Caprazene | 740805-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Caprazene
• 英文别名: (2S)-2-[[(2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxyoxolan-2-yl]oxy-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-1,4-dimethyl-3-oxo-2,7-dihydro-1,4-diazepine-5-carboxylic acid
• CAS: 740805-17-8
• 化学式: C₂₂H₃₁N₅O₁₂
• 分子量: 557.5
• InChiKey: NNRRJUQQUMBTMH-LCMDQALXSA-N

物化性质

• 熔点：
  210-211 °C (decomp)(Solv: acetone (67-64-1); water (7732-18-5))
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -7
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  245
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  (2S,5S,6S)-2-[(S)-[(2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxyoxolan-2-yl]oxy-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-1,4-dimethyl-6-[(3S)-15-methyl-3-[(3S)-3-methyl-5-oxo-5-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxypentanoyl]oxyhexadecanoyl]oxy-3-oxo-1,4-diazepane-5-carboxylic acid 在 丙酮 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以to afford 96.3 mg of caprazene as a colorless solid (99% yield)的产率得到Caprazene
  参考文献：
  名称：

  Antibacterial agent and therapeutic agent for Johne's disease containing the same

  摘要：

  本发明提供了一种针对分枝杆菌亚种结核分枝杆菌（Mycobacterium avium subsp. paratuberculosis）具有高抗菌活性的抗菌剂。具体而言，本发明的抗菌剂具有高抗菌活性的是一种卡普拉扎霉素衍生物，例如以下一般式（II）所表示的衍生物：其中Me是甲基基团；R1是直链或基本直链的烷基基团，具有5到21个碳原子，直链或基本直链的烯基基团，具有5到21个碳原子，具有5到12个碳原子的环烷基团，或在对位上用具有1到14个碳原子的直链烷基团，具有1到9个碳原子的直链烷氧基团或具有5到12个碳原子的环烷基团取代的苯基团。

  公开号：

  US20090209744A1

文献信息

• Caprazene as novel compound and derivatives thereof, and caprazol as novel compound and derivatives thereof
  申请人：Miyake Toshiaki

  公开号：US20060178319A1

  公开（公告）日：2006-08-10

  Caprazene and caprazol could be synthesized by hydrolysis of a caprazamycin. There could be synthesized a caprazene-1′″- amide derivative of the formula (II) and a caprazene-1′″-ester derivative of the formula (III) from caprazene. Further, there could be synthesized a caprazol-1′″-amide derivative of the formula (V) and a caprazol-1′″-amide-3′″-ester derivative and a caprazol-3′″-ester derivative, etc. from caprazol. Furthermore, an imidazolidinone derivative could be synthesized from the ring-opened product of the 1,4-diazepinone ring of caprazol. The novel caprazene derivative, novel caprazol derivative and novel imidazolidinone derivative now synthesized exhibit excellent antibacterial activities against a variety of bacteria, including acid-fast bacteria.

  Caprazene和caprazol可以通过水解caprazamycin来合成。可以从caprazene合成公式（II）的caprazene-1′″-酰胺衍生物和公式（III）的caprazene-1′″-酯衍生物。此外，可以从caprazol合成公式（V）的caprazol-1′″-酰胺衍生物，caprazol-1′″-酰胺-3′″-酯衍生物和caprazol-3′″-酯衍生物等。此外，可以从caprazol的1,4-二氮杂环酮环的开环产物合成咪唑烷酮衍生物。现在合成的新型caprazene衍生物，新型caprazol衍生物和新型咪唑烷酮衍生物对各种细菌，包括抗酸菌，具有优异的抗菌活性。
• Antibacterial agent and therapeutic agent for johne's disease containing the same
  申请人：Microbial Chemistry Research Foundation

  公开号：US08058247B2

  公开（公告）日：2011-11-15

  An antibacterial agent having high antibacterial activity against Mycobacterium avium subsp. paratuberculosis is provided. Specifically, the antibacterial agent of the present invention having high antibacterial activity against Mycobacterium avium subsp. paratuberculosis is a caprazamycin derivative represented, for example, by the following general formula (II): wherein Me is a methyl group; and R1 is a straight or substantially straight chain alkyl group having 5 to 21 carbon atoms, a straight or substantially straight chain alkenyl group having 5 to 21 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, or a phenyl group substituted at the para-position with a straight chain alkyl group having 1 to 14 carbon atoms, a straight chain alkoxy group having 1 to 9 carbon atoms or a cycloalkyl group having 5 to 12 carbon atoms.

