(2S,4S,2'S)-Itraconazole | 848585-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (2S,4S,2'S)-Itraconazole
• 英文别名: 2-[(2S)-butan-2-yl]-4-[4-[4-[4-[[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one
• CAS: 848585-71-7
• 化学式: C₃₅H₃₈Cl₂N₈O₄
• 分子量: 705.644
• InChiKey: VHVPQPYKVGDNFY-PGTZCRIKSA-N

物化性质

• 沸点：
  850.0±75.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (S)-2-(sec-butyl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 、 (2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-4-tozyloxymethyl-1,3-dioxolane 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 以62%的产率得到(2S,4S,2'S)-Itraconazole
  参考文献：
  名称：

  Impact of Absolute Stereochemistry on the Antiangiogenic and Antifungal Activities of Itraconazole

  摘要：

  Itraconazole is used clinically as an antifungal agent and has recently been shown to possess antiangiogenic acitivity. Itraconazole has three chiral centers that give rise to eight stereoisomers. The complete role of stereochemistry in the two activities of itraconazole, however, has not been addressed adequately. For the first time, all eight stereoisomers of itraconazole (la h) have been synthesized and evaluated for activity against human endothelial cell proliferation and for antifungal activity against five fungal strains. Distinct antiangiogenic and antifungal activity profiles of the trans stereoisomers, especially 1e and If, suggest different molecular mechanisms underlying the antiangiogenic and antifungal activities of itraconazole.

  DOI：

  10.1021/ml1000068

文献信息

• CHIRALLY PURE ISOMERS OF ITRACONAZOLE FOR USE AS ANGIOGENESIS INHIBITORS
  申请人：Liu Jun O.

  公开号：US20130102614A1

  公开（公告）日：2013-04-25

  Described herein are methods of inhibiting angiogenesis, and treating and preventing disorders associated with angiogenesis by administering anti-angiogenesis compounds to a subject.

  本文描述了通过向受试者施用抗血管生成化合物来抑制血管生成并治疗和预防与血管生成相关的疾病的方法。
• US9095589B2
  申请人：——

  公开号：US9095589B2

  公开（公告）日：2015-08-04
• [EN] CHIRALLY PURE ISOMERS OF ITRACONAZOLE FOR USE AS ANGIOGENESIS INHIBITORS<br/>[FR] ISOMÈRES CHIRALEMENT PURS D'ITRACONAZOLE DESTINÉS À ÊTRE UTILISÉS COMME INHIBITEURS D'ANGIOGENÈSE
  申请人：UNIV JOHNS HOPKINS MED

  公开号：WO2013155218A1

  公开（公告）日：2013-10-17

  Described herein are methods of inhibiting angiogenesis, and treating and preventing disorders associated with angiogenesis by administering anti-angiogenesis compounds to a subject.