5-ethyl-1-(2-iodophenyl)-4-heptanone | 872835-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-ethyl-1-(2-iodophenyl)-4-heptanone
• 英文别名: 4-Heptanone, 5-ethyl-1-(2-iodophenyl)-；5-ethyl-1-(2-iodophenyl)heptan-4-one
• CAS: 872835-39-7
• 化学式: C₁₅H₂₁IO
• 分子量: 344.236
• InChiKey: BZLGTUVEDOKUAG-UHFFFAOYSA-N

物化性质

• 沸点：
  388.4±25.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-ethyl-1-(2-iodophenyl)-4-heptanone 、 甲基三苯基溴化膦 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 2.0h， 以76%的产率得到1-[4-(1-ethylpropyl)-4-penten-1-yl]-2-iodobenzene
  参考文献：
  名称：

  [EN] 2,3-BENZOXAZIN DERIVATIVES AS NON-STEROIDAL GLUCOCORTICOID RECEPTOR MODULATORS
  [FR] DERIVES DE 2,3-BENZOXAZINE UTILISES EN TANT QUE MODULATEURS NON STEROIDIENS DU RECEPTEUR GLUCOCORTICOIDE

  摘要：

  本发明提供了式(I)的化合物，其中R1代表1-乙基丙基、1-甲基乙基或2-甲基丙基；或其生理功能衍生物；包括这些化合物的药物组合物，这些化合物用于制造药物，特别用于治疗炎症和/或过敏症状，以及用于制备这些化合物的过程和制造这些化合物的化学中间体。

  公开号：

  WO2006000398A1
• 作为产物：
  描述：

  1-ethylpropylzinc bromide 在 四(三苯基膦)钯 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 6.33h， 生成 5-ethyl-1-(2-iodophenyl)-4-heptanone
  参考文献：
  名称：

  Dissociated Nonsteroidal Glucocorticoid Receptor Modulators; Discovery of the Agonist Trigger in a Tetrahydronaphthalene−Benzoxazine Series

  摘要：

  The tetrahydronaphthalene-benzoxazine glucocorticoid receptor (GR) partial agonist 4b was optimized to produce potent full agonists of GR. Aromatic ring substitution of the tetrahydronaphthalene leads to weak GR antagonists. Discovery of an "agonist trigger" substituent on the saturated ring of the tetrahydronaphthalene leads to increased potency and efficacious GR agonism. These compounds are efficacy selective in an NFkB GR agonist assay ( representing transrepression effects) over an MMTV GR agonist assay ( representing transactivation effects). 52 and 60 have NFkB pIC(50) = 8.92 (105%) and 8.69 (92%) and MMTV pEC(50) = 8.20 (47%) and 7.75 (39%), respectively. The impact of the trigger substituent on agonism is modeled within GR and discussed. 36, 52, and 60 have anti-inflammatory activity in a mouse model of inflammation after topical dosing with 52 and 60, having an effect similar to that of dexamethasone. The original lead was discovered by a manual agreement docking method, and automation of this method is also described.

  DOI：

  10.1021/jm060302x

文献信息

• [EN] 2,3-BENZOXAZIN DERIVATIVES AS NON-STEROIDAL GLUCOCORTICOID RECEPTOR MODULATORS<br/>[FR] DERIVES DE 2,3-BENZOXAZINE UTILISES EN TANT QUE MODULATEURS NON STEROIDIENS DU RECEPTEUR GLUCOCORTICOIDE
  申请人：GLAXO GROUP LTD

  公开号：WO2006000398A1

  公开（公告）日：2006-01-05

  The present invention provides compounds of formula (I), wherein R1 represents 1-ethylpropyl, 1-methylethyl or 2-methylpropyl; or a physiologically functional derivative thereof; pharmaceutical compositions comprising the compounds, the use of the compounds for the manufacture of medicaments particularly for the treatment of inflammatory and/or allergic conditions, processes for the preparation of the compounds, and chemical intermediates in the processes for the manufacture of the compounds.

  本发明提供了式(I)的化合物，其中R1代表1-乙基丙基、1-甲基乙基或2-甲基丙基；或其生理功能衍生物；包括这些化合物的药物组合物，这些化合物用于制造药物，特别用于治疗炎症和/或过敏症状，以及用于制备这些化合物的过程和制造这些化合物的化学中间体。
• Dissociated Nonsteroidal Glucocorticoid Receptor Modulators; Discovery of the Agonist Trigger in a Tetrahydronaphthalene−Benzoxazine Series
  作者：Mike Barker、Margaret Clackers、Royston Copley、Derek A. Demaine、Davina Humphreys、Graham G. A. Inglis、Michael J. Johnston、Haydn T. Jones、Michael V. Haase、David House、Richard Loiseau、Lesley Nisbet、Francois Pacquet、Philip A. Skone、Stephen E. Shanahan、Dan Tape、Victoria M. Vinader、Melanie Washington、Iain Uings、Richard Upton、Iain M. McLay、Simon J. F. Macdonald

  DOI：10.1021/jm060302x

  日期：2006.7.1

  The tetrahydronaphthalene-benzoxazine glucocorticoid receptor (GR) partial agonist 4b was optimized to produce potent full agonists of GR. Aromatic ring substitution of the tetrahydronaphthalene leads to weak GR antagonists. Discovery of an "agonist trigger" substituent on the saturated ring of the tetrahydronaphthalene leads to increased potency and efficacious GR agonism. These compounds are efficacy selective in an NFkB GR agonist assay ( representing transrepression effects) over an MMTV GR agonist assay ( representing transactivation effects). 52 and 60 have NFkB pIC(50) = 8.92 (105%) and 8.69 (92%) and MMTV pEC(50) = 8.20 (47%) and 7.75 (39%), respectively. The impact of the trigger substituent on agonism is modeled within GR and discussed. 36, 52, and 60 have anti-inflammatory activity in a mouse model of inflammation after topical dosing with 52 and 60, having an effect similar to that of dexamethasone. The original lead was discovered by a manual agreement docking method, and automation of this method is also described.