disodium phenoxycarbonylphosphonate | 74270-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: disodium phenoxycarbonylphosphonate
• CAS: 74270-30-7
• 化学式: C₇H₅O₅P*2Na
• 分子量: 246.067
• InChiKey: WXVXIDWIJZVBSZ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.49
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  dimethyl (phenoxycarbonyl)phosphonate 在 三甲基溴硅烷 、 Amberlite IRC 50 (Na⁺ form) 作用下， 反应 3.0h， 以88%的产率得到disodium phenoxycarbonylphosphonate
  参考文献：
  名称：

  Synthesis of esters of phosphonoformic acid and their antiherpes activity

  摘要：

  Aliphatic and aromatic mono-, di-, and triesters of phosphonoformic acid (foscarnet) were synthesized. The triesters were prepared by the Michaelis-Arbuzov reaction and were hydrolyzed to di- and monoesters. The compounds were tested for antiviral activity on isolated herpes simplex virus type 1 (HSV-1) DNA polymerase, in a HSV-1 plaque reduction assay, and on a cutaneous HSV-1 infection in guinea pigs. None of the esters inhibited the activity of isolated HSV-1 polymerases. Monoesters with a free carboxylic group and diesters with an aromatic carboxylic ester function were active against the cutaneous herpes infection. Mono- and diesters with an aromatic phosphonic ester group also showed activity in the plaque-reduction assay. However, mono- and diesters with an aromatic phosphonic ester group also showed activity in the plaque-reduction assay. However, mono- and diesters with aliphatic carboxylic ester groups were inactive in all test systems. The results show that all three acidic groups of phosphonoformic acid must be free in order to get antiviral activity at the enzyme level. However, certain esters of this acid may be biotransformed to the acid itself to give antiherpes activity.

  DOI：

  10.1021/jm00356a028

文献信息

• Phosphonoformic acid esters
  申请人：Astra Lakemedel Aktiebolag

  公开号：US04372894A1

  公开（公告）日：1983-02-08

  A compound of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different, and each is selected from the group consisting of hydrogen and phenyl groups of the formula ##STR2## wherein R.sub.4 and R.sub.5 are the same or different and each is selected from the group consisting of hydrogen, halogen, alkyl having 1, 2, or 3 carbon atoms, alkoxy having 1, 2, or 3 carbon atoms, alkoxycarbonyl having 2-7 carbon atoms; and alkylcarbonyl groups having 2-7 carbon atoms; or R.sub.4 and R.sub.5 together from a straight saturated alkylene chain having 3 or 4 carbon atoms and being bound to adjacent positions, i.e. 2,3- or 3,4- in the phenyl ring; provided that one of R.sub.1 and R.sub.2 is a phenyl group of the formula II when R.sub.3 is H; and physiologically acceptable salts and optical isomers thereof; methods for preparation of the compounds, pharmaceutical compositions containing them, and their medicinal use.

  式##STR1##的化合物，其中R.sub.1、R.sub.2和R.sub.3相同或不同，且每个均选自由氢和苯基组成的群，该群的式为##STR2##，其中R.sub.4和R.sub.5相同或不同，每个均选自由氢、卤素、具有1、2或3个碳原子的烷基、具有1、2或3个碳原子的烷氧基、具有2-7个碳原子的烷氧羰基；和具有2-7个碳原子的烷基羰基；或者R.sub.4和R.sub.5一起形成直链饱和的具有3或4个碳原子的烷基链，并与相邻位置即苯环中的2,3-或3,4-相连；前提是当R.sub.3为H时，R.sub.1和R.sub.2中的一个是式II的苯基；以及其生理上可接受的盐和光学异构体；制备这些化合物的方法，含有它们的药物组合物，以及它们的药用。
• Metal-Cation-Mediated Hydrolysis of Phosphonoformate Diesters:  Chemoselectivity and Catalysis¹
  作者：Robert A. Moss、Hugo Morales-Rojas、Saketh Vijayaraghavan、Jingzhi Tian

  DOI：10.1021/ja030437h

  日期：2004.9.1

  methyl (9), and diphenyl (10) phosphonoformate diesters are substantially accelerated by Ce(IV), Th(IV), Zr(IV), and Hf(IV) cations. Chemoselectivity is observed, whereby Zr(IV) and Hf(IV) principally direct P-OR hydrolysis, whereas Th(IV) and Ce(IV) mainly direct C-OR hydrolysis. Leaving group efficiency (OMe vs OPh) modulates the chemoselectivity. The metal cations also mediate further hydrolytic reactions

  Ce(IV)、Th(IV) 显着加速二甲基 (7)、甲基苯基 (8)、苯基甲基 (9) 和二苯基 (10) 膦酰甲酸二酯在 D(2)O (pD 1.7-3.1) 中的水解)、Zr(IV) 和 Hf(IV) 阳离子。观察到化学选择性，其中 Zr(IV) 和 Hf(IV) 主要指导 P-OR 水解，而 Th(IV) 和 Ce(IV) 主要指导 C-OR 水解。离开组效率（OMe 与 OPh）调节化学选择性。金属阳离子还介导了最初生成的膦酰甲酸酯单酯 14、15、18 和 20 的进一步水解反应。 P-OR/C-OR 选择性的起源根据可能存在于溶液和反应动力学。
• Acyloxymethyl and 4-acyloxybenzyl diester prodrugs of phosphonoformate
  作者：Andrew D. Briggs、Michel Camplo、Sally Freeman、Jan Lundström、Brian G. Pring

  DOI：10.1016/0040-4020(96)00906-4

  日期：1996.11

  (pivaloyloxymethoxycarbonyl)phosphonate 4, sodium 4-acyloxybenzyl phenoxycarbonylphosphonates 14a-c and sodium 4-acyloxybenzyl benzyloxycarbonylphosphonates 15a,b have been prepared as bioreversible prodrugs of the antiviral phosphonoformate 1. Their hydrolyses, in vivo systemic bioavailability and antiviral activity are reported. Of the compounds evaluated 4 was the best prodrug.

  新戊酰氧基钠（新戊酰氧基）膦4，钠4-酰氧基phenoxycarbonylphosphonates 14A-C和钠4-酰氧基benzyloxycarbonylphosphonates 15A，B已经制备作为抗病毒的磷酰前药生物可逆1。报告了它们的水解，体内全身生物利用度和抗病毒活性。在所评估的化合物中，有4种是最好的前药。