(3aR,4R,7S,7aS)-2-(6-(prop-2-yn-1-ylamino)hexyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione | 1259533-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3aR,4R,7S,7aS)-2-(6-(prop-2-yn-1-ylamino)hexyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
• CAS: 1259533-52-2
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: YNSKODMOFUXARD-SYMSYNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3aR,4R,7S,7aS)-2-(6-(prop-2-yn-1-ylamino)hexyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 2,5-dioxopyrrolidin-1-yl 4-((6-((3aR,4R,7S,7aS)-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl)hexyl)(prop-2-yn-1-yl)amino)-4-oxobutanoate
  参考文献：
  名称：

  Drug-Loaded, Bivalent-Bottle-Brush Polymers by Graft-through ROMP

  摘要：

  Graft through ring-opening metathesis polymerization (ROMP) using ruthenium N heterocyclic carbene catalysts has enabled the synthesis of bottle-brush polymers with unprecedented ease and control Here we report the first bivalent-brush polymers, these materials were prepared by graft through ROMP of drug-loaded poly(ethylene glycol) (PEG) based macromonomers (MMs) Anticancer drugs doxorubicin (DOX) and camptothecin (CT) were attached to a norbornene alkyne-PEG MM via a photocleavable linker ROMP of either or both drug loaded MMs generated brush homo and copolymers with low polydispersities and defined molecular weights Release of free DOX and CT from these materials was initiated by exposure to 365 nm light All of the CT and DOX polymers were at least 10 fold more toxic to human cancer cells after photoinitiated drug release while a copolymer carrying both CT and DOX displayed 30-fold increased toxicity upon irradiation Graft through ROMP of drug loaded macromonomers provides a general method for the systematic study of structure function relationships for stimuli responsive polymers in biological systems

  DOI：

  10.1021/ma1021506
• 作为产物：
  描述：

  exo-N-(6-hydroxyhexyl)-5-norbornene-2,3-dicarboximide 在 草酰氯 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.55h， 生成 (3aR,4R,7S,7aS)-2-(6-(prop-2-yn-1-ylamino)hexyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
  参考文献：
  名称：

  Drug-Loaded, Bivalent-Bottle-Brush Polymers by Graft-through ROMP

  摘要：

  Graft through ring-opening metathesis polymerization (ROMP) using ruthenium N heterocyclic carbene catalysts has enabled the synthesis of bottle-brush polymers with unprecedented ease and control Here we report the first bivalent-brush polymers, these materials were prepared by graft through ROMP of drug-loaded poly(ethylene glycol) (PEG) based macromonomers (MMs) Anticancer drugs doxorubicin (DOX) and camptothecin (CT) were attached to a norbornene alkyne-PEG MM via a photocleavable linker ROMP of either or both drug loaded MMs generated brush homo and copolymers with low polydispersities and defined molecular weights Release of free DOX and CT from these materials was initiated by exposure to 365 nm light All of the CT and DOX polymers were at least 10 fold more toxic to human cancer cells after photoinitiated drug release while a copolymer carrying both CT and DOX displayed 30-fold increased toxicity upon irradiation Graft through ROMP of drug loaded macromonomers provides a general method for the systematic study of structure function relationships for stimuli responsive polymers in biological systems

  DOI：

  10.1021/ma1021506