(9H-fluoren-9-yl)methyl (5-oxopentyl)carbamate | 952661-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl (5-oxopentyl)carbamate
• 英文别名: 9H-fluoren-9-ylmethyl N-(5-oxopentyl)carbamate
• CAS: 952661-21-1
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: VTIAGIQUBAUOJO-UHFFFAOYSA-N

物化性质

• 沸点：
  524.4±33.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl (5-oxopentyl)carbamate 在 三乙胺 、 乙酰氯 、 三氟乙酸 、 silver(l) oxide 作用下， 以 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  A Versatile Annulation Protocol toward Novel Constrained Phosphinic Peptidomimetics

  摘要：

  [GRAPHICS]The development of a novel 3-center 2-component annulation reaction between alpha,omega-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting alpha,omega-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochernistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structrures.

  DOI：

  10.1021/jo071081l
• 作为产物：
  描述：

  9H-芴-9-基甲基(5-羟基戊基)氨基甲酸酯 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (9H-fluoren-9-yl)methyl (5-oxopentyl)carbamate
  参考文献：
  名称：

  A Versatile Annulation Protocol toward Novel Constrained Phosphinic Peptidomimetics

  摘要：

  [GRAPHICS]The development of a novel 3-center 2-component annulation reaction between alpha,omega-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting alpha,omega-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochernistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structrures.

  DOI：

  10.1021/jo071081l

文献信息

• Probing the Plasticity in the Active Site of Protein N-terminal Methyltransferase 1 Using Bisubstrate Analogues
  作者：Dongxing Chen、Cheng Dong、Guangping Dong、Karthik Srinivasan、Jinrong Min、Nicholas Noinaj、Rong Huang

  DOI：10.1021/acs.jmedchem.0c00770

  日期：2020.8.13

  The bisubstrate analogue strategy is a promising approach to develop potent and selective inhibitors for protein methyltransferases. Herein, the interactions of a series of bisubstrate analogues with protein N-terminal methyltransferase 1 (NTMT1) were examined to probe the molecular properties of the active site of NTMT1. Our results indicate that a 2-C to 4-C atom linker enables its respective bisubstrate

  双底物类似物策略是开发蛋白质甲基转移酶的有效和选择性抑制剂的有前途的方法。在此，研究了一系列双底物类似物与蛋白质 N 端甲基转移酶 1 (NTMT1) 的相互作用，以探测 NTMT1 活性位点的分子特性。我们的结果表明，2-C 到 4-C 原子接头使其各自的双底物类似物能够占据 NTMT1 的底物和辅因子结合位点，但具有 5-C 原子接头的双底物类似物仅与底物结合相互作用位点并起到基底的作用。此外，4-C 原子接头是最佳的，并产生最有效的抑制剂 ( K i,app= 130 ± 40 pM) 对于迄今为止的 NTMT1，显示对其他甲基转移酶甚至其同源物 NTMT2 的选择性超过 3000 倍。这项研究揭示了 NTMT1 活性位点可塑性的分子基础。此外，我们的研究概述了开发任何甲基转移酶双底物抑制剂的一般指导。