nortopsentin D

• 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 D
• 英文别名: 3-[2-(1H-indol-3-yl)-1H-imidazol-5-yl]-1H-indole
• 化学式: C₁₉H₁₄N₄
• 分子量: 298.347
• InChiKey: WTHCAOFPCFIQLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 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 D
  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

• Methods for making bis-heterocyclic alkaloids
  申请人：——

  公开号：US20030232988A1

  公开（公告）日：2003-12-18

  Methods for making bis-heterocyclic compounds, especially bis-heterocyclic compounds having five and six-membered heterocyclic linkers are described. Also described are methods for making an alpha amino ketone synthon that enables facile syntheses of bisindole compounds, including topsentins and dragmacidins. 1

  制备双杂环化合物的方法，特别是具有五元和六元杂环连接基的双杂环化合物。还描述了制备α-氨基酸酮合成子（synthon）的方法，该方法能够实现bisindole化合物，包括topsentins和dragmacidins的简便合成。
• A Concise Synthesis of Topsentin A and Nortopsentins B and D
  作者：Fumiko Y. Miyake、Kenichi Yakushijin、David A. Horne

  DOI：10.1021/ol000124g

  日期：2000.7.1

  [reaction: see text] A concise synthesis of topsentin A (R(1) = R(2) = H) and nortopsentins B (R(1) = Br, R(2) = H) and D (R(1) = R(2) = H) is described from oxotryptamine 5 via reduction of acyl cyanide 4. Regiospecific bromination of 3-cyanoindole afforded 6-bromo-3-cyanoindole (10) as the major product.

  [反应：请参见文本]托普汀A（R（1）= R（2）= H）和降钙素B（R（1）= Br，R（2）= H）和D（R（1）的简明合成通过还原酰基氰化物4，由氧代草胺5描述了R 2 ＝ R（2）＝ H）。3-氰基吲哚的区域特异性溴化得到6-溴-3-氰基吲哚（10）作为主要产物。
• Microwave-assisted Regioselective Synthesis of 2,4-Disubstituted Imidazoles: Nortopsentin D Synthesized by Minimal Effort
  作者：Pilar M. Fresneda、Pedro Molina、Miguel A. Sanz

  DOI：10.1055/s-2001-10767

  日期：——

  A two step regioselective synthesis of 2,4-disubstituted imidazoles based on the reaction of α-azidoacetyl indoles with carboxylic acids in the presence of tertiary phosphines followed by cyclization of the resulting ketoamides by the action of ammonium acetate under microwave irradiation is described. The method has successfully been applied to the synthesis of the antifungal nortopsentin D [2,4-bis(3-indolyl)imidazole].

  基于α-叠氮乙酰基吲哚与羧酸在三苯膦存在下的反应，随后通过乙酸铵在微波照射下引发的酮酰胺环化，描述了一种2,4-二取代咪唑的区域选择性两步合成方法。该方法已成功应用于抗真菌药物nortopsentin D [2,4-双(3-吲哚基)咪唑]的合成。
• 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。
• Successive diarylation at the carbon positions (2/4 and 2/5) of 1H-imidazole and its application to the total synthesis of nortopsentin D
  作者：Ikuo Kaswasaki、Masayuki Yamashita、Shunsaku Ohta

  DOI：10.1039/c39940002085

  日期：——

  Nortopsentin D, an antifungal 2,4-diinodolylimidazole, is synthesized by use of a successive and regioselective diarylation, in which N-protected 2,4,5-tri- and 4,5-di-bromoimidazole derivatives are treated with N-silylated 3-indolylboric acid in the presence of a palladium(o) catalyst.

  Nortopsentin D 是一种抗真菌的 2,4-二吲哚基咪唑，它是通过连续和区域选择性二芳基化反应合成的。在这种反应中，N 保护的 2,4,5- 三溴咪唑和 4,5- 二溴咪唑衍生物与 N-硅烷化的 3-吲哚硼酸在钯（邻）催化剂存在下进行处理。