Benzoic acid, 4-[(3-chlorofuro[2,3-b]quinolin-4-yl)amino]- | 690633-00-2

• 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: Benzoic acid, 4-[(3-chlorofuro[2,3-b]quinolin-4-yl)amino]-
• 英文别名: 4-[(3-chlorofuro[2,3-b]quinolin-4-yl)amino]benzoic acid
• CAS: 690633-00-2
• 化学式: C₁₈H₁₁ClN₂O₃
• 分子量: 338.75
• InChiKey: AHPRJCULOGJNPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-dichlorofuro[2,3-b]quinoline 、 对氨基苯甲酸 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以53%的产率得到Benzoic acid, 4-[(3-chlorofuro[2,3-b]quinolin-4-yl)amino]-
  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

• Synthesis and anti-inflammatory evaluation of 4-anilinofuro[2,3- b ]quinoline and 4-phenoxyfuro[2,3- b ]quinoline derivatives. Part 3
  作者：Yeh-Long Chen、I-Li Chen、Chih-Ming Lu、Cherng-Chyi Tzeng、Lo-Ti Tsao、Jih-Pyang Wang

  DOI：10.1016/j.bmc.2003.10.051

  日期：2004.1

  Mast cells, neutrophils and macrophages are important inflammatory cells that have been implicated in the pathogenesis of acute and chronic inflammatory diseases. To explore a novel anti-inflammatory agent, we have synthesized certain 4-anilinofuro[2,3-b]quinoline and 4-phenoxyfuro[2,3-b]quinoline derivatives and evaluated their anti-inflammatory activities by reaction of 3,4-dichlorofuro[2,3-b]quinoline with appropriate Ar-NH2 or Ar-OH. Compounds 6a and 15 were proved to be more potent than the reference inhibitor, mepacrine for the inhibition of rat peritoneal mast cell degranulation with IC50 values of 6.5 and 16.4 muM, respectively. Compounds 2b, 6a, 10, and 15 also showed potent inhibitory activity (IC50 = 7.2-29.4 muM) for the secretion of lysosomal enzyme and beta-glucuronidase from neutrophils. These results also indicated that oxime derivatives are more potent than the respective ketone precursors (6a greater than or equal to 2a; 7a greater than or equal to 3), and the substituent such as Me at the oxime decreased inhibitory activity (6a greater than or equal to 6b; 7a greater than or equal to 7b). Among these derivatives, compound 6a showed the most potent activity with IC50 values of 6.5-11.6 muM for the inhibition of mast cell degranulation and neutrophil degranulation. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.