Synthesis of New Quinoline-Piperonal Hybrids as Potential Drugs against Alzheimer's Disease

被引：21
|
作者：
Brum, Juliana de Oliveira C. [1 ]
Neto, Denise Cristian F. [1 ]
de Almeida, Joyce Sobreiro E. D. [2 ]
Lima, Joselia Alencar [2 ,3 ]
Kuca, Kamil [4 ]
Franca, Tanos Celmar C. [2 ,4 ]
Figueroa-Villar, Jose D. [1 ]
机构：
[1] Mil Inst Engn, Dept Chem, Med Chem Grp, Praca Gen Tiburcio 80, BR-22290270 Rio De Janeiro, RJ, Brazil
[2] Mil Inst Engn, Lab Mol Modeling Appl Chem & Biol Def LMCBD, Praca Gen Tiburcio 80, BR-22290270 Rio De Janeiro, RJ, Brazil
[3] Univ Fed Maranhao, Grad Program Adult Hlth, Ave Portugueses 1966, BR-65080805 Sao Luis, MA, Brazil
[4] Univ Hradec Kralove, Fac Sci, Dept Chem, Rokitanskeho 62, Hradec Kralove 50003, Czech Republic
来源：
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES | 2019年 / 20卷 / 16期
关键词：
piperonal; quinolines; guanil-hydrazones; acetylcholinesterase; Alzheimer's disease; CHOLINESTERASE-INHIBITORS; ACETYLCHOLINESTERASE INHIBITORS; SWISS-PDBVIEWER; DESIGN; MODEL; REACTIVATION; DOCKING;
D O I：
10.3390/ijms20163944
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Six quinoline-piperonal hybrids were synthesized and evaluated as potential drugs against Alzheimer's disease (AD). Theoretical analysis of the pharmacokinetic and toxicological properties of the compounds suggest that they present good oral bio-availability and are also capable of penetrating the blood-brain barrier, qualifying as leads for new drugs against AD. Evaluation of their inhibitory capacity against acetyl- and butyrilcholinesterases (AChE and BChE) through Ellmann's test showed that three compounds present promising results with one of them being capable of inhibiting both enzymes. Further docking studies of the six compounds synthesized helped to elucidate the main interactions that may be responsible for the inhibitory activities observed.
引用
收藏
页数：15
相关论文
共 50 条
  • [1] Synthesis and evaluation of quinoline analogs as potential drugs in Alzheimer's disease
    Malik, Seema
    Sangwan, Abhijeet
    Piplani, Poonam
    Marco Coutelles, Jose
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [2] Synthesis of furocoumarin-stilbene hybrids as potential multifunctional drugs against multiple biochemical targets associated with Alzheimer's disease
    Agbo, Emmanuel N.
    Gildenhuys, Samantha
    Choong, Yee Siew
    Mphahlele, Malose J.
    More, Garland K.
    BIOORGANIC CHEMISTRY, 2020, 101
  • [3] A Template for New Drugs against Alzheimer's Disease
    Aguzzi, Adriano
    Gitler, Aaron D.
    CELL, 2013, 154 (06) : 1182 - 1184
  • [4] New tacrine-acridine hybrids as promising multifunctional drugs for potential treatment of Alzheimer's disease
    Chufarova, Nina
    Czarnecka, Kamila
    Skibinski, Robert
    Cuchra, Magda
    Majsterek, Ireneusz
    Szymanski, Pawel
    ARCHIV DER PHARMAZIE, 2018, 351 (07)
  • [5] New trends in the design of drugs against Alzheimer's disease
    Francotte, P
    Graindorge, E
    Boverie, S
    de Tullio, P
    Pirotte, B
    CURRENT MEDICINAL CHEMISTRY, 2004, 11 (13) : 1757 - 1778
  • [6] Design, synthesis and evaluation of novel feruloyl-donepezil hybrids as potential multitarget drugs for the treatment of Alzheimer's disease
    Dias, Kris Simone T.
    de Paula, Cynthia T.
    dos Santos, Thiago
    Souza, Isis N. O.
    Boni, Marina S.
    Guimaraes, Marcos J. R.
    da Silva, Fernanda M. R.
    Castro, Newton G.
    Neves, Gilda A.
    Veloso, Clarice C.
    Coelho, Marcio M.
    de Melo, Ivo Souza F.
    Giusti, Fabiana C. V.
    Giusti-Paiva, Alexandre
    da Silva, Marcelo L.
    Dardenne, Laurent E.
    Guedes, Isabella A.
    Pruccoli, Letizia
    Morroni, Fabiana
    Tarozzi, Andrea
    Viegas, Claudio, Jr.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 130 : 440 - 457
  • [7] Design and synthesis of tacrine-phenothiazine hybrids as multitarget drugs for Alzheimer’s disease
    Ai-ling Hui
    Yan Chen
    Shi-jing Zhu
    Chang-sheng Gan
    Jian Pan
    An Zhou
    Medicinal Chemistry Research, 2014, 23 : 3546 - 3557
  • [8] Design and synthesis of tacrine-phenothiazine hybrids as multitarget drugs for Alzheimer's disease
    Hui, Ai-ling
    Chen, Yan
    Zhu, Shi-jing
    Gan, Chang-sheng
    Pan, Jian
    Zhou, An
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (07) : 3546 - 3557
  • [9] Quinoline and imidazole dimers and their hybrids as new potential anti-cancer drugs
    Pottier, Laurent
    Le Calve, Benjamin
    De Neve, Nancy
    Nshimyumukiza, Prosper
    Dewelle, Janique
    Lefranc, Florence
    Mijatovic, Tatjana
    Kiss, Robert
    CANCER RESEARCH, 2009, 69
  • [10] New Tacrine Hybrids with Natural-Based Cysteine Derivatives as Multitargeted Drugs for Potential Treatment of Alzheimer's Disease
    Keri, Rangappa S.
    Quintanova, Catarina
    Chaves, Silvia
    Silva, Diana F.
    Cardoso, Sandra M.
    Santos, M. Amelia
    CHEMICAL BIOLOGY & DRUG DESIGN, 2016, 87 (01) : 101 - 111
12345