7-methyl-3-nitro-quinolin-4-ol | 50332-60-0

• 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: 7-methyl-3-nitro-quinolin-4-ol
• 英文别名: 7-Methyl-3-nitro-chinolin-4-ol；7-methyl-3-nitro-4-quinolinol；4-Hydroxy-7-methyl-3-nitrochinolin；7-Methyl-3-nitroquinolin-4-ol；7-methyl-3-nitro-1H-quinolin-4-one
• CAS: 50332-60-0
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: UHNGNAKCLOWVMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  349.2±37.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methyl-3-nitro-quinolin-4-ol 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-chloro-7-methyl-3-nitro-quinoline
  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-甲基-4-喹诺酮 在 硝酸 作用下， 以 丙酸 为溶剂， 生成 7-methyl-3-nitro-quinolin-4-ol
  参考文献：
  名称：

  Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs

  摘要：

  Thiazolo-, oxazolo-和selenazolo[4,5-c]quinolin-4-胺及其类似物的描述包括制造方法和新型中间体的使用。这些化合物是免疫调节剂，能诱导细胞因子生物合成，包括干扰素和/或肿瘤生物合成、坏死因子，并抑制T辅助型2型免疫应答。这些化合物在治疗病毒性和肿瘤性疾病方面也很有用。

  公开号：

  US06110929A1

文献信息

• Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4- amines and analogs thereof
  申请人：3M Innovative Properties Company

  公开号：US20030195224A1

  公开（公告）日：2003-10-16

  Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.

  本文描述了噻唑啉、噁唑啉和硒唑啉[4,5-c]喹啉-4-胺及其类似物，包括制造方法和新型中间体的用途。这些化合物是免疫调节剂，可诱导细胞因子生物合成，包括干扰素和/或肿瘤生物合成、坏死因子，并抑制T辅助型2免疫反应。这些化合物还可用于治疗病毒和肿瘤性疾病。
• Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof
  申请人：3M Innovative Properties Company

  公开号：US20030045545A1

  公开（公告）日：2003-03-06

  Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.

  本文描述了噻唑-、噁唑-和硒唑- [4,5-c]喹啉-4-胺及其类似物，包括制造方法和新型中间体的用途。这些化合物是免疫调节剂，可诱导细胞因子生物合成，包括干扰素和/或肿瘤生物合成、坏死因子，并抑制T-helper型2免疫反应。此外，这些化合物还可用于治疗病毒和肿瘤性疾病。
• Oxazolo, thiazolo and selenazolo [4,5-C]-quinolin-4-amines and analogs thereof
  申请人：3M Innovative Properties Company

  公开号：US06809203B2

  公开（公告）日：2004-10-26

  Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.

  本文描述了噻唑并吡唑、氧唑并吡唑和硒唑并[4,5-c]喹啉-4-胺及其类似物，包括其制造方法和新型中间体的使用。这些化合物是免疫调节剂，可诱导细胞因子的生物合成，包括干扰素和/或肿瘤坏死因子，并抑制T辅助型2型免疫应答。此外，这些化合物还可用于治疗病毒和肿瘤性疾病。
• Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof
  申请人：3M Innovative Properties Company

  公开号：US06440992B1

  公开（公告）日：2002-08-27

  Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.

  本文描述了噻唑、噁唑和硒唑[4,5-c]喹啉-4-胺及其类似物，包括制备方法和新型中间体的用途。这些化合物是免疫调节剂，能够诱导细胞因子生物合成，包括干扰素和/或肿瘤坏死因子，并抑制T-helper-2型免疫反应。这些化合物还可用于治疗病毒性和肿瘤性疾病。
• Oxazolo, thiazolo and selenazolo [4,5-c]quinolin-4-amines and analogs thereof
  申请人：3M Innovative Properties Company

  公开号：US06627638B2

  公开（公告）日：2003-09-30

  Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.

  本文介绍了噻唑啉、噁唑啉和硒唑啉[4,5-c]喹啉-4-胺及其类似物，包括制备方法和新型中间体的用途。这些化合物是免疫调节剂，能诱导细胞因子生物合成，包括干扰素和/或肿瘤坏死因子，并抑制T-helper型2免疫应答。此外，这些化合物还可用于治疗病毒性和肿瘤性疾病。