4-Chloro-7-methoxy-3-nitro-quinoline | 1026963-05-2

• 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: 4-Chloro-7-methoxy-3-nitro-quinoline
• 英文别名: 4-Chloro-7-methoxy-3-nitroquinoline
• CAS: 1026963-05-2
• 化学式: C₁₀H₇ClN₂O₃
• mdl: MFCD17170303
• 分子量: 238.63
• InChiKey: HOCSOOBRPRKXSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Chloro-7-methoxy-3-nitro-quinoline 在 platinum on activated charcoal 过氧乙酸 、 氨 、 氢气 、 magnesium sulfate 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 1-Isobutyl-7-methoxy-1H-imidazo[4,5-c]quinolin-4-ylamine
  参考文献：
  名称：

  Synthesis and Structure−Activity-Relationships of 1H-Imidazo[4,5-c]quinolines That Induce Interferon Production

  摘要：

  1H-Imidazo-[4,5-c]quinolines were prepared while investigating novel nucleoside analogues as potential antiviral agents. While these compounds showed no direct antiviral activity when tested in a number of cell culture systems, some demonstrated potent inhibition of virus lesion development in an intravaginal guinea pig herpes simplex virus-2 assay. We have determined that the in vivo antiviral activity can be attributed to the ability of these molecules to induce the production of cytokines, especially interferon (IFN), in this model. Subsequently, we found that the compounds also induce in vitro production of IFN in human peripheral blood mononuclear cells (hPBMCs). The in vitro results reported herein and the in vivo results reported previously led to the discovery of imiquimod, 26, which was developed as a topical agent and has been approved for the treatment of genital warts, actinic keratosis, and superficial basal cell carcinoma.

  DOI：

  10.1021/jm049211v
• 作为产物：
  描述：

  7-甲氧基-3-硝基喹啉-4-醇 在 三氯氧磷 作用下， 生成 4-Chloro-7-methoxy-3-nitro-quinoline
  参考文献：
  名称：

  融合的咪唑并吡啶的合成与构效关系：一系列苯二氮杂ze受体配体

  摘要：

  合成了2-Arylimidazo [4,5-c]喹啉和类似的稠合咪唑并吡啶，并评价为苯并二氮杂receptor受体配体。与吡唑并喹啉如CGS-9896相比，与受体的亲和力受2-位芳基庞大性的影响。在2-位具有异恶唑部分的衍生物显示出高结合亲和力和体内活性。在咪唑并[4,5-c]喹啉系列中，在6-位的取代降低或消除了活性。除7-卤代类似物外，大多数具有未取代异恶唑基的衍生物均表现出拮抗或反向激动剂活性。另一方面，5-甲基异恶唑-3-基或3-甲基异恶唑-5-基衍生物通常表现出激动剂活性。在与非芳族环稠合的咪唑并吡啶中观察到对异恶唑部分的类似取代作用。根据详细的药理评估，S-8510，2-（3-异恶唑基）-3,6,7,9-四氢咪唑并[4,5-d]吡喃++ + [4,3-b]吡啶一磷酸具有弱的反向激动剂选择活性作为治疗老年性痴呆某些症状的治疗候选药物。

  DOI：

  10.1021/jm9600609

文献信息

• Synthesis and Structure−Activity Relationships of Fused Imidazopyridines:  A New Series of Benzodiazepine Receptor Ligands
  作者：Susumu Takada、Takashi Sasatani、Nobuo Chomei、Makoto Adachi、Toshio Fujishita、Masami Eigyo、Shunji Murata、Kazuo Kawasaki、Akira Matsushita

  DOI：10.1021/jm9600609

  日期：1996.1.1

  synthesized and evaluated as benzodiazepine receptor ligands. Affinity to the receptors was greatly affected by the bulkiness of the aryl group at the 2-position, compared to the pyrazoloquinolines such as CGS-9896. Derivatives with an isoxazole moiety at the 2-position showed high binding affinity and in vivo activity. In the imidazo[4,5-c]quinoline series, substitution at the 6-position decreased or abolished

  合成了2-Arylimidazo [4,5-c]喹啉和类似的稠合咪唑并吡啶，并评价为苯并二氮杂receptor受体配体。与吡唑并喹啉如CGS-9896相比，与受体的亲和力受2-位芳基庞大性的影响。在2-位具有异恶唑部分的衍生物显示出高结合亲和力和体内活性。在咪唑并[4,5-c]喹啉系列中，在6-位的取代降低或消除了活性。除7-卤代类似物外，大多数具有未取代异恶唑基的衍生物均表现出拮抗或反向激动剂活性。另一方面，5-甲基异恶唑-3-基或3-甲基异恶唑-5-基衍生物通常表现出激动剂活性。在与非芳族环稠合的咪唑并吡啶中观察到对异恶唑部分的类似取代作用。根据详细的药理评估，S-8510，2-（3-异恶唑基）-3,6,7,9-四氢咪唑并[4,5-d]吡喃++ + [4,3-b]吡啶一磷酸具有弱的反向激动剂选择活性作为治疗老年性痴呆某些症状的治疗候选药物。
• 一种芳杂环类化合物及其制备方法和用途
  申请人：上海翊石医药科技有限公司

  公开号：CN116262750A

  公开（公告）日：2023-06-16

  本发明涉及作为ENPP1抑制剂的芳杂环类化合物以及所述化合物的制备方法及用途。
• Synthesis and Structure−Activity-Relationships of 1<i>H</i>-Imidazo[4,5-<i>c</i>]quinolines That Induce Interferon Production
  作者：John F. Gerster、Kyle J. Lindstrom、Richard L. Miller、Mark A. Tomai、Woubalem Birmachu、Shannon N. Bomersine、Shiela J. Gibson、Linda M. Imbertson、Joel R. Jacobson、Roy T. Knafla、Peter V. Maye、Nickolas Nikolaides、Folakemi Y. Oneyemi、Gwen J. Parkhurst、Sharon E. Pecore、Michael J. Reiter、Lisa S. Scribner、Tracy L. Testerman、Natalie J. Thompson、Tammy L. Wagner、Charles E. Weeks、Jean-Denis Andre、Daniel Lagain、Yvon Bastard、Michel Lupu

  DOI：10.1021/jm049211v

  日期：2005.5.1

  1H-Imidazo-[4,5-c]quinolines were prepared while investigating novel nucleoside analogues as potential antiviral agents. While these compounds showed no direct antiviral activity when tested in a number of cell culture systems, some demonstrated potent inhibition of virus lesion development in an intravaginal guinea pig herpes simplex virus-2 assay. We have determined that the in vivo antiviral activity can be attributed to the ability of these molecules to induce the production of cytokines, especially interferon (IFN), in this model. Subsequently, we found that the compounds also induce in vitro production of IFN in human peripheral blood mononuclear cells (hPBMCs). The in vitro results reported herein and the in vivo results reported previously led to the discovery of imiquimod, 26, which was developed as a topical agent and has been approved for the treatment of genital warts, actinic keratosis, and superficial basal cell carcinoma.