(1R,4aR,7S)-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-1-phenanthrenecarbaldehyde | 233749-77-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,4aR,7S)-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-1-phenanthrenecarbaldehyde
• 英文别名: (1R,4aR,7S,8aS,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carbaldehyde
• CAS: 233749-77-4
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: BDYOIDJEWCGJCN-ZDNSCYFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (1R,4aR,7S)-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-1-phenanthrenecarbaldehyde 在 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成 3-((1S,4aR,7S,8aS,10aR)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-1-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Pimarane cyclooxygenase 2 (COX-2) inhibitor and its structure–activity relationship

  摘要：

  The structure-activity relationship and molecular modelings of a novel pimarane COX-2 inhibitor are reported. Particularly, a series of linker extended analogues designed on the basis of these studies exhibited significantly enhanced COX-2 inhibitory activities and selectivities. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00004-x
• 作为产物：
  描述：

  ent-pimara-9(11),15-dien-19-ol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,4aR,7S)-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-1-phenanthrenecarbaldehyde
  参考文献：
  名称：

  Pimarane cyclooxygenase 2 (COX-2) inhibitor and its structure–activity relationship

  摘要：

  The structure-activity relationship and molecular modelings of a novel pimarane COX-2 inhibitor are reported. Particularly, a series of linker extended analogues designed on the basis of these studies exhibited significantly enhanced COX-2 inhibitory activities and selectivities. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00004-x

文献信息

• Interleukin-1 and tumor necrosis factor-alpha modulators; syntheses of such modulators and methods of using such modulators
  申请人：Palladino Michael A.

  公开号：US20080064753A1

  公开（公告）日：2008-03-13

  Described herein are chemical compounds and pharmaceutical compositions, including novel chemical compounds and pharmaceutical compositions thereof, useful in the treatment of various diseases and disease states. Also described are methods of synthesizing natural products and novel, structurally-related chemical compounds. More particularly, disclosed are new analogs of and processes for the preparation of compounds and pharmaceutical compositions thereof useful in the treatment of, for example, inflammation, cancer, multiple myeloma, cachexia, cardiovascular disease, anti-infectious, diabetes, otitis media, sinusitis and transplant rejection.

  本文描述了一些化合物和药物组合物，包括新颖的化合物和药物组合物，它们可用于治疗各种疾病和疾病状态。同时，还描述了合成天然产物和新的、结构相关的化合物的方法。更具体地，披露了新的模拟物和制备它们的化合物和药物组合物的过程，这些化合物和药物组合物可用于治疗炎症、癌症、多发性骨髓瘤、消瘦症、心血管疾病、抗感染、糖尿病、中耳炎、鼻窦炎和移植排斥等疾病。
• INTERLEUKIN-1 AND TUMOR NECROSIS FACTOR-ALPHA MODULATORS; SYNTHESES OF SUCH MODULATORS AND METHODS OF USING SUCH MODULATORS
  申请人：Palladino Michael A.

  公开号：US20110160309A1

  公开（公告）日：2011-06-30

  Described herein are chemical compounds and pharmaceutical compositions, including