cis-Hexahydropyrrolo[3,4-B]pyrrol-6(6AH)-one | 1523530-51-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-Hexahydropyrrolo[3,4-B]pyrrol-6(6AH)-one
• 英文别名: (3aS,6aS)-2,3,3a,4,5,6a-hexahydro-1H-pyrrolo[2,3-c]pyrrol-6-one
• CAS: 1523530-51-9
• 化学式: C₆H₁₀N₂O
• 分子量: 126.158
• InChiKey: OWUKCNLPZKSUSF-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-二氯苯磺酰氯 、 cis-Hexahydropyrrolo[3,4-B]pyrrol-6(6AH)-one 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以41%的产率得到
  参考文献：
  名称：

  Constraining the amide bond in N-Sulfonylated dipeptide VLA-4 antagonists

  摘要：

  The integrin VLA-4 is implicated in several inflammatory disease states. In search of non-peptidic antagonists of VLA-4, rotational constraints were imposed on the amide bond of prototypical N-sulfonylated dipeptide VLA-4 antagonists. By judicious structural modi. cation of the side chains, trisubstituted imidazoles with moderate binding potencies were obtained, for example, 19, VLA-4 IC50 = 237 nM. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.045
• 作为产物：
  描述：

  1-benzylhexahydropyrrolo[3,4-b]pyrrol-6-(1H)-one 在 palladium on activated charcoal 甲酸 、 氢气 作用下， 以 甲醇 为溶剂， 以99%的产率得到cis-Hexahydropyrrolo[3,4-B]pyrrol-6(6AH)-one
  参考文献：
  名称：

  Constraining the amide bond in N-Sulfonylated dipeptide VLA-4 antagonists

  摘要：

  The integrin VLA-4 is implicated in several inflammatory disease states. In search of non-peptidic antagonists of VLA-4, rotational constraints were imposed on the amide bond of prototypical N-sulfonylated dipeptide VLA-4 antagonists. By judicious structural modi. cation of the side chains, trisubstituted imidazoles with moderate binding potencies were obtained, for example, 19, VLA-4 IC50 = 237 nM. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.045

文献信息

• Constraining the amide bond in N-Sulfonylated dipeptide VLA-4 antagonists
  作者：Linda L. Chang、Ginger X. Yang、Ermengilda McCauley、Richard A. Mumford、John A. Schmidt、William K. Hagmann

  DOI：10.1016/j.bmcl.2008.01.045

  日期：2008.3

  The integrin VLA-4 is implicated in several inflammatory disease states. In search of non-peptidic antagonists of VLA-4, rotational constraints were imposed on the amide bond of prototypical N-sulfonylated dipeptide VLA-4 antagonists. By judicious structural modi. cation of the side chains, trisubstituted imidazoles with moderate binding potencies were obtained, for example, 19, VLA-4 IC50 = 237 nM. (C) 2008 Elsevier Ltd. All rights reserved.