(2-oxochromen-7-yl) N-methyl-N-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]carbamate | 1051926-20-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (2-oxochromen-7-yl) N-methyl-N-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]carbamate
• CAS: 1051926-20-5
• 化学式: C₁₉H₂₄N₂O₆
• 分子量: 376.409
• InChiKey: PCWQJWXTNMPSOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2-oxochromen-7-yl) N-methyl-N-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 C₁₄H₁₆N₂O₄
  参考文献：
  名称：

  A new fluorogenic probe for the selective detection of carbon monoxide in aqueous medium based on Pd(0) mediated reaction

  摘要：

  一种基于香豆素的荧光探针PCO-1，在pH 8.0的缓冲溶液中通过基于Pd(0)介导的分子内环化-消除途径选择性地检测一氧化碳。

  DOI：

  10.1039/c5cc00902b
• 作为产物：
  描述：

  N-[(叔-丁氧基)羰基]-N,N'-二甲基乙二胺 在 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 41.0h， 生成 (2-oxochromen-7-yl) N-methyl-N-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]carbamate
  参考文献：
  名称：

  A new fluorogenic probe for the selective detection of carbon monoxide in aqueous medium based on Pd(0) mediated reaction

  摘要：

  一种基于香豆素的荧光探针PCO-1，在pH 8.0的缓冲溶液中通过基于Pd(0)介导的分子内环化-消除途径选择性地检测一氧化碳。

  DOI：

  10.1039/c5cc00902b

文献信息

• A comparative study of the self-immolation of para-aminobenzylalcohol and hemithioaminal-based linkers in the context of protease-sensitive fluorogenic probes
  作者：Yves Meyer、Jean-Alexandre Richard、Bruno Delest、Pauline Noack、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1039/b926316k

  日期：——

  This study focuses on the disassembly-behavior of self-immolative pro-fluorescent linkers under physiological conditions and through an enzyme-initiated domino reaction. The targeted linkers are based on para-aminobenzylalcohol (PABA) or hemithioaminal derivatives of para-carboxybenzaldehyde or glyoxilic acid. We found that a fine tuning of the kinetic properties could be obtained through the modulation of the linker structure, giving either a fast signal response or free-adaptable systems suitable for the design of protease-sensitive fluorogenic probes or prodrug systems.

  这项研究聚焦于生理条件下以及通过酶促多米诺反应，自灭活型前荧光接头的行为解离过程。目标接头基于对氨基苯甲醇（PABA）或对羧基苯甲醛或乙醛酸的半硫代胺醇衍生物。我们发现，通过调节接头结构，可以精细调整其动力学特性，从而实现快速信号响应或自由适配系统，适用于设计蛋白酶敏感的荧光探针或前药系统。
• A trifunctional self-immolative spacer enables drug release with two non-sequential enzymatic cleavages
  作者：Alberto Dal Corso、Simone Arosio、Noemi Arrighetti、Paola Perego、Laura Belvisi、Luca Pignataro、Cesare Gennari

  DOI：10.1039/d1cc02895b

  日期：——

  The enzymatic dephosphorylation of a self-immolative spacer accelerates cargo release and acts as an additional and independent trigger in protease-sensitive prodrugs.

  自焚间隔的自催化脱磷酸作用加速了货物的释放，并在蛋白酶敏感的前药中起到一种额外的、独立的触发作用。

• Development of a New Nonpeptidic Self-Immolative Spacer. Application to the Design of Protease Sensing Fluorogenic Probes
  作者：Yves Meyer、Jean-Alexandre Richard、Marc Massonneau、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1021/ol800198f

  日期：2008.4.1

  The design and synthesis of novel self-immolative spacer systems aiming at the release of phenol-containing compounds are described. The newly designed traceless linkers proved to be conveniently stable under physiological conditions and operate through spontaneous decomposition of an hemithioaminal intermediate under neutral aqueous conditions. Their utility was then illustrated by the preparation of original fluorogenic substrates of penicillin amidase whose strong fluorescence is unveiled through enzyme-initiated domino reactions.