2-chloro-N-(2-hydroxybenzyll)acetamide | 618886-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-chloro-N-(2-hydroxybenzyll)acetamide
• 英文别名: Chloracetylaminomethylphenole；2-chloro-N-[(2-hydroxyphenyl)methyl]acetamide
• CAS: 618886-56-9
• 化学式: C₉H₁₀ClNO₂
• 分子量: 199.637
• InChiKey: NXSMGQPKNZVURX-UHFFFAOYSA-N

物化性质

• 沸点：
  431.0±35.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(2-hydroxybenzyll)acetamide 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以1.28 g的产率得到4,5-二氢-1,4-苯并氧氮杂卓-3(2H)-酮
  参考文献：
  名称：

  Synthesis, SAR studies, and evaluation of 1,4-benzoxazepine derivatives as selective 5-HT1A receptor agonists with neuroprotective effect: Discovery of Piclozotan

  摘要：

  A new series of 1,4-benzoxazepine derivatives was designed, synthesized, and evaluated for binding to 5-HT1A receptor and cerebral anti-ischemic effect. A lot of compounds exhibited nanomolar affinity for 5-HT1A receptor with good selectivity over both dopamine D, and alpha(1)-adrenergic receptors. Among these compounds, 3-chloro-4-[4-[4-(2-pyridinyl)-1,2,3,6-tetrahydropyridin-1-y]butyl]-1, 4-benzoxazepin-5(4H)-one (50: SUN N4057 (Piclozotan) as 2HCl salt) showed remarkable neuroprotective activity in a transient middle cerebral artery occlusion (t-MCAO) model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.046
• 作为产物：
  描述：

  (氨基甲基)-苯酚 、 氯乙酰氯 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以88%的产率得到2-chloro-N-(2-hydroxybenzyll)acetamide
  参考文献：
  名称：

  [EN] DESIGN, SYNTHESIS AND EVALUATION OF PROCASPASE ACTIVATING COMPOUNDS AS PERSONALIZED ANTI-CANCER DRUGS
  [FR] CONCEPTION, SYNTHÈSE ET ÉVALUATION DE COMPOSÉS ACTIVATEURS DE PROCASPASE EN TANT QUE MÉDICAMENTS ANTICANCÉREUX PERSONNALISÉS

  摘要：

  本发明公开了涉及诱导细胞死亡（例如癌细胞）的组合物和方法。公开了用于合成和使用这些化合物的相关方法，包括在癌症治疗中使用化合物以及在细胞中选择性诱导凋亡。公开了具有比其他化合物更低神经毒性效应的化合物。

  公开号：

  WO2010091382A1

文献信息

• Epoxidizable Fatty Amide–Phenol Conjugates
  作者：Jonathan A. Zerkowski、Michael J. Haas

  DOI：10.1007/s11746-011-1785-0

  日期：2011.8

  also prepared: one acrylamide, one styrene derivative, and two types of AB2 diamino acids, all of which contain oleic units that are sites for epoxidation and crosslinking. Fatty acid aryl ethers were prepared using hydroxy fatty acids. These molecules are intended to serve as augmented analogues of epoxidized vegetable oil. Their amide groups should lead to intermolecular aggregation through hydrogen

  本文报道了一系列新型化合物的合成，其中羧酸已通过酰胺甲基单元与苯酚连接。例如，已将一种，两种或三种脂肪酸选择性地连接到苯酚上，产率超过75％。所使用的脂肪酸是油酸，其随后被环氧化。可以将其他官能团例如氨基酸结合到这些化合物中。还制备了适合聚合的单体实例：一种丙烯酰胺，一种苯乙烯衍生物和两种类型的AB 2二氨基酸，全部都含有油酸单元，这些单元是环氧化和交联的位点。使用羟基脂肪酸制备脂肪酸芳基醚。这些分子旨在用作环氧化植物油的增强类似物。它们的酰胺基应通过氢键导致分子间聚集，共价包括其他官能团的选择可能会允许调节由它们构成的薄膜，涂层或固体的宏观材料性能。
• DESIGN, SYNTHESIS AND EVALUATION OF PROCASPASE ACTIVATING COMPOUNDS AS PERSONALIZED ANTI-CANCER DRUGS
  申请人：Hergenrother Paul J.

  公开号：US20120040995A1

  公开（公告）日：2012-02-16

  Compositions and methods are disclosed in embodiments relating to induction of cell death such as in cancer cells. Compounds and related methods for synthesis and use thereof, including the use of compounds in therapy for the treatment of cancer and selective induction of apoptosis in cells are disclosed. Compounds are disclosed that have lower neurotoxicity effects than other compounds.

  本实施例揭示了与诱导细胞死亡有关的组合物和方法，例如在癌细胞中。揭示了合成和使用相关化合物的方法，包括在治疗癌症和选择性诱导细胞凋亡方面使用化合物的方法。揭示了具有比其他化合物更低神经毒性影响的化合物。
• PROCASPASE ACTIVATING COMPOUNDS
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20150344452A1

  公开（公告）日：2015-12-03

  Compositions and methods are disclosed in embodiments relating to induction of cell death such as in cancer cells. Compounds and related methods for synthesis and use thereof, including the use of compounds in therapy for the treatment of cancer and selective induction of apoptosis in cells are disclosed. Compounds are disclosed that have lower neurotoxicity effects than other compounds.

  本实施例揭示了与细胞死亡诱导有关的组合物和方法，例如在癌细胞中。揭示了合成和使用相关化合物的方法，包括在治疗癌症和选择性诱导细胞凋亡方面使用化合物的方法。揭示了具有较低神经毒性效应的化合物。
• Procaspase-3 Activation as an Anti-Cancer Strategy: Structure−Activity Relationship of Procaspase-Activating Compound 1 (PAC-1) and Its Cellular Co-Localization with Caspase-3
  作者：Quinn P. Peterson、Danny C. Hsu、David R. Goode、Chris J. Novotny、Ryan K. Totten、Paul J. Hergenrother

  DOI：10.1021/jm900722z

  日期：2009.9.24

  A goal of personalized medicine as applied to oncology is to identify compounds that exploit a defined molecular defect in a cancerous cell. A compound called procaspase-activating compound I (PAC-1) was reported that enhances the activity of procaspase-3 in vitro and induces apoptotic death in cancer cells in culture and in mouse xenograft models. Experimental evidence indicates that PAC-1 activates procaspase-3 in vitro through chelation of inhibitory zinc ions. Described herein is the synthesis and biological activity of a family of PAC-1 derivatives where key functional groups have been systematically altered. Analysis of these compounds reveals a strong correlation between the in vitro procaspase-3 activating effect and their ability to induce death in cancer cells in culture. Importantly, we also show that a fluorescently labeled version of PAC-1 co-localizes with sites of caspase-3 activity in cancer cells. The data presented herein further bolster the hypothesis that PAC-1 induces apoptosis in cancer cells through the direct activation of procaspase-3, has implications for the design and discovery of next-generation procaspase-3 activating compounds, and sheds light on the anti-apoptotic role of cellular zinc.
• US8778945B2
  申请人：——

  公开号：US8778945B2

  公开（公告）日：2014-07-15