(2S)-N-[3-(N-benzylindol-3-yl)propanoyl]camphorsultam | 943154-69-6

• 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: (2S)-N-[3-(N-benzylindol-3-yl)propanoyl]camphorsultam
• 英文别名: (1R)-N-3-(N-benzylindol-3-ylpropanoyl)camphorsultam；(1R)-N-3-(N-benzylindoylpropanoyl)camphorsultam；3-(1-benzylindol-3-yl)-1-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]propan-1-one；3-(1-benzylindol-3-yl)-1-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]propan-1-one
• CAS: 943154-69-6
• 化学式: C₂₈H₃₂N₂O₃S
• 分子量: 476.64
• InChiKey: CBRHYOHAOKBJIM-ULNCZQIZSA-N

物化性质

• 熔点：
  123 °C
• 沸点：
  665.4±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-N-[3-(N-benzylindol-3-yl)propanoyl]camphorsultam 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.25h， 生成 (2S)-N-{(2R)-3-(N-benzylindol-3-yl)-2-[(dibenzylamino)methyl]propanoyl}camphorsultam
  参考文献：
  名称：

  Synthesis and Evaluation of Analogues of N-Phthaloyl-l-tryptophan (RG108) as Inhibitors of DNA Methyltransferase 1

  摘要：

  DNA methyltransferases (DNMT) are promising drug targets in cancer provided that new, more specific, and chemically stable inhibitors are discovered. Among the non-nucleoside DNMT inhibitors, N-phthaloyl-L-tryptophan 1 (RG108) was first identified as inhibitor of DNMT1. Here, 1 analogues were synthesized to understand its interaction with DNMT. The indole, carboxylate, and phthalimide moieties were modified. Homologated and conformationally constrained analogues were prepared. The latter were synthesized from prolinohomotryptophan derivatives through a methodology based amino-zinc-ene-enolate cyclization. All compounds were tested for their ability to inhibit DNMT1 in vitro. Among them, constrained compounds 16-18 and NPys derivatives 10-11 were found to be at least 10-fold more potent than the reference compound. The cytotoxicity on the tumor, DU145 cell line of the most potent inhibitors was correlated to their inhibitory potency. Finally, docking studies were conducted in order to understand their binding mode. This study provides insights for the design of the next-generation of DNMT inhibitors.

  DOI：

  10.1021/jm401419p
• 作为产物：
  描述：

  3-吲哚丙酸 在 N-甲基吗啉 、 sodium hydride 、 氯甲酸异丁酯 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 (2S)-N-[3-(N-benzylindol-3-yl)propanoyl]camphorsultam
  参考文献：
  名称：

  用于合成 β2-氨基酸的新型可扩展不对称氨基甲基化反应

  摘要：

  β-氨基酸是设计拟肽的有用工具，开发其合成的新方法，尤其是 β2-氨基酸的合成，仍然是一个重要的挑战。在这里，我们报告了一种新的可扩展路线，该路线基于 Mannich 型亚胺鎓亲电试剂对甲硅烷基乙烯酮 N,O-缩醛的氨甲基化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600926

文献信息

• Aminomethylation of chiral silyl enol ethers: access to β2-homotryptophane and β2-homolysine derivatives
  作者：Roba Moumné、Maud Larregola、Youcef Boutadla、Solange Lavielle、Philippe Karoyan

  DOI：10.1016/j.tetlet.2008.05.131

  日期：2008.8

  We describe here the aminomethylation of chiral silyl enol ether derivatives using iminium ion. The choice of judicious precursors with adequate protecting groups for the silylation/aminomethylation step was required to achieve the synthesis of beta(2)-homotryptophane in few steps. The same methodology was used to prepare a beta(2)-homolysine derivative. (C) 2008 Elsevier Ltd. All rights reserved.