2-(Diphenoxyphosphorylmethyl)isoindole-1,3-dione | 178860-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(Diphenoxyphosphorylmethyl)isoindole-1,3-dione
• CAS: 178860-98-5
• 化学式: C₂₁H₁₆NO₅P
• 分子量: 393.336
• InChiKey: YXUBPLBOUFXFOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(Diphenoxyphosphorylmethyl)isoindole-1,3-dione 在 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 二苯基氨基甲基膦酸酯
  参考文献：
  名称：

  天门冬氨酸和谷氨酸二苯基膦酸酯类似物的合成及其蛋白酶抑制性能。

  摘要：

  描述了天门冬氨酸和谷氨酸的二苯基膦酸酯类似物的合成及其对金黄色葡萄球菌V8蛋白酶和颗粒酶B的抑制活性。该研究揭示了在这些类似物的合成中保护基团相容性的困难。两个类似物，乙酰基。发现AspP（OPh）2和Acetyl.GluP（OPh）2充当V8蛋白酶的不可逆灭活剂，但对颗粒酶B无活性。

  DOI：

  10.1016/s0960-894x(98)00272-8
• 作为产物：
  描述：

  N-溴甲基邻苯二甲酰亚胺 、 phosphorous acid ethyl ester-diphenyl ester 以 xylene 为溶剂， 反应 120.0h， 生成 2-(Diphenoxyphosphorylmethyl)isoindole-1,3-dione
  参考文献：
  名称：

  天门冬氨酸和谷氨酸二苯基膦酸酯类似物的合成及其蛋白酶抑制性能。

  摘要：

  描述了天门冬氨酸和谷氨酸的二苯基膦酸酯类似物的合成及其对金黄色葡萄球菌V8蛋白酶和颗粒酶B的抑制活性。该研究揭示了在这些类似物的合成中保护基团相容性的困难。两个类似物，乙酰基。发现AspP（OPh）2和Acetyl.GluP（OPh）2充当V8蛋白酶的不可逆灭活剂，但对颗粒酶B无活性。

  DOI：

  10.1016/s0960-894x(98)00272-8

文献信息

• Synthesis of diphenyl phosphonate analogues of tyrosine and tryptophan and derived peptides as chymotrypsin inhibitors
  作者：Carol Bergin、Robert Hamilton、Brian Walker、Brian J. Walker

  DOI：10.1039/cc9960001155

  日期：——

  The synthesis of α-aminophosphonate analogues of tyrosine and tryptophan, e.g. 4 and 5 respectively, and their incorporation into proline-containing dipeptides is reported; of the sequences synthesised, the dipeptide Z-Pro-TrpP(OPh)2 is the only derivative that functions as an irreversible inactivator of the serine proteinase chymotrypsin, in contrast, the tyrosine analogue 4 behaves as a competitive reversible inhibitor of the enzyme and the tryptophan analogue 5 behaves as a slow-binding inhibitor.

  报告了酪氨酸和色氨酸的 α-氨基膦酸盐类似物（如 4 和 5）的合成及其与含脯氨酸二肽的结合；在合成的序列中，二肽 Z-Pro-TrpP(OPh)2 是唯一的衍生物。在合成的序列中，Z-Pro-TrpP(OPh)2 是唯一一种可作为丝氨酸蛋白酶糜蛋白酶不可逆灭活剂的衍生物，相反，酪氨酸类似物 4 是该酶的竞争性可逆抑制剂，而色氨酸类似物 5 则是一种慢结合抑制剂。
• Synthesis and proteinase inhibitory properties of diphenyl phosphonate analogues of aspartic and glutamic acids
  作者：Robert Hamilton、Brian Walker、Brian J. Walker

  DOI：10.1016/s0960-894x(98)00272-8

  日期：1998.7

  The synthesis of diphenyl phosphonate analogues of aspartic and glutamic acid, and their inhibitory activity against S. aureus V8 protease and granzyme B, is described. The study has revealed difficulties with protecting group compatibility in the synthesis of these analogues. Two analogues, Acetyl. AspP (OPh)2 and Acetyl.GluP (OPh)2 were found to function as irreversible inactivators of V8 proteinase

  描述了天门冬氨酸和谷氨酸的二苯基膦酸酯类似物的合成及其对金黄色葡萄球菌V8蛋白酶和颗粒酶B的抑制活性。该研究揭示了在这些类似物的合成中保护基团相容性的困难。两个类似物，乙酰基。发现AspP（OPh）2和Acetyl.GluP（OPh）2充当V8蛋白酶的不可逆灭活剂，但对颗粒酶B无活性。
• PHOSPHORUS NITROGEN FLAME RETARDANT, METHOD THEREOF AND MATERIAL COMPRISING THE SAME
  申请人：ZHOU Chongfu

  公开号：US20220127533A1

  公开（公告）日：2022-04-28

  Provided are phosphorus nitrogen flame retardants represented by Formula III, a method of preparing the flame retardants without using any solvent, and various materials comprising the flame retardants. Rb and Rc are independently of each other selected from hydrogen, substituted or unsubstituted alkyl such as C1-C18 alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic alkyl, substituted or unsubstituted heterocycles, substituted or unsubstituted aryl such as C6˜C18 aryl, substituted or unsubstituted heteroaryl such as C3˜C18 heteroaryl, and acyl radical. The invention exhibits numerous technical merits such as excellent flame retardant efficacy, good compatibility with polymers, lower migration to material surface, excellent hydrolysis resistance, low smoke and low toxicity during burning, simpler preparation process, fewer by-products, shorter reaction time, higher yield, and no environmental impact, among others.
• Towards the identification of unknown neuropeptide precursor-processing enzymes: Design and synthesis of a new family of dipeptidyl phosphonate activity probes for substrate-based protease identification
  作者：Eduard Sabidó、Teresa Tarragó、Ernest Giralt

  DOI：10.1016/j.bmc.2010.09.066

  日期：2010.12

  Specific proteolytic processing of inactive precursors is an exquisite cellular mechanism that triggers the activation of numerous physiologic peptides and proteins. This process ensures the generation of biologically active peptides, such as many neuropeptides and peptide hormones, in the appropriate cellular compartments at the right time, and its failure leads to several pathological conditions. Identification of the proteases involved in this limited proteolysis is, therefore, an essential step for the subsequent establishment of new therapeutic targets. As a first effort along this line, we synthesized eight new dipeptidyl phosphonate activity-based probes and used them to explore the soluble proteome from mouse brain and pituitary gland for substrate-based protease identification both by in-gel analysis and mass spectrometry. (C) 2010 Elsevier Ltd. All rights reserved.