3,4-dichlorofuro[2,3-b]quinoline | 118726-20-8

• 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: 3,4-dichlorofuro[2,3-b]quinoline
• 英文别名: 3,4-dichloro-furo[2,3-b]quinoline；3,4-Dichlor-furo[2,3-b]chinolin
• CAS: 118726-20-8
• 化学式: C₁₁H₅Cl₂NO
• 分子量: 238.073
• InChiKey: AKXSRYATWZCGBW-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C(Solv: ethanol (64-17-5))
• 沸点：
  371.2±37.0 °C(Predicted)
• 密度：
  1.510±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dichlorofuro[2,3-b]quinoline 在 Lindlar's catalyst 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 21.0h， 生成 4-Furo[2,3-b]quinolin-4-yloxybenzaldehyde
  参考文献：
  名称：

  Synthesis and anti-inflammatory evaluation of 4-anilinofuro[2,3- b ]quinoline and 4-phenoxyfuro[2,3- b ]quinoline derivatives. Part 3

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2003.10.051
• 作为产物：
  描述：

  furo[2,3-b]quinoline-3,4(2H,9H)-dione 在 水 、 三氯氧磷 作用下， 反应 4.0h， 以79%的产率得到3,4-dichlorofuro[2,3-b]quinoline
  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

• Synthesis and anticancer evaluation of certain 4-anilinofuro[2,3-]quinoline and 4-anilinofuro[3,2-]quinoline derivatives
  作者：Y CHEN、I CHEN、T WANG、C HAN、C TZENG

  DOI：10.1016/j.ejmech.2005.04.003

  日期：2005.9

  4-anilinofuro[2,3-b]quinoline and angular 4-anilinofuro[3,2-c]quinoline derivatives were synthesized and evaluated in vitro against the full panel of NCI's 60 cancer cell lines. For the linear 4-anilinofuro[2,3-b]quinoline derivatives, 1-[4-(furo[2,3-b]quinolin-4-ylamino)phenyl]ethanone (5a) is the most cytotoxic with a mean GI50 value of 0.025 microM. Substitution at either furo[2,3-b]quinoline ring (2a

  合成了某些线性4-苯胺呋喃[2,3-b]喹啉和角4-苯胺呋喃[3,2-c]喹啉衍生物，并在体外针对NCI的60种癌细胞系进行了评估。对于线性4-苯胺基呋喃[2,3-b]喹啉衍生物，1- [4-（呋喃[2,3-b]喹啉-4-基氨基）苯基]乙酮（5a）具有最高的细胞毒性，平均GI50值为0.025 microM。在呋喃[2,3-b]喹啉环（2a，2b和5b）或4-苯胺基部分（3-7）处取代导致细胞毒性降低。对于角4-苯胺基呋喃[3,2-c]喹啉衍生物，（E）-1- [3-（呋喃[3,2-c]喹啉-4-基氨基）苯基]乙酮肟（14a）表现出强抑制作用在UO-31，UACC-257和UACC-62上具有GI50活性，GI50值分别为0.03，<0.01和<0.01 microM。观察到与其甲基对应物14b相同的细胞毒性谱，其中针对UO-31，UACC-257和UACC-62的GI50值分别为<0.01、0
• 4-Anilino&lsqb;2,3-b&rsqb;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。
• Umwandlung des Dictamnins in Isomere mit angul�rer Struktur
  作者：H. Tuppy、F. B�hm

  DOI：10.1007/bf00899585

  日期：——
• 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 9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives. Part 2
  作者：Yeh-Long Chen、I-Li Chen、Chih-Ming Lu、Cherng-Chyi Tzeng、Lo-Ti Tsao、Jih-Pyang Wang

  DOI：10.1016/s0968-0896(03)00439-5

  日期：2003.9

  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 9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives and evaluated their anti-inflammatory activities. The title compounds were synthesized by reaction of either 9-chloroacridine or 3,4-dichlorofuro[2,3-b]quinoline with appropriate Ar-OH and their anti-inflammatory activities were studied on inhibitory effects on the activation of mast cells, neutrophils and macrophages. Four 9-(4formylphenoxy)acridine derivatives 2b-2e were proved to be more potent than the reference inhibitor, mepacrine for the inhibition of rat peritoneal mast cell degranulation with IC50 values of 6.1, 5.9, 13.5, and 4.7 muM, respectively. Compounds 2c, 3b, 3c, and 5a also showed potent inhibitory activity (IC50 = 4.3-18.3 muM) for the secretion of lysosomal enzyme and P-glucuronidase from neutrophils. In addition, 2d, 3a, and 4 inhibited TNF-alpha formation from the N9 cells (the brain resident macrophages) with IC50 vales less then 10 muM. These results indicated that acridine derivatives exhibited more potent anti-inflammatory activities than their respective furo[2,3-b]quinoline counterparts (4 vs 9; 5a vs 10a; 5b vs 10b). (C) 2003 Elsevier Ltd. All rights reserved.