(1S,6R)-1-[(1S,2S)-3-(4-acetylpiperazin-1-yl)-1,2-dihydroxy-2-methylpropyl]-6-hydroxy-5-methylidene-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione | 153789-65-2

• 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: (1S,6R)-1-[(1S,2S)-3-(4-acetylpiperazin-1-yl)-1,2-dihydroxy-2-methylpropyl]-6-hydroxy-5-methylidene-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione
• CAS: 153789-65-2
• 化学式: C₁₈H₂₈N₄O₇
• 分子量: 412.443
• InChiKey: OMBUIVLYULPILZ-RUGDWHBFSA-N

物化性质

• 沸点：
  808.2±65.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  152
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,6R)-1-[(1S,2S)-3-(4-acetylpiperazin-1-yl)-1,2-dihydroxy-2-methylpropyl]-6-hydroxy-5-methylidene-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以99%的产率得到2-<4-<(trifluoroacetyl)amino>phenyl>-1-(4-nitrophenyl)-1,2-(E)-epoxypropane
  参考文献：
  名称：

  Esterolytic antibodies induced to haptens with a 1,2-amino alcohol functionality

  摘要：

  Three structurally related haptens 1-3 were designed and synthesized with the goal of generating antibodies for the hydrolysis of ester 4a and amide 4b. These haptens contain a 1,2-amino alcohol functionality which replaces the ester/amide moiety of the substrates. A number of catalytic antibodies were generated, and the Michaelis-Menten kinetics constants of three representative catalytic antibodies induced to each of haptens 1-3 were determined. These catalytic antibodies accelerated the hydrolysis of ester 4a with k(cat)/k(un) = approximately 3 X 10(3), and their catalytic activities were effectively inhibited by the addition of their respective haptens. To evaluate the structural influences of the hapten on antibody binding and specificity as well as catalytic activity, a total of 18 antibodies including the above catalytic antibodies and three representative noncatalytic antibodies from each group were selected, and their dissociation constants with their respective haptens, amide 4b, and products were determined. The studies have shown that (1) the structural variations among the three haptens induce no significant changes in catalytic activity of antibodies while they slightly influence the antibody binding and specificity for the substrate and products and (2) a high probability (reaching nearly 50%) of finding catalytic activity among the monoclonal antibodies raised to hapten 1 is found, suggesting that the induction of a charged complementary amino acid residue in close proximity to the reaction site may be important to generation of catalytic antibodies.

  DOI：

  10.1021/ja00081a008
• 作为产物：
  描述：

  1-乙酰哌嗪 、 bicyclomycin 3'-O-methanesulfonate 以 甲醇 为溶剂， 反应 2.5h， 以29%的产率得到(1S,6R)-1-[(1S,2S)-3-(4-acetylpiperazin-1-yl)-1,2-dihydroxy-2-methylpropyl]-6-hydroxy-5-methylidene-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione
  参考文献：
  名称：

  双环霉素 C(3') 胺的合成和反应性

  摘要：

  制备了新型双环霉素 C(3') 叔胺 6-8，其中吗啉、N-乙酰哌嗪和 N-carboethoxypiperazine 分别安装在双环霉素 (1) 的 C(3') 站点上。以前合成双环霉素 C(3') 胺的尝试没有成功。发现化合物 68 在中性和碱性溶液中比 1 更具反应性。在这些条件下，发生了新的环断裂过程以产生单取代的乙内酰脲（即 15、18、19）和 α-亚甲基-γ-丁内酯（17）。提出了形成乙内酰脲 15、18 和 19 以及丁内酯 17 的途径，并提供了支持这些假设的证据。讨论了这种环断裂过程在未来药物设计中的潜在意义

  DOI：

  10.1021/ja00081a006

文献信息

• Synthesis and reactivity of bicyclomycin C(3') amines
  作者：Hyeung-Geun Park、Marco A. Vela、Harold Kohn

  DOI：10.1021/ja00081a006

  日期：1994.1

  The novel bicyclomycin C(3') tertiary amines 6-8 were prepared in which morpholine, N-acetylpiperazine, and N-carboethoxypiperazine were installed at the C(3') site in bicyclomycin (1), respectively. Previous attempts to synthesize bicyclomycin C(3') amines were unsuccessful. Compounds 68 were found to be more reactive than 1 in neutral and basic solutions. Under these conditions, a novel ring fragmentation

  制备了新型双环霉素 C(3') 叔胺 6-8，其中吗啉、N-乙酰哌嗪和 N-carboethoxypiperazine 分别安装在双环霉素 (1) 的 C(3') 站点上。以前合成双环霉素 C(3') 胺的尝试没有成功。发现化合物 68 在中性和碱性溶液中比 1 更具反应性。在这些条件下，发生了新的环断裂过程以产生单取代的乙内酰脲（即 15、18、19）和 α-亚甲基-γ-丁内酯（17）。提出了形成乙内酰脲 15、18 和 19 以及丁内酯 17 的途径，并提供了支持这些假设的证据。讨论了这种环断裂过程在未来药物设计中的潜在意义
• Esterolytic antibodies induced to haptens with a 1,2-amino alcohol functionality
  作者：Hiroaki Suga、Oguz Ersoy、Takeshi Tsumuraya、Jung Lee、Anthony J. Sinskey、Satoru Masamune

  DOI：10.1021/ja00081a008

  日期：1994.1

  Three structurally related haptens 1-3 were designed and synthesized with the goal of generating antibodies for the hydrolysis of ester 4a and amide 4b. These haptens contain a 1,2-amino alcohol functionality which replaces the ester/amide moiety of the substrates. A number of catalytic antibodies were generated, and the Michaelis-Menten kinetics constants of three representative catalytic antibodies induced to each of haptens 1-3 were determined. These catalytic antibodies accelerated the hydrolysis of ester 4a with k(cat)/k(un) = approximately 3 X 10(3), and their catalytic activities were effectively inhibited by the addition of their respective haptens. To evaluate the structural influences of the hapten on antibody binding and specificity as well as catalytic activity, a total of 18 antibodies including the above catalytic antibodies and three representative noncatalytic antibodies from each group were selected, and their dissociation constants with their respective haptens, amide 4b, and products were determined. The studies have shown that (1) the structural variations among the three haptens induce no significant changes in catalytic activity of antibodies while they slightly influence the antibody binding and specificity for the substrate and products and (2) a high probability (reaching nearly 50%) of finding catalytic activity among the monoclonal antibodies raised to hapten 1 is found, suggesting that the induction of a charged complementary amino acid residue in close proximity to the reaction site may be important to generation of catalytic antibodies.