  本发明提供一种对分枝杆菌亚种牛结核分枝杆菌具有高抗菌活性的抗菌剂。具体而言，本发明具有高抗菌活性的抗菌剂是一种卡普拉唑霉素衍生物，例如以下通式（II）所表示：其中Me是甲基基团；R1是一种直链或基本直链的烷基基团，具有5到21个碳原子，一种直链或基本直链的烯基基团，具有5到21个碳原子，一种具有5到12个碳原子的环烷基团，或者在对位上用一种直链烷基基团，具有1到14个碳原子，一种直链烷氧基基团，具有1到9个碳原子或者一种具有5到12个碳原子的环烷基团进行取代的苯基团。
• CAPRAZENE AS A NOVEL COMPOUND AND DERIVATIVES THEREOF, AND CAPRAZOL AS A NOVEL COMPOUND AND DERIVATIVES THEREOF
  申请人：MEIJI SEIKA KAISHA, LTD.

  公开号：US20140005371A1

  公开（公告）日：2014-01-02

  A caprazene compound is provided which is the compound represented by the following formula (Ia): wherein Me stands for methyl group, and A is a hydrogen atom, and wherein said compound has the 1 H-NMR and 13 C-NMR data as set forth in Table 15.

  提供了一种caprazene化合物，其化学式表示如下（Ia）： 其中Me代表甲基基团，A代表氢原子，该化合物在表15中具有1H-NMR和13C-NMR数据。
• Antibacterial agent and therapeutic agent for Johne's disease containing the same
  申请人：Takahashi Yoshiaki

  公开号：US20090209744A1

  公开（公告）日：2009-08-20

  An antibacterial agent having high antibacterial activity against Mycobacterium avium subsp. paratuberculosis is provided. Specifically, the antibacterial agent of the present invention having high antibacterial activity against Mycobacterium avium subsp. paratuberculosis is a caprazamycin derivative represented, for example, by the following general formula (II): wherein Me is a methyl group; and R 1 is a straight or substantially straight chain alkyl group having 5 to 21 carbon atoms, a straight or substantially straight chain alkenyl group having 5 to 21 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, or a phenyl group substituted at the para-position with a straight chain alkyl group having 1 to 14 carbon atoms, a straight chain alkoxy group having 1 to 9 carbon atoms or a cycloalkyl group having 5 to 12 carbon atoms.

  本发明提供了一种针对分枝杆菌亚种结核分枝杆菌（Mycobacterium avium subsp. paratuberculosis）具有高抗菌活性的抗菌剂。具体而言，本发明的抗菌剂具有高抗菌活性的是一种卡普拉扎霉素衍生物，例如以下一般式（II）所表示的衍生物：其中Me是甲基基团；R1是直链或基本直链的烷基基团，具有5到21个碳原子，直链或基本直链的烯基基团，具有5到21个碳原子，具有5到12个碳原子的环烷基团，或在对位上用具有1到14个碳原子的直链烷基团，具有1到9个碳原子的直链烷氧基团或具有5到12个碳原子的环烷基团取代的苯基团。
• ANTI-XDR-TB DRUG, ANTI-MDR-TB DRUG, AND COMBINATION ANTI-TUBERCULOSIS DRUG
  申请人：TAKAHASHI YOSHIAKI

  公开号：US20110237530A1

  公开（公告）日：2011-09-29

  A method for treating an individual infected with XDR-TB, the method including administering to the individual an anti-XDR-TB drug which comprises a compound having a structure expressed by Structural Formula (1) below: