Citation: Mei Wenwen, Guo Yuewei, Li Jia, Cai Meiyi, Ma Wenquan, Gong Jingxu, Wang Xuedong. Synthesis and Protein-Tyrosine Phosphatase 1B Inhibitory Activity Evaluation of Indolepropyl Based 1,3,4-Oxadiazole Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(3): 533-539. doi: 10.6023/cjoc201509024 shu

Synthesis and Protein-Tyrosine Phosphatase 1B Inhibitory Activity Evaluation of Indolepropyl Based 1,3,4-Oxadiazole Derivatives

Mei Wenwen ^a,b ,
Guo Yuewei ^b ,
Li Jia ^b ,
Cai Meiyi ^a ,
Ma Wenquan ^c ,
Gong Jingxu ^b,, ,
Wang Xuedong ^a,,

1.
a College of Pharmacy, Weifang Medical University, Weifang 261053;
2.
b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
3.
c Weifang Biomedical Innovation and Entrepreneurship Service Center, Weifang 261205

Corresponding author: Gong Jingxu, Wang Xuedong,
Received Date: 21 September 2015
Available Online: 12 November 2015
Fund Project: 国家海洋"863"项目(Nos. 2013AA092902, 2012AA092105) (Nos. 2013AA092902, 2012AA092105)国家自然科学基金(Nos. 81520108028, 81273430, 41306130, 41506187, 81302692, 41476063) (Nos. 81520108028, 81273430, 41306130, 41506187, 81302692, 41476063)山东省自然科学基金(No. U1406402) (No. U1406402)上海市科委项目(Nos. 14431901100, 15431901000) (Nos. 14431901100, 15431901000)新药研究国家重点实验室/上海药物所自主项目(Nos. SIMM1501ZZ-03, CASIMM0120152039)资助项目. (Nos. SIMM1501ZZ-03, CASIMM0120152039)

A series of indolepropyl based 1,3,4-oxadiazole derivatives were synthesized by esterification, hydrazidation, cyclization and substitution using indolebutyric acid as starting material. The inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) was evaluated. The results indicated that five compounds displayed obviously inhibitory effect against PTP1B in vitro, for instance, compound 5g exhibited the strongest PTP1B inhibitory activity with an IC₅₀ value of 6.74 μg· mL^-1 . It was the first example of indolealkyl based oxadiazole derivatives showing PTP1B inhibitory activity.
- 1,3,4-oxadiazole,
- synthesis,
- PTP1B inhibitory activity
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