7-苄氧基-4-羟基喹啉-3-羧酸乙酯 | 17825-15-9

• 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: 7-苄氧基-4-羟基喹啉-3-羧酸乙酯
• 英文名称: ethyl 7-(benzyloxy)-4-quinolone-3-carboxylate
• 英文别名: 7-(benzyloxy)-4-hydroxyquinoline-3-carboxylic acid ethyl ester；ethyl 7-(benzyloxy)-4-hydroxyquinoline-3-carboxylate；Ethyl-7-benzyloxy-4-hydroxychinolin-3-carboxylat；ethyl 4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate
• CAS: 17825-15-9
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: AJFAAXMCFXOPOM-UHFFFAOYSA-N

物化性质

• 熔点：
  295 °C
• 沸点：
  475.4±40.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  7-苄氧基-4-羟基喹啉-3-羧酸乙酯 在 palladium 10% on activated carbon 氢气 、 potassium carbonate 作用下， 以 甲醇 、 DMF (N,N-dimethyl-formamide) 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 53.0h， 生成 1-ethyl-7-hydroxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  [EN] MACROLIDES SUBSTITUDED AT THE 4"-POSITION
  [FR] MACROLIDES SUBSTITUES EN POSITION 4''

  摘要：

  本发明涉及在式(I)的4'位置被取代的14-或15-元大环内酯及其药学上可接受的衍生物，以及它们的制备过程和在人体或动物体内治疗或预防全身或局部微生物感染中的用途。

  公开号：

  WO2004101585A1
• 作为产物：
  描述：

  3-苄氧基苯胺 以 二苯醚 为溶剂， 反应 2.5h， 生成 7-苄氧基-4-羟基喹啉-3-羧酸乙酯
  参考文献：
  名称：

  Computer-Aided Molecular Modeling, Synthesis, and Biological Evaluation of 8-(Benzyloxy)-2-phenylpyrazolo[4,3-c]quinoline as a Novel Benzodiazepine Receptor Agonist Ligand

  摘要：

  Using computer-aided conformational analysis, based on molecular dynamics simulation, cluster analysis, and Monte Carlo techniques, we have designed and synthesized compounds in which a benzyloxy substituent has been incorporated into a series of pyrazoloquinoline benzodiazepine receptor (BZR) ligands, Earlier studies had shown that the benzyloxy group could act as part of the agonist pharmacophoric determinant in the beta-carboline ring system. Furthermore, the agonist beta-carboline had been correlated with a binding site orientation and volume fit for an agonist 6-phenylimidazobenzodiazepine carboxylate. The present study was undertaken to determine whether the benzyloxy substituent could be used as an agonist pharmacophoric descriptor for the phenylpyrazolo[4,3-c]quinolin-3-one BZR ligands, The results of a determination of GABA shift ratios for the synthetic ligands indicate that 8-(benzyloxy)-2-phenylpyrazolo[4,3-c]quinolin-3-one can be predicted to be an agonist at the BZR.

  DOI：

  10.1021/jm00006a014

文献信息

• [EN] CARBAMATE LINKED MACROLIDES USEFUL FOR THE TREATMENT OF MICROBIAL INFECTIONS<br/>[FR] MACROLIDES A LIAISON CARBAMATE UTILISES DANS LE TRAITEMENT DES INFECTIONS MICROBIENNES
  申请人：PLIVA ISTRAZIVACKI INST D O O

  公开号：WO2005108413A1

  公开（公告）日：2005-11-17

  The present invention relates to 14- or 15-membered macrolides substituted at the 4' position of formula (I) and pharmaceutically acceptable derivatives thereof, to processes for their preparation and their use in therapy or prophylaxis of systemic or topical microbial infections in a human or animal body.

  本发明涉及在式(I)的4'位置被取代的14-或15-元大环内酯及其药学上可接受的衍生物，以及它们的制备过程和在人体或动物体内治疗或预防全身或局部微生物感染中的用途。
• Macrolides substituted at the 4"-position
  申请人：Alihodzic Sulejman

  公开号：US20070213283A1

  公开（公告）日：2007-09-13

  The present invention relates to 14- or 15-membered macrolides substituted at the 4″ position of formula (I) and pharmaceutically acceptable derivatives thereof, to processes for their preparation and their use in therapy or prophylaxis of systemic or topical microbial infections in a human or animal body.

  本发明涉及在式（I）的4″位取代的14或15元大环内酯及其药学上可接受的衍生物，以及其制备过程和在人或动物体内治疗或预防全身或局部微生物感染的用途。
• Carbamate Linked Macrolides Useful For The Treatment Of Microbial Infections
  申请人：Alihodzic Sulejman

  公开号：US20080249033A1

  公开（公告）日：2008-10-09

  The present invention relates to 14- or 15-membered macrolides substituted at the 4″ position of formula (I) and pharmaceutically acceptable derivatives thereof, to processes for their preparation and their use in therapy or prophylaxis of systemic or topical microbial infections in a human or animal body.

  本发明涉及在公式（I）的4″位置取代的14或15元大环内酯及其药学上可接受的衍生物，以及它们的制备过程和在人或动物体内治疗或预防系统性或局部微生物感染的用途。
• MACROLONE COMPOUNDS
  申请人：Forrest Andrew Keith

  公开号：US20090062218A1

  公开（公告）日：2009-03-05

  A compound of formula (I) compositions comprising same, processes for their preparation and use of said compounds, particularly in the treatment of microbial infections.

  一种化合物的公式(I)，包括该化合物的组合物，其制备过程以及该化合物的用途，特别是用于治疗微生物感染。
• Discovery of novel quinoline scaffold selective estrogen receptor degraders (SERDs) for treatment of ER positive breast cancer with enhanced antiproliferative bioactivity through immunogenic cell death (ICD) effects
  作者：Yunlong Lu、Zhenlin Liang、Lijuan Liu、Yanyu Zhou、Chao Liu、Zhihao Zhao、Tianpeng Zheng、Qianming Du、Wukun Liu

  DOI：10.1016/j.ejmech.2024.116534

  日期：2024.9

  approach for estrogen receptor (ER)-positive breast cancer. Currently, cyclin-dependent kinase 4/6 (CDK4/6) inhibitors are combined with aromatase inhibitors (AIs) or selective estrogen receptor degraders (SERDs) as first-line therapy for advanced ER-positive breast cancer. Herein, a new family of quinoline scaffold SERDs was synthesized and evaluated in MCF-7 cells. Among them, compounds and exhibited

  联合疗法被证明是治疗雌激素受体（ER）阳性乳腺癌的有效方法。目前，细胞周期蛋白依赖性激酶4/6（CDK4/6）抑制剂与芳香酶抑制剂（AI）或选择性雌激素受体降解剂（SERD）联合作为晚期ER阳性乳腺癌的一线治疗。在此，合成了一个新的喹啉支架 SERD 家族，并在 MCF-7 细胞中进行了评估。其中，化合物 和 单独使用以及与 ribociclib（CDK4/6 抑制剂）联合使用均表现出显着的 MCF-7 抑制作用。同时，化合物可有效降解ER并抑制ER下游信号通路。有趣的是，化合物和 MCF-7 细胞中的损伤相关分子模式 (DAMP) 诱导内质网应激 (ERS) 并引发免疫原性细胞死亡 (ICD)。这些发现强调了口服 SERD 在 ER 阳性乳腺癌治疗中的免疫相关和增强的抗增殖作用。