5-(tetrahydro-4H-pyran-4-yloxy)-benzofuran-2-carboxylic acid | 871109-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-(tetrahydro-4H-pyran-4-yloxy)-benzofuran-2-carboxylic acid
• 英文别名: 5-(Oxan-4-yloxy)-1-benzofuran-2-carboxylic acid
• CAS: 871109-57-8
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: ZAADXIDTSZTEAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(tetrahydro-4H-pyran-4-yloxy)-benzofuran-2-carboxylic acid 、 (1R,2S,10R,12R,13S)-10-(aminomethyl)-8,19-dihydroxy-5,7,16,18-tetramethoxy-6,17,21-trimethyl-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),5,7,15(20),16,18-hexaene-12-carbonitrile 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 水 为溶剂， 以60%的产率得到N-[[(1R,2S,10R,12R,13S)-12-cyano-8,19-dihydroxy-5,7,16,18-tetramethoxy-6,17,21-trimethyl-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),5,7,15(20),16,18-hexaen-10-yl]methyl]-5-(oxan-4-yloxy)-1-benzofuran-2-carboxamide
  参考文献：
  名称：

  Evaluation of antitumor properties of novel saframycin analogs in vitro and in vivo

  摘要：

  Novel analogs of (-)-saframycin A are described. The analogs are shown to be potent inhibitors of the in vitro growth of several tumor cells in a broad panel and promising as leads for further optimization. The first in vivo studies in a solid tumor model (HCT-116) reveal potent antitumor activity with associated toxicity of daily administration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.085
• 作为产物：
  描述：

  5-(tetrahydro-4H-pyran-4-yloxy)-benzofuran-2-carboxylic acid methyl ester 在 lithium hydroxide 、 水 、 盐酸 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 2.0h， 以99%的产率得到5-(tetrahydro-4H-pyran-4-yloxy)-benzofuran-2-carboxylic acid
  参考文献：
  名称：

  [EN] SAFRAMYCIN ANALOGS AS THERAPEUTIC AGENTS IN THE TREATMENT OF CANCER
  [FR] NOUVEAUX ANALOGUES DE SAFRAMYCINE UTILISES EN TANT QU'AGENTS THERAPEUTIQUES

  摘要：

  公开号：

  WO2005118584A3

文献信息

• [EN] SAFRAMYCIN ANALOGS AS THERAPEUTIC AGENTS IN THE TREATMENT OF CANCER<br/>[FR] NOUVEAUX ANALOGUES DE SAFRAMYCINE UTILISES EN TANT QU'AGENTS THERAPEUTIQUES
  申请人：AXYS PHARM INC

  公开号：WO2005118584A3

  公开（公告）日：2006-03-23
• [EN] NOVEL SAFRAMYCIN ANALOGS AS THERAPEUTIC AGENTS<br/>[FR] NOUVEAUX ANALOGUES DE SAFRAMYCINE UTILISES EN TANT QU'AGENTS THERAPEUTIQUES
  申请人：AXYS PHARM INC

  公开号：WO2005118584A2

  公开（公告）日：2005-12-15

  The present invention is directed to saframcyin analogs that are useful in the treatment of cancer. Pharmaceutical compositions and processes for preparing these compounds are also disclosed.
• WO2006/66183
  申请人：——

  公开号：——

  公开（公告）日：——
• Evaluation of antitumor properties of novel saframycin analogs in vitro and in vivo
  作者：Jeffrey R. Spencer、Martin Sendzik、Jason Oeh、Peter Sabbatini、Stacie A. Dalrymple、Catherine Magill、Hyunjin M. Kim、Penglie Zhang、Neil Squires、Katherine G. Moss、Juthamas Sukbuntherng、Doris Graupe、John Eksterowicz、Peter R. Young、Andrew G. Myers、Michael J. Green

  DOI：10.1016/j.bmcl.2006.06.085

  日期：2006.9

  Novel analogs of (-)-saframycin A are described. The analogs are shown to be potent inhibitors of the in vitro growth of several tumor cells in a broad panel and promising as leads for further optimization. The first in vivo studies in a solid tumor model (HCT-116) reveal potent antitumor activity with associated toxicity of daily administration. (c) 2006 Elsevier Ltd. All rights reserved.