3,4-dihydro-N-[(2S)-3-[(2-methoxyphenyl)thio]-2-methylpropyl]-2H-(3S)-1,5-benzoxathiepin-3-amine | 866760-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4-dihydro-N-[(2S)-3-[(2-methoxyphenyl)thio]-2-methylpropyl]-2H-(3S)-1,5-benzoxathiepin-3-amine
• 英文别名: (3S)-N-{(2S)-3-[(2-methoxyphenyl)sulfanyl]-2-methylpropyl}-3,4-dihydro-2H-1,5-benzoxathiepin-3-amine；3-(R)-[3-(2-methoxyphenylthio)-2-(R)-methylpropyl]amino-3,4-dihydro-2H-1,5-benzoxathiepine；(3S)-N-[(2S)-3-(2-methoxyphenyl)sulfanyl-2-methylpropyl]-3,4-dihydro-2H-1,5-benzoxathiepin-3-amine
• CAS: 866760-21-6
• 化学式: C₂₀H₂₅NO₂S₂
• 分子量: 375.556
• InChiKey: HZQHAAFWVRDHMZ-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S)-3-[(2-methoxyphenyl)thio]-2-methyl-propanal 、 3-(S)-amino-1,5-benzoxathiepine 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 3,4-dihydro-N-[(2S)-3-[(2-methoxyphenyl)thio]-2-methylpropyl]-2H-(3S)-1,5-benzoxathiepin-3-amine
  参考文献：
  名称：

  Sodium Late Current Blockers in Ischemia Reperfusion: Is the Bullet Magic?

  摘要：

  We describe the discovery of the first selective, potent, and voltage-dependent inhibitor of the late current mediated by the cardiac sodium channel Na(V)1.5. The compound 3,4-dihydro-N-[(2S)-3-[(2-methoxyphenyl)thio]-2-methylpropyll-2H-(3R)-1,5-benzoxathiepin-3-amine, 2a (F 15845), was identified from a novel family of 3-amino-1,5-benzoxathiepine derivatives. The late sodium current inhibition and antiischemic effects of 2a were studied in various models in vitro and in vivo. In a rabbit model of ischemia-reperfusion, 2a exhibited more potent antiischemic effects than reference compounds KC 12291, ranolazine, and ivabradine. Thus, after a single administration, 2a almost abolished ST segment elevation in response to a transient coronary occlusion. Further, the antiischemic activity of 2a is maintained over a wide range of doses and is not associated with any hemodynamic changes, contrary to conventional antiischemic agents. The unique pharmacological profile of 2a opens new and promising opportunities for the treatment of ischemic heart diseases.

  DOI：

  10.1021/jm800100z

文献信息

• Synthesising Method and Benzoxathiepine Intermediates
  申请人：Vacher Bernard

  公开号：US20080234499A1

  公开（公告）日：2008-09-25

  The invention relates to preparing derivatives of formula (1), wherein, in particular R 1 and R 2 , identical or different, represent a hydrogen, flourine or chlorine atom, a hydroxy group, an alkyl radical and an alkoxy radical, R 3 is an alkyl radical, a hydroxy group, or a methoxy radical, R 4 is a hydrogen atom or a methyl radical and R 5 and R 6 , identical or different, represent a hydrogen atom, an alkyl radical, an alkoxy radical, an alkylthio radical, and an alkylamino radical. The inventive method consists in reducing an amid of formula (9).

  该发明涉及制备式（1）的衍生物，其中，特别是R1和R2，相同或不同，代表氢、氟或氯原子、羟基、烷基基团和烷氧基团，R3是烷基基团、羟基或甲氧基团，R4是氢原子或甲基基团，R5和R6，相同或不同，代表氢原子、烷基基团、烷氧基团、烷硫基团和烷基氨基团。该创新方法在于还原式（9）的酰胺。
• PROCEDE DE SYNTHESE ET INTERMEDIAIRES DE BENZOXATHIEPINES
  申请人：PIERRE FABRE MEDICAMENT

  公开号：EP1735297B1

  公开（公告）日：2007-10-03
• US7902381B2
  申请人：——

  公开号：US7902381B2

  公开（公告）日：2011-03-08