4873-09-0Relevant articles and documents
Preparation process of triallyl isocyanurate (by machine translation)
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Paragraph 0010; 0013-0030, (2020/07/02)
The preparation process is characterized in that allyl alcohol is used as a raw material, allyl alcohol and p-toluenesulfonyl chloride are prepared into allyl tosylate through an acid binding agent; and the prepared allyl tosylate is reacted with sodium cyanate, a phase transfer catalyst and a polar solvent to obtain triallyl isocyanurate. To the preparation method, allyl alcohol is adopted as the raw material, atmospheric pollution is reduced, the reaction rate is higher, the yield of triallyl isocyanurate is improved, the environment is protected, and the energy-saving and consumption-reducing effect is remarkable. (by machine translation)
Facile synthesis of 1-Alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications
Lakshman, Mahesh K.,Singh, Manish K.,Kumar, Mukesh,Chamala, Raghu Ram,Yedulla, Vijayender R.,Wagner, Domenick,Leung, Evan,Yang, Lijia,Matin, Asha,Ahmad, Sadia
, p. 1919 - 1932 (2014/11/07)
(1H-Benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), 1H-benzo[d][1,2,3]triazol-1-yl 4- methylbenzenesulfonate (Bt-OTs), and 3H-[1,2,3]triazolo[4,5-b]pyridine-3-yl 4-methylbenzenesulfonate (At-OTs) are classically utilized in peptide synthesis for amide-bond formation. However, a previously undescribed reaction of these compounds with alcohols in the presence of a base, leads to 1-alkoxy-1H-benzo- (Bt-OR) and 7-azabenzotriazoles (At-OR). Although BOP undergoes reactions with alcohols to furnish 1-alkoxy-1H-benzotriazoles, Bt-OTs proved to be superior. Both, primary and secondary alcohols undergo reaction under generally mild reaction conditions. Correspondingly, 1-alkoxy-1H-7-azabenzotriazoles were synthesized from At-OTs. Mechanistically, there are three pathways by which these peptide-coupling agents can react with alcohols. From 31P{1H}, [18O]-labeling, and other chemical experiments, phosphonium and tosylate derivatives of alcohols seem to be intermediates. These then react with BtO- and AtO- produced in situ. In order to demonstrate broader utility, this novel reaction has been used to prepare a series of acyclic nucleoside-like compounds. Because BtO- is a nucleofuge, several Bt-OCH2Ar substrates have been evaluated in nucleophilic substitution reactions. Finally, the possible formation of Pd πallyl complexes by departure of BtO- has been queried. Thus, alpha-allylation of three cyclic ketones was evaluated with 1-(cinnamyloxy)-1H-benzo[d][1,2,3]triazole, via in situ formation of pyrrolidine enamines and Pd catalysis.
Structure guided design of a series of sphingosine kinase (SphK) inhibitors
Gustin, Darin J.,Li, Yihong,Brown, Matthew L.,Min, Xiaoshan,Schmitt, Mike J.,Wanska, Malgorzata,Wang, Xiaodong,Connors, Richard,Johnstone, Sheere,Cardozo, Mario,Cheng, Alan C.,Jeffries, Shawn,Franks, Brendon,Li, Shyun,Shen, Shanling,Wong, Mariwil,Wesche, Holger,Xu, Guifen,Carlson, Timothy J.,Plant, Matthew,Morgenstern, Kurt,Rex, Karen,Schmitt, Joanna,Coxon, Angela,Walker, Nigel,Kayser, Frank,Wang, Zhulun
, p. 4608 - 4616 (2013/08/15)
Sphingosine-1-phosphate (S1P) signaling plays a vital role in mitogenesis, cell migration and angiogenesis. Sphingosine kinases (SphKs) catalyze a key step in sphingomyelin metabolism that leads to the production of S1P. There are two isoforms of SphK and observations made with SphK deficient mice show the two isoforms can compensate for each other's loss. Thus, inhibition of both isoforms is likely required to block SphK dependent angiogenesis. A structure based approach was used to design and synthesize a series of SphK inhibitors resulting in the identification of the first potent inhibitors of both isoforms of human SphK. Additionally, to our knowledge, this series of inhibitors contains the only sufficiently potent inhibitors of murine SphK1 with suitable physico-chemical properties to pharmacologically interrogate the role of SphK1 in rodent models and to reproduce the phenotype of SphK1 (-/-) mice.