Synthesis of limonene β-amino alcohol derivatives in support of new antileishmanial therapies

被引:16
|
作者
Ferrarini, Stela R. [1 ]
Graebin, Cedric S. [1 ]
Limberger, Jones [2 ]
Canto, Romulo F. S. [1 ]
Dias, Daiane O. [1 ]
da Rosa, Ricardo G. [2 ]
Madeira, Maria de Fatima [3 ]
Eifler-Lima, Vera L. [1 ]
机构
[1] Univ Fed Rio Grande do Sul, Lab Sintese Organ Med, BR-90610000 Porto Alegre, RS, Brazil
[2] Univ Fed Rio Grande do Sul, Lab Catalise Metais Transicao, BR-90610000 Porto Alegre, RS, Brazil
[3] Fiocruz MS, Serv Parasitol Clin, Inst Pesquisa Clin Evandro Chagas, BR-21045900 Rio De Janeiro, Brazil
来源
MEMORIAS DO INSTITUTO OSWALDO CRUZ | 2008年 / 103卷 / 08期
关键词
limonene; beta-amino alcohol; synthesis; leishmaniasis; Leishmania braziliensis; neglected diseases;
D O I
10.1590/S0074-02762008000800005
中图分类号
R38 [医学寄生虫学]; Q [生物科学];
学科分类号
07 ; 0710 ; 09 ; 100103 ;
摘要
A series of seven limonene beta-amino alcohol derivatives has been regioselectively synthesised in moderate to good yields. Two of these compounds were found to be significantly effective against in vitro cultures of the Leishmania (Viannia) braziliensis promastigote form in the micromolar range. The activities found for 3b and 3f were about 100-fold more potent than the standard drug, Pentamidine, in the same test, while limonene did not display any activity. This is the first report of antileishmanial activity by limonene beta-amino alcohol derivatives.
引用
收藏
页码:773 / 777
页数:5
相关论文
共 50 条
  • [21] Antileishmanial Thioureas: Synthesis, Biological Activity and in Silico Evaluations of New Promising Derivatives
    Viana, Gil Mendes
    Soares, Deivid Costa
    Santana, Marcos Vinicius
    do Amaral, Lilian Henriques
    Meireles, Paloma Wetler
    Nunes, Raquel Pinto
    Rodrigues Pereira da Silva, Luiz Claudio
    de Sequeira Aguiar, Lucia Cruz
    Rodrigues, Carlos Rangel
    de Sousa, Valeria Pereira
    Castro, Helena Carla
    Abreu, Paula Alvarez
    Sathler, Plinio Cunha
    Saraiva, Elvira Maria
    Cabral, Lucio Mendes
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2017, 65 (10) : 911 - 919
  • [22] Synthesis and preliminary evaluation of new ursolic and oleanolic acids derivatives as antileishmanial agents
    Gnoatto, Simone C. B.
    Dalla Vechia, Luciana
    Lencina, Claiton L.
    Dassonville-Klimpt, Alexandra
    Da Nascimento, Sophie
    Mossalayi, Djavad
    Guillon, Jean
    Gosmann, Grace
    Sonnet, Pascal
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2008, 23 (05) : 604 - 610
  • [23] Synthesis of lupeol derivatives and their antileishmanial and antitrypanosomal activities
    Machado, Vanessa R.
    Sandjo, Louis P.
    Pinheiro, Giovanni L.
    Moraes, Milene H.
    Steindel, Mario
    Pizzolatti, Moacir G.
    Biavatti, Maique W.
    NATURAL PRODUCT RESEARCH, 2018, 32 (03) : 275 - 281
  • [24] Synthesis of a New Chiral Cyclicβ-Amino Alcohol
    Zong Xuan SHEN
    Jing LIANG
    Ya Wen ZHANG(School of Chemistry and Chemical Engineering
    Chinese Chemical Letters, 2000, (01) : 9 - 10
  • [25] Synthesis of a new chiral cyclic β-amino alcohol
    Shen, ZX
    Liang, J
    Zhang, YW
    CHINESE CHEMICAL LETTERS, 2000, 11 (01) : 9 - 10
  • [26] Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity
    Clarkson, C
    Musonda, CC
    Chibale, K
    Campbell, WE
    Smith, P
    BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (20) : 4417 - 4422
  • [27] Design, synthesis and cytotoxic activities of novel β-amino alcohol derivatives
    Bai, Bing
    Li, Xing-Yao
    Li, Yan
    Zhu, Hua-Jie
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (08) : 2302 - 2304
  • [28] Synthesis and therapeutic application of beta-amino alcohol derivatives
    Boumzour, Wiame
    El Youssfi, Safaa
    El Hammoumi, Mohamed Merouane
    Maazouz, Oussama
    Nassri, Aziz
    El Bachiri, Abdelhadi
    JOURNAL OF MOLECULAR STRUCTURE, 2025, 1321
  • [29] In Silico Toxicological Evaluation of New Antileishmanial Derivatives
    Miceli, L. A.
    Lira, M-. L. F.
    Marra, R. K. F.
    Borges, J. C.
    Gomes, A. P.
    Bello, M. L.
    Rodrigues, C. R.
    Bernardino, A. M. R.
    Amaral, V. F.
    Castro, H. C.
    INTERNATIONAL JOURNAL OF TOXICOLOGY, 2019, 38 (01) : 34 - 35
  • [30] Regarding a new alcohol derived from limonene
    Genvresse, P
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES, 1901, 132 : 414 - 416