84044-04-2Relevant academic research and scientific papers
A novel theranostic activity-based probe targeting kallikrein 7 for the diagnosis and treatment of skin diseases
Bisyris, Evangelos,Zingkou, Eleni,Kordopati, Golfo G.,Matsoukas, Minos,Magriotis, Plato A.,Pampalakis, Georgios,Sotiropoulou, Georgia
, p. 6507 - 6510 (2021/07/07)
We applied a newin silicoapproach for using protease-substrate motifs to design a kallikrein 7 (KLK7)-specific phosphonate activity-based probe (ABP) to quantify the active KLK7in situ. Epidermal application of the ABP-inhibitor onSpink5?/?Klk5
Catalytic asymmetric 1,2-addition of α-isothiocyanato phosphonates: Synthesis of chiral β-hydroxy- or β-amino-substituted α-amino phosphonic acid derivatives
Cao, Yi-Ming,Shen, Fang-Fang,Zhang, Fu-Ting,Zhang, Jin-Long,Wang, Rui
supporting information, p. 1862 - 1866 (2014/03/21)
α-Amino phosphonic acid derivatives are considered to be the most important structural analogues of α-amino acids and have a very wide range of applications. However, approaches for the catalytic asymmetric synthesis of such useful compounds are very limited. In this work, simple, efficient, and versatile organocatalytic asymmetric 1,2-addition reactions of α-isothiocyanato phosphonate were developed. Through these processes, derivatives of β-hydroxy-α-amino phosphonic acid and α,β-diamino phosphonic acid, as well as highly functionalized phosphonate-substituted spirooxindole, can be efficiently constructed (up to 99 % yield, d.r. >20:1, and >99 % ee). This novel method provides a new route for the enantioselective functionalization of α-phosphonic acid derivatives. Correct chirality critical: Organocatalytic asymmetric Adol-type and Mannich-type reactions of α-isothiocyanato phosphonate have been realized. Michael addition was also applicable under the same catalytic conditions. This versatile approach provides a new route for the synthesis of diverse highly optically active functionalized α-amino phosphonic acid derivatives. Copyright
Synthesis of phosphonodipeptide conjugates of ursolic acid and their homologs
Deng, Sheng-Lou,Baglin, Isabelle,Nour, Mohammed,Cave, Christian
, p. 55 - 65 (2008/04/05)
To prepare novel derivatives of naturally bioactive 3β-hydroxy-urs-12- en-28-oic acid (ursolic acid) with unusual properties and broad spectrum of activities, a number of chemical reactions were conducted. First, a variety of a-aminophosphonates were prepared by a series of reactions involving the three-component Mannich type reaction as a key step. Second, an array of phosphonodipeptides and their homologs was synthesized through multistep reactions including condensation of phthalic anhydride with glycine or β-alanine, chlorination of N-blocked amino acids, coupling of acid chloride with α-aminophosphonates and sequential hydrazinolysis. Finally, new classes of phosphonodipeptide conjugates of ursolic acid and their homologs were obtained by condensation of 3β-acetoxy-urs-12-en-28-oyl chloride with phosphonodipeptides and their homologs.
