(E)-1-(4-(furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone O-3-(dimethylamino)propyl oxime | 1310569-77-7

• 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: (E)-1-(4-(furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone O-3-(dimethylamino)propyl oxime
• 英文别名: N-[4-[(E)-N-[3-(dimethylamino)propoxy]-C-methylcarbonimidoyl]phenyl]furo[2,3-b]quinolin-4-amine
• CAS: 1310569-77-7
• 化学式: C₂₄H₂₆N₄O₂
• 分子量: 402.496
• InChiKey: NXIKGKJXCGTHBQ-WPWMEQJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(N,N-dimethylamino)propoxyamine hydrochloride 、 1-(4-(furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以75%的产率得到(E)-1-(4-(furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone O-3-(dimethylamino)propyl oxime
  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

• 4-ANILINOFURO[2,3-B]QUINOLINE DERIVATIVES, THEIR PREPARATION PROCESSES, AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：Tzeng Cherng-Chyi

  公开号：US20130172336A1

  公开（公告）日：2013-07-04

  Disclosed herein are novel 4-anilinofuro[2,3-b]quinoline derivatives of formula (I): or a pharmaceutically acceptable salt thereof, wherein each of the substituents is given the definition as set forth in the Specification and Claims. Also disclosed are the preparation processes of these derivatives and their uses in the manufacture of pharmaceutical compositions and in the treatment of cancers.

  本文披露了新型的4-苯胺基呋喃[2,3-b]喹啉衍生物，其化学式为(I):或其药学上可接受的盐，其中每个取代基的定义如规范和权利要求中所述。还披露了这些衍生物的制备过程以及它们在制造药物组合物和治疗癌症方面的用途。
• US8952033B2
  申请人：——

  公开号：US8952033B2

  公开（公告）日：2015-02-10
• 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.