1-(7-((1-azido-3,6,9,12-tetraoxapentadecan-15-yl)oxy)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-benzoylpiperazin-1-yl)ethane-1,2-dione | 1430096-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1-(7-((1-azido-3,6,9,12-tetraoxapentadecan-15-yl)oxy)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-benzoylpiperazin-1-yl)ethane-1,2-dione
• CAS: 1430096-94-8
• 化学式: C₃₂H₄₁N₇O₉
• 分子量: 667.719
• InChiKey: DYRXQTOYTHEBNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  48.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  190.51
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-(7-((1-azido-3,6,9,12-tetraoxapentadecan-15-yl)oxy)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-benzoylpiperazin-1-yl)ethane-1,2-dione 、 1-(4-(2,5,8,11,14-pentaoxaheptadec-16-yn-1-yl)benzoyl)azetidin-2-one 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三(3-羟丙基三唑甲基)胺 作用下， 以 水 、 叔丁醇 为溶剂， 反应 3.0h， 以69%的产率得到1-(4-benzoylpiperazin-1-yl)-2-[4-methoxy-7-[3-[2-[2-[2-[2-[4-[2-[2-[2-[2-[[4-(2-oxoazetidine-1-carbonyl)phenyl]methoxy]ethoxy]ethoxy]ethoxy]ethoxymethyl]triazol-1-yl]ethoxy]ethoxy]ethoxy]ethoxy]propoxy]-1H-pyrrolo[2,3-c]pyridin-3-yl]ethane-1,2-dione
  参考文献：
  名称：

  Chemically Programmed Antibodies As HIV-1 Attachment Inhibitors

  摘要：

  Herein, we describe the design and application of two small-molecule anti-HIV compounds for the creation of chemically programmed antibodies. N-Acyl-beta-lactam derivatives of two previously described molecules BMS-378806 and BMS-488043 that inhibit the interaction between HIV-1 gp120 and T-cells were synthesized and used to program the binding activity of aldolase antibody 38C2. Discovery of a successful linkage site to BMS-488043 allowed for the synthesis of chemically programmed antibodies with affinity for HIV-1 gp120 and potent HIV-1 neutralization activity. Derivation of a successful conjugation strategy for this family of HIV-1 entry inhibitors enables its application in chemically programmed antibodies and vaccines and may facilitate the development of novel bispecific antibodies and topical microbicides.

  DOI：

  10.1021/ml400097z
• 作为产物：
  描述：

  4-bromo-7-prop-2-enoxy-1H-pyrrolo[2,3-c]pyridine 在 aluminum (III) chloride 、 copper(l) iodide 、 dimethyl sulfide borane 、 四丁基氟化铵 、 水 、 sodium hydride 、 乙二胺 、 N,N-二异丙基乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 74.5h， 生成 1-(7-((1-azido-3,6,9,12-tetraoxapentadecan-15-yl)oxy)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-benzoylpiperazin-1-yl)ethane-1,2-dione
  参考文献：
  名称：

  Chemically Programmed Antibodies As HIV-1 Attachment Inhibitors

  摘要：

  Herein, we describe the design and application of two small-molecule anti-HIV compounds for the creation of chemically programmed antibodies. N-Acyl-beta-lactam derivatives of two previously described molecules BMS-378806 and BMS-488043 that inhibit the interaction between HIV-1 gp120 and T-cells were synthesized and used to program the binding activity of aldolase antibody 38C2. Discovery of a successful linkage site to BMS-488043 allowed for the synthesis of chemically programmed antibodies with affinity for HIV-1 gp120 and potent HIV-1 neutralization activity. Derivation of a successful conjugation strategy for this family of HIV-1 entry inhibitors enables its application in chemically programmed antibodies and vaccines and may facilitate the development of novel bispecific antibodies and topical microbicides.

  DOI：

  10.1021/ml400097z