Antimicrobial activity of allylic thiocyanates derived from the Morita-Baylis-Hillman reaction

被引:16
|
作者
Sa, Marcus Mandolesi [1 ]
Ferreira, Misael [1 ]
Lima, Emerson Silva [2 ]
Dos Santos, Ivanildes [3 ]
Orlandi, Patrcia Puccinelli [3 ]
Fernandes, Luciano [4 ]
机构
[1] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC, Brazil
[2] Univ Fed Amazonas, Fac Ciencias Farmaceut, Manaus, Amazonas, Brazil
[3] Fundacao Oswaldo Cruz, Ctr Pesquisa Leonidas & Maria Deane, Coordenacao Biodiversidade Saude, Manaus, Amazonas, Brazil
[4] Univ Tecnol Fed Parana, Dept Engn Quim, Ponta Grossa, PR, Brazil
关键词
antimicrobial; allylic thiocyanate; Morita-Baylis-Hillman reaction; MRSA; BIOLOGICAL EVALUATION; ASSISTED SYNTHESIS; TRYPANOSOMA-CRUZI; AQUEOUS-MEDIUM; DERIVATIVES; INHIBITORS; AGENTS; ANTIBIOTICS; RESISTANCE; CHEMISTRY;
D O I
10.1590/S1517-83822014000300007
中图分类号
Q93 [微生物学];
学科分类号
071005 ; 100705 ;
摘要
Bacterial resistance to commonly used antibiotics has been recognized as a significant global health issue. In this study, we carried out the screening of a family of allylic thiocyanates for their action against a diversity of bacteria and fungi with a view to developing new antimicrobial agents. Allylic thiocyanates bearing halogenated aryl groups, which were readily obtained in two steps from the Morita-Baylis-Hillman adducts, showed moderate-to-high activity against selective pathogens, including a methicillin-resistant S. aureus (MRSA) strain. In particular cases, methyl (Z)-3-(2,4-dichlorophenyl)-2-(thiocyanomethyl)-2-propenoate exhibited antimicrobial activity comparable to the reference antibiotic Imipenem.
引用
收藏
页码:807 / 812
页数:6
相关论文
共 50 条
  • [1] Synthesis of multifunctionalized allyl isothiocyanates via isomerization of Morita-Baylis-Hillman adduct-derived allylic thiocyanates
    Shin, Sang Gyu
    Oh, Hyun-Woo
    Kim, Byung Chang
    Ok, Jaeseung
    Lee, Seung In
    Youn, Sung Pyo
    Bae, Hyun Hee
    Park, Ji Yoon
    Han, Jin Woo
    Lee, Chang Hoon
    SYNTHETIC COMMUNICATIONS, 2025, 55 (03) : 251 - 258
  • [2] Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbonates
    Formanek, Bedrich
    Simek, Michal
    Kamlar, Martin
    Cisarova, Ivana
    Vesely, Jan
    SYNTHESIS-STUTTGART, 2019, 51 (04): : 907 - 920
  • [3] Sila Morita-Baylis-Hillman reaction of cyclopropenes
    Chuprakov, Stepan
    Malyshev, Denis A.
    Trofimov, Alexander
    Gevorgyan, Vladimir
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (48) : 14868 - 14869
  • [4] Nicholas cations in the Morita-Baylis-Hillman reaction
    Campbell, Mark
    Krafft, Marie E.
    Kerrigan, Sean
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [5] Recent extensions of the Morita-Baylis-Hillman reaction
    Ma, Guang-Ning
    Jiang, Jia-Jun
    Shi, Min
    Wei, Yin
    CHEMICAL COMMUNICATIONS, 2009, (37) : 5496 - 5514
  • [6] Decarboxylative Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbamates
    Docekal, Vojtech
    Simek, Michal
    Dracinsky, Martin
    Vesely, Jan
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (51) : 13441 - 13445
  • [7] Leishmanicidal activity of Morita-Baylis-Hillman adducts
    Santana Vieira, Ana Carolina
    Santos, Mariana da Silva
    Leite, Anderson Brandao
    da Silva, Amanda Evelyn
    Agra Cavalcante-Silva, Luiz Henrique
    Augusto Pereira, Gabrielle de Souza
    Gomes Marques, Sany Delany
    de Oliveira Santos, Barbara Viviana
    Fernandes Duarte, Alysson Wagner
    de Queiroz, Aline Cavalcante
    de Luna-Freire, Kristerson Reinaldo
    Alexandre-Moreira, Magna Suzana
    PARASITOLOGY RESEARCH, 2022, 121 (02) : 751 - 762
  • [8] Asymmetric Allylic Alkylation of Isatin-Derived Morita-Baylis-Hillman Carbonates with Nitroalkanes
    Chen, Guo-Ying
    Zhong, Fangrui
    Lu, Yixin
    ORGANIC LETTERS, 2012, 14 (15) : 3955 - 3957
  • [9] Asymmetric organocatalytic Morita-Baylis-Hillman reaction and asymmetric organocatalytic transformations of Morita-Baylis-Hillman adducts. An update
    Pellissier, Helene
    TETRAHEDRON, 2025, 172
  • [10] Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction
    Wei Yin
    Shi Min
    CHINESE SCIENCE BULLETIN, 2010, 55 (17): : 1699 - 1711