Synthesis of novel triazole-linked mefloquine derivatives: Biological evaluation against Plasmodium falciparum

被引：28
|
作者：
Hamann, Anton R. [1 ]
de Kock, Carmen [2 ]
Smith, Peter J. [2 ]
van Otterlo, Willem A. L. [1 ]
Blackie, Margaret A. L. [1 ]
机构：
[1] Univ Stellenbosch, Dept Chem & Polymer Sci, ZA-7602 Matieland, South Africa
[2] Univ Cape Town, Groote Schuur Hosp, Dept Pharmacol, ZA-7700 Rondebosch, South Africa
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 23期
基金：
新加坡国家研究基金会; 英国医学研究理事会;
关键词：
2,8-Bis(trifluoromethyl) quinoline; 1,2,3-Triazole; P; falciparum; CuAAC chemistry; ACTIVITY IN-VITRO; ANTIMALARIAL ACTIVITY; MALARIA PARASITES; DESIGN; CHLOROQUINE; EXPLORATION; RESISTANCE; CHEMISTRY; HYBRIDS; VIVO;
D O I：
10.1016/j.bmcl.2014.10.015
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Using 2,8-bis(trifluoromethyl) quinoline, the pharmacophore of mefloquine, as scaffold, eleven novel triazole-linked compounds have been synthesised by the application of CuAAC chemistry. The in vitro biological activity of the compounds on the Plasmodium falciparum chloroquine-sensitive strain NF54 was then determined. The compounds all showed IC(50)s in the lower mu M range with (1R, 3S, 5R)- N-{[1-( 2,8bis( trifluoromethyl) quinoline-4-yl)-1H-1,2,3-triazol-4-yl] methyl} adamantan-2-amine (29) exhibiting the best activity of 1.00 mu M. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5466 / 5469
页数：4
相关论文
共 50 条
  • [21] Synthesis and anti-Plasmodium falciparum evaluation of novel pyrazolopyrimidine derivatives
    Flávia F. Silveira
    Lívia M. Feitosa
    João C. M. Mafra
    Maria de Lourdes G. Ferreira
    Kamilla R. Rogerio
    Leonardo J. M. Carvalho
    Nubia Boechat
    Luiz C. S. Pinheiro
    Medicinal Chemistry Research, 2018, 27 : 1876 - 1884
  • [22] Triazole-linked thiazolidinedione-Benzothiazole hybrids: Design and biological evaluation as AChE inhibitors
    Almatary, Aya M.
    Al-Sanea, Mohammad M.
    Nasr, Eman E.
    Haikal, Abdullah
    Thompson, Gary S.
    Abood, Amira
    Ibrahim, Mahmoud A. A.
    Elgazar, Abdullah A.
    Hamdi, Abdelrahman
    BIOORGANIC CHEMISTRY, 2025, 157
  • [23] Triazole-linked phenyl derivatives: Redox mechanisms and in situ electrochemical evaluation of interaction with dsDNA
    Pontinha, A. Dora R.
    Lombardo, Caterina M.
    Neidle, Stephen
    Oliveira-Brett, Ana Maria
    BIOELECTROCHEMISTRY, 2015, 101 : 97 - 105
  • [24] Synthesis of Thiazolidinedione- and Triazole-Linked Organoselenocyanates and Evaluation of Anticancer Activities Against Breast Cancer with Mechanistic Investigations
    Pal, Nikita
    Banerjee, Kaustav
    Sarkar, Shilpi
    Mandal, Tapas K.
    Bhabak, Krishna P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2025, 31 (11)
  • [25] Exploring anticancer properties of new triazole-linked benzenesulfonamide derivatives against colorectal carcinoma: Synthesis, cytotoxicity, and in silico insights
    Kurt, Belma Zengin
    Ozmen, Ozge
    Civelek, Dilek Ozrurk
    Senol, Halil
    Sonmez, Fatih
    BIOORGANIC & MEDICINAL CHEMISTRY, 2025, 119
  • [26] Synthesis of triazole-linked pseudo-starch fragments
    Nepogodiev, Sergey A.
    Dedola, Simone
    Marmuse, Laurence
    de Oliveira, Marcelo T.
    Field, Robert A.
    CARBOHYDRATE RESEARCH, 2007, 342 (3-4) : 529 - 540
  • [27] Synthesis and Biological Evaluation of Novel Triazole Derivatives as Strigolactone Biosynthesis Inhibitors
    Kawada, Kojiro
    Takahashi, Ikuo
    Arai, Minori
    Sasaki, Yasuyuki
    Asami, Tadao
    Yajima, Shunsuke
    Ito, Shinsaku
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2019, 67 (22) : 6143 - 6149
  • [28] Design, synthesis and biological evaluation of novel triazole, urea and thiourea derivatives of quinoline against Mycobacterium tuberculosis
    Upadhayaya, Ram Shankar
    Kulkarni, Girish M.
    Vasireddy, Nageswara Rao
    Vandavasi, Jaya Kishore
    Dixit, Shailesh S.
    Sharma, Vivek
    Chattopadhyaya, Jyoti
    BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (13) : 4681 - 4692
  • [29] Synthesis of New Cyclomarin Derivatives and Their Biological Evaluation towards Mycobacterium Tuberculosis and Plasmodium Falciparum
    Kiefer, Alexander
    Bader, Chantal D.
    Held, Jana
    Esser, Anna
    Rybniker, Jan
    Empting, Martin
    Mueller, Rolf
    Kazmaier, Uli
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (37) : 8894 - 8902
  • [30] Synthesis of stable triazole-linked glycopeptide mimics.
    Rutjes, FPJT
    Kuijpers, BHM
    Groothuys, S
    Quaedflieg, PJLM
    Blaauw, RH
    van Delft, FL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U533 - U533
12345