1-(4-(3-chlorofuro[2,3-b]quinolin-4-ylamino)phenyl)ethanone | 629164-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(3-chlorofuro[2,3-b]quinolin-4-ylamino)phenyl)ethanone
• 英文别名: 1-[4-(3-chlorofuro[2,3-b]quinolin-4-ylamino)phenyl]ethanone；1-[4-[(3-chlorofuro[2,3-b]quinolin-4-yl)amino]phenyl]ethanone
• CAS: 629164-70-1
• 化学式: C₁₉H₁₃ClN₂O₂
• 分子量: 336.777
• InChiKey: VERRUNYNHQDERO-UHFFFAOYSA-N

物化性质

• 熔点：
  245-247 °C
• 沸点：
  524.5±50.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-(3-chlorofuro[2,3-b]quinolin-4-ylamino)phenyl)ethanone 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以78%的产率得到1-(4-(furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone
  参考文献：
  名称：

  4-ANILINO[2,3-b]QUINOLINE DERIVATIVES,THEIR PREPARATION PROCECC ANDPHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME

  摘要：

  本文披露了一种新颖的4-苯胺基[2,3-b]喹啉衍生物，化学式如下：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中的用途。

  公开号：

  US20040072856A1
• 作为产物：
  描述：

  3,4-dichlorofuro[2,3-b]quinoline 、 4-氨基苯乙酮 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以75%的产率得到1-(4-(3-chlorofuro[2,3-b]quinolin-4-ylamino)phenyl)ethanone
  参考文献：
  名称：

  4-ANILINO[2,3-b]QUINOLINE DERIVATIVES,THEIR PREPARATION PROCECC ANDPHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME

  摘要：

  本文披露了一种新颖的4-苯胺基[2,3-b]喹啉衍生物，化学式如下：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中的用途。

  公开号：

  US20040072856A1

文献信息

• 4-Anilino[2,3-b]quinoline derivatives, their preparation processes and pharmaceutical compositions comprising the same
  申请人：Kaohsiung Medical University

  公开号：US06750223B2

  公开（公告）日：2004-06-15

  Disclosed herein are 4-anilino[2,3-b]quinoline derivatives of formula (I): wherein each of R1, R2, R3 and Y is given the definition as set forth in the Specification and Claims. These compounds of formula (I) have been found to have the ability to inhibit growth of a variety of tumor/cancer cells, especially leukemia, colon, melanoma and breast cancer cells. Also, disclosed are preparation processes of these compounds of formula (I) and pharmaceutical compositions comprising said compositions of formula (I).

  本文公开了式(I)的4-苯胺基[2,3-b]喹啉衍生物，其中R1、R2、R3和Y的定义如说明书和权利要求所述。已发现这些式(I)化合物具有抑制多种肿瘤/癌细胞生长的能力，尤其是白血病、结肠癌、黑色素瘤和乳腺癌细胞。此外，还公开了这些式(I)化合物的制备方法和包含该式(I)化合物的制药组合物。
• 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。
• [EN] 4-ANILINOFURO[2,3-b]QUINOLINE DERIVATIVES, THEIR PREPARATION PROCESSES, AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME<br/>[FR] DÉRIVÉS DE 4-ANILINOFURO[2,3-B]QUINOLINE, PROCÉDÉS D'ÉLABORATION CORRESPONDANTS, ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT
  申请人：UNIV KAOHSIUNG MEDICAL

  公开号：WO2012102965A1

  公开（公告）日：2012-08-02

  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.

  本文披露了一种新的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格书和权利要求所述。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。
• 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.
• 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.