8Z-4'-demethylaplysinopsin | 117490-38-7

• 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: 8Z-4'-demethylaplysinopsin
• CAS: 117490-38-7
• 化学式: C₁₃H₁₂N₄O
• 分子量: 240.264
• InChiKey: AAMOMFNMMXXVGM-WDZFZDKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18.0
• 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：
  74.48
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (E)-2'-demethylaplysinopsin 以 甲醇 为溶剂， 反应 3.0h， 生成 8Z-4'-demethylaplysinopsin
  参考文献：
  名称：

  Australian marine sponge alkaloids as a new class of glycine-gated chloride channel receptor modulator

  摘要：

  Chemical analysis of a specimen of the sponge lanthella cf. flabelliformis returned two new sesquiterpene glycinyl lactams, ianthellalactams A (1) and B (2), the known sponge sesquiterpene dictyodendrillin (3) and its ethanolysis artifact ethyl dictyodendrillin (4), and five known sponge indole alkaloids, aplysinopsin (5), 8E-3'-deimino-3'-oxoaplysinopsin (6), 8Z-3'-deimino-3'-oxoaplysinopsin (7), dihydroaplysinopsin (8) and tubastrindole B (9). The equilibrated mixture 6/7 exhibited glycine-gated chloride channel receptor (GlyR) antagonist activity with a bias towards alpha 3 over alpha 1 GlyR, while tubastrindole B (9) exhibited a bias towards alpha 1 over alpha 3 GlyR. At low- to sub-micromolar concentrations, 9 was also a selective potentiator of alpha 1 GlyR, with no effect on alpha 3 GlyR-a pharmacology that could prove useful in the treatment of movement disorders such as spasticity and hyperekplexia. Our investigations into the GlyR modulatory properties of 1-9 were further supported by the synthesis of a number of structurally related indole alkaloids. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.061

文献信息

• Novel Aplysinopsin-Type Alkaloids from Scleractinian Corals of the Family Dendrophylliidae of the Mediterranean and the Philippines. Configurational-assignment criteria, stereospecific synthesis, and photoisomerization
  作者：Graziano Guella、Ines Mancini、Helmut Zibrowius、Francesco Pietra

  DOI：10.1002/hlca.19880710412

  日期：1988.6.15

  scleractinian coral Tubastraea sp. (Dendrophylliidae) collected at Palawan, Philippines, 3′-deimino-3′-oxoaplysinopsin (4) and 6-bromo-3′-deimino-3′-oxoaplysinopsin (6) are now isolated as 5:2 mixtures of (E/Z) stereoisomers. The 3′-deimino-2′,4′-bis(demethyl)-3′-oxoaplysinopsin (7) and 6-bromo-3′-demino-2′,4-bis(demethyl)-3′-oxoaplysinopsin (5) are isolated as 2:3 and 1:1 (E/Z) mixtures, respectively

  来自巩膜珊瑚Tubastraea sp。（3）-deimino-3'-oxoaplysinopsin（4）和6-bromo-3'-deimino-3'-oxoaplysinopsin（6）收集于菲律宾巴拉望岛（Dendrophylliidae），现以（E / Z）立体异构体。3'-deimino-2'，4'-双（去甲基）-3'-氧皂甙酶（7）和6-bromo-3'-demino-2'，4-双（去甲基）-3'-氧皂甙酶（5）分别以2：3和1：1（E / Z）混合物的形式从另一种树突藻（Leptopsammia pruvoti）中分离出来，收集在法国地中海沿岸的马赛附近。通过合成可获得用于完整结构确定所需的大量这些化合物和相关化合物。因此，吲哚-3-羧甲醛（9）或其6-溴衍生物14与乙内酰脲（15），3-甲基乙内酰脲（11）或1，3-二甲基乙内酰脲（10）的缩合产生具有高立体特异性的普遍的天然
• Australian marine sponge alkaloids as a new class of glycine-gated chloride channel receptor modulator
  作者：Walter Balansa、Robiul Islam、Daniel F. Gilbert、Frank Fontaine、Xue Xiao、Hua Zhang、Andrew M. Piggott、Joseph W. Lynch、Robert J. Capon

  DOI：10.1016/j.bmc.2013.04.061

  日期：2013.7

  Chemical analysis of a specimen of the sponge lanthella cf. flabelliformis returned two new sesquiterpene glycinyl lactams, ianthellalactams A (1) and B (2), the known sponge sesquiterpene dictyodendrillin (3) and its ethanolysis artifact ethyl dictyodendrillin (4), and five known sponge indole alkaloids, aplysinopsin (5), 8E-3'-deimino-3'-oxoaplysinopsin (6), 8Z-3'-deimino-3'-oxoaplysinopsin (7), dihydroaplysinopsin (8) and tubastrindole B (9). The equilibrated mixture 6/7 exhibited glycine-gated chloride channel receptor (GlyR) antagonist activity with a bias towards alpha 3 over alpha 1 GlyR, while tubastrindole B (9) exhibited a bias towards alpha 1 over alpha 3 GlyR. At low- to sub-micromolar concentrations, 9 was also a selective potentiator of alpha 1 GlyR, with no effect on alpha 3 GlyR-a pharmacology that could prove useful in the treatment of movement disorders such as spasticity and hyperekplexia. Our investigations into the GlyR modulatory properties of 1-9 were further supported by the synthesis of a number of structurally related indole alkaloids. (C) 2013 Elsevier Ltd. All rights reserved.