3-diphenylphosphoryl-4-(aminocarbonyl)benzoic acid | 1314804-26-6

• 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: 3-diphenylphosphoryl-4-(aminocarbonyl)benzoic acid
• CAS: 1314804-26-6
• 化学式: C₂₀H₁₆NO₄P
• 分子量: 365.325
• InChiKey: AFPDQIHMICFXCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.46
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-(二苯基膦基)-4-(甲氧基羰基)苯甲酸 在 二乙烯三胺五醋酸 、 sodium 1-(N-isopropylamino)diazen-1-ium-1,2-diolate 作用下， 反应 4.0h， 生成 3-diphenylphosphoryl-4-(aminocarbonyl)benzoic acid
  参考文献：
  名称：

  Rapid and Selective Nitroxyl (HNO) Trapping by Phosphines: Kinetics and New Aqueous Ligations for HNO Detection and Quantitation

  摘要：

  Recent studies distinguish the biological and pharmacological effects of nitroxyl (HNO) from its oxidized/deprotonated product nitric oxide (center dot NO), but the lack of HNO detection methods limits the understanding its in vivo mechanisms and the identification of endogenous sources. We previously demonstrated that reaction of HNO with triarylphosphines provides aza-ylides and HNO-derived amides, which may serve as stable HNO biomarkers. We now report a kinetic analysis for the trapping of HNO by phosphines, ligations of enzyme-generated HNO, and compatibility studies illustrating the selectivity of phosphines for HNO over other physiologically relevant nitrogen oxides. Quantification of HNO using phosphines is demonstrated using an HPLC-based assay and ligations of phosphine carbamates generate HNO-derived ureas. These results further demonstrate the potential of phosphine probes for reliable biological detection and quantification of HNO.

  DOI：

  10.1021/ja203652z

文献信息

• Stoichiometric Nitroxyl Photorelease Using the (6-Hydroxy-2-naphthalenyl)methyl Phototrigger
  作者：Yang Zhou、Ruth B. Cink、Alexander J. Seed、M. Cather Simpson、Paul Sampson、Nicola E. Brasch

  DOI：10.1021/acs.orglett.8b04099

  日期：2019.2.15

  The design and synthesis of a photoactivatable HNO donor incorporating the (6-hydroxynaphthalen-2-yl)methyl (6,2-HNM) photocage coupled to the trifluoromethanesulfonamidoxy analogue of the well-established HNO generator Piloty’s acid is described. The photoactive HNO donor stoichiometrically generates HNO (∼98%) at neutral pH conditions, and evidence for concerted C–O and N–S bond cleavage was obtained

  描述了结合（6-羟基萘-2-基）甲基（6,2-HNM）光笼与成熟的HNO生成器Piloty酸的三氟甲烷磺酰胺氧基类似物偶联的光活化HNO供体的设计和合成。在中性pH条件下，光活性HNO供体化学计量生成HNO（约98％），并且获得了协调的C-O和N-S键裂解的证据。甲磺酰氨基氧基类似物主要经历不希望的N–O键断裂。
• Nitroxyl donating and visualization with a coumarin-based fluorescence probe
  作者：Jiajun Chen、Yunxi Cui、Peixuan Wu、Rohan Dassanayake、Peng Yu、Kun Fu、Zhicheng Sun、Yuanyuan Liu、Yang Zhou

  DOI：10.1016/j.saa.2024.124317

  日期：2024.8

  physiological conditions (pH 7.4 and 37 °C), the CD1 HNO donor can readily decompose with a half-life of ∼90 min. The corresponding stoichiometry HNO from the CD1 donor was confirmed using both Vitamin B and phosphine compound traps. In addition to HNO releasing, specifically, the degradation product 2-oxo-2H-chromene-6-sulfinate (CS1) was generated as a fluorescent marker during the decomposition. Therefore

  硝酰基（HNO）是一氧化氮（NO）的单电子还原产物，在临床试验中治疗充血性心力衰竭引起了人们的极大兴趣。在本文中，我们描述了第一个基于香豆素的化合物-羟基-2-氧代-2H-色烯-6-磺酰胺（CD1）作为双功能HNO供体，它可以释放HNO信号分子和荧光报告分子。在生理条件下（pH 7.4 和 37 °C），CD1 HNO 供体很容易分解，半衰期约为 90 分钟。使用维生素 B 和磷化氢化合物陷阱确认了来自 CD1 供体的相应化学计量 HNO。具体来说，除了释放 HNO 之外，在分解过程中还产生了作为荧光标记的降解产物 2-oxo-2H-chromene-6-sulfinate (CS1)。因此，可以通过荧光产生来准确监测 HNO 的释放量。与CD1供体相比，荧光强度增加了约4.9倍。根据生理条件下 CS1 的荧光产生，确定 HNO 释放的检测浓度限为 ∼0.13 μM。此外，CD1供体的生物
• <i>O</i>²-Sulfonylethyl Protected Isopropylamine Diazen-1-ium-1,2-diolates as Nitroxyl (HNO) Donors: Synthesis, β-Elimination Fragmentation, HNO Release, Positive Inotropic Properties, and Blood Pressure Lowering Studies
  作者：Zhangjian Huang、Jatinder Kaur、Atul Bhardwaj、Nasser Alsaleh、Julie A. Reisz、Jenna F. DuMond、S. Bruce King、John M. Seubert、Yihua Zhang、Edward E. Knaus

  DOI：10.1021/jm301303p

  日期：2012.11.26

  New types of nonexplosive O-2-sulfonylethyl protected (-CH2CH2SO2R; R = OMe, NHOMe, NHOBn, Me) derivatives of isopropylamine diazen-1-ium-1,2-diolate (IPA/NO) (2-5) were developed that are designed to act as novel HNO donors. These compounds, with suitable half lives (6.6-17.1 h) at pH 7.4, undergo a base induced beta-elimination reaction that releases a methyl vinyl sulfone product and the, parent IPA/NO anion which subsequently preferentially releases HNO (46-61% range). Importantly, the O-2-methylsulfonylethyl compound 5 exhibited a significant in vitro inotropic effect up to 283% of the baseline value and increased the rates of contraction and relaxation but did not induce a chronotropic effect. Furthermore; compound 5 (22.5 mg/kg po dose). provided a significant reduction in blood pressure up to 6 h after drug administration. All these data suggest that O-2-sulfonylethyl protected derivatives of IPA/NO, which are efficient HNO donors, could have potential applications to treat cardiovascular disease(s) such as congestive heart failure.