ethyl (E,4S)-7-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-4-[(2-methylpropan-2-yl)oxycarbonylamino]hept-2-enoate | 952065-51-9

• 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: ethyl (E,4S)-7-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-4-[(2-methylpropan-2-yl)oxycarbonylamino]hept-2-enoate
• CAS: 952065-51-9
• 化学式: C₂₅H₄₄N₄O₈
• 分子量: 528.646
• InChiKey: BFDFPMNVDTZACF-ZWKQNVPVSA-N

物化性质

• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  154
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl (E,4S)-7-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-4-[(2-methylpropan-2-yl)oxycarbonylamino]hept-2-enoate 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 miraziridine A diethyl ester
  参考文献：
  名称：

  Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B

  摘要：

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.082
• 作为产物：
  描述：

  Boc-L-鸟氨酸 在 lithium aluminium tetrahydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.33h， 生成 ethyl (E,4S)-7-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-4-[(2-methylpropan-2-yl)oxycarbonylamino]hept-2-enoate
  参考文献：
  名称：

  Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B

  摘要：

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.082

文献信息

• Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B
  作者：Hiroyuki Konno、Kanako Kubo、Hidefumi Makabe、Emi Toshiro、Naoyuki Hinoda、Kazuto Nosaka、Kenichi Akaji

  DOI：10.1016/j.tet.2007.06.082

  日期：2007.9

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.