(S)-4-amino-1,1,1,2,2,-pentafluoro-5-methyl-3-hexanone hydrochloride | 135837-29-5

• 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: (S)-4-amino-1,1,1,2,2,-pentafluoro-5-methyl-3-hexanone hydrochloride
• 英文别名: H-Val-CF2CF3.hydrochloride；(4S)-4-amino-1,1,1,2,2-pentafluoro-5-methylhexan-3-one;hydrochloride
• CAS: 135837-29-5
• 化学式: C₇H₁₀F₅NO*ClH
• 分子量: 255.615
• InChiKey: WAVLGLCPGHJLPW-WCCKRBBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-4-amino-1,1,1,2,2,-pentafluoro-5-methyl-3-hexanone hydrochloride 、 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (t-Butoxycarbonyl)-l-valyl-N-(1,1,1,2,2-pentafluoro-5-methyl-3-oxo-4-hexanyl)proline amide
  参考文献：
  名称：

  Inhibition of Human Neutrophil Elastase with Peptidyl Electrophilic Ketones. 2. Orally Active PG-Val-Pro-Val Pentafluoroethyl Ketones

  摘要：

  Valylprolylvalyl pentafluoroethyl ketones with different N-protecting groups were evaluated in vitro and in vivo as inhibitors of human neutrophil elastase (HNE). Several of these compounds were found to be orally active in HNE-induced rat and hamster lung hemorrhage models. The compound with 4-(4-morpholinylcarbonyl)benzoyl as the protecting group, 71 (MDL 101,146), was studied in greater detail. Hydration and epimerization studies were performed on 71 and related compounds in various media, including human blood serum. Highperformance liquid chromatography studies on a reversed-phase system as a measure of the Lipophilicity of 71. and related compounds revealed a small range of relative retention times wherein the orally active compounds fell. The K-i value determined for 71 vs HNE was 25 nM.

  DOI：

  10.1021/jm00052a013
• 作为产物：
  描述：

  N-Boc-L-缬氨酸 在 N-甲基吗啉 、 盐酸 、 methyllithium lithium bromide 、 氯甲酸异丁酯 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (S)-4-amino-1,1,1,2,2,-pentafluoro-5-methyl-3-hexanone hydrochloride
  参考文献：
  名称：

  Efficient preparation of peptidyl pentaflouroethly ketones

  摘要：

  A concise method for the preparation of alpha-amino pentafluoroethyl ketone salts from amino acids is described. These intermediates are useful for the preparation of peptidyl pentafluoroethyl ketones.

  DOI：

  10.1016/s0040-4039(00)92063-x

文献信息

• Orally-active elastase inhibitors
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05478811A1

  公开（公告）日：1995-12-26

  This invention relates to novel morpholinourea and related derivatives of pentafluoroethyl peptides which are orally active elastase inhibitors. These compounds are useful in the treatment of various inflammatory diseases and emphysema.

  本发明涉及一种新型的吗啉脲和五氟乙基肽相关衍生物，它们是口服活性的弹性蛋白酶抑制剂。这些化合物在治疗各种炎症性疾病和肺气肿方面具有用途。
• Perfluoroalkyl ketone inhibitors of elastase and processes for making
  申请人：Hoechst Marion Roussel, Inc.

  公开号：US06008196A1

  公开（公告）日：1999-12-28

  This invention relates to compounds which are inhibitors of elastase, particularly human neutrophil elastase, and to novel processes for making the same. As inhibitors of human neutrophil elastase, the compounds are useful in the treatment of a patient afflicted with a neutrophil associated inflammatory disease.

  本发明涉及一种抑制弹性蛋白酶的化合物，特别是人类中性粒细胞弹性蛋白酶的抑制剂，并涉及制备该化合物的新型方法。作为人类中性粒细胞弹性蛋白酶的抑制剂，这些化合物在治疗患有中性粒细胞相关炎症疾病的患者中非常有用。