(6-bromo-7-hydroxycoumarin-4-yl)methyl 4-nitrophenyl carbonate | 485318-64-7

• 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: (6-bromo-7-hydroxycoumarin-4-yl)methyl 4-nitrophenyl carbonate
• 英文别名: (6-Bromo-7-hydroxy-2-oxochromen-4-yl)methyl (4-nitrophenyl) carbonate
• CAS: 485318-64-7
• 化学式: C₁₇H₁₀BrNO₈
• 分子量: 436.172
• InChiKey: DESXBJZIRDHVDC-UHFFFAOYSA-N

物化性质

• 沸点：
  621.7±55.0 °C(Predicted)
• 密度：
  1.737±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (6-bromo-7-hydroxycoumarin-4-yl)methyl 4-nitrophenyl carbonate 、 多巴胺 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以897 mg的产率得到N-[(6-溴-7-羟基香豆素-4-基)甲氧基羰基]多巴胺
  参考文献：
  名称：

  [8- [双（羧甲基）氨基甲基] -6-溴-7-羟基香豆素-4-基]甲基部分作为具有COOH，NH 2，OH和C═O官能团的化合物的光敏保护基

  摘要：

  我们引入了基于香豆素的可光活化保护基的变体，并将其示例性地用于羧酸，胺，苯酚和羰基化合物的笼蔽。笼状化合物可在长波紫外线/可见光照射下有效地光解。与相应的（6-bromo-7-hydroxycoumarin-4-yl）methyl（Bhc）衍生物相比，新型香豆素型笼状化合物的特征在于（i）在水性缓冲液中的溶解度显着提高，（ii）较低的p K a香豆素发色团的C 7羟基的最大分子量，因此允许在较低的pH下有效地释放光，并且（iii）在光保护的羰基化合物的情况下，具有更高的光解量子产率。光解的第一步以约10 9 s -1的速率常数发生。

  DOI：

  10.1021/jo100368w
• 作为产物：
  描述：

  6-溴-4-(氯甲基)-7-羟基-2H-色烯-2-酮 在 4-二甲氨基吡啶 作用下， 以 水 、 乙腈 为溶剂， 反应 105.0h， 生成 (6-bromo-7-hydroxycoumarin-4-yl)methyl 4-nitrophenyl carbonate
  参考文献：
  名称：

  Photo-Control of nitric oxide synthase activity using a caged isoform specific inhibitor

  摘要：

  Nitric oxide (NO) plays a critical role in a number of physiological processes and is produced in mammalian cells by nitric oxide synthase (NOS) isozymes. Because of the diverse functions of NO, pharmaceutical interventions which seek to abrogate adverse effects of excess NOS activity must not interfere with the normal regulation of NO levels in the body. A method has been developed For the control of NOS enzyme activity using the localized photochemical release of a caged isoform- specific NOS inhibitor. The caged form of an iNOS inhibitor has been synthesized and tested for photosensitivity and potency. UV and multiphoton uncaging were verified using a hemoglobin-based assay. IC50 values were determined for the inhibitor (70 +/- 11 nM), the caged inhibitor (1098 +/- 172 nM), the UV uncaged inhibitor (67 +/- 26 nM) and the multiphoton uncaged inhibitor (73 +/- 11 nM). UV irradiation of the caged inhibitor resulted in a 86% reduction in iNOS activity after 5 min. Multiphoton uncaging had an apparent first order time constant of 0.007 +/- 0.001 min(-1). A therapeutic range exists, with molar excess of inhibitor to enzyme from 3- to 7-fold, over which the full dynamic range of the inhibition can be exploited. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00050-0

文献信息

• Chemically Amplified Response Strategies for Medical Sciences
  申请人：Almutairi Adah

  公开号：US20120259267A1

  公开（公告）日：2012-10-11

  Compositions are provided in which dendrimers and/or nanoparticles are synthesized with multi-photon responsive elements and self-immolative oligomers. The compositions may be utilized to selectively deliver Payloads within tissue by irradiating the compositions. The compositions may also be used to amplify sensitivity to irradiation.
• US8828383B2
  申请人：——

  公开号：US8828383B2

  公开（公告）日：2014-09-09
• US9724417B2
  申请人：——

  公开号：US9724417B2

  公开（公告）日：2017-08-08
• Photo-Control of nitric oxide synthase activity using a caged isoform specific inhibitor
  作者：H Montgomery

  DOI：10.1016/s0968-0896(02)00050-0

  日期：2002.6

  Nitric oxide (NO) plays a critical role in a number of physiological processes and is produced in mammalian cells by nitric oxide synthase (NOS) isozymes. Because of the diverse functions of NO, pharmaceutical interventions which seek to abrogate adverse effects of excess NOS activity must not interfere with the normal regulation of NO levels in the body. A method has been developed For the control of NOS enzyme activity using the localized photochemical release of a caged isoform- specific NOS inhibitor. The caged form of an iNOS inhibitor has been synthesized and tested for photosensitivity and potency. UV and multiphoton uncaging were verified using a hemoglobin-based assay. IC50 values were determined for the inhibitor (70 +/- 11 nM), the caged inhibitor (1098 +/- 172 nM), the UV uncaged inhibitor (67 +/- 26 nM) and the multiphoton uncaged inhibitor (73 +/- 11 nM). UV irradiation of the caged inhibitor resulted in a 86% reduction in iNOS activity after 5 min. Multiphoton uncaging had an apparent first order time constant of 0.007 +/- 0.001 min(-1). A therapeutic range exists, with molar excess of inhibitor to enzyme from 3- to 7-fold, over which the full dynamic range of the inhibition can be exploited. (C) 2002 Elsevier Science Ltd. All rights reserved.
• [8-[Bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxycoumarin-4-yl]methyl Moieties as Photoremovable Protecting Groups for Compounds with COOH, NH₂, OH, and C═O Functions
  作者：Volker Hagen、Funda Kilic、Janina Schaal、Brigitte Dekowski、Reinhard Schmidt、Nico Kotzur

  DOI：10.1021/jo100368w

  日期：2010.5.7

  exemplarily for caging of a carboxylic acid, an amine, a phenol, and a carbonyl compound. The caged compounds are efficiently photolyzed at long-wavelength UV/vis irradiation. Compared to the corresponding (6-bromo-7-hydroxycoumarin-4-yl)methyl (Bhc) derivatives, the novel coumarin-type caged compounds are distinguished by (i) dramatically increased solubilities in aqueous buffers, (ii) lower pKa values

  我们引入了基于香豆素的可光活化保护基的变体，并将其示例性地用于羧酸，胺，苯酚和羰基化合物的笼蔽。笼状化合物可在长波紫外线/可见光照射下有效地光解。与相应的（6-bromo-7-hydroxycoumarin-4-yl）methyl（Bhc）衍生物相比，新型香豆素型笼状化合物的特征在于（i）在水性缓冲液中的溶解度显着提高，（ii）较低的p K a香豆素发色团的C 7羟基的最大分子量，因此允许在较低的pH下有效地释放光，并且（iii）在光保护的羰基化合物的情况下，具有更高的光解量子产率。光解的第一步以约10 9 s -1的速率常数发生。