3-苯甲酰氨基-7-羟基-2H-1-苯并吡喃-2-酮 | 126940-57-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 3-苯甲酰氨基-7-羟基-2H-1-苯并吡喃-2-酮
• 英文名称: 3-benzoylamino-7-hydroxy-2H-1-benzopyran-2-one
• 英文别名: N-(7-hydroxy-2-oxo-2H-1-benzopyran-3-yl)benzamide；N-(7-hydroxy-2-oxo-2H-chromen-3-yl)benzamide；N-(7-hydroxy-2-oxochromen-3-yl)benzamide
• CAS: 126940-57-6
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: VYNNYDYTRZLFQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-苯甲酰氨基-7-羟基-2H-1-苯并吡喃-2-酮 在 盐酸 、 水 、 碳酸氢钠 作用下， 以 丙醇 、 水 为溶剂， 反应 10.0h， 以87.7%的产率得到3-氨基-7-羟基香豆素
  参考文献：
  名称：

  Coumarin derivative

  摘要：

  一种增强基于DNA损伤作用的癌症治疗效果的药物，其包含以下通式（I）所表示的化合物作为活性成分： 其中，X表示单键或可以被取代的C1至C6烷基链；A表示可以被取代的C1至C6烷基链、可以被取代的C6至C10芳基链，或者可以被取代的4至10成员的单环或双环不饱和、部分饱和或完全饱和的杂环基团，其中所述的杂环基团包含1至4个从氮原子、氧原子和硫原子组成的杂原子。

  公开号：

  US20050054717A1
• 作为产物：
  描述：

  methyl 2-benzoylamino-3-dimethylaminopropenoate 、 间苯二酚 以 溶剂黄146 为溶剂， 反应 6.0h， 以73%的产率得到3-苯甲酰氨基-7-羟基-2H-1-苯并吡喃-2-酮
  参考文献：
  名称：

  Stanovnik, Branko; Svete, Jurij; Tisler, Miha, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1273 - 1276

  摘要：

  DOI：

文献信息

• Simplified aminocoumarin analogues as anticancer agents: Amino isosteric replacement in the noviose moiety resulted in substantial enhancement of antiproliferative activity
  作者：Ting Zhang、Zheng Yan、Yun-Feng Li、Nan Wang

  DOI：10.1016/j.cclet.2013.04.046

  日期：2013.8

  Simplified aminocoumarin analogues, either noviosylated or simple basic heterocycle attached 3-amidocoumarin compounds, are known to be promising anticancer agents targeting the C-terminal ATP-binding site of Hsp90. In this study, 3'-amino isosteric replacement in the noviose moiety of two known noviose containing Hsp90 C-terminal inhibitors was synthetically realized for the first time. In vitro evaluation of these compounds suggested that the introduction of a basic amino group into the noviose subunit resulted in significant improvement of their cytotoxicities. (C) 2013 Yun-Feng Li and Nan Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Novobiocin-related compounds: synthesis of 3-benzoylamino-2-oxo-2H-1-benzopyran-7-yl d-glycopyranosides by the trichloroacetimidate methodology
  作者：Marjan Ješelnik、Janez Plavec、Slovenko Polanc、Marijan Kočevar

  DOI：10.1016/s0008-6215(00)00142-7

  日期：2000.10

  A general stereoselective method for the synthesis of 4-deoxynovobiocin-related glycosides is described. 3-Benzoylamino-2H-1-benzopyran-7-yl 2,3,4,6-tetra-O-acetyl-D-glycopyranosides of glucose, galactose and mannose were synthesised from appropriate O-glycosyltrichloroacetimidates and N-(7-hydroxy-2-oxo-2H-1-benzopyran-3-yl)benzamides in boiling methylene chloride in the presence of boron trifluoride etherate. Heating of these products in a mixture of triethylamine and methanol gave the corresponding deprotected 3-benzoylamino-2-oxo-2H-1-benzopyran-7-yl beta-D-glycopyranosides. (C) 2000 Elsevier Science Ltd. All rights reserved.
• STANOVNIK, BRANKO;SVETE, JURIJ;TISLER, MIHA, J. HETEROCYCL. CHEM., 26,(1989) N, C. 1273-1275
  作者：STANOVNIK, BRANKO、SVETE, JURIJ、TISLER, MIHA

  DOI：——

  日期：——
• US7411076B2
  申请人：——

  公开号：US7411076B2

  公开（公告）日：2008-08-12
• Coumarin derivative
  申请人：Muto Susumu

  公开号：US20050054717A1

  公开（公告）日：2005-03-10

  A medicament for enhancing an effect of a cancer therapy based on a mode of action of DNA injury, which comprises as an active ingredient a compound represented by the following general formula (I): wherein X represents a single bond or a C 1 to C 6 alkylene group which may be substituted; A represents a C 1 to C 6 alkyl group which may be substituted, a C 6 to C 10 aryl group which may be substituted, or a 4 to 10-membered monocyclic or bicyclic and unsaturated, partly saturated, or completely saturated heterocyclic group which may be substituted, wherein said heterocyclic group comprises as ring-constituting atoms 1 to 4 hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom.

  一种增强基于DNA损伤作用的癌症治疗效果的药物，其包含以下通式（I）所表示的化合物作为活性成分： 其中，X表示单键或可以被取代的C1至C6烷基链；A表示可以被取代的C1至C6烷基链、可以被取代的C6至C10芳基链，或者可以被取代的4至10成员的单环或双环不饱和、部分饱和或完全饱和的杂环基团，其中所述的杂环基团包含1至4个从氮原子、氧原子和硫原子组成的杂原子。