One-Step Synthesis of Chiral Oxindole-type Analogues with Potent Anti-inflammatory and Analgesic Activities

Scientific Reports
Yulong SunRui Wang

Abstract

Here we report a facile approach to synthesize highly optically active oxindole-type analogues with both high yield and enantioselectivity. This single-step synthesis strategy represents a substantial improvement upon existing methods that are often involved with multi-step routes and have suboptimal atomic economy. One such compound, namely Q4c, showed remarkable in vivo anti-inflammatory activity with efficiency approaching to that of a steroidal compound dexamethasone. Moreover, Q4c alleviated pain in mouse models with comparable activity to morphine. Further investigation suggested that nitric oxide signaling pathway is involved in the anti-inflammatory and analgesic activities of Q4c. Notably, this is the first time that chiral oxindole-type analogues have been identified to be both anti-inflammatory and analgesic, and our study also paved the way for future development of oxindoles as drug candidates in this field.

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Citations

Apr 9, 2019·ChemSusChem·Mubarak B DambattaLouis C Morrill
Jun 28, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mezna Saleh AltowyanH A Al-Ghulikah
Oct 18, 2016·International Journal of Oncology·Su Jung HwangHyo-Jong Lee
Nov 4, 2020·BMC Complementary Medicine and Therapies·Zhennan WangAi-Qun Jia
Apr 30, 2020·Saudi Journal of Biological Sciences·Mezna Saleh AltowyanH A Al-Ghulikah

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