3-乙基-4-氧代-4H-苯并吡喃-2-羧酸 | 801138-61-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 3-乙基-4-氧代-4H-苯并吡喃-2-羧酸
• 英文名称: 3-Ethyl-4-oxo-4H-chromene-2-carboxylic acid
• 英文别名: 3-ethyl-4-oxochromene-2-carboxylic acid
• CAS: 801138-61-4
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: QVEGBFBXTRGKKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±42.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-乙基-4-氧代-4H-苯并吡喃-2-羧酸 在 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-[(2S)-4-amino-3,4-dioxo-1-phenylbutan-2-yl]-3-ethyl-4-oxochromene-2-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of chromone carboxamides as calpain inhibitors

  摘要：

  Excessive calpain activations contribute to serious cellular damage and have been found in many pathological conditions. Novel chromone carboxamides derived from ketoamides were prepared and evaluated for mu-calpain inhibition. Among synthesized, compound 2i was the most potent calpain inhibitor with an IC50 value of 0.24 +/- 0.11 mu M comparable to the activity of peptide aldehyde calpain inhibitor MDL 28,170. Furthermore, compound 2i showed higher selectivity for mu-calpain over two related cysteine proteases cathepsin B and cathepsin L, suggesting the chromone ring as a good scaffold for selective mu-calpain inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.095
• 作为产物：
  描述：

  Ethyl 3-ethyl-4-oxochromene-2-carboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 3-乙基-4-氧代-4H-苯并吡喃-2-羧酸
  参考文献：
  名称：

  Synthesis and biological evaluation of chromone carboxamides as calpain inhibitors

  摘要：

  Excessive calpain activations contribute to serious cellular damage and have been found in many pathological conditions. Novel chromone carboxamides derived from ketoamides were prepared and evaluated for mu-calpain inhibition. Among synthesized, compound 2i was the most potent calpain inhibitor with an IC50 value of 0.24 +/- 0.11 mu M comparable to the activity of peptide aldehyde calpain inhibitor MDL 28,170. Furthermore, compound 2i showed higher selectivity for mu-calpain over two related cysteine proteases cathepsin B and cathepsin L, suggesting the chromone ring as a good scaffold for selective mu-calpain inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.095

文献信息

• CHROMEN-4-ON-DERIVATE
  申请人：Merck Patent GmbH

  公开号：EP1856084A1

  公开（公告）日：2007-11-21
• [DE] CHROMEN-4-ON-DERIVATE<br/>[EN] CHROMEN-4-ONE DERIVATIVES<br/>[FR] DERIVES DE CHROMENE-4-ONE
  申请人：MERCK PATENT GMBH

  公开号：WO2006094601A1

  公开（公告）日：2006-09-14

  [EN] The invention relates to chromen-4-one derivatives, the production thereof, and the use of the same for the care, preservation or improvement of the general state of the skin or especially the hair, and for the prophylaxis of time-induced and/or light-induced ageing processes of the human skin or especially human hair. The invention also relates to preparations with an active content of such chromen-4-one derivatives.
  [FR] La présente invention concerne des dérivés de chromène-4-one, leur production et leur utilisation pour traiter, conserver ou améliorer l'état général de la peau ou en particulier des cheveux et pour prévenir contre les processus de vieillissement dus au temps et/ou à la lumière de la peau chez l'homme, en particulier des cheveux chez l'homme. Cette invention concerne également des préparations comprenant une teneur efficace en dérivés de chromène-4-one de ce type.
  [DE] Die vorliegende Erfindung betrifft Chromen-4-on-Derivate, ihre Herstellung und Verwendung zur Pflege, Konservierung oder Verbesserung des allgemeinen Zustandes der Haut oder insbesondere der Haare und zur Prophylaxe gegen zeit- und/oder lichtinduzierte Alterungsprozesse der menschlichen Haut oder insbesondere menschlicher Haare. Ferner betrifft die Erfindung Zubereitungen mit einem wirksamen Gehalt an solchen Chromen-4-on-Derivaten.
• Synthesis and biological evaluation of chromone carboxamides as calpain inhibitors
  作者：Kwang Seob Lee、Seon Hee Seo、Yong Ha Lee、Ha Dong Kim、Moon Ho Son、Bong Young Chung、Jae Yeol Lee、Changbae Jin、Yong Sup Lee

  DOI：10.1016/j.bmcl.2005.03.095

  日期：2005.6

  Excessive calpain activations contribute to serious cellular damage and have been found in many pathological conditions. Novel chromone carboxamides derived from ketoamides were prepared and evaluated for mu-calpain inhibition. Among synthesized, compound 2i was the most potent calpain inhibitor with an IC50 value of 0.24 +/- 0.11 mu M comparable to the activity of peptide aldehyde calpain inhibitor MDL 28,170. Furthermore, compound 2i showed higher selectivity for mu-calpain over two related cysteine proteases cathepsin B and cathepsin L, suggesting the chromone ring as a good scaffold for selective mu-calpain inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.