diethyl N-(2-propyl)carbamoylphosphonate | 700867-59-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl N-(2-propyl)carbamoylphosphonate
• 英文别名: isopropylcarbamoyl-phosphonic acid diethyl ester；Isopropylcarbamoyl-phosphonsaeure-diaethylester；1-diethoxyphosphoryl-N-propan-2-ylformamide
• CAS: 700867-59-0
• 化学式: C₈H₁₈NO₄P
• 分子量: 223.209
• InChiKey: ZULFTPNTEBKTDC-UHFFFAOYSA-N

物化性质

• 沸点：
  100-102 °C(Press: 1 Torr)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl N-(2-propyl)carbamoylphosphonate 在 三甲基溴硅烷 、 甲醇 作用下， 以 乙腈 为溶剂， 生成 N-2-propylcarbamoylphosphonic acid
  参考文献：
  名称：

  氨基甲酰基膦酸酯，一类新的体内活性基质金属蛋白酶抑制剂。1.烷基和环烷基氨基甲酰基膦酸。

  摘要：

  基质金属蛋白酶（MMP）是一类20多种依赖锌的酶，它们水解结缔组织，并参与多种疾病，这些疾病与不良的组织分解有关。本文报告了基于氨基甲酰基膦酸功能的一类新型MMP抑制剂的合成，表征和生物学评估。我们报告一系列10开链N-烷基氨基甲酰基膦酸（范围从R = C（1）到C（6）基团），八个N-环烷基氨基甲酰基膦酸（范围从环丙基到环辛基环）和四个N，N-二烷基氨基甲酰基膦酸酸。在三种体外模型中评估了这些化合物，这些模型包括：（a）跨重构基膜的体外侵袭，（b）测定重组MMP-1，MMP-2，MMP-3的IC（50）值， MMP-8和MMP-9酶，（c）体外毛细血管形成模型，其是血管生成的模型。还在体内鼠黑色素瘤模型中测试了几种化合物。得出以下一般结论：大多数化合物对MMP-2的选择性优于其他MMP亚型。环烷基氨基甲酰基膦酸比类似的开链烷基化合物更有效。N-环戊基氨基甲酰基膦酸（3m）显示出在环烷基衍

  DOI：

  10.1021/jm030386z
• 作为产物：
  描述：

  (甲氧羰基)膦酸二乙酯 、 异丙胺 生成 diethyl N-(2-propyl)carbamoylphosphonate
  参考文献：
  名称：

  Carbamoylphosphonates¹

  摘要：

  DOI：

  10.1021/ja01619a040

文献信息

• Carbamoylphosphonate MMP inhibitors. Part 4: The influence of chirality and geometrical isomerism on the potency and selectivity of inhibition
  作者：Eli Breuer、Yiffat Katz、Rivka Hadar、Reuven Reich

  DOI：10.1016/j.tetasy.2004.07.002

  日期：2004.8

  Matrix metalloproteinases (MMPs) are a family of over twenty zinc-dependent enzymes that hydrolyze connective tissue and are involved in a variety of diseases, which are associated with undesired tissue breakdown. Previously we described the synthesis of a series of achiral alkyl and cycloalkylcarbamoylphosphonic acids and their biological evaluation. Herein we report the effect of chirality and geometrical isomerism on the potency and selectivity of inhibition. The inhibitory potencies of pairs of enantiomeric and stereoisomeric alkyl and cycloalkylcarbamoylphosphonic acids were evaluated on recombinant MMP-1, MMP-2, MMP-3. MMP-8, and MMP-9 enzymes. The results show that the enantiomers and stereoisomers studied differ considerably in their inhibitory potencies and selectivities on the enzyme subtypes studied. Such a result is consistent with the assumption that the carbamoylphosphonates interact with a chiral environment such as an enzyme. (C) 2004 Elsevier Ltd. All rights reserved.
• Plant-growth-regulating<i>N</i>-(phosphonoacetyl)amines
  作者：Piotr Wieczorek、Dorota Miliszkiewicz、Barbara Lejczak、Miroslaw Soroka、Pawel Kafarski

  DOI：10.1002/ps.2780400110

  日期：1994.1

  AbstractA series of N‐(phosphonacetyl)amine derivatives were synthesized and screened for plant‐growth regulating activity on Lepidium sativum L. and Cucumis sativus L. Aromatic N‐(phosphonoacetyl)amines. which may be considered as possible analogues of N‐acylaniline herbicides obtained by replacement of their acyl group by the phosphonacetyl moiety, exhibited significant or moderate herbicidal activity. In contrast, N‐(phosphonoacetyl)amino acids and N‐(phosphonoacetyl)aminophosphonic acids promoted the growth of L. sativum and C. sativus roots.