tert-butyl 3-[(2S)-2-amino-3-hydroxypropyl]indole-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl 3-[(2S)-2-amino-3-hydroxypropyl]indole-1-carboxylate
• 化学式: C₁₆H₂₂N₂O₃
• 分子量: 290.362
• InChiKey: CYCBCFFLYXJCEF-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  77.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三光气 、 tert-butyl 3-[(2S)-2-amino-3-hydroxypropyl]indole-1-carboxylate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以234 mg的产率得到(S)-1-tert-butoxycarbonyl-3-(2-oxo-oxazolidin-4-ylmethyl)-indole
  参考文献：
  名称：

  Copper-Catalyzed Cyclization of Iodo-tryptophans: A Straightforward Synthesis of Pyrroloindoles

  摘要：

  Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, affording a wide range of polysubstituted, enantioenriched tetrahydropyrrolo[2,3-b]indoles. Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems.

  DOI：

  10.1021/ol8015513
• 作为产物：
  描述：

  N-carbobenzyloxy-1-tert-butoxycarbonyl-L-tryptophanol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 tert-butyl 3-[(2S)-2-amino-3-hydroxypropyl]indole-1-carboxylate
  参考文献：
  名称：

  Copper-Catalyzed Cyclization of Iodo-tryptophans: A Straightforward Synthesis of Pyrroloindoles

  摘要：

  Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, affording a wide range of polysubstituted, enantioenriched tetrahydropyrrolo[2,3-b]indoles. Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems.

  DOI：

  10.1021/ol8015513

文献信息

• Substrate-guided optimization of the syringolins yields potent proteasome inhibitors with activity against leukemia cell lines
  作者：Kyle A. Totaro、Dominik Barthelme、Peter T. Simpson、Robert T. Sauer、Jason K. Sello

  DOI：10.1016/j.bmc.2015.07.041

  日期：2015.9

  Natural products that inhibit the proteasome have been fruitful starting points for the development of drug candidates. Those of the syringolin family have been underexploited in this context. Using the published model for substrate mimicry by the syringolins and knowledge about the substrate preferences of the proteolytic subunits of the human proteasome, we have designed, synthesized, and evaluated syringolin analogs. As some of our analogs inhibit the activity of the proteasome with second-order rate constants 5-fold greater than that of the methyl ester of syringolin B, we conclude that the substrate mimicry model for the syringolins is valid. The improvements in in vitro potency and the activities of particular analogs against leukemia cell lines are strong bases for further development of the syringolins as anti-cancer drugs. (c) 2015 Elsevier Ltd. All rights reserved.