tert-butyl (S)-1-((E)-((8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-7,8,9,11-tetrahydro-1H-cyclopenta[a]phenanthren-3 (2H,6H,10H,12H,13H,14H,15H,16H,17H)-ylidene)aminooxy)-3-methyl-1-oxobutan-2-ylcarbamate | 1364711-11-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: tert-butyl (S)-1-((E)-((8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-7,8,9,11-tetrahydro-1H-cyclopenta[a]phenanthren-3 (2H,6H,10H,12H,13H,14H,15H,16H,17H)-ylidene)aminooxy)-3-methyl-1-oxobutan-2-ylcarbamate
• 英文别名: tert-butyl (S)-1-((E)-((8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-7,8,9,11-tetrahydro-1H-cyclopenta[a]phenanthren-3(2H,6H,10H,12H,13H,14H,15H,16H,17H)-ylidene)aminooxy)-3-methyl-1-oxobutan-2-ylcarbamate；[(E)-[(8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ylidene]amino] (2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 1364711-11-4
• 化学式: C₃₁H₄₈N₂O₅
• 分子量: 528.733
• InChiKey: BVVZDYAFJRFFFG-JAOSEMGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-1-((E)-((8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-7,8,9,11-tetrahydro-1H-cyclopenta[a]phenanthren-3 (2H,6H,10H,12H,13H,14H,15H,16H,17H)-ylidene)aminooxy)-3-methyl-1-oxobutan-2-ylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 pregn-4-ene-3,20-dione 3-O-(L-valine)-E-oxime
  参考文献：
  名称：

  Water-Soluble Progesterone Analogues Are Effective, Injectable Treatments in Animal Models of Traumatic Brain Injury

  摘要：

  After more than 30 years of research and 30 failed clinical trials with as many different treatments, progesterone is the first agent to demonstrate robust clinical efficacy as a treatment for traumatic brain injuries. It is currently being investigated in two, independent phase III clinical trials in hospital settings; however, it presents a formidable solubility challenge that has so far prevented the identification of a formulation that would be suitable for emergency field response use or battlefield situations. Accordingly, we have designed and tested a novel series of water-soluble analogues that address this critical need. We report here the synthesis of C-20 oxime conjugates of progesterone as therapeutic agents for traumatic brain injuries with comparable efficacy in animal models of traumatic brain injury and improved solubility and pharmacokinetic profiles. Pharmacodynamic analysis reveals that a nonprogesterone steroidal analogue may be primarily responsible for the observed activity.

  DOI：

  10.1021/ml200303r
• 作为产物：
  描述：

  (8S,9S,10R,13S,14S,17S,E)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one oxime 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 20.5h， 生成 tert-butyl (S)-1-((E)-((8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-7,8,9,11-tetrahydro-1H-cyclopenta[a]phenanthren-3 (2H,6H,10H,12H,13H,14H,15H,16H,17H)-ylidene)aminooxy)-3-methyl-1-oxobutan-2-ylcarbamate
  参考文献：
  名称：

  PROGESTERONE ANALOGS AND USES RELATED THERETO

  摘要：

  该披露涉及孕酮衍生物及其相关用途。在某些实施例中，该披露涉及本文披露的化合物及其用途，用于管理由创伤性脑损伤或中风引起的炎症。

  公开号：

  US20130210785A1

文献信息

• [EN] PROGESTERONE PHOSPHATE ANALOGS AND USES RELATED THERETO<br/>[FR] ANALOGUES DE PHOSPHATES DE PROGESTÉRONE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2015023593A1

  公开（公告）日：2015-02-19

  This disclosure relates to progesterone phophate derivatives and uses related thereto. In certain embodiments, the disclosure relates to compounds disclosed herein and uses for managing inflammation such as those resulting from traumatic brain injury or stroke.

  本公开涉及孕酮磷酸盐衍生物及其相关用途。在某些实施方式中，本公开涉及本文所披露的化合物及其用于管理炎症的用途，例如由创伤性脑损伤或中风引起的炎症。
• Progesterone Phosphate Analogs and Uses Related Thereto
  申请人：EMORY UNIVERSITY

  公开号：US20160194351A1

  公开（公告）日：2016-07-07

  This disclosure relates to progesterone phophate derivatives and uses related thereto. In certain embodiments, the disclosure relates to compounds disclosed herein and uses for managing inflammation such as those resulting from traumatic brain injury or stroke.

  本公开涉及孕酮磷酸酯衍生物及其相关用途。在某些实施例中，本公开涉及本文所披露的化合物及其用于管理炎症，例如由创伤性脑损伤或中风引起的炎症。
• Progesterone analogs and uses related thereto
  申请人：EMORY UNIVERSITY

  公开号：US10336787B2

  公开（公告）日：2019-07-02

  This disclosure relates to progesterone derivatives and uses related thereto. In certain embodiments, the disclosure relates to compounds disclosed herein and uses for managing inflammation resulting from traumatic brain injury or stroke.

  本公开涉及黄体酮衍生物及其相关用途。在某些实施方案中，本公开涉及本文公开的化合物以及用于控制创伤性脑损伤或中风引起的炎症的用途。
• Progesterone phosphate analogs and uses related thereto
  申请人：EMORY UNIVERSITY

  公开号：US11053276B2

  公开（公告）日：2021-07-06

  This disclosure relates to progesterone phophate derivatives and uses related thereto. In certain embodiments, the disclosure relates to compounds disclosed herein and uses for managing inflammation such as those resulting from traumatic brain injury or stroke.

  本公开涉及黄体酮磷酸盐衍生物及其相关用途。在某些实施方案中，本公开涉及本文公开的化合物以及用于控制炎症（如脑外伤或中风引起的炎症）的用途。
• PROGESTERONE PHOSPHATE ANALOGS AND USES RELATED THERETO
  申请人：EMORY UNIVERSITY

  公开号：US20200255470A1

  公开（公告）日：2020-08-13

  This disclosure relates to progesterone phophate derivatives and uses related thereto. In certain embodiments, the disclosure relates to compounds disclosed herein and uses for managing inflammation such as those resulting from traumatic brain injury or stroke.