(Z)-2-甲基-3-[(1,3,4,5-四氢-4β-(甲基氨基)苯并[cd]吲哚)-5α-基]-2-丙烯-1-醇 | 1150-44-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 中文名称: (Z)-2-甲基-3-[(1,3,4,5-四氢-4β-(甲基氨基)苯并[cd]吲哚)-5α-基]-2-丙烯-1-醇
• 英文名称: Isochanoclavin-(I)
• 英文别名: Isochanoclavine I；(Z)-2-methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol
• CAS: 1150-44-3
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: SAHHMCVYMGARBT-NFNYYWLXSA-N

物化性质

• 熔点：
  181 °C
• 沸点：
  470.1±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  48
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2-甲基-3-[(1,3,4,5-四氢-4β-(甲基氨基)苯并[cd]吲哚)-5α-基]-2-丙烯-1-醇 在 potassium carbonate 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 以90%的产率得到曲麦角碱
  参考文献：
  名称：

  Simple Total Syntheses of (-)-Ergot Alkaloids and Thier (+)-Enantiomers by a Common Synthesis Method Utilizing Optical Resolution

  摘要：

  The first and simple total syntheses of (-)-isochanoclavine-I ((-)-1b), (-)-agroclavine ((-)-3), (-)-agroclavine-I ((-)-4), and (-)-norchanoclavine-I ((-)-5C) and their (+)-enantiomers are achieved from indole-3-carboxaldehyde (8) by a common synthesis method utilizing optical resolution. Absolute configuration of (-)-agroclavine-I is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-I (1c) are also included.

  DOI：

  10.3987/com-97-7821
• 作为产物：
  描述：

  (-)-6,7-secoagroclavine 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 以29%的产率得到(Z)-2-甲基-3-[(1,3,4,5-四氢-4β-(甲基氨基)苯并[cd]吲哚)-5α-基]-2-丙烯-1-醇
  参考文献：
  名称：

  Simple Total Syntheses of (-)-Ergot Alkaloids and Thier (+)-Enantiomers by a Common Synthesis Method Utilizing Optical Resolution

  摘要：

  The first and simple total syntheses of (-)-isochanoclavine-I ((-)-1b), (-)-agroclavine ((-)-3), (-)-agroclavine-I ((-)-4), and (-)-norchanoclavine-I ((-)-5C) and their (+)-enantiomers are achieved from indole-3-carboxaldehyde (8) by a common synthesis method utilizing optical resolution. Absolute configuration of (-)-agroclavine-I is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-I (1c) are also included.

  DOI：

  10.3987/com-97-7821

文献信息

• 6-Substituted-4-dialkylaminotetrahydrobenz(c,d)indoles
  申请人：ELI LILLY AND COMPANY

  公开号：EP0153083A2

  公开（公告）日：1985-08-28

  (± )-4-Substituted-amino-6-substituted-1,3,4,5-tetra- hydrobenz[c,dlindoles, or a pharmaceutically-acceptable salt thereof, are central serotonin agonists.

  (±)-4-取代-氨基-6-取代-1,3,4,5-四氢苯并[c,dlindoles 或其药学上可接受的盐是中枢羟色胺激动剂。
• Chanoclavine-producing endophytic fungi of the genus Neotyphodium, and artificially endophyte-infected plants
  申请人：MAYEKAWA MANUFACTURING CO., LTD.

  公开号：EP1142986A3

  公开（公告）日：2002-06-12

  The invention relates to provision of plant(s) not showing livestock toxicity and having strong resistance to pests due to symbiotic fungi with which the plant(s) is/are infected, said symbiotic fungus comprising a filamentous fungus preferably belonging to the genus Neotyphodium, said filamentous fungus preferably having a final metabolic product of chanoclavine, which fungus is artificially introduced into a plant to infect the plant.

  本发明涉及提供不会对牲畜产生毒性并对害虫具有很强抵抗力的植物，这是由于植物感染了共生真菌，所述共生真菌包括丝状真菌，最好属于新担子菌属，所述丝状真菌最好具有一种最终代谢产物--香黄素，人工将该真菌引入植物以感染该植物。
• Increased production of terpenes and terpenoids
  申请人：Evolva SA

  公开号：US10190140B2

  公开（公告）日：2019-01-29

  This invention provides recombinant cells and methods for producing terpenes and terpenoids by increasing production or accumulation or both of isoprenoid precursors thereof.

  本发明提供了通过增加异戊烯类化合物前体的产量或积累或两者兼而有之来生产萜烯和萜类化合物的重组细胞和方法。
• Production of lysergic acid by genetic modification of a fungus
  申请人：West Virigina University

  公开号：US10370689B2

  公开（公告）日：2019-08-06

  The present invention provides a method of producing lysergic acid and other ergot alkaloids by genetic modification of a fungus. A strain of fungus comprising Aspergillus fumigatus (A. fumigatus) or any fungus having a pathway similar to Aspergillus fumigatus and expressing one or more genes of the ergot alkaloid biosynthesis pathway from one or more fungus selected from the group consisting of Epichloë festucae var. lolii×Epichloë typhina isolate Lp1 (E. sp. Lp1); Claviceps species; Claviceps africana (C. africana); Claviceps gigantea (C. gigantea); Epichloë coenophiala and Periglandula species, wherein gene easA or gene easM is inactivated in said A. fumigatus or said fungus having a pathway similar to Aspergillus fumigatus, is provided.

  本发明提供了一种通过遗传修饰真菌生产麦角酸和其他麦角生物碱的方法。一株真菌包括烟曲霉（A. fumigatus）或任何具有与烟曲霉相似途径的真菌，并表达麦角生物碱生物合成途径的一个或多个基因，该基因来自选自Epichloë festucae var.lolii×Epichloë typhina isolate Lp1 (E. sp. Lp1)；Claviceps species；Claviceps africana (C.africana)；Claviceps gigantea (C.gigantea)；Epichloë coenophiala 和 Periglandula species，其中基因 easA 或基因 easM 在所述烟曲霉或所述具有与烟曲霉相似途径的真菌中失活。
• Selection of symbiota by screening multiple host-symbiont associations
  申请人：Agriculture Victoria Services Pty Ltd

  公开号：US10631516B2

  公开（公告）日：2020-04-28

  The present invention relates to new methods of selecting and breeding organisms, in particular organisms which exhibit symbiotic behaviour with symbionts, and to new organisms and symbiota developed thereby, such as plant or grass and endophyte symbiota. Multiple symbionts are deployed in multiple organisms and selected for improved symbiotic compatibility and performance early in the breeding process. Methods include producing improved organisms from germplasm, by inoculating host organism germplasm libraries with symbionts selected from symbiont libraries and selecting improved host organisms exhibiting desired symbiota characteristics, and selection of organism-symbiont associations with a desired genetic and metabolic profile by metagenomic analysis of nucleic acid libraries from an organism or organism-symbiont association.

  本发明涉及选择和培育生物的新方法，特别是与共生体表现出共生行为的生物，以及由此培育出的新生物和共生体，如植物或草和内生菌共生体。多种共生体在多个生物体内配置，并在育种过程的早期进行筛选，以提高共生体的兼容性和性能。方法包括：用从共生体文库中选出的共生体接种宿主生物种质文库，并选择具有所需共生体特征的改良宿主生物，以及通过对来自生物或生物-共生体结合体的核酸文库进行元基因组分析，选择具有所需遗传和代谢特征的生物-共生体结合体，从而从种质中培育出改良生物。