Nortopsentin-C | 134029-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Nortopsentin-C
• 英文别名: 6-bromo-3-[2-(1H-indol-3-yl)-1H-imidazol-5-yl]-1H-indole
• CAS: 134029-45-1
• 化学式: C₁₉H₁₃BrN₄
• 分子量: 377.243
• InChiKey: OWBTWZBJRVBXIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.3
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-氰基吲哚 在 萘 、 盐酸羟胺 、 氢气 、 sodium 、 sodium hydride 、 碳酸氢钠 、 potassium hydrogencarbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 27.17h， 生成 Nortopsentin-C
  参考文献：
  名称：

  Marine-Natural-Product Development: First Discovery of Nortopsentin Alkaloids as Novel Antiviral, Anti-phytopathogenic-Fungus, and Insecticidal Agents

  摘要：

  Nortopsentin alkaloids were found to have potent antiviral, anti-phytopathogenic-fungus, and insecticidal activities for the first time. Antiviral-activity tests revealed that these compounds were very sensitive to substituents, so a series of nortopsentin derivatives were designed, synthesized, and systematically evaluated for their antiviral activities against TMV, their fungicidal activities, and their insecticidal activities on the basis of a structural-diversity-derivation strategy. Compounds 2e (in vivo inactivation-, curative-, and protective-activity inhibitory rates of 50, 59, and 56%, respectively, at 500 mu g/mL) and 2k (in vivo inactivation-, curative-, and protective-activity inhibitory rates of 60, 58, and 52%, respectively, at 500 mu g/mL), with excellent antiviral activities and good physicochemical properties, emerged as new lead compounds for novel-antiviral-agent development. Further fungicidal-activity tests revealed that these alkaloids displayed broad-spectrum fungicidal activities. Compounds 2f, 2h, and 2j emerged as new lead compounds for antifungal-activity research. Additionally, all the compounds displayed good insecticidal activities against five kinds of insects, including Mythimna separate, Helicoverpa armigera, Ostrinia nubilalis, Plutella xylostella, and Culex pipiens pallens.

  DOI：

  10.1021/acs.jafc.8b00507

文献信息

• Total Synthesis of Nortopsentins A-D, Marine Alkaloids.
  作者：Ikuo KAWASAKI、Masayuki YAMASHITA、Shunsaku OHTA

  DOI：10.1248/cpb.44.1831

  日期：——

  Nortopsentins A-D, antifungal 1, 4-bisindolylimidazole marine alkaloids isolated from a sponge, were synthesized through palladium-catalyzed cross-coupling of 3-indolylboronic and 6-bromo-3-indolylboronic acids with halogenoimidazoles as the key reaction.

  以卤代咪唑为关键反应，通过钯催化 3-吲哚硼酸和 6-溴-3-吲哚硼酸的交叉偶联合成了从海绵中分离出的抗真菌 1，4-双吲哚基咪唑海洋生物碱 Nortopsentins A-D。
• Use for topsentin compounds and pharmaceutical compositions containing
  申请人：Regents of the Univ. of California

  公开号：US05290777A1

  公开（公告）日：1994-03-01

  A novel use for the class of biologically active bis-indole alkaloid compounds, which have been named topsentins, nortopsentins, or dragmacidins, pharmaceutical compositions containing them, methods of producing the compounds, and methods of using the compounds are disclosed. Specifically, the novel utility pertains to the anti-inflammatory properties exhibited by the bis-indole compounds and their analogs.

  揭示了一种对生物活性双吲哚生物碱化合物类别的新用途，这些化合物被命名为topsentins、nortopsentins或dragmacidins，包含它们的药物组合物，生产这些化合物的方法以及使用这些化合物的方法。具体而言，这种新的用途涉及到双吲哚化合物及其类似物所表现的抗炎性能。
• EP0686154B1
  申请人：——

  公开号：EP0686154B1

  公开（公告）日：1998-04-22
• Marine-Natural-Product Development: First Discovery of Nortopsentin Alkaloids as Novel Antiviral, Anti-phytopathogenic-Fungus, and Insecticidal Agents
  作者：Xiaofei Ji、Jincheng Guo、Yuxiu Liu、Aidang Lu、Ziwen Wang、Yongqiang Li、Shaoxiang Yang、Qingmin Wang

  DOI：10.1021/acs.jafc.8b00507

  日期：2018.4.25

  Nortopsentin alkaloids were found to have potent antiviral, anti-phytopathogenic-fungus, and insecticidal activities for the first time. Antiviral-activity tests revealed that these compounds were very sensitive to substituents, so a series of nortopsentin derivatives were designed, synthesized, and systematically evaluated for their antiviral activities against TMV, their fungicidal activities, and their insecticidal activities on the basis of a structural-diversity-derivation strategy. Compounds 2e (in vivo inactivation-, curative-, and protective-activity inhibitory rates of 50, 59, and 56%, respectively, at 500 mu g/mL) and 2k (in vivo inactivation-, curative-, and protective-activity inhibitory rates of 60, 58, and 52%, respectively, at 500 mu g/mL), with excellent antiviral activities and good physicochemical properties, emerged as new lead compounds for novel-antiviral-agent development. Further fungicidal-activity tests revealed that these alkaloids displayed broad-spectrum fungicidal activities. Compounds 2f, 2h, and 2j emerged as new lead compounds for antifungal-activity research. Additionally, all the compounds displayed good insecticidal activities against five kinds of insects, including Mythimna separate, Helicoverpa armigera, Ostrinia nubilalis, Plutella xylostella, and Culex pipiens pallens.