2-amino-4-methoxy-3-pentyloxybenzaldehyde | 219607-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-amino-4-methoxy-3-pentyloxybenzaldehyde
• 英文别名: 2-amino-4-methoxy-3-pentoxybenzaldehyde
• CAS: 219607-44-0
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: HOVQIIGVBKXWRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  382.7±42.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-methoxy-3-pentyloxybenzaldehyde 在 哌啶 、 盐酸 、 氯化亚砜 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 7-Methoxy-2-oxo-8-pentyloxy-1,2-dihydro-quinoline-3-carboxylic acid benzylamide
  参考文献：
  名称：

  Synthesis and SAR Studies of 2-Oxoquinoline Derivatives as CB2 Receptor Inverse Agonists

  摘要：

  The highly CB2 selective cannabinoid receptor inverse agonist, 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid N-benzo[1,3]dioxol-5-ylmethyl)amide (JTE-907; 9b), served as the lead compound for investigating the structure-activity relationships of its analogues and in the search for more potent and effective CB2 receptor inverse agonists. A series of aromatic amides of 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid 6 was synthesized, and the CB2 receptor activities of the compounds were determined by a [S-35]GTP(gamma)S-binding assay using membranes of CHO cells stably transfected with the human CB2 receptor. As a result, all the compounds were defined as full CB2 receptor inverse agonists, and additionally, except for two 3,4-dihydroxyphenylalkylamides, they were found to be equally potent as SR144528.

  DOI：

  10.1021/jm050879z
• 作为产物：
  描述：

  3-羟基-4-甲氧基-2-硝基苯甲醛 在 盐酸 、 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 2-amino-4-methoxy-3-pentyloxybenzaldehyde
  参考文献：
  名称：

  Synthesis and SAR Studies of 2-Oxoquinoline Derivatives as CB2 Receptor Inverse Agonists

  摘要：

  The highly CB2 selective cannabinoid receptor inverse agonist, 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid N-benzo[1,3]dioxol-5-ylmethyl)amide (JTE-907; 9b), served as the lead compound for investigating the structure-activity relationships of its analogues and in the search for more potent and effective CB2 receptor inverse agonists. A series of aromatic amides of 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid 6 was synthesized, and the CB2 receptor activities of the compounds were determined by a [S-35]GTP(gamma)S-binding assay using membranes of CHO cells stably transfected with the human CB2 receptor. As a result, all the compounds were defined as full CB2 receptor inverse agonists, and additionally, except for two 3,4-dihydroxyphenylalkylamides, they were found to be equally potent as SR144528.

  DOI：

  10.1021/jm050879z

文献信息

• Synthesis and in vitro biological evaluation of carbon-11-labeled quinoline derivatives as new candidate PET radioligands for cannabinoid CB2 receptor imaging
  作者：Mingzhang Gao、Min Wang、Kathy D. Miller、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.bmc.2010.02.011

  日期：2010.3

  family of potential antitumor agents, and cannabinoid receptor 2 (CB2) is believed to be over-expressed in tumor cells. This study was designed to develop new radioligands for imaging of CB2 receptor in cancer using biomedical imaging technique positron emission tomography (PET). Carbon-11-labeled 2-oxoquinoline and 2-chloroquinoline derivatives, [11C]6a–d and [11C]9a–d, were prepared by O-[11C]methylation

  最近有人提出将大麻素作为潜在的抗肿瘤药物的新家族，并且认为大麻素受体2（CB2）在肿瘤细胞中过表达。这项研究旨在利用生物医学成像技术正电子发射断层扫描（PET）开发用于癌症中CB2受体成像的新型放射性配体。碳11标记的2-氧喹啉和2-氯喹啉衍生物[ 11 C] 6a - d和[ 11 C] 9a - d是通过使用[ 11 C] CH对相应的前体进行O- [ 11 C]甲基化制备的3OTf在基本条件下并通过简化的固相萃取（SPE）方法进行分离，以[ 11 C] CO 2为基础，以40％至50％的放射化学收率进行了分离，并将衰变校正为轰击结束（EOB）。EOB的总合成时间为15–20分钟，放射化学纯度> 99％，合成结束时的比活（EOS）为111–185 GBq /μmol。放射性配体结合试验表明，化合物6f，6b和9f表现出强大的体外结合亲和力，纳摩尔摩尔K i值，对CB2的选择性至少100-2000倍。
• 2-oxoquinoline compounds and medicinal uses thereof
  申请人：Japan Tobacco Inc.

  公开号：US06509352B1

  公开（公告）日：2003-01-21

  A 2-oxoquinoline compound or its pharmaceutically acceptable salt of general formula [I]:   (wherein each symbol in the formula is as determined in the description), and its pharmaceutical use. The compound [I] of the present invention and its pharmaceutically acceptable salts selectively act on cannabinoid receptors, particularly on peripheral type cannabinoid receptors, and have fewer side effects on the central nervous system, having great immunosuppressive action, anti-inflammatory action or antiallergic action. Therefore, these compounds are useful as cannabinoid receptors (particularly peripheral type cannabinoid receptors) modulator, immunosuppressants, anti-inflammatory agents, and antiallergic agents.

  通用公式为[I]的2-氧喹啉化合物或其药用可接受的盐：（其中公式中的每个符号如描述中确定），及其药用。本发明的化合物[I]及其药用可接受的盐选择性作用于大麻素受体，特别是外周型大麻素受体，对中枢神经系统的副作用较少，具有很强的免疫抑制作用、抗炎作用或抗过敏作用。因此，这些化合物可用作大麻素受体（特别是外周型大麻素受体）调节剂、免疫抑制剂、抗炎剂和抗过敏剂。
• 2-oxoquinoline compounds and pharmaceutical uses thereof
  申请人：——

  公开号：US20030191069A1

  公开（公告）日：2003-10-09

  A 2-oxoquinoline compound or its pharmaceutically acceptable salt of general formula [I]: 1 (wherein each symbol in the formula is as determined in the description), and its pharmaceutical use. The compound [I] of the present invention and its pharmaceutically acceptable salts selectively act on cannabinoid receptors, particularly on peripheral type cannabinoid receptors, and have fewer side effects on the central nervous system, having great immunosuppressive action, anti-inflammatory action or antiallergic action. Therefore, these compounds are useful as cannabinoid receptors (particularly peripheral type cannabinoid receptors) modulator, immunosuppressants, anti-inflammatory agents, and antiallergic agents.

  一种2-氧基喹啉化合物或其药学上可接受的盐，其通式为[I]:1（其中公式中的每个符号如说明中所确定的那样），以及其医药用途。本发明的化合物[I]及其药学上可接受的盐，能够选择性地作用于大麻素受体，特别是外周型大麻素受体，并且对中枢神经系统的副作用较少，具有很强的免疫抑制作用、抗炎作用或抗过敏作用。因此，这些化合物可用作大麻素受体（特别是外周型大麻素受体）调节剂、免疫抑制剂、抗炎剂和抗过敏剂。
• 2-OXOQUINOLINE COMPOUNDS AND MEDICINAL USES THEREOF
  申请人：Japan Tobacco Inc.

  公开号：EP1142877A1

  公开（公告）日：2001-10-10

  A 2-oxoquinoline compound or its pharmaceutically acceptable salt of general formula [I]: (wherein each symbol in the formula is as determined in the description), and its pharmaceutical use. The compound [I] of the present invention and its pharmaceutically acceptable salts selectively act on cannabinoid receptors, particularly on peripheral type cannabinoid receptors, and have fewer side effects on the central nervous system, having great immunosuppressive action, anti-inflammatory action or antiallergic action. Therefore, these compounds are useful as cannabinoid receptors (particularly peripheral type cannabinoid receptors) modulator, immunosuppressants, anti-inflammatory agents, and antiallergic agents.

  通式[I]的 2-氧代喹啉化合物或其药学上可接受的盐： (其中式中各符号由说明中确定）及其药物用途。 本发明的化合物[I]及其药学上可接受的盐选择性地作用于大麻素受体，特别是外周型大麻素受体，对中枢神经系统的副作用较小，具有很好的免疫抑制作用、抗炎作用或抗过敏作用。因此，这些化合物可用作大麻素受体（特别是外周型大麻素受体）调节剂、免疫抑制剂、抗炎剂和抗过敏剂。
• US6509352B1
  申请人：——

  公开号：US6509352B1

  公开（公告）日：2003-01-21