Citation: FENG Jian-An, JIANG Xue-Hua. Synthesis and Evaluation of Two Novel Naphthol Derivatives as Novel Cholinesterase Inhibitors[J]. Chinese Journal of Structural Chemistry, ;2016, 35(3): 371-374. doi: 10.14102/j.cnki.0254-5861.2011-0881 shu

Synthesis and Evaluation of Two Novel Naphthol Derivatives as Novel Cholinesterase Inhibitors

FENG Jian-An ,
JIANG Xue-Hua ^,

1.
West China School of Pharmacy, Sichuan University, Chengdu 610041, China

Corresponding author: JIANG Xue-Hua,
Received Date: 3 July 2015
Available Online: 1 December 2015

Two novel naphthol derivatives (1 and 2) were synthesized and characterized via IR, ¹H NMR, and HRMS. The structure of compound 2 was verified by single-crystal X-ray crystallography. It crystallizes in monoclinic, space group C2/c with a = 21.6725(9), b = 6.0127(3), c = 25.5405(14) Å, β = 94.716(5)°, V = 3316.9(3) Å³, Z = 8, F(000) = 1384, D_c = 1.511 Mg/m³, M_r = 377.22 and μ = 2.487 mm^-1. In addition, their cholinesterase inhibitory activities in vitro toward Electrophorus electricus acetylcholinesterase (eelAChE) and horse serum butyrylcholinesterase (eqBChE) were further determined. The results showed that compound 1 as a new acetylcholinesterase (AChE) inhibitor displayed higher AChE inhibitory activity (IC₅₀ = 1.4 μM), which could be considered for Alzheimer’s disease therapeutics.
- naphthol,
- crystal,
- cholinesterase
1. [1]
  (1) Walsh, D. M.; Selkoe, D. J. Deciphering the molecular basis of memory failure in Alzheimer's disease. Neuron 2004, 44, 181-193.
2. [2]
  (2) Selkoe, D. J.; Podlisny, M. B. Deciphering the genetic basis of Alzheimer's disease. Annu. Rev. Genomics Hum. Genet. 2002, 3, 67-99.
3. [3]
  (3) Terry, A. V.; Buccafusco, J. J. The cholinergic hypothesis of age and Alzheimer's disease-related cognitive deficits: recent challenges and their implications for novel drug development. J. Pharmacol. Exp. Ther. 2003, 306, 821-827.
4. [4]
  (4) Jacobsen, J. S.; Reinhart, P.; Pangalos, M. N. Current concepts in therapeutic strategies targeting cognitive decline and disease modification in Alzheimer's disease. NeuroRx 2005, 2, 612-626.
5. [5]
  (5) Mori, H. Untangling Alzheimer's disease from fibrous lesions of neurofibrillary tangles and senile plaques. Neuropathology 2000, 20, S55-60.
6. [6]
  (6) Khan, A. T.; Lal, M.; Ali, S.; Khan, M. M. One-pot three-component reaction for the synthesis of pyran annulated heterocyclic compounds using DMAP as a catalyst. Tetra. Lett. 2011, 52, 5327-5332.
7. [7]
  (7) Eshghi, H.; Zohuri, G. H.; Sandaroos, R.; Damavandi, S. Synthesis of novel benzo[f]chromene compounds catalyzed by ionic liquid. Heterocycl. Commun. 2012, 18, 67-70.
8. [8]
  (8) Sandaroos, R.; Damavandi, S. Ultrasound-assisted one-pot synthesis of disubstituted and trisubstituted 1H-benzo[f]chromene derivatives catalyzed by 4-nitro-2, 6-diacetylpyridinebis(2, 4, 6-trimethylaniline)FeCl₂. Res. Chem. Intermed. 2013, 39, 4167-4174.
9. [9]
  (9) Sheldrick, G. M. SHELXL 97, Program for the Refinement of Crystal Structure. University of Göttingen, Germany 1997.
10. [10]
  (10) Ellman, G. L.; Courtney, K. D.; Andres, V.; Featherstone, R. M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88-95.
1. [1]
  Jiakun Bai , Junhui Jia , Aisen Li . An elastic organic crystal with piezochromic luminescent behavior. Chinese Journal of Structural Chemistry, 2024, 43(6): 100323-100323. doi: 10.1016/j.cjsc.2024.100323
2. [2]
  Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
3. [3]
  Jun Lu , Jinrui Yan , Yaohao Guo , Junjie Qiu , Shuangliang Zhao , Bo Bao . Controlling solid form and crystal habit of triphenylmethanol by antisolvent crystallization in a microfluidic device. Chinese Chemical Letters, 2024, 35(4): 108876-. doi: 10.1016/j.cclet.2023.108876
4. [4]
  Ce Liang , Qiuhui Sun , Adel Al-Salihy , Mengxin Chen , Ping Xu . Recent advances in crystal phase induced surface-enhanced Raman scattering. Chinese Chemical Letters, 2024, 35(9): 109306-. doi: 10.1016/j.cclet.2023.109306
5. [5]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
6. [6]
  Fengyu Zhang , Yali Liang , Zhangran Ye , Lei Deng , Yunna Guo , Ping Qiu , Peng Jia , Qiaobao Zhang , Liqiang Zhang . Enhanced electrochemical performance of nanoscale single crystal NMC811 modification by coating LiNbO₃. Chinese Chemical Letters, 2024, 35(5): 108655-. doi: 10.1016/j.cclet.2023.108655
7. [7]
  Na Wang , Wang Luo , Huaiyi Shen , Huakai Li , Zejiang Xu , Zhiyuan Yue , Chao Shi , Hengyun Ye , Leping Miao . Crystal engineering regulation achieving inverse temperature symmetry breaking ferroelasticity in a cationic displacement type hybrid perovskite system. Chinese Chemical Letters, 2024, 35(5): 108696-. doi: 10.1016/j.cclet.2023.108696
8. [8]
  Zhijia Zhang , Shihao Sun , Yuefang Chen , Yanhao Wei , Mengmeng Zhang , Chunsheng Li , Yan Sun , Shaofei Zhang , Yong Jiang . Epitaxial growth of Cu_2-xSe on Cu (220) crystal plane as high property anode for sodium storage. Chinese Chemical Letters, 2024, 35(7): 108922-. doi: 10.1016/j.cclet.2023.108922
9. [9]
  Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
10. [10]
  Zhi-Yuan Yue , Hua-Kai Li , Na Wang , Shan-Shan Liu , Le-Ping Miao , Heng-Yun Ye , Chao Shi . Dehydration-triggered structural phase transition-associated ferroelectricity in a hybrid perovskite-type crystal. Chinese Chemical Letters, 2024, 35(10): 109355-. doi: 10.1016/j.cclet.2023.109355
11. [11]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
12. [12]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
13. [13]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
14. [14]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(932)
HTML views(44)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return