Articles

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

  • Mei Wenwen ,
  • Guo Yuewei ,
  • Li Jia ,
  • Cai Meiyi ,
  • Ma Wenquan ,
  • Gong Jingxu ,
  • Wang Xuedong
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  • a College of Pharmacy, Weifang Medical University, Weifang 261053;
    b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
    c Weifang Biomedical Innovation and Entrepreneurship Service Center, Weifang 261205

Received date: 2015-09-21

  Revised date: 2015-11-12

  Online published: 2015-12-04

Supported by

Project supported by the National Marine "863" Projects (Nos. 2013AA092902 and 2012AA092105), the National Natural Science Foundation of China (Nos. 81520108028, 81273430, 41306130, 41506187, 81302692, 41476063), the NSFC-Shandong Joint Fund for Marine Science Research Centers (No. U1406402), the Science and Technology Commission of Shanghai Municipality Project (Nos. 14431901100, 15431901000), the State Key Laboratory of Drug Research/Shanghai Institute of Materia Medica Projects (Nos. SIMM1501ZZ-03, CASIMM0120152039).

Abstract

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.

Cite this article

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

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