N-[2-(3,5-dichloro-4-hydroxyphenyl)ethyl]acetamide | 437712-24-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[2-(3,5-dichloro-4-hydroxyphenyl)ethyl]acetamide
• CAS: 437712-24-8
• 化学式: C₁₀H₁₁Cl₂NO₂
• 分子量: 248.109
• InChiKey: AUTHFAYMAPBODC-UHFFFAOYSA-N

物化性质

• 沸点：
  427.9±45.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  N-[2-(3,5-dichloro-4-hydroxyphenyl)ethyl]acetamide 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 2-(3,5-dichloro-4-hydroxyphenyl)ethylamine hydrochloride
  参考文献：
  名称：

  Ezrin inhibitors and methods of making and using

  摘要：

  该发明涵盖了包含以下化合物的化合物和药物组合物（I）的药物组合物，或其药用盐或前药，这些化合物对于抑制细胞中的ezrin蛋白或抑制癌细胞的生长是有用的。

  公开号：

  US09522908B2
• 作为产物：
  描述：

  酪胺盐酸盐 在 磺酰氯 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 16.0h， 生成 N-[2-(3,5-dichloro-4-hydroxyphenyl)ethyl]acetamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of ezrin inhibitors targeting metastatic osteosarcoma

  摘要：

  Respiratory failure due to pulmonary metastasis is the major cause of death for patients with osteosarcoma. However, the molecular basis for metastasis of osteosarcoma is poorly understood. Recently, ezrin, a member of the ERM family of proteins, has been associated with osteosarcoma metastasis to the lungs. The small molecule NSC 668394 was identified to bind to ezrin, inhibit in vitro and in vivo cell migration, invasion, and metastatic colony survival. Reported herein are the design and synthesis of analogues of NSC 668394, and subsequent functional ezrin inhibition studies. The binding affinity was characterized by surface plasmon resonance technique. Cell migration and invasion activity was determined by electrical cell impedance methodology. Optimization of a series of heterocyclic-dione analogues led to the discovery of compounds 21k and 21m as potential novel antimetastatic agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.003

文献信息

• Identification of 4-benzylamino-2-[(4-morpholin-4-ylphenyl)amino]pyrimidine-5-carboxamide derivatives as potent and orally bioavailable STAT6 inhibitors
  作者：Shinya Nagashima、Hiroshi Nagata、Masahiro Iwata、Masaki Yokota、Hiroyuki Moritomo、Masaya Orita、Sadao Kuromitsu、Akiko Koakutsu、Keiko Ohga、Makoto Takeuchi

  DOI：10.1016/j.bmc.2008.05.031

  日期：2008.7.1

  Signal transducers and activators of transcription 6 (STAT6) is a key regulator of the type 2 helper T (Th2) cell immune response and a potential therapeutic target for allergic diseases such as asthma and atopic diseases. To search for potent and orally bioavailable STAT6 inhibitors, we synthesized a series of 4-benzylaminopyrimidine-5- carboxamide derivatives and evaluated their STAT6 inhibitory activities. Among these compounds, 2-[(4-morpholin-4-ylphenyl)amino]-4-[(2,3,6- trifluorobenzyl)amino]pyrimidine-5-carboxamide (25y, YM-341619, AS1617612) showed potent STAT6 inhibition with an IC(50) of 0.70 nM, and also inhibited Th2 differentiation in mouse spleen T cells induced by interleukin (IL)-4 with an IC(50) of 0.28 nM without affecting type 1 helper T (Th1) cell differentiation induced by IL-12. In addition, compound 25y showed an oral bioavailability of 25% in mouse. (c) 2008 Elsevier Ltd. All rights reserved.
• Cytotoxic, antifouling bromotyramines: A synthetic study on simple marine natural products and Their analogues
  作者：Ryan C. Schoenfeld、Susan Conova、Daniel Rittschof、Bruce Ganem

  DOI：10.1016/s0960-894x(02)00022-7

  日期：2002.3

  Synthesis and biological evaluation of two naturally-occurring bromotyramines. moloka'iamine 1 and 3,5-dibromo-4-methoxy-beta-phenethylamine 2, together with several analogues, have been completed. Bromotyramine 2 is cytotoxic, and was found to be a potent antifoulant. Analogues 15 and 16 also displayed significant cytotoxic and antifouling activities. (C) 2002 Elsevier Science Ltd. All rights reserved.
• NOVEL EZRIN INHIBITORS AND METHODS OF MAKING AND USING
  申请人：GEORGETOWN UNIVERSITY

  公开号：US20140135325A1

  公开（公告）日：2014-05-15

  The invention encompasses compound and pharmaceutical composition comprising the compound of the following Formula (I): or pharmaceutically acceptable salts or prodrugs thereof, that are useful for inhibiting ezrin protein in a cell or for inhibiting the growth of a cancer cell.
• Novel Ezrin Inhibitors and Methods of Making and Using
  申请人：Georgetown University

  公开号：US20180148437A1

  公开（公告）日：2018-05-31

  The invention encompasses compound and pharmaceutical composition comprising the compound of the following Formula (I): or pharmaceutically acceptable salts or prodrugs thereof, that are useful for inhibiting ezrin protein in a cell or for inhibiting the growh of a cancer cell.
• US9522908B2
  申请人：——

  公开号：US9522908B2

  公开（公告）日：2016-12-20