SYNTHESIS, CHARACTERIZATION, AND BIOLOGICAL EVALUATION OF SOME NOVEL GLYCOSYL 1,3,4-THIADIAZOLE DERIVATIVES AS ACETYLCHOLINESTERASE INHIBITORS

被引：11
作者：
Liu, Wei-wei [1 ,2 ,3 ]
Li, Qu-xiang [2 ]
Shi, Da-hua [1 ,3 ]
Cao, Zhi-ling [1 ,3 ]
Cheng, Feng-chang
Tao, Chuan-zhou [1 ,3 ]
Yin, Long [1 ]
Wang, Xuan [1 ]
机构：
[1] Huaihai Inst Technol, Sch Chem Engn, Lianyungang 222005, Peoples R China
[2] China Univ Min & Technol, Xuzhou 221116, Peoples R China
[3] Jiangsu Marine Resources Dev Res Inst, Lianyungang 222005, Peoples R China
来源：
HETEROCYCLES | 2015年 / 91卷 / 02期
关键词：
D-Glucosamine; 1,3,4-Thiadiazole; Acetylcholinesterase Inhibitor; POTENTIAL ANTIBACTERIAL; ANTIDEPRESSANT; ANALOGS;
D O I：
10.3987/COM-14-13134
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The corresponding 4-substituted glycosyl thiosemicarbazide derivatives (6a-61) were obtained by the reaction of glycosyl isothiocyanate 4 with various hydrazides. Further cyclization with the system of p-TsCl/TEA led to the formation of N-glycosyl-5-substituted 1,3,4-thiadiazole-2-amine (7a-71). Subsequent removal of the acetyl groups were conducted using the system of NaOMe/MeOH. The chemical structures of all new products were confirmed by JR. H-1 NMR and ESI-HRMS. The acetylcholinesterase (AChE) inhibitory activities of those compounds were tested by Ellman's method. Among them, the compound 8h possessed the best acetylcholinesterase-inhibition activity with IC50 of 18.38 +/- 0.89 mu M.
引用
收藏
页码：275 / 286
页数：12
相关论文
共 50 条
  • [31] Design, synthesis and insecticidal activity of new 1,3,4-thiadiazole and 1,3,4-thiadiazolo[3,2-a]pyrimidine derivatives under solvent-free conditions
    Ismail, Mahmoud F.
    Madkour, Hassan M. F.
    Salem, Marwa S.
    Mohamed, Ali M. M.
    Aly, Aly Fahmy
    SYNTHETIC COMMUNICATIONS, 2021, 51 (17) : 2644 - 2660
  • [32] Synthesis, Characterization, and Biological Evaluation of Some Novel Quinoxaline Derivatives as Antiviral Agents
    El-Zahabi, Heba S. A.
    ARCHIV DER PHARMAZIE, 2017, 350 (05)
  • [33] Design, synthesis and pharmacological evaluation of some novel indanone derivatives as acetylcholinesterase inhibitors for the management of cognitive dysfunction
    Piplani, Poonam
    Jain, Ankit
    Devi, Dhiksha
    Anjali
    Sharma, Anuradha
    Silakari, Pragati
    BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (01) : 215 - 224
  • [34] A convenient synthesis of 1,3,4-thiadiazole and 1,3,4-oxadiazole based peptidomimetics employing diacylhydrazines derived from amino acids
    Nagendra, G.
    Lamani, Ravi S.
    Narendra, N.
    Sureshbabu, Vommina V.
    TETRAHEDRON LETTERS, 2010, 51 (48) : 6338 - 6341
  • [35] Synthesis, Nematicidal Activity, and 3D-QSAR of Novel 1,3,4-Oxadiazole/ Thiadiazole Thioether Derivatives
    Chen, Jixiang
    Gan, Xiuhai
    Yi, Chongfen
    Wang, Shaobo
    Yang, Yuyuan
    He, Fangcheng
    Hu, Deyu
    Song, Baoan
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (10) : 939 - 944
  • [36] SYNTHESIS AND BIOLOGICAL EVALUATION OF SULFONAMIDE-BASED 1,3,4-OXADIAZOLE DERIVATIVES
    Kavitha, Selvaraj
    Nasarullah, Zulfareen
    Kannan, Kulanthai
    BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2019, 33 (02) : 307 - 319
  • [37] New Antimicrobial Nitro Heteroaryl-1,3,4-Thiadiazole Derivatives Containing Piperazinyl Benzonitrile Moiety: Synthesis and in silico Study
    Tahghighi, Azar
    Aghaee, Sara
    Bakhteari, Elnaz
    Azerang, Parisa
    Abdouss, Majid
    Eslamifar, Ali
    Foroumadi, AliReza
    JOURNAL OF COMPUTATIONAL BIOPHYSICS AND CHEMISTRY, 2022, 21 (02): : 249 - 257
  • [38] Synthesis, biological evaluation and molecular modeling of 1,3,4-thiadiazol-2-amide derivatives as novel antitubulin agents
    Li, Yu-Jing
    Qin, Ya-Juan
    Makawana, Jigar A.
    Wang, Yan-Ting
    Zhang, Yan-Qing
    Zhang, Ya-Liang
    Yang, Meng-Ru
    Jiang, Ai-Qin
    Zhu, Hai-Liang
    BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (15) : 4312 - 4322
  • [39] Design, synthesis and biological evaluation of novel 1, 3, 4-oxadiazole derivatives as potent neuraminidase inhibitors
    Yu, Wei
    Cheng, Li Peng
    Pang, Wan
    Guo, Ling Ling
    BIOORGANIC & MEDICINAL CHEMISTRY, 2022, 57
  • [40] Synthesis, Antimicrobial Evaluation and Docking Study of Some Pyrazole Bearing [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazole Derivatives
    Shingare, Ramesh M.
    Patil, Yogesh S.
    Sangshetti, Jaiprakash N.
    Damale, Manoj G.
    Rajani, Dhanji P.
    Madje, Balaji R.
    CHEMISTRYSELECT, 2018, 3 (14): : 3899 - 3903
12345