Synthesis of azomethines derived from cinnamaldehyde and vanillin: in vitro aetylcholinesterase inhibitory, antioxidant and insilico molecular docking studies

被引:39
作者
Chigurupati, Sridevi [1 ]
Selvaraj, Manikandan [2 ]
Mani, Vasudevan [3 ]
Mohammad, Jahidul I. [4 ]
Selvarajan, Kesavanarayanan K. [5 ]
Akhtar, Shaikh S. [1 ]
Marikannan, Maharajan [6 ]
Raj, Suthakaran [7 ]
Teh, Lay K. [2 ,5 ]
Salleh, Mohd Z. [2 ,5 ]
机构
[1] AIMST Univ, Fac Pharm, Bedong 08100, Kedah, Malaysia
[2] Univ Teknol MARA UiTM, Integrat Pharmacogen Inst iPROMISE, Puncak Alam Campus, Bandar Puncak Alam 42300, Selangor Darul, Malaysia
[3] Qassim Univ, Dept Pharmacol & Toxicol, Coll Pharm, Buraydah 51452, Saudi Arabia
[4] CUCMS, Dept Pharmacol, Fac Med, Cyberjaya 63000, Malaysia
[5] Univ Hail, Dept Pharmacol & Toxicol, Coll Pharm, Hail 2440, Saudi Arabia
[6] Int Med Univ, Sch Pharm, Kuala Lumpur 57000, Malaysia
[7] Teegala Ram Reddy Coll Pharm, Dept Pharmaceut Chem, Fac Pharm, Hyderabad 500097, Andhra Pradesh, India
关键词
Schiff bases; Cinnamaldehyde; Vanillin; Azomethines DPPH; Molecular docking; Acetylcholine esterase; SCHIFF-BASES; CHOLINESTERASE-INHIBITORS; DERIVATIVES; DISCOVERY;
D O I
10.1007/s00044-017-2104-6
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In the present study, we report the synthesis of azomethines derived from cinnamaldehyde (C1-C3) and vanillin (V1-V3) using ethanol as a green solvent in the presence of triethyl amine. The synthesized compounds were characterized and investigated for their free radical scavenging activity and anti-Alzheimer properties by DPPH and acetylcholinesterase (AChE) inhibition assays. The anti-Alzheimer properties of the compounds were determined by molecular docking and ADME predictions. Compounds, C1 and V1 were found to be potential with IC50 values of 0.01 +/- 0.09 A mu M and 0.31 +/- 0.03 A mu M respectively. The antioxidant activity of C1 in terms of DPPH and ABTS was found to be 16.22 +/- 0.02 A mu M and 17.2 +/- 0.02 A mu M, whereas V1 showed antioxidant activities at 14.07 +/- 0.02 A mu M and 15.06 +/- 0.03 A mu M respectively. In silico studies based on molecular docking and ADME predictions revealed the significance of azomethine derivatives as the potent anti-Alzheimer agents.
引用
收藏
页码:807 / 816
页数:10
相关论文
共 35 条
[1]   Efficient Synthesis and Discovery of Schiff Bases as Potent Cholinesterase Inhibitors [J].
Abd Razik, Basma M. ;
Osman, Hasnah ;
Ezzat, Mohammed O. ;
Basiri, Alireza ;
Salhin, Abdussalam ;
Kia, Yalda ;
Murugaiyah, Vikneswaran .
MEDICINAL CHEMISTRY, 2016, 12 (06) :527-536
[2]  
[Anonymous], 2013, INT J ORG CHEM, DOI [DOI 10.4236/IJOC.2013.33A008, 10.4236/ijoc. 2013.33A008]
[3]  
[Anonymous], 2015, MAESTR SCHROD REL 20
[4]   Natural and synthetic antioxidants: An updated overview [J].
Augustyniak, Agnieszka ;
Bartosz, Grzegorz ;
Cipak, Ana ;
Duburs, Gunars ;
Horakova, L'ubica ;
Luczaj, Wojciech ;
Majekova, Magdalena ;
Odysseos, Andreani D. ;
Rackova, Lucia ;
Skrzydlewska, Elzbieta ;
Stefek, Milan ;
Strosova, Miriam ;
Tirzitis, Gunars ;
Venskutonis, Petras Rimantas ;
Viskupicova, Jana ;
Vraka, Panagiota S. ;
Zarkovic, Neven .
FREE RADICAL RESEARCH, 2010, 44 (10) :1216-1262
[5]  
Bendale A.R., 2011, Der Pharma Chem, V3, P34
[6]   STUDYING NEWLY SYNTHESIZED AND DEVELOPED 4-HYDROXY-3-METHOXYBENZALDEHYDESCHIFF BASES BY UV SPECTROPHOTOMETRY AND HIGH PERFORMANCE LIQUID CHROMATOGRAPHY [J].
Chigurupati, Sridevi ;
Muralidharan, Selvadurai ;
Cin, Lim Sue ;
Raser, Wei Yin ;
Santhi, Kumaraswamy ;
Kesavanarayanan, Krishnan Selvarajan .
PHARMACEUTICAL CHEMISTRY JOURNAL, 2017, 50 (12) :851-856
[7]   Identification of novel acetylcholinesterase inhibitors: Indolopyrazoline derivatives and molecular docking studies [J].
Chigurupati, Sridevi ;
Selvaraj, Manikandan ;
Mani, Vasudevan ;
Selvarajan, Kesavanarayanan Krishnan ;
Mohammad, Jahidul Islam ;
Kaveti, Balaji ;
Bera, Hriday ;
Palanimuthu, Vasanth Raj ;
Teh, Lay Kek ;
Salleh, Mohd Zaki .
BIOORGANIC CHEMISTRY, 2016, 67 :9-17
[8]   A NEW AND RAPID COLORIMETRIC DETERMINATION OF ACETYLCHOLINESTERASE ACTIVITY [J].
ELLMAN, GL ;
COURTNEY, KD ;
ANDRES, V ;
FEATHERSTONE, RM .
BIOCHEMICAL PHARMACOLOGY, 1961, 7 (02) :88-&
[9]  
Elseweidy MM, 2017, CYTOKINE
[10]   Glide: A new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy [J].
Friesner, RA ;
Banks, JL ;
Murphy, RB ;
Halgren, TA ;
Klicic, JJ ;
Mainz, DT ;
Repasky, MP ;
Knoll, EH ;
Shelley, M ;
Perry, JK ;
Shaw, DE ;
Francis, P ;
Shenkin, PS .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (07) :1739-1749