N-(7-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl)-benzamide | 312911-49-2

• 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
• 英文名称: N-(7-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl)-benzamide
• 英文别名: N-(7-hydroxy-8-methyl-2-oxochromen-3-yl)benzamide
• CAS: 312911-49-2
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: BZJWEQGYYCYRGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  N-(7-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl)-benzamide 在 三氟化硼乙醚 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 3-benzoylamino-8-methyl-2-oxo-2H-1-benzopyran-7-yl β-D-galactopyranoside
  参考文献：
  名称：

  Novobiocin-related compounds: synthesis of 3-benzoylamino-2-oxo-2H-1-benzopyran-7-yl d-glycopyranosides by the trichloroacetimidate methodology

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(00)00142-7
• 作为产物：
  描述：

  (Z)-2-phenyl-4-(chloromethylene)-5(4H)-oxazolone 、 2,6-二羟基甲苯 在 三氯化铝 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(7-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl)-benzamide
  参考文献：
  名称：

  Novobiocin-related compounds: synthesis of 3-benzoylamino-2-oxo-2H-1-benzopyran-7-yl d-glycopyranosides by the trichloroacetimidate methodology

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(00)00142-7

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.