(-)-(2S)-4-acetyl-2-<(methanesulfonyl)oxy>-6-hydroxy-1,2,3,4-tetrahydrobenzoquinoline | 144192-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (-)-(2S)-4-acetyl-2-<(methanesulfonyl)oxy>-6-hydroxy-1,2,3,4-tetrahydrobenzoquinoline
• 英文别名: (-)-(2S)-3-acetyl-2-<(methylsulfonyl)oxy>-5-hydroxy-1,2,3,4-tetrahydrobenzoquinoline；(-)-(2S)-3-acetyl-2-[(methylsulfonyl)oxy]-5-hydroxy-1,2,3,4-tetrahydrobenzo[f]quinoline；[(2S)-4-acetyl-6-hydroxy-2,3-dihydro-1H-benzo[f]quinolin-2-yl] methanesulfonate
• CAS: 144192-02-9
• 化学式: C₁₆H₁₇NO₅S
• 分子量: 335.381
• InChiKey: AMPGTOIOUUESEM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(2S)-4-acetyl-2-<(methanesulfonyl)oxy>-6-hydroxy-1,2,3,4-tetrahydrobenzoquinoline 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 (+)-(8bR,9aS)-2-<(1H-indol-2-yl)carbonyl>-1,2,9,9a-tetrahydrocyclopropabenzindol-4-one
  参考文献：
  名称：

  CBI-PDE-I-二聚体的合成和生化评估，CBI-PDE-I-二聚体是（+）-CC-1065的苯甲酰化类似物，在小鼠中也产生延迟的毒性。

  摘要：

  开发了一种实用的CBI（2）合成方法，并将其应用于CC-1065的苯甲酰化类似物的合成，包括CBI-PDE-I-二聚体（13）和CBI-双吲哚[（+）-A'BC]。显示CBI-PDE-I-二聚体具有与（+）-CC-1065类似的DNA序列选择性和对DNA的结构作用。特别重要的是观察到的与（+）-CC-1065的未烷基化亚基的吡咯烷环相关的双链缠绕效应，并可能与其延迟的毒性作用有关。还比较了CBI-PDE-I-二聚体与（+）-CC-1065在解旋酶II抑制双链解开和T4连接酶进行切口密封方面的效果，发现在数量上相似。CBI化合物的体外和体内效力与相应的CPI衍生物非常接近。最后，

  DOI：

  10.1021/jm00066a004
• 作为产物：
  描述：

  3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydro-4H-benzoquinoline 在 4-二甲氨基吡啶 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 (-)-(2S)-4-acetyl-2-<(methanesulfonyl)oxy>-6-hydroxy-1,2,3,4-tetrahydrobenzoquinoline
  参考文献：
  名称：

  Synthesis of CBI-PDE-I-dimer, the benzannelated analog of CC-1065

  摘要：

  A practical synthesis of CBI (2), utilizing inexpensive starting materials, was developed and applied to the synthesis of benzannelated analogs of CC-1065, in particular CBI-PDE-I-dimer (13) and CBI-bis-indole (17). While a Sharpless asymmetric dihydroxylation reaction proved effective at providing optically active intermediates, a more classical resolution procedure was used to prepare materials of higher optical purity. A novel cyclization employing a six-membered-ring intermediate (12) was employed to construct the cyclopropyl ring in CBI. Like CC-1065, CBI-PDE-I-dimer appears to cause delayed toxicity in mice.

  DOI：

  10.1021/jo00049a035

文献信息

• Synthesis of CBI-PDE-I-dimer, the benzannelated analog of CC-1065
  作者：Paul A. Aristoff、Paul D. Johnson

  DOI：10.1021/jo00049a035

  日期：1992.11

  A practical synthesis of CBI (2), utilizing inexpensive starting materials, was developed and applied to the synthesis of benzannelated analogs of CC-1065, in particular CBI-PDE-I-dimer (13) and CBI-bis-indole (17). While a Sharpless asymmetric dihydroxylation reaction proved effective at providing optically active intermediates, a more classical resolution procedure was used to prepare materials of higher optical purity. A novel cyclization employing a six-membered-ring intermediate (12) was employed to construct the cyclopropyl ring in CBI. Like CC-1065, CBI-PDE-I-dimer appears to cause delayed toxicity in mice.
• Synthesis and biochemical evaluation of the CBI-PDE-I-dimer, a benzannelated analog of (+)-CC-1065 that also produces delayed toxicity in mice
  作者：Paul A. Aristoff、Paul D. Johnson、Daekyu Sun、Laurence H. Hurley

  DOI：10.1021/jm00066a004

  日期：1993.7

  A practical synthesis of CBI (2) was developed and applied to the synthesis of benzannelated analogs of CC-1065, including CBI-PDE-I-dimer (13) and CBI-bis-indole [(+)-A'BC]. The CBI-PDE-I-dimer was shown to have similar DNA sequence selectivity and structural effects on DNA as (+)-CC-1065. Of particular importance was the observed duplex winding effect that has been associated with the pyrrolidine

  开发了一种实用的CBI（2）合成方法，并将其应用于CC-1065的苯甲酰化类似物的合成，包括CBI-PDE-I-二聚体（13）和CBI-双吲哚[（+）-A'BC]。显示CBI-PDE-I-二聚体具有与（+）-CC-1065类似的DNA序列选择性和对DNA的结构作用。特别重要的是观察到的与（+）-CC-1065的未烷基化亚基的吡咯烷环相关的双链缠绕效应，并可能与其延迟的毒性作用有关。还比较了CBI-PDE-I-二聚体与（+）-CC-1065在解旋酶II抑制双链解开和T4连接酶进行切口密封方面的效果，发现在数量上相似。CBI化合物的体外和体内效力与相应的CPI衍生物非常接近。最后，