Stereoselective Synthesis of α‐Aminophosphonic Acids through Pudovik and Kabachnik‐Fields Reaction

Author:

Ordóñez Mario,Viveros‐Ceballos José Luis,Estudillo Iván Romero‐

Publisher

InTech

Reference48 articles.

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2. (a) Yamato M, Koguchi T, Okachi R, Yamada K, Nakayama K, Kase H, Karasawa A, Shuto K. K‐26, a novel inhibitor of angiotensin I converting enzyme produced by an actinomycete K‐26. The Journal of Antibiotics 1986;39:44–52; (b) Ntai I, Bachmann BO. Identification of ACE pharmacophore in the phosphonopeptide metabolite K‐26. Bioorganic & Medicinal Chemistry Letters. 2008;18;3068–3071

3. (a) Kukhar VP, Hudson HR, editors. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity. Chichester: Wiley; 2000; (b) Orsini F, Sello G, Sisti M. Aminophosphonic acids and derivatives. Synthesis and biological applications. Current Medicinal Chemistry. 2010;17:264–289; (c) Lejczak B, Kafarski P. Biological activity of aminophosphonic acids and their short peptides. Topics in Heterocyclic Chemistry. 2009;20:31–63; (d) Sienczyk M, Oleksyszyn J. Irreversible inhibition of serine proteases‐design and in vivo activity of diaryl α‐aminophosphonate derivatives. Current Medicinal Chemistry. 2009;16:1673–1687; (e) Moonen K, Laureyn I, Stevens CV. Synthetic methods for azaheterocyclic phosphonates and their biological activity. Chemical Reviews. 2004;104:6177–6215; (f) Hiratake J, Oda J. Aminophosphonic and aminoboronic acids as key elements of a transition state analogue inhibitor of enzymes. Bioscience, Biotechnology, and Biochemistry. 1997;61:211–218; (g) Kafarski P, Lejczak B. Biological activity of aminophosphonic acids. Phosphorus, Sulfur, and Silicon and the Related Elements. 1991;63:193–215

4. Mucha A, Kafarski P, Berlicki L. Remarkable potential of the α‐aminophosphonate/phosphinate structural motif in medicinal chemistry. Journal of Medicinal Chemistry. 2011;54:5955–5980

5. (a) Mikolajczyk M. Acyclic and cyclic aminophosphonic acids: Asymmetric syntheses mediated by chiral sulfinyl auxiliarity. Journal of Organometallic Chemistry. 2005;690:2488–2486; (b) Huang J, Chen R. An overview of recent advances on the synthesis and biological activity of α‐aminophosphonic acid derivatives. Heteroatom Chemistry. 2000;11:480–492; (c) Patel DV, Rielly‐Gauvin K, Ryono DE, Free CA, Rogers WL, Smith SA, DeForrest JM, Oehl RS, Petrillo Jr EW. α‐Hydroxy phosphinyl‐based inhibitors of human renin. Journal of Medicinal Chemistry. 1995;38:4557–4569; (d) Allen JG, Atherton FR, Hall MJ, Hassall CH, Holmes SW, Lambert RW, Nisbet LJ, Ringrose PS. Phosphonopeptides as antibacterial agents: alaphosphin and related phosphonopeptides. Antimicrobial Agents and Chemotherapy. 1979, 15, 684–695; (e) Atherton FR, Hall MJ, Hassall CH, Lambert RW, Lloyd WJ, Ringrose PS. Phosphonopeptides as antibacterial agents: Mechanism of action of alaphosphin. Antimicrobial Agents and Chemotherapy. 1979;15:696–705

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