6-(苄氧基)-4-氯-7-甲氧基喹啉 | 516526-43-5

• 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
• 中文名称: 6-(苄氧基)-4-氯-7-甲氧基喹啉
• 英文名称: 6-(benzyloxy)-4-chloro-7-methoxyquinoline
• 英文别名: 4-chloro-7-methoxy-6-phenylmethoxyquinoline
• CAS: 516526-43-5
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: VKIDMVXAAMVIKE-UHFFFAOYSA-N

物化性质

• 沸点：
  434.8±40.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(苄氧基)-4-氯-7-甲氧基喹啉 在 氢氧化钯 氢气 、 水 、 氯仿 、 Sodium sulfate-III 作用下， 以 triethylamine N,N-dimethylformamide 为溶剂， 反应 6.0h， 以to give 6-hydroxy-7-methoxyquinoline (258 mg, yield 84%)的产率得到6-Hydroxy-7-methoxyquinoline
  参考文献：
  名称：

  COMPOUND HAVING TGFBETA INHIBITORY ACTIVITY AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

  摘要：

  本发明提供了由式(I)表示的化合物及其药学上可接受的盐和溶剂： 其中，X代表CH或N；Z代表—O—、—NH—或—C(═O)—；R和R′代表氢原子、羟基、卤素原子、可选取代的烷基、可选取代的烯基、可选取代的烷氧基、氨基、氨基甲酰基或可选取代的杂环基；A代表可选取代的特定环烷基或杂环基。本发明的化合物具有优异的TGFβ抑制活性。

  公开号：

  US20090312313A1
• 作为产物：
  描述：

  4-甲氧基-3-羟基苯乙酮 在 盐酸 、 4-二甲氨基吡啶 、 硝酸 、 sodium methylate 、 铁粉 、 potassium carbonate 、 三氯氧磷 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 6-(苄氧基)-4-氯-7-甲氧基喹啉
  参考文献：
  名称：

  Identification of novel quinoline analogues bearing thiazolidinones as potent kinase inhibitors for the treatment of colorectal cancer

  摘要：

  In this investigation, a novel series of quinoline analogues bearing thiazolidinones were designed and synthesized based on our previous study. Among them, the most potent compound 11k, 4-((4-(4-(3-(2-(2,6-difluorophenyl)-4-oxothiazolidin-3-yl)ureido)phenoxy)-6-methoxyquinolin-7-yl)oxy)-N-iso-propylpiperidine-1-carboxamide, possessed submicromolar c-Met and Ron inhibitory activities. In addition, enzymatic assays against a mini-panel of kinases (c-Kit, B-Raf, c-Src, IGF1R, PDGFR alpha and AXL) were performed, the results showed that compound 11k exhibited moderate inhibitory activity against PDGFR alpha, c-Src and AXL. MTT assay revealed in vitro antitumor activities against HT-29 cells of compound 11k with an IC50 value of 0.31 mu M which was 9.3- and 34.2-fold more potent than that of Regorafenib (IC50 = 2.87 mu M) and Cabozantinib (IC50 = 10.6 mu M). Preliminary antitumor mechanisms were also investigated by cellular assays. Considerable cytotoxicity, antiproliferation and induction of apoptosis of compound 11k in a dose- and time-dependent manner were confirmed by IncuCyte live-cell imaging assays. Treatment with compound 11k caused slight G2-or M-phase arrest in HT-29 cells. Further cell selectivity of compound 11k showed that it was not active against human normal colorectal mucosa epithelial cell FHC at 10.0 mu g/mL. The above results support further structural modification of compound 11k to improve its inhibitory activity, which will lead to more potent anticancer agents. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112643

文献信息

• 一种具有含氮杂环结构的化合物及其制备方 法和用途
  申请人：成都海博为药业有限公司

  公开号：CN111763215B

  公开（公告）日：2021-05-18

  本发明公开了一种具有含氮杂环结构的化合物及其制备方法和用途，该类化合物对表皮生长因子受体抑制剂EGFR具有明显的抑制作用，可作为EGFR抑制剂，用于制备治疗由EGFR介导的疾病的药物，所述由EGFR介导的疾病包括但不限于恶性肿瘤等，具有广阔的应用前景。
• Compound having tgfß inhibitory activity and medicinal composition containing the same
  申请人：Shimizu Kiyoshi

  公开号：US20060111375A1

  公开（公告）日：2006-05-25

  The present invention provides compounds represented by formula (I) and pharmaceutically acceptable salts and solvates thereof: wherein X represents CH or N; Z represents —O—, —NH— or —C(═O)—; R and R′ represent a hydrogen atom, hydroxyl, a halogen atom, optionally substituted alkyl, optionally substituted alkenyl optionally substituted alkoxy, amino, aminocarbonyl, or an optionally substituted heterocyclic group; and A represents an optionally substituted specific carbocyclic or heterocyclic group. The compounds according to the present invention have excellent TGFβ inhibitory activity.

  本发明提供了以下公式（I）所表示的化合物及其药学上可接受的盐和溶剂： 其中，X代表CH或N；Z代表-O-，-NH-或-C（=O）-；R和R'代表氢原子，羟基，卤原子，可选择取代的烷基，可选择取代的烯基，可选择取代的烷氧基，氨基，氨基甲酰基或可选择取代的杂环基；A代表可选择取代的特定环烷基或杂环基。本发明的化合物具有出色的TGFβ抑制活性。
• Quinoline or quinazoline derivatives inhibiting auto-phosphorylation of fibroblast growth factor receptors
  申请人：Miwa Atsushi

  公开号：US20050049264A1

  公开（公告）日：2005-03-03

  An objective of the present invention is to provide novel compounds which have inhibitory activity against autophosphorylation of an FGF receptor family and, when orally or intraveneously administered, can suppress the growth of cancer cells. The compounds of the present invention are represented by formula (I) or a pharmaceutically acceptable salt or solvate thereof: wherein X represents CH or N; Z represents O or S; Q represents NR 10 , CR 11 R 2 , carbonyl, O, S(═O)m, wherein m is 0 to 2, or urea; R 1 to R 3 each independently represent H, OH, halogen, nitro, amino, alkyl, alkoxy or the like in which the alkyl and alkoxy groups are optionally substituted; R 4 represents H; R 5 to R 8 each independently represent H, halogen, alkyl, or alkoxy; and R 9 represents an optionally substituted carbocyclic or heterocyclic group.

  本发明的目标是提供新型化合物，其具有对FGF受体家族自磷酸化的抑制活性，并在口服或静脉注射时能够抑制癌细胞的生长。本发明的化合物由公式（I）或其药学上可接受的盐或溶剂表示：其中X代表CH或N; Z代表O或S; Q代表NR10，CR11R2，羰基，O，S（═O）m，其中m为0到2，或脲基; R1至R3各自独立地表示H、OH、卤素、硝基、氨基、烷基、烷氧基或其类似物，其中烷基和烷氧基基团可选择性地被取代; R4表示H; R5至R8各自独立地表示H、卤素、烷基或烷氧基; R9表示一个可选择性取代的碳环或杂环基团。
• Quinoline Derivatives and Quinazoline Derivatives Inhibiting Autophosphrylation of Flt3 and Medicinal Compositions Containing the Same
  申请人：Miwa Atsushi

  公开号：US20080207617A1

  公开（公告）日：2008-08-28

  An objective of the present invention is to provide compounds and pharmaceuticals useful for the treatment of disease where the inhibition of autophosphorylation of FMS-like tyrosine kinase 3(Flt3) is therapeutically effective. The present invention relates to a pharmaceutical composition for use in the treatment or prevention of diseases where the inhibition of autophosphorylation of Flt3 therapeutically or prophylactically effective, which comprises a compound represented by formula (I) or a pharmaceutically acceptable salt or solvate thereof: wherein X represents CH or N; Z represents O or S; R 1 , R 2 , and R 3 represent H, OH, or optionally substituted alkoxy; R 4 represents H; R 5 , R 6 , R 7 , and R 8 represent H, Hal, alkyl or the like; and R 9 represents, e.g., alkyl substituted by t-butyl or the like.

  本发明的目标是提供化合物和药物，用于治疗抑制FMS样酪氨酸激酶3（Flt3）自磷酸化在治疗上具有疗效的疾病。本发明涉及一种药物组合物，用于治疗或预防抑制Flt3自磷酸化在治疗或预防上具有疗效的疾病，所述药物组合物包括以下公式（I）所表示的化合物或其药学上可接受的盐或溶剂：其中X代表CH或N；Z代表O或S；R1、R2和R3代表H、OH或可选取代的烷氧基；R4代表H；R5、R6、R7和R8代表H、卤素、烷基或类似物；R9代表例如被t-丁基或类似物取代的烷基。
• Compound having TGFβ inhibitory activity and medicinal composition containing the same
  申请人：Kirin Beer Kabushiki Kaisha

  公开号：US07560558B2

  公开（公告）日：2009-07-14

  The present invention provides compounds represented by formula (I) and pharmaceutically acceptable salts and solvates thereof: wherein X represents CH or N; Z represents —O—, —NH— or —C(═O)—; R and R′ represent a hydrogen atom, hydroxyl, a halogen atom, optionally substituted alkyl, optionally substituted alkenyl optionally substituted alkoxy, amino, aminocarbonyl, or an optionally substituted heterocyclic group; and A represents an optionally substituted specific carbocyclic or heterocyclic group. The compounds according to the present invention have excellent TGFβ inhibitory activity.

  本发明提供了由式（I）表示的化合物及其药学上可接受的盐和溶剂化物：其中，X代表CH或N；Z代表—O—，—NH—或—C（═O）—；R和R'代表氢原子、羟基、卤素原子、可选取代的烷基、可选取代的烯基、可选取代的烷氧基、氨基、氨基甲酰基或可选取代的杂环基；A代表可选取代的特定碳环或杂环基。根据本发明的化合物具有优异的TGFβ抑制活性。