3-fluorophenyl 6-hexamethylenetetrammoniomethyl-2-oxo-2H-1-benzopyran-3-carboxylate; chloride | 1104642-51-4

• 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: 3-fluorophenyl 6-hexamethylenetetrammoniomethyl-2-oxo-2H-1-benzopyran-3-carboxylate; chloride
• 英文别名: (3-Fluorophenyl) 2-oxo-6-(3,5,7-triaza-1-azoniatricyclo[3.3.1.13,7]decan-1-ylmethyl)chromene-3-carboxylate;chloride
• CAS: 1104642-51-4
• 化学式: C₂₃H₂₂FN₄O₄*Cl
• 分子量: 472.903
• InChiKey: OZWDAJWKRBHHPX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.84
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-fluorophenyl 6-hexamethylenetetrammoniomethyl-2-oxo-2H-1-benzopyran-3-carboxylate; chloride 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 (3-Fluorophenyl) 6-(aminomethyl)-2-oxochromene-3-carboxylate;hydrochloride
  参考文献：
  名称：

  6-Substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives in a new approach of the treatment of cancer cell invasion and metastasis

  摘要：

  Novel 6-substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives were synthesized and their potency in reducing the invasive behaviour of HT 1080 fibrosarcoma cells was evaluated. Structure-activity relationships were deduced from biological results and will be used in further design of new active compounds. In particular, the acetoxymethyl substituent found at the 6-position of previously described active compounds can be replaced by an acetamidomethyl substituent without loss of potency; while the presence of an aryl ester function at the 3-position was preferred to a thioester or an amide function to induce marked biological activity. This work confirms the interest of aryl esters of 6-substituted coumarin-3-carboxylic acids as potential new anti-cancer agents. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.024
• 作为产物：
  描述：

  乌洛托品 、 3-fluorophenyl 6-chloromethyl-2-oxo-2H-1-benzopyran-3-carboxylate 以 氯仿 为溶剂， 反应 18.0h， 以65%的产率得到3-fluorophenyl 6-hexamethylenetetrammoniomethyl-2-oxo-2H-1-benzopyran-3-carboxylate; chloride
  参考文献：
  名称：

  6-Substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives in a new approach of the treatment of cancer cell invasion and metastasis

  摘要：

  Novel 6-substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives were synthesized and their potency in reducing the invasive behaviour of HT 1080 fibrosarcoma cells was evaluated. Structure-activity relationships were deduced from biological results and will be used in further design of new active compounds. In particular, the acetoxymethyl substituent found at the 6-position of previously described active compounds can be replaced by an acetamidomethyl substituent without loss of potency; while the presence of an aryl ester function at the 3-position was preferred to a thioester or an amide function to induce marked biological activity. This work confirms the interest of aryl esters of 6-substituted coumarin-3-carboxylic acids as potential new anti-cancer agents. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.024

文献信息

• 6-Substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives in a new approach of the treatment of cancer cell invasion and metastasis
  作者：Isabelle Kempen、Marc Hemmer、Stéphane Counerotte、Lionel Pochet、Pascal de Tullio、Jean-Michel Foidart、Silvia Blacher、Agnès Noël、Francis Frankenne、Bernard Pirotte

  DOI：10.1016/j.ejmech.2008.01.024

  日期：2008.12

  Novel 6-substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives were synthesized and their potency in reducing the invasive behaviour of HT 1080 fibrosarcoma cells was evaluated. Structure-activity relationships were deduced from biological results and will be used in further design of new active compounds. In particular, the acetoxymethyl substituent found at the 6-position of previously described active compounds can be replaced by an acetamidomethyl substituent without loss of potency; while the presence of an aryl ester function at the 3-position was preferred to a thioester or an amide function to induce marked biological activity. This work confirms the interest of aryl esters of 6-substituted coumarin-3-carboxylic acids as potential new anti-cancer agents. (C) 2008 Elsevier Masson SAS. All rights reserved.