烯丙基4-氨基-3-羟基苯甲酸酯 | 273939-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 烯丙基4-氨基-3-羟基苯甲酸酯
• 英文名称: allyl 4-amino-3-hydroxybenzoate
• 英文别名: Prop-2-en-1-yl 4-amino-3-hydroxybenzoate；prop-2-enyl 4-amino-3-hydroxybenzoate
• CAS: 273939-62-1
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: JIRCSZFJNFUJRM-UHFFFAOYSA-N

物化性质

• 沸点：
  388.7±32.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  烯丙基4-氨基-3-羟基苯甲酸酯 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium hydride 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 allyl 4-(2-aminoacetamido)-3-(benzyloxy)benzoate
  参考文献：
  名称：

  固相合成Tris-Benzamides作为α-螺旋模拟物

  摘要：

  模仿α螺旋的小分子引起了极大的兴趣，因为大量的蛋白质间相互作用在界面处使用了螺旋结构。为了产生α-螺旋模拟物的文库，开发了一种有效的固相合成方法来生产三苯甲酰胺。tris-benzamide支架设计用于放置位于i，i + 4和i处的三个侧链官能团α螺旋的+ 7个位置，模拟一个螺旋面。合成策略涉及简单且重复的反应，包括去除烯丙基酯，通过O→N酰基迁移形成酰胺键以及O-烷基化。以高纯度（83-99％）制备了一个包含20个含有各种官能团的tris-benzamides的小型文库，以证明合成方法的多功能性。这种方法可以轻松快速地构建α-螺旋模拟物，这将有助于鉴定目标蛋白质的小分子。

  DOI：

  10.1021/co100056c
• 作为产物：
  描述：

  4-氨基-3-羟基苯甲酸 、 3-溴丙烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 烯丙基4-氨基-3-羟基苯甲酸酯
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists

  摘要：

  The thiazolidinediones (TZD) typified by rosiglitazone are the only approved therapeutics targeting PPAR gamma for the treatment of type-2 diabetes (T2DM). Unfortunately, despite robust insulin sensitizing properties, they are accompanied by a number of severe side effects including congestive heart failure, edema, weight gain, and osteoporosis. We recently identified PPAR gamma antagonists that bind reversibly with high affinity but do not induce transactivation of the receptor, yet they act as insulin sensitizers in mouse models of diabetes (SR1664).(1) This Letter details our synthetic exploration around this novel series of PPAR gamma antagonists based on an N-biphenylmethylindole scaffold. Structure-activity relationship studies led to the identification of compound 46 as a high affinity PPAR gamma antagonist that exhibits antidiabetic properties following oral administration in diet-induced obese mice.

  DOI：

  10.1021/acsmedchemlett.5b00218

文献信息

• NOVEL COMPOUNDS
  申请人：AstraZeneca AB

  公开号：EP1135377A1

  公开（公告）日：2001-09-26
• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES
  申请人：ASTRAZENECA UK LTD

  公开号：WO2000034254A1

  公开（公告）日：2000-06-15

  Compounds of formula (I) are disclosed, processes for their preparation, pharmaceutical compositions containing the compounds and the use of the compounds as pharmaceuticals. There are also provided chemical intermediates useful for the preparation of the compounds. The compounds are useful as pharmaceuticals, especially for the treatment of inflammatory disease.
• Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists
  作者：Alice Asteian、Anne-Laure Blayo、Yuanjun He、Marcel Koenig、Youseung Shin、Dana S. Kuruvilla、Cesar A. Corzo、Michael D. Cameron、Li Lin、Claudia Ruiz、Susan Khan、Naresh Kumar、Scott Busby、David P. Marciano、Ruben D. Garcia-Ordonez、Patrick R. Griffin、Theodore M. Kamenecka

  DOI：10.1021/acsmedchemlett.5b00218

  日期：2015.9.10

  The thiazolidinediones (TZD) typified by rosiglitazone are the only approved therapeutics targeting PPAR gamma for the treatment of type-2 diabetes (T2DM). Unfortunately, despite robust insulin sensitizing properties, they are accompanied by a number of severe side effects including congestive heart failure, edema, weight gain, and osteoporosis. We recently identified PPAR gamma antagonists that bind reversibly with high affinity but do not induce transactivation of the receptor, yet they act as insulin sensitizers in mouse models of diabetes (SR1664).(1) This Letter details our synthetic exploration around this novel series of PPAR gamma antagonists based on an N-biphenylmethylindole scaffold. Structure-activity relationship studies led to the identification of compound 46 as a high affinity PPAR gamma antagonist that exhibits antidiabetic properties following oral administration in diet-induced obese mice.
• Solid-Phase Synthesis of Tris-Benzamides as α-Helix Mimetics
  作者：Tae-Kyung Lee、Jung-Mo Ahn

  DOI：10.1021/co100056c

  日期：2011.3.14

  use helical structures at the interface. With a goal of generating libraries of α-helix mimetics, an efficient solid-phase synthetic method was developed to produce tris-benzamides. The tris-benzamide scaffold was designed to place three side-chain functional groups found at the i, i + 4, and i + 7 positions of an α-helix, emulating one helical face. The synthetic strategy involves simple and iterative

  模仿α螺旋的小分子引起了极大的兴趣，因为大量的蛋白质间相互作用在界面处使用了螺旋结构。为了产生α-螺旋模拟物的文库，开发了一种有效的固相合成方法来生产三苯甲酰胺。tris-benzamide支架设计用于放置位于i，i + 4和i处的三个侧链官能团α螺旋的+ 7个位置，模拟一个螺旋面。合成策略涉及简单且重复的反应，包括去除烯丙基酯，通过O→N酰基迁移形成酰胺键以及O-烷基化。以高纯度（83-99％）制备了一个包含20个含有各种官能团的tris-benzamides的小型文库，以证明合成方法的多功能性。这种方法可以轻松快速地构建α-螺旋模拟物，这将有助于鉴定目标蛋白质的小分子。