4-methoxy-2-nitro-3-pentyloxybenzaldehyde | 194360-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxy-2-nitro-3-pentyloxybenzaldehyde
• 英文别名: 4-methoxy-2-nitro-3-pentoxybenzaldehyde
• CAS: 194360-76-4
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: QASURIZUCHQSBK-UHFFFAOYSA-N

物化性质

• 熔点：
  26-27 °C
• 沸点：
  427.0±45.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-2-nitro-3-pentyloxybenzaldehyde 在 哌啶 、 盐酸 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 0.25h， 生成 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid
  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：

  异香兰素 在 nitronium tetrafluoborate 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 4-methoxy-2-nitro-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。
• Cannabinoid receptor inverse agonists and neutral antagonists as therapeutic agents for the treatment of bone disorders
  申请人：Ralston Hamilton Stuart

  公开号：US20060172019A1

  公开（公告）日：2006-08-03

  The present invention pertains to cannabinoid (CB) receptor inverse agonists and neutral antagonists, and especially CB1 and CB2 inverse agonists and neutral antagonists; such as, for example, certain pyrazole compounds; their use in the inhibition of osteoclasts (for example, the inhibition of the survival, formation, and/or activity of osteoclasts), and/or in the inhibition of bone resorption; their use in connection with treatment of bone disorders, such as conditions mediated by osteoclasts (e.g., increased osteoclast activity) and/or characterised by (e.g., increased) bone resorption, such as osteoporosis (e.g., osteoporosis not associated with inflammation; e.g., osteoporosis associated with a genetic predisposition, sex hormone deficiency, or ageing), cancer associated bone disease, and Paget's disease of bone.

  本发明涉及大麻素（CB）受体的反向激动剂和中性拮抗剂，尤其是CB1和CB2的反向激动剂和中性拮抗剂，例如某些吡唑化合物；它们用于抑制破骨细胞（例如抑制破骨细胞的存活、形成和/或活动），和/或抑制骨吸收；它们用于治疗骨疾病，例如由破骨细胞介导的疾病（例如破骨细胞活性增加）和/或以（例如增加的）骨吸收为特征的疾病，例如骨质疏松症（例如与炎症无关的骨质疏松症；例如与遗传倾向、性激素缺乏或衰老有关的骨质疏松症）、癌症相关骨疾病和Paget骨病。
• Compounds and pharmaceutical use thereof
  申请人：Japan Tobacco Inc.

  公开号：US06017919A1

  公开（公告）日：2000-01-25

  The compounds of the formula (I) ##STR1## wherein each symbol is as defined in the specification, pharmaceutically acceptable salts thereof and pharmaceutical use thereof. The Compound (I) and pharmaceutically acceptable salts thereof of the present invention selectively act on cannabinoid receptors, particularly peripheral receptors, cause less side effects on the central system, and have superior immunoregulating action, antiinflammatory action, antiallergic action and therapeutic effect on nephritis. Therefore, they are useful as cannabinoid receptor, particularly peripheral cannabinoid receptor activators and antagonists, immunoregulators, therapeutic agents for autoimmune diseases, antiinflammatory agents, antiallergic agents and therapeutic agents for nephritis.

  以下为翻译结果： 公式（I）的化合物：##STR1## 其中每个符号如规范中所定义，其药学上可接受的盐和药物用途。本发明的化合物（I）及其药学上可接受的盐，可选择性地作用于大麻素受体，尤其是周围受体，对中枢神经系统产生较少的副作用，并具有优越的免疫调节作用、抗炎作用、抗过敏作用和治疗肾炎的疗效。因此，它们可用作大麻素受体，特别是周围大麻素受体的激动剂和拮抗剂、免疫调节剂、自身免疫性疾病治疗剂、抗炎剂、抗过敏剂和肾炎治疗剂。