99767-90-5Relevant academic research and scientific papers
Synthesis and bioactivities evaluation of L-pyroglutamic acid analogues from natural product lead
Gang, Fang-li,Zhu, Feng,Li, Xiao-ting,Wei, Jie-lu,Wu, Wen-jun,Zhang, Ji-wen
, p. 4644 - 4649 (2018/08/21)
A series of L-pyroglutamic acid analogues from natural product lead were designed and synthesized, as well as their antifungal activities against Phytophthora infestans, neuritogenic activities, antibacterial activities and anti-inflammatory activities are described. The bioassays and SAR study showed that the majority of L-pyroglutamic acid esters have a significant antifungal activity against P. infestans, especially 2d and 2j demonstrated the best activities with EC50 values of 1.44 and 1.21 μg mL?1, which were about seven times that of commercial azoxystrobin (7.85 μg mL?1). Moreover, compounds 2e, 2g and 4d displayed anti-inflammatory activity against LPS-induced NO production in BV-2 microglial cells; neuritogenic activity in NGF-induced PC-12 cells is the same activity. This study demonstrates that compounds 2d and 2j are potential drugs to control P. infestans.
Five- and six-membered ring opening of pyroglutamic diketopiperazine
Parrish, Dennis A.,Mathias, Lon J.
, p. 1820 - 1826 (2007/10/03)
A variety of ring-opening reactions of pyroglutamic diketopiperazine at both the five-membered and six-membered rings is described. Mild, basic conditions facilitate nucleophilic attack by amines at the diketopiperazine carbonyls giving pyroglutamides in excellent yield. Reaction with nucleophiles under acidic conditions give bis-glutamate derivatives of 2,5-diketopiperazine (DKP). These reactions provide simple, two-step sequences to pyroglutamides and symmetrical diketopiperazines from commercial pyroglutamic acid with control of product dictated by reaction conditions, catalyst, and nucleophile.
