3990-05-4Relevant articles and documents
Method for reducing carboxylic acid compound into aldehyde
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Paragraph 0036-0039, (2020/02/27)
The invention discloses a method for reducing a carboxylic acid compound into aldehyde. In a nitrogen atmosphere, in an organic solvent, a ligand/Cu catalyst, the carboxylic acid compound, an anhydride compound and hydrosilane are added by a one-pot method, a reaction is performed under the condition of the temperature of 20-120 DEG C for 2-20 h, after the reaction is completed, quenching and column chromatography separation are performed to obtain the product. The carboxylic acid compound can be successfully converted into aldehyde through one-pot reaction, especially unsaturated carboxylic acid can be reduced, and the reaction yield is generally relatively high. Compared with the prior art, the method has the outstanding advantages that the cheap copper salt is used as a catalyst, so that the experiment cost is greatly reduced. Meanwhile, the used method enlarges the application range of the reaction substrate, improves the compatibility of functional groups, and provides a new synthesis way for reducing the carboxylic acid compound into aldehyde.
Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2
Mostyn, Shannon N.,Carland, Jane E.,Shimmon, Susan,Ryan, Renae M.,Rawling, Tristan,Vandenberg, Robert J.
, p. 1949 - 1959 (2017/09/26)
It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50 of 9 μM and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GlyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 μM. This novel class of compounds show considerable promise as a first generation of GlyT2 transport inhibitors.
Design, synthesis, and pharmacological evaluation of bis-2-(5- phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl sulfide 3 (BPTES) analogs as glutaminase inhibitors
Shukla, Krupa,Ferraris, Dana V.,Thomas, Ajit G.,Stathis, Marigo,Duvall, Bridget,Delahanty, Greg,Alt, Jesse,Rais, Rana,Rojas, Camilo,Gao, Ping,Xiang, Yan,Dang, Chi V.,Slusher, Barbara S.,Tsukamoto, Takashi
, p. 10551 - 10563 (2013/02/22)
Bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl sulfide (BPTES) is a potent and selective allosteric inhibitor of kidney-type glutaminase (GLS) that has served as a molecular probe to determine the therapeutic potential of GLS inhibition. In an attempt to identify more potent GLS inhibitors with improved drug-like molecular properties, a series of BPTES analogs were synthesized and evaluated. Our structure-activity relationship (SAR) studies revealed that some truncated analogs retained the potency of BPTES, presenting an opportunity to improve its aqueous solubility. One of the analogs, N-(5-{2-[2-(5-amino-[1,3,4] thiadiazol-2-yl)-ethylsulfanyl]-ethyl}-[1,3,4]thiadiazol-2-yl) -2-phenyl-acetamide 6, exhibited similar potency and better solubility relative to BPTES and attenuated the growth of P493 human lymphoma B cells in vitro as well as in a mouse xenograft model.
