6-bromo-2'-demethylaplysinopsin (Z)

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-bromo-2'-demethylaplysinopsin (Z)
• 英文别名: (Z)-6-bromo-2'-demethylaplysinopsin；(Z)-2-amino-4-((6-bromo-1H-indol-3-yl)methylene)-1-methyl-1H-imidazol-5(4H)-one；(5Z)-2-amino-5-[(6-bromo-1H-indol-3-yl)methylidene]-3-methylimidazol-4-one
• 化学式: C₁₃H₁₁BrN₄O
• 分子量: 319.161
• InChiKey: AKOYYWJWILIASW-WCIBSUBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.98
• 氢给体数：
  3.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  6-溴吲哚-3-甲醛 在 甲酸 、 氨 、 sodium ethanolate 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 110.0h， 生成 6-bromo-2'-demethylaplysinopsin (Z)
  参考文献：
  名称：

  Iminophosphorane-mediated imidazole ring formation: A new and general entry to aplysinopsin-type alkaloids of marine origin.

  摘要：

  Aza Wittig-type reactions of iminophosphoranes 21, derived from ethyl alpha-azido-beta-(3-indolyl)propenoates and triphenylphosphine, with methyl isocyanate, carbon dioxide or carbon disulfide provide the corresponding heterocumulenes 22, 25 and 28 which undergo cyclization by the action of nitrogenous reagents completing the assemblage of the framework of aplysinopsin. Further deprotection leads to naturally occurring aplysinopsin analogues.

  DOI：

  10.1016/s0040-4020(01)85082-1

文献信息

• Aplysinopsin-type alkaloids fromDendrophyllia sp., a scleractinian coral of the family dendrophylliidae of the philippines, facile photochemical (Z/E) photoisomerization and thermal reversal
  作者：Graziano Guella、Ines Mancini、Helmut Zibrowius、Francesco Pietra

  DOI：10.1002/hlca.19890720703

  日期：1989.11.1

  The dendrophylliid Dendrophyllia sp. of Palawan contains the indole alkaloids 2′-demethylaplysinopsin (4) and 2′-demethyl-3′-N-methylaplysinopsin (6) and their 6-bromo analogues in H (Z/E) ratio larger than 95:5; these mixtures undergo facile photoisomerization to give mixtures richer in the (E) stereoisomer which undergo thermal isomerization to give back the original mixtures.

  树突藻Dendrophyllia sp。巴拉望岛含有吲哚生物碱2'-脱甲基皂苷（4）和2'-脱甲基-3'- N-甲基皂苷（6）及其6-溴类似物的H（Z / E）比大于95：5；这些混合物容易进行光异构化，得到富含（E）立体异构体的混合物，然后进行热异构化，得到原来的混合物。
• In vitro structure–activity relationships of aplysinopsin analogs and their in vivo evaluation in the chick anxiety–depression model
  作者：Kevin Lewellyn、Dobroslawa Bialonska、Melissa J. Loria、Stephen W. White、Kenneth J. Sufka、Jordan K. Zjawiony

  DOI：10.1016/j.bmc.2013.09.011

  日期：2013.11

  Aplysinopsins are tryptophan-derived natural products that have been isolated from a variety of marine organisms and have been shown to possess a range of biological activities. In vitro receptor binding assays showed that of the 12 serotonin receptor subtypes, analogues showed a high affinity for the 5-HT2B and 5-HT2C receptor subtypes, with selectivity for 5-HT2B over 5-HT2C. While no conclusions could be drawn about the number and position of N-methylations, bromination at C-4 and C-5 of the indole ring resulted in greater binding affinities, with K-i's as low as 35 nM. This data, combined with previous knowledge of the CNS activity of aplysinopsin analogs, suggested that these compounds may have potential as leads for antidepressant drugs. Compounds 3c, 3u, and 3x were evaluated in the chick anxiety-depression model to assess their in vivo efficacy. Compound 3c showed a modest antidepressant effect at a dose of 30 nM/kg in the animal model. (C) 2013 Elsevier Ltd. All rights reserved.
• GUELLA, GRAZIANO;MANCIN, INES;ZIBROWIUS, HELMUT;PIETRA, FRANCESCO, HELV. CHIM. ACTA., 72,(1989) N, C. 1440-1450
  作者：GUELLA, GRAZIANO、MANCIN, INES、ZIBROWIUS, HELMUT、PIETRA, FRANCESCO

  DOI：——

  日期：——
• Iminophosphorane-mediated imidazole ring formation: A new and general entry to aplysinopsin-type alkaloids of marine origin.
  作者：Pedro Molina、Pedro Almendros、Pilar M. Fresneda

  DOI：10.1016/s0040-4020(01)85082-1

  日期：1994.2

  Aza Wittig-type reactions of iminophosphoranes 21, derived from ethyl alpha-azido-beta-(3-indolyl)propenoates and triphenylphosphine, with methyl isocyanate, carbon dioxide or carbon disulfide provide the corresponding heterocumulenes 22, 25 and 28 which undergo cyclization by the action of nitrogenous reagents completing the assemblage of the framework of aplysinopsin. Further deprotection leads to naturally occurring aplysinopsin analogues.