Synthesis and antituberculosis activity of new fatty acid amides

被引:57
|
作者
Montes D'Oca, Caroline Da Ros [1 ]
Coelho, Tatiane [2 ]
Marinho, Tamara Germani [1 ]
Lopes Hack, Carolina Rosa [1 ]
Duarte, Rodrigo da Costa [1 ]
da Silva, Pedro Almeida [2 ]
Montes D'Oca, Marcelo Goncalves [1 ]
机构
[1] Univ Fed Rio Grande, Escola Quim & Alimentos, Lab Kolbe Sintese Organ, Rio Grande, RS, Brazil
[2] Univ Fed Rio Grande, Fac Med, Lab Micobacteriol, Rio Grande, RS, Brazil
关键词
Mycobacterium tuberculosis; Fatty acid amides; Ricinoleic acid; FAMEs; ENDOCANNABINOID SYSTEM; MYCOBACTERIUM-TUBERCULOSIS; ANANDAMIDE; OLEAMIDE; CANCER; TARGET;
D O I
10.1016/j.bmcl.2010.06.149
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
This work reports the synthesis of new fatty acid amides from C16: 0, 18: 0, 18: 1, 18: 1 (OH), and 18: 2 fatty acids families with cyclic and acyclic amines and demonstrate for the first time the activity of these compounds as antituberculosis agents against Mycobacterium tuberculosis H(37)Rv, M. tuberculosis rifampicin resistance (ATCC 35338), and M. tuberculosis isoniazid resistance (ATCC 35822). The fatty acid amides derivate from ricinoleic acid were the most potent one among a series of tested compounds, with a MIC 6.25 mu g/mL for resistance strains. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5255 / 5257
页数:3
相关论文
共 50 条
  • [1] MICROSOMAL SYNTHESIS OF FATTY ACID AMIDES
    BACHUR, NR
    UDENFRIEND, S
    JOURNAL OF BIOLOGICAL CHEMISTRY, 1966, 241 (06) : 1308 - +
  • [2] SYNTHESIS AND HERBICIDAL ACTIVITY OF SOME NEW HETEROCYCLIC ACID AMIDES
    Kaur, Pardeep
    Sharma, Sunita
    Joshi, Sukesha
    Aggarwal, Navneet
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 27 (02) : 129 - 135
  • [3] A Convenient Protocol for the Synthesis of Fatty Acid Amides
    Johansson, Silje J. R.
    Johannessen, Tonje
    Ellefsen, Christiane F.
    Ristun, Mali S.
    Antonsen, Simen
    Hansen, Trond V.
    Stenstrom, Yngve
    Nolsoe, Jens M. J.
    SYNLETT, 2019, 30 (02) : 213 - 217
  • [4] Synthesis and Antituberculosis Activity of New Hydrazide Derivatives
    Kaplancikli, Zafer A.
    Turan-Zitouni, Gulhan
    Ozdemir, Ahmet
    Teulade, Jean-Claude
    ARCHIV DER PHARMAZIE, 2008, 341 (11) : 721 - 724
  • [5] Synthesis and antituberculosis activity of new thiazolylhydrazone derivatives
    Turan-Zitouni, Guelhan
    Oezdemir, Ahmet
    Kaplancikli, Zafer Asim
    Benkli, Kadriye
    Chevallet, Pierre
    Akalin, Gulsen
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (05) : 981 - 985
  • [6] Toxocara canis: Larvicidal activity of fatty acid amides
    Mata-Santos, Tais
    Montes D'Oca, Caroline da Ros
    Mata-Santos, Hilton Antonio
    Fenalti, Juliana
    Pinto, Nitza
    Coelho, Tatiane
    Berne, Maria Elisabeth
    Almeida da Silva, Pedro Eduardo
    Montes D'Oca, Marcelo Goncalves
    Scaini, Carlos James
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (03) : 739 - 741
  • [7] Synthesis of fatty acid amides from Sichuan pepper
    Toy, Patrick
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [8] Pharmacological activity of fatty acid amides is regulated, but not mediated, by fatty acid amide hydrolase in vivo
    Lichtman, AH
    Hawkins, EG
    Griffin, G
    Cravatt, BF
    JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2002, 302 (01): : 73 - 79
  • [9] Synthesis and antiinflammatory activity of quinopimaric acid amides
    Flekhter O.B.
    Tret'yakova E.V.
    Galin F.Z.
    Karachurina L.T.
    Spirikhin L.V.
    Zarudii F.S.
    Tolstikov G.A.
    Pharmaceutical Chemistry Journal, 2002, 36 (8) : 428 - 431
  • [10] Synthesis of fatty acid amides, fatty acid esters, and their derivatives using halogenating agents and triphenylphosphine
    Pongpipatt, Paweena
    Chavasiri, Warinthorn
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238