N-{2[N-(tert-butoxycarbonyl)aminoethyl]}-3-{N'-[N-2-(tert-butoxycarbonyl)aminoethyl]carbamoyl}-trans-propenamide | 140686-30-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-{2[N-(tert-butoxycarbonyl)aminoethyl]}-3-{N'-[N-2-(tert-butoxycarbonyl)aminoethyl]carbamoyl}-trans-propenamide
• CAS: 140686-30-2
• 化学式: C₁₈H₃₂N₄O₆
• 分子量: 400.475
• InChiKey: AAITWRARWVJNSP-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  134.86
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-{2[N-(tert-butoxycarbonyl)aminoethyl]}-3-{N'-[N-2-(tert-butoxycarbonyl)aminoethyl]carbamoyl}-trans-propenamide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以88%的产率得到N-(2-aminoethyl)-3-trans-propenamide dihydrochloride
  参考文献：
  名称：

  Search for the pharmacophore of the K+ channel blocker, apamin

  摘要：

  The suggestion that the arginine residues, 13Arg and 14Arg, in the octadecapeptide apamin 1 are critically important to its action in blocking Ca2+-dependent K+ channels (and hence part of the 'pharmacophore') has been investigated by examining small peptides containing Arg-Arg or Lys-Arg. Bisguanidine derivatives modelled on the Arg-Arg partial pharmacophore have also been synthesised and tested; in particular, N-(2-guanidinoethyl)-3[N1-(2-guanidinoethyl)carbamoyl]-trans-propenamide 11 and its higher homologue 12. None of the compounds showed more than weak activity (K(i) > 10(-5) M) indicating that although the Arg-Arg fragment may be necessary, it is not a sufficient atom grouping for the pharmacophore.

  DOI：

  10.1016/0223-5234(91)90133-8
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.08h， 生成 N-{2[N-(tert-butoxycarbonyl)aminoethyl]}-3-{N'-[N-2-(tert-butoxycarbonyl)aminoethyl]carbamoyl}-trans-propenamide
  参考文献：
  名称：

  Search for the pharmacophore of the K+ channel blocker, apamin

  摘要：

  The suggestion that the arginine residues, 13Arg and 14Arg, in the octadecapeptide apamin 1 are critically important to its action in blocking Ca2+-dependent K+ channels (and hence part of the 'pharmacophore') has been investigated by examining small peptides containing Arg-Arg or Lys-Arg. Bisguanidine derivatives modelled on the Arg-Arg partial pharmacophore have also been synthesised and tested; in particular, N-(2-guanidinoethyl)-3[N1-(2-guanidinoethyl)carbamoyl]-trans-propenamide 11 and its higher homologue 12. None of the compounds showed more than weak activity (K(i) > 10(-5) M) indicating that although the Arg-Arg fragment may be necessary, it is not a sufficient atom grouping for the pharmacophore.

  DOI：

  10.1016/0223-5234(91)90133-8

文献信息

• Design and synthesis of a transition state analogue for the Diels–Alder reaction
  作者：Paramjit S. Arora、Que N. Van、Michael Famulok、A.J. Shaka、James S. Nowick

  DOI：10.1016/s0968-0896(98)00072-8

  日期：1998.9

  dienophile 3 are based upon fumaramide. The fumaramide system should destabilize the initially formed boat conformer of Diels-Alder product 4 and stabilize a half-chair conformer. The conversion of the initially formed boat conformer to the half-chair conformer is designed to help prevent Diels-Alder product 4 from binding strongly to catalysts selected to strongly bind TSA 1. This feature should minimize product

  本文描述了Diels-Alder反应的三阳离子过渡态类似物（TSA 1）的设计和合成。TSA 1包含一个模拟Diels-Alder过渡态船形的双环[2.2.1]庚烯环系统，旨在通过氢键和盐桥与抗体，核酸和印迹聚合物紧密结合。本文还描述了Diels-Alder反应底物（二烯2和亲二烯体3）的合成，以及用于监测Diels-Alder产物4形成的灵敏HPLC分析。它们基于马来酰亚胺，TSA 1和亲二烯体3基于富马酰胺。富马酰胺系统应使Diels-Alder产品4最初形成的船用构形器不稳定，并使半椅构形器稳定。最初形成的船用顺应剂向半椅顺应剂的转化旨在帮助防止Diels-Alder产品4与选定的与TSA 1牢固结合的催化剂牢固结合。此功能应将产品抑制作用降至最低，这可能是产品中的一个问题。 Diels-Alder反应的催化。