N-prenyl-cyclo-L-tryptophyl-L-proline | 73093-48-8

• 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: N-prenyl-cyclo-L-tryptophyl-L-proline
• 英文别名: (3S,8aS)-3-[[1-(3-methylbut-2-enyl)indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 73093-48-8
• 化学式: C₂₁H₂₅N₃O₂
• 分子量: 351.448
• InChiKey: UHDXIZKDEGWFRD-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-prenyl-L-tryptophyl-L-proline methyl ester 在 2-羟基吡啶 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以59%的产率得到N-prenyl-cyclo-L-tryptophyl-L-proline
  参考文献：
  名称：

  Synthesis and evaluation of microtubule assembly inhibition and cytotoxicity of prenylated derivatives of cyclo-l-Trp-l-Pro

  摘要：

  The synthesis of three isoprenylated derivatives of cyclo-L-Trp-L-Pro is described. These substances have been evaluated for cytotoxic activity in rat normal fibroblast 3Y1 cells and have also been evaluated in vitro for the inhibition of microtubule assembly. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00171-1

文献信息

• Efficient Synthesis of<i>N</i>-Prenylpyrroloindoline and<i>N</i>-Prenylindole Alkaloids Based on a New Four-Reaction Anionic Domino Process
  作者：Pilar López-Alvarado、Esmeralda Caballero、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1021/ol061631m

  日期：2006.9

  Treatment of 2,5-diketopiperazines or carbamates derived from tryptophan or tryptamine with iodomethyltrimethylsilane followed by lithium hexamethyldisilazane and a prenyl halide produced stereoselectively derivatives of the hexahydropyrrolo[2,3-b]indole system bearing prenyl substituents both at C-3a and at the indoline nitrogen in a one-pot procedure involving a novel four-reaction anionic domino

  用碘甲基三甲基硅烷，然后用六甲基二硅氮烷锂和异戊烯基卤化物处理色氨酸或色胺中的2,5-二酮哌嗪或氨基甲酸酯，生成六氢吡咯并[2,3-b]吲哚体系的立体选择性衍生物，C-3a和C-3a均带有异戊烯基取代基一锅法中使用二氢吲哚氮，涉及一种新颖的四反应性阴离子多米诺工艺。该反应应用于N-异戊烯基前列腺素B的制备，并实现了生物活性海洋天然产物（+/-）-去氟氟乙胺B的非常有效的正式全合成。
• Bioinspired Indole Prenylation Reactions in Water
  作者：Satomi Tanaka、Shinya Shiomi、Hayato Ishikawa

  DOI：10.1021/acs.jnatprod.7b00464

  日期：2017.8.25

  chemistry, organic chemistry, and biochemistry. We have developed a direct bioinspired indole prenylation reaction using DMAPP or its equivalents as the electrophile in homogeneous aqueous acidic media in the absence of enzyme to provide prenylated indole products. After establishing the bioinspired indole prenylation reaction, this was then used to achieve the synthesis of a series of natural products, namely

  衍生自二甲基二烯丙基二磷酸酯（DMAPP）的异戊二烯单元是许多天然产物（包括萜类，类胡萝卜素，类固醇和天然橡胶）中的重要基序。了解DMAPP的化学特性是天然产物化学，有机化学和生物化学中的重要主题。我们已经开发出一种直接的生物启发型吲哚异戊二烯化反应，使用DMAPP或其等同物作为亲电试剂，在均质水性酸性介质中，在不存在酶的情况下提供了异戊二烯化的吲哚产物。建立所述仿生吲哚异戊烯化反应后，然后将其用于实现一系列天然产物，即，的合成Ñ -prenylcyclo-升-tryptophyl-升-脯氨酸，tryprostatins，rhinocladins和terezine D.
• Synthesis and evaluation of microtubule assembly inhibition and cytotoxicity of prenylated derivatives of cyclo-l-Trp-l-Pro
  作者：Juan F Sanz-Cervera、Emily M Stocking、Takeo Usui、Hiroyuki Osada、Robert M Williams

  DOI：10.1016/s0968-0896(00)00171-1

  日期：2000.10

  The synthesis of three isoprenylated derivatives of cyclo-L-Trp-L-Pro is described. These substances have been evaluated for cytotoxic activity in rat normal fibroblast 3Y1 cells and have also been evaluated in vitro for the inhibition of microtubule assembly. (C) 2000 Elsevier Science Ltd. All rights reserved.