4-(3-chloro-7-methoxyfuro[2,3-b]quinolin-4-ylamino)-N-(2-hydroxyethyl)benzamide | 1310570-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(3-chloro-7-methoxyfuro[2,3-b]quinolin-4-ylamino)-N-(2-hydroxyethyl)benzamide
• 英文别名: 4-[(3-chloro-7-methoxyfuro[2,3-b]quinolin-4-yl)amino]-N-(2-hydroxyethyl)benzamide
• CAS: 1310570-11-6
• 化学式: C₂₁H₁₈ClN₃O₄
• 分子量: 411.845
• InChiKey: ZPJSOSKXJIQRAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  96.6
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-dichloro-7-methoxyfuro[2,3-b]quinoline 、 对氨基苯甲酰氨基乙醇 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以56%的产率得到4-(3-chloro-7-methoxyfuro[2,3-b]quinolin-4-ylamino)-N-(2-hydroxyethyl)benzamide
  参考文献：
  名称：

  Discovery of 4-Anilinofuro[2,3-b]quinoline Derivatives as Selective and Orally Active Compounds against Non-Small-Cell Lung Cancers

  摘要：

  We have reported the preparation and anticancer evaluation of certain 4-anilinofuro-[2,3-b]quinolines. However, drawbacks such as lack of selective cytotoxicity, poor oral bioavailability, and poor water solubility exhibited by these compounds prompted us to search for newer derivatives. Among them, (E)-1-(4-(furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone O-2-aminoethyloxime (13a) is selectively active against the growth of NCI-H460 and is highly water-soluble (63 mu g/mL). Its hydrochloride salt, 13a center dot HCl exhibited not only excellent water solubility (1049 ug/mL) but also a high oral bioavailability (57.1%). Compound 13a may cause cancer cell apoptosis through inducing mitotic arrest and mitotic catastrophe mechanism. Xenographic studies indicated the tumor size with 13a center dot HCl treated nude mice was significantly lower than control. Further evaluation in an orthotopic lung cancer model indicated that 13a center dot HCl can be absorbed readily through oral administration, distributed to lung tissue, and exhibited significant efficacy in inhibiting the growth of lung cancers.

  DOI：

  10.1021/jm200046z

文献信息

• Discovery of 4-Anilinofuro[2,3-<i>b</i>]quinoline Derivatives as Selective and Orally Active Compounds against Non-Small-Cell Lung Cancers
  作者：Yu-Wen Chen、Yeh-Long Chen、Chih-Hua Tseng、Chih-Chung Liang、Chia-Ning Yang、Yun-Chin Yao、Pei-Jung Lu、Cherng-Chyi Tzeng

  DOI：10.1021/jm200046z

  日期：2011.7.14

  We have reported the preparation and anticancer evaluation of certain 4-anilinofuro-[2,3-b]quinolines. However, drawbacks such as lack of selective cytotoxicity, poor oral bioavailability, and poor water solubility exhibited by these compounds prompted us to search for newer derivatives. Among them, (E)-1-(4-(furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone O-2-aminoethyloxime (13a) is selectively active against the growth of NCI-H460 and is highly water-soluble (63 mu g/mL). Its hydrochloride salt, 13a center dot HCl exhibited not only excellent water solubility (1049 ug/mL) but also a high oral bioavailability (57.1%). Compound 13a may cause cancer cell apoptosis through inducing mitotic arrest and mitotic catastrophe mechanism. Xenographic studies indicated the tumor size with 13a center dot HCl treated nude mice was significantly lower than control. Further evaluation in an orthotopic lung cancer model indicated that 13a center dot HCl can be absorbed readily through oral administration, distributed to lung tissue, and exhibited significant efficacy in inhibiting the growth of lung cancers.