds showed lower activity. The results merit the antimicrobial promise of the 2-(((2-ether)amino)methylene)-dimedone analogs. SN - 1096-1208 UR - https://www.unboundmedicine.com/medline/citation/29233781/Synthesis_and_in_vitro_evaluation_of_2____2_ether_amino_methylene__dimedone_derivatives_as_potential_antimicrobial_agents_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0882-4010(17)31100-2 DB - PRIME DP - Unbound Medicine ER -