5-[(E)-(1H-indol-3-yl)methylidene]-1-methylimidazolidine-2,4-dione | 91902-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-[(E)-(1H-indol-3-yl)methylidene]-1-methylimidazolidine-2,4-dione
• 英文别名: 8E-3'-deimino-4'-demethyl-3'-oxoaplysinopsin；5-indol-3-ylmethylene-1-methyl-imidazolidine-2,4-dione；5-Indol-3-ylmethylen-1-methyl-imidazolidin-2,4-dion；(5E)-5-(1H-indol-3-ylmethylidene)-1-methylimidazolidine-2,4-dione
• CAS: 91902-09-9
• 化学式: C₁₃H₁₁N₃O₂
• 分子量: 241.249
• InChiKey: PQHURGADVOOPAU-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 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：
  65.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-[(E)-(1H-indol-3-yl)methylidene]-1-methylimidazolidine-2,4-dione 以 甲醇 为溶剂， 反应 3.0h， 生成 8Z-3'-deimino-4'-demethyl-3'-oxoaplysinopsin
  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
• 作为产物：
  描述：

  甲酰乙内脲 、 3-吲哚甲醛 反应 0.75h， 以46%的产率得到5-[(E)-(1H-indol-3-yl)methylidene]-1-methylimidazolidine-2,4-dione
  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

• A simple synthesis of aplysinopsin analogues by dimethylamine substitution in N,N-(dimethylamino)methylidene derivatives of five-membered heterocycles
  作者：Renata Jakše、Simon Rečnik、Jurij Svete、Amalija Golobič、Ljubo Golič、Branko Stanovnik

  DOI：10.1016/s0040-4020(01)00838-9

  日期：2001.9

  Some new aplysinopsin analogues were prepared by a simple coupling of N,N-(dimethylamino)methylidene substituted hydantoin, thiohydantoin, and thiazolone derivatives, with indole derivatives. Configuration around the exocyclic CC double bond was determined on the basis of long-range heteronuclear coupling constants using 2D HMBC correlation technique.

  通过将N，N-（二甲基氨基）亚甲基取代的乙内酰脲，硫代乙内酰脲和噻唑酮衍生物与吲哚衍生物简单偶联，制备了一些新的皂素类似物。基于远距离异核偶联常数，使用2D HMBC相关技术确定了环外CC双键周围的构型。
• Gordon; Jackson, Journal of Biological Chemistry, 1935, vol. 110, p. 151,156
  作者：Gordon、Jackson

  DOI：——

  日期：——
• 359. The synthesis of r-α-methylamino-β-3-indolylpropionic acid
  作者：Eric John Miller、William Robson

  DOI：10.1039/jr9380001910

  日期：——
• The Preparation of Sarcosine and Methyl α-Methylamino-β-(3-indolyl)-propionate
  作者：F. F. Blicke、Paul E. Norris

  DOI：10.1021/ja01641a032

  日期：1954.6