Recent synthesis of aminophosphonic acids as potential biological importance

被引：191

作者：

Naydenova, Emilia D. ^{[1
]}

Todorov, Petar T. ^{[1
]}

Troev, Kolio D. ^{[2
]}

机构：

[1] Univ Chem Technol & Met, Dept Organ Chem, BU-1756 Sofia, Bulgaria

[2] Bulgarian Acad Sci, Inst Polymer, BU-1113 Sofia, Bulgaria

来源：

AMINO ACIDS | 2010年 / 38卷 / 01期

关键词：

alpha-Aminophosphonic acids; N-(phosphonomethyl) glycine; Phosphorus trichloride; Dimethyl-H-phosphonate; Biological activity; ALPHA-AMINO-PHOSPHONATES; BEARING HETEROCYCLIC MOIETY; KABACHNIK-FIELDS REACTION; POLY(URETHANE PHOSPHONATE); 1-AMINOPHOSPHONIC ACIDS; SHIKIMATE PATHWAY; ONE-POT; GLYPHOSATE; ESTERS; BIS(AMINOPHOSPHONATE);

D O I：

10.1007/s00726-009-0254-7

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Aminophosphonic acids are an important group of medicinal compounds, and their synthesis has been a focus of considerable attention in synthetic organic chemistry as well as medicinal chemistry. Although the phosphonic and carboxylic acid groups differ considerably with respect to shape, size, and acidity, alpha-aminophosphonic acids are considered to be structural analogues of the corresponding amino acids and the transition state mimics peptide hydrolysis. This review summarizes recent developments in the synthesis, characterization and biological activity of alpha-aminophosphonic acid and N-analogues. An account of both uses will be presented, emphasizing one of the potential future developments, and some implications in medicinal chemistry are also disclosed. In addition, a brief account on the characterization of N-(phosphonomethyl) glycine derivatives will be presented.

引用

页码：23 / 30

页数：8

共 78 条

[1] THE SITE OF THE INHIBITION OF THE SHIKIMATE PATHWAY BY GLYPHOSATE .2. INTERFERENCE OF GLYPHOSATE WITH CHORISMATE FORMATION INVIVO AND INVITRO [J].

AMRHEIN, N ;

DEUS, B ;

GEHRKE, P ;

STEINRUCKEN, HC .

PLANT PHYSIOLOGY, 1980, 66 (05) :830-834

[2]

[Anonymous], 1997, ACS MONOGRAPH

[3]

Baird D.D., 1971, P N CENTRAL WEED CON, P64

[4] Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot [J].

Bhattacharya, Asish K. ;

Rana, Kalpeshkumar C. .

TETRAHEDRON LETTERS, 2008, 49 (16) :2598-2601

[5] EXPLORATION OF N-PHOSPHONOALKYL-SPACED, N-PHOSPHONOALKENYL-SPACED, AND N-(PHOSPHONOALKYL)PHENYL-SPACED ALPHA-AMINO-ACIDS AS COMPETITIVE N-METHYL-D-ASPARTIC ACID ANTAGONISTS [J].

BIGGE, CF ;

JOHNSON, G ;

ORTWINE, DF ;

DRUMMOND, JT ;

RETZ, DM ;

BRAHCE, LJ ;

COUGHENOUR, LL ;

MARCOUX, FW ;

PROBERT, AW .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (08) :1371-1384

[6] An efficient synthesis of 1-aminophosphonic acids and esters bearing heterocyclic moiety [J].

Boduszek, B .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1995, 104 (1-4) :63-70

[7] 1-aminophosphonic acids and esters bearing heterocyclic moiety .2. Pyridine, pyrrole and imidazole derivatives [J].

Boduszek, B .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 113 (1-4) :209-218

[8] One-pot synthesis of α-amino phosphonates from α-amino acids and β-amino alcohols [J].

Boto, A ;

Gallardo, JA ;

Hernández, R ;

Saavedra, CJ .

TETRAHEDRON LETTERS, 2005, 46 (45) :7807-7811

[9]

CHERKASOV RA, 1998, RUSS CHEM REV, V67, P857, DOI [DOI 10.1070/RC1998V067N10ABEH000421, 10.1070/RC1998v067n10ABEH000421]

[10]

CHYKALIUK P, 1980, BIBLIO GLYPHOSATE

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