Enantioselective synthesis of functionalized αα-aminophosphonic acid derivatives

Author:

Maestro Aitor1,del Corte Xabier1,Martinez de Marigorta Edorta1,Palacios Francisco1,Vicario Javier1

Affiliation:

1. Departamento de Química Orgánica I, Facultad de Farmacia, University of the Basque Country, Vitoria-Gasteiz, Spain

Funder

Ministerio de Economía, Industria y Competitividad

Gobierno Vasco

Publisher

Informa UK Limited

Subject

Inorganic Chemistry,Organic Chemistry,Biochemistry

Reference14 articles.

1. a) Van der Jeught, K.; Stevens, C. V. Direct Phosphonylation of Aromatic Azaheterocycles. Chem. Rev. 2009, 109, 2672. b) Berlicki, L.; Kafarski, P. Computer-Aided Analysis and Design of Phosphonic and Phosphinic Enzyme Inhibitors as Potential Drugs and Agrochemicals. Curr. Org. Chem. 2005, 9, 1829. c) Kafarski, P.; Lejczak, B. Aminophosphonic Acids of Potential Medical Importance. Cur. Med. Chem: Anti-Cancer Ag. 2001, 1, 301.

2. a) Hirschmann, R.; Smith, III, A. B.; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Venkovic, S. J. Peptide Synthesis Catalyzed by an Antibody Containing a Binding Site for Variable Amino Acids. Science 1994, 265, 234. b) Macchiarulo, A. R.; Pellicciari. Exploring the Other Side of Biologically Relevant Chemical Space: Insights into Carboxylic, Sulfonic and Phosphonic Acid Bioisosteric Relationships. J. Mol. Graphics Modell. 2007, 26, 728. c) Sieńczyk, M.; Winiarski, L.; Kasperkiewicz, P.; Psurski, M.; Wietrzyk, J.; Oleksyszyn, J. Synthesis and Activity Study of Phosphonamidate Dipeptides as Potential Inhibitors of VanX. Bioorg. Med. Chem. Lett. 2011, 21, 7224. d) Atherton, F. R.; Hassall, C. H.; Lambert, R. W. Synthesis and Structure-activity Relationships of Antibacterial Phosphonopeptides Incorporating (1-Aminoethyl)Phosphonic Acid and (Aminomethyl)Phosphonic Acid. J. Med. Chem. 1986, 29, 29. e) Yao, G.; Ye, M.; Huang, R.; Li, Y.; Pan, Y.; Xu, Q.; Liao, Z.; Wang, H. Synthesis and Antitumor Activities of Novel Rhein α-Aminophosphonates Conjugates. Bioorg. Med. Chem. Lett. 2014, 24, 501. f) Bonarska, D.; Kleszczyńska, H. Sarapuk. Antioxidative Activity of Some Phenoxy and Organophosphorous Compounds. J. Cell Mol. Biol. Lett. 2002, 7, 929.

3. a) Nguyen, L. A.; He, H.; Pham-Huy, C. Chiral Drugs: An Overview. Int. J. Biomedical Sci. 2002, 6, 85. b) Kasprzyk-Hordern, B. Pharmacologically Active Compounds in the Environment and Their Chirality. Chem. Soc. Rev. 2010, 39, 4466.

4. a) Stamper, C.; Bennett, B.; Edwards, T.; Holz, R. C.; Ringe, D.; Petsko, G. Inhibition of the Aminopeptidase from Aeromonas proteolytica by l-Leucinephosphonic Acid. Spectroscopic and Crystallographic Characterization of the Transition State of Peptide Hydrolysis. Biochemistry 2001, 40, 7035. b) Kafarski, P.; Lejczak, B.; Szewczyk, J. Optically Active 1 Amino Alkane Phosphonic Acids Di Benzoyl l Tartaric Anhydride as an Effective Agent for the Resolution of Racemic Di Phenyl 1 Amino Alkane Phosphonates. Can. J. Chem. 1983, 61, 2425. c) Solodenko, V. A.; Kukhar, V. P. Stereoselective Papain-catalyzed Synthesis of Alafosfalin. Tetrahedron Lett. 1989, 32, 66. d) Polyak, M. S. Antibiotics of the Phosphonic Acid Group. Antibiot. Med. Biotekhnol. 1987, 32, 66.

5. Recent Advances in the Catalytic Asymmetric Construction of Phosphorus-Substituted Quaternary Carbon Stereocenters

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3