(1R,5R-1-(12'-azidododecanoyl)-4-hydroxy-4-methyl-6-oxa-3-azabicyclo[3.1.0]hexan-2-one | 1039366-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (1R,5R-1-(12'-azidododecanoyl)-4-hydroxy-4-methyl-6-oxa-3-azabicyclo[3.1.0]hexan-2-one
• CAS: 1039366-95-4
• 化学式: C₁₇H₂₈N₄O₄
• 分子量: 352.434
• InChiKey: HLJBEGCIWDSXTF-NZEUDUFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  25.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  127.69
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,5R-1-(12'-azidododecanoyl)-4-hydroxy-4-methyl-6-oxa-3-azabicyclo[3.1.0]hexan-2-one 、 (+)生物素-N-琥珀酰亚胺基酯 在 palladium hydroxide - carbon 氢气 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 以88%的产率得到5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[12-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-12-oxododecyl]pentanamide
  参考文献：
  名称：

  Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation

  摘要：

  Epolactaene, isolated from cultured Penicillium sp. BM 1689-P mycelium, induces neurite outgrowth and arrests the cell cycle of the human neuroblastoma cell line, SH-SY5Y, at the G1 phase. We have found that epolactaene and its derivatives induce apoptosis in the human leukemia B-cell line, BALL-1. In this study, we prepared fluorescent and biotinylated epolactaene derivatives. We characterized the cellular location and the identification of BALL-1 proteins that reacted with these compounds. The results obtained from the reaction of epolactaene or its derivative with N-acetylcysteine methyl ester indicate that these compounds induce the disulfide formation and the alpha-position of the epoxylactam core is the reactive site. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.029
• 作为产物：
  描述：

  (2S,3S)-3-[(S)-1-hydroxyethyl]-2-(12'-azidododecanoyl)oxirane-2-carboxamide 在 二甲基亚砜 、 三氟乙酸酐 、 三乙胺 、 lithium hydroxide 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 1.25h， 以72%的产率得到(1R,5R-1-(12'-azidododecanoyl)-4-hydroxy-4-methyl-6-oxa-3-azabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation

  摘要：

  Epolactaene, isolated from cultured Penicillium sp. BM 1689-P mycelium, induces neurite outgrowth and arrests the cell cycle of the human neuroblastoma cell line, SH-SY5Y, at the G1 phase. We have found that epolactaene and its derivatives induce apoptosis in the human leukemia B-cell line, BALL-1. In this study, we prepared fluorescent and biotinylated epolactaene derivatives. We characterized the cellular location and the identification of BALL-1 proteins that reacted with these compounds. The results obtained from the reaction of epolactaene or its derivative with N-acetylcysteine methyl ester indicate that these compounds induce the disulfide formation and the alpha-position of the epoxylactam core is the reactive site. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.029