Emindole SB

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Emindole SB
• 英文别名: entinclole SB；(1S,12S,15R,16S,17S,20S)-1,16,20-trimethyl-16-(4-methylpent-3-enyl)-3-azapentacyclo[10.8.0.02,10.04,9.015,20]icosa-2(10),4,6,8-tetraen-17-ol
• 化学式: C₂₈H₃₉NO
• 分子量: 405.624
• InChiKey: XOLHQUYGSUGTQA-DFGZTGKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 Emindole SB 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 24.0h， 以2 mg的产率得到
  参考文献：
  名称：

  Indole-Diterpenoids with Anti-H1N1 Activity from the Aciduric Fungus Penicillium camemberti OUCMDZ-1492

  摘要：

  An aciduric fungal strain, Penicillium camemberti OUCMDZ-1492, was isolated from an acidic marine niche, mangrove soil and mud, around the roots of Rhizophora apiculata. Six new indole-diterpenoids (1-6), along with five known analogues, emindole SB (7), 21-isopentenylpaxilline (8), paspaline (9), paxilline (10), and dehydroxypaxilline (11), were isolated from the fermentation broth of P. camemberti OUCMDZ-1492 grown at pH 5.0. On the basis of spectroscopic analyses, CD spectra, quantum ECD calculations, and chemical methods, new structures 1-6 were established as 3-deoxo-4b-deoxypaxilline, 4a-demethylpaspaline-4a-carboxylic acid, 4a-demethylpaspaline-3,4,4a-triol, 2'-hydroxypaxilline, 9,10-diisopentenylpaxilline, and (6S,7R,10E,14E)-16-(1H-indol-3-yl)-2,6,10,14-tetramethylhexadeca-2,10,14-triene-6,7-diol, respectively. Compounds 1-3 and 5-10 exhibited significant activity against the H1N1 virus with IC50 values of 28.3, 38.9, 32.2, 73.3, 34.1, 26.2, 6.6, 77.9, and 17.7 mu M, respectively. The results showed that 3-oxo, 4b-hydroxy, and 9-isopentenyl substitutions tend to increase the anti-H1N1 activity of hexacyclic indole-diterpenoids.

  DOI：

  10.1021/np400304q
• 作为产物：
  描述：

  在 盐酸 、 iron(III)-acetylacetonate 、 Lindlar's catalyst 、 isopropylphenylsilane 、 氢气 、 叔丁基锂 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 二甲基亚砜 、 甲苯 、 正戊烷 为溶剂， 反应 6.25h， 生成 Emindole SB
  参考文献：
  名称：

  Paxilline 吲哚二萜的简明方法

  摘要：

  描述了一种合成的帕克西林吲哚二萜的方法。通往五环核心的途径依赖于酮的新区域选择性烯基化和串联自由基加成 - 醛醇反应序列以访问邻位四元立体中心。Emindole SB 是该家族中最简单的成员，通过 11 个步骤从市售材料合成，以证明这种方法的应用。

  DOI：

  10.1021/jacs.5b11129

文献信息

• Indoloditerpenes from a Marine-Derived Fungal Strain of <i>Dichotomomyces cejpii</i> with Antagonistic Activity at GPR18 and Cannabinoid Receptors
  作者：Henrik Harms、Viktor Rempel、Stefan Kehraus、Marcel Kaiser、Peter Hufendiek、Christa E. Müller、Gabriele M. König

  DOI：10.1021/np400850g

  日期：2014.3.28

  A marine-derived strain of Dichotomomyces cejpii produces the new compounds emindole SB beta-mannoside (1) and 27-O-methylasporyzin C (2), as well as the known indoloditerpenes JBIR-03 (3) and emindole SB (4). Indo le derivative 1 was found to be a CB2 antagonist, while 2 was identified as the first selective GPR18 antagonist with an indole structure. Compound 4 was found to be a nonselective CB1/CB2 antagonist. The new natural indole derivatives may serve as lead structures for the development of GPR18- and CB receptor-blocking drugs.
• Systems and Methods for Identifying and Expressing Gene Clusters
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20200040347A1

  公开（公告）日：2020-02-06

  Methods for identifying biosynthetic gene clusters that include genes for producing compounds that interact with specific target proteins are disclosed. Some methods relate to bioinformatics methods for identifying and/or prioritizing biosynthetic gene clusters. Related systems, components, and tools for the identification and expression of such gene clusters are also disclosed.
• A Concise Approach to Paxilline Indole Diterpenes
  作者：David T. George、Eric J. Kuenstner、Sergey V. Pronin

  DOI：10.1021/jacs.5b11129

  日期：2015.12.16

  A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and a tandem radical addition-aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this

  描述了一种合成的帕克西林吲哚二萜的方法。通往五环核心的途径依赖于酮的新区域选择性烯基化和串联自由基加成 - 醛醇反应序列以访问邻位四元立体中心。Emindole SB 是该家族中最简单的成员，通过 11 个步骤从市售材料合成，以证明这种方法的应用。
• Indole-Diterpenoids with Anti-H1N1 Activity from the Aciduric Fungus <i>Penicillium camemberti</i> OUCMDZ-1492
  作者：Yaqin Fan、Yi Wang、Peipei Liu、Peng Fu、Tonghan Zhu、Wei Wang、Weiming Zhu

  DOI：10.1021/np400304q

  日期：2013.7.26

  An aciduric fungal strain, Penicillium camemberti OUCMDZ-1492, was isolated from an acidic marine niche, mangrove soil and mud, around the roots of Rhizophora apiculata. Six new indole-diterpenoids (1-6), along with five known analogues, emindole SB (7), 21-isopentenylpaxilline (8), paspaline (9), paxilline (10), and dehydroxypaxilline (11), were isolated from the fermentation broth of P. camemberti OUCMDZ-1492 grown at pH 5.0. On the basis of spectroscopic analyses, CD spectra, quantum ECD calculations, and chemical methods, new structures 1-6 were established as 3-deoxo-4b-deoxypaxilline, 4a-demethylpaspaline-4a-carboxylic acid, 4a-demethylpaspaline-3,4,4a-triol, 2'-hydroxypaxilline, 9,10-diisopentenylpaxilline, and (6S,7R,10E,14E)-16-(1H-indol-3-yl)-2,6,10,14-tetramethylhexadeca-2,10,14-triene-6,7-diol, respectively. Compounds 1-3 and 5-10 exhibited significant activity against the H1N1 virus with IC50 values of 28.3, 38.9, 32.2, 73.3, 34.1, 26.2, 6.6, 77.9, and 17.7 mu M, respectively. The results showed that 3-oxo, 4b-hydroxy, and 9-isopentenyl substitutions tend to increase the anti-H1N1 activity of hexacyclic indole-diterpenoids.