(2-{4-[(E)-3-(4-bromophenyl)acryloylamino]-3-fluorophenyl}benzooxazol-5-yl) acetic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2-{4-[(E)-3-(4-bromophenyl)acryloylamino]-3-fluorophenyl}benzooxazol-5-yl) acetic acid
• 英文别名: (2-{4-[(E)-3-(4-bromophenyl)acryloylamino]-3-fluorophenyl}benzooxazol-5-yl)acetic acid；OGT2115；trans 2-[4-[3-(4-bromophenyl)-2-propenamido]-3-fluorophenyl]benzoxazol-5-ylacetic acid；(E)-2-(2-(4-(3-(4-bromophenyl)acrylamido)-3-fluorophenyl)benzo[d]oxazol-5-yl)acetic acid；2-[2-[4-[[(E)-3-(4-bromophenyl)prop-2-enoyl]amino]-3-fluorophenyl]-1,3-benzoxazol-5-yl]acetic acid
• 化学式: C₂₄H₁₆BrFN₂O₄
• 分子量: 495.304
• InChiKey: LKBXWNYXDMSFQU-ONNFQVAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基-3-硝基苯乙酸 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 生成 (2-{4-[(E)-3-(4-bromophenyl)acryloylamino]-3-fluorophenyl}benzooxazol-5-yl) acetic acid
  参考文献：
  名称：

  Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: novel classes of heparanase inhibitor

  摘要：

  Using a furanylthiazole acetic acid as a starting point, a novel series of benzoxazol-5-yl acetic acid derivatives have been identified as heparanase inhibitors. Several compounds possess an IC50 of similar to 200 nM against heparanase, for example, trans 2-[4-[3-(3,4-dichlorophenylamino)-3-oxo-1-propenyl]-2-fluorophenyl]benzoxazol-5-yl acetic acid (16e). Several of the compounds show anti-angiogenic properties. Improvement to the DMPK profile of compounds has provided compounds of potential use in in vivo models. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.014

文献信息

• [EN] HEPARANASE INHIBITORS AND USE THEREOF<br/>[FR] INHIBITEURS D'HÉPARANASE ET LEUR UTILISATION
  申请人：BETA THERAPEUTICS PTY LTD

  公开号：WO2018107200A1

  公开（公告）日：2018-06-21

  The invention relates to functionalized quinazoline compounds, pharmaceutical compositions comprising such compounds, and the use of such compounds as heparanase inhibitors for the treatment of diseases or conditions related to heparanse activity.

  本发明涉及功能化喹唑啉化合物，包括此类化合物的药物组合物，以及此类化合物作为肝素酶抑制剂用于治疗与肝素酶活性相关的疾病或状况的使用。
• Synthetic Route to a Benzooxazole Derivative with Heparanase Inhibitory Activity
  作者：Chiara Da Pieve、Pravin Patel、Sotiris Missailidis

  DOI：10.1080/00397910902994186

  日期：2010.2.2

  The synthesis of a benzooxazol-5-yl acetic acid derivative (9) with strong heparanase and angiogenesis inhibitory activity, and thus possible commercial interest, is described in detail.
• FGF-8 FOR USE IN TREATING DISEASES OR DISORDERS OF ENERGY HOMEOSTASIS
  申请人：Technische Universität München

  公开号：EP3104873B1

  公开（公告）日：2019-09-04
• METHODS OF TREATING OCULAR DISORDERS
  申请人：Beta Therapeutics Pty. Ltd.

  公开号：EP3554505A1

  公开（公告）日：2019-10-23
• Methods of Treating Ocular Disorders
  申请人：NELMS Keats

  公开号：US20200093852A1

  公开（公告）日：2020-03-26

  This invention relates to the use of a heparanase inhibitor for treating, or inhibiting the progression or development of, an ocular inflammatory disorder, such as age-related macular degeneration, diabetic retinopathy, retinitis pigmentosa, retinal 5 vein occlusion, retinoblastoma, uveitis, macular edema, dry eye, ocular inflammation associated with an infection or keratoconus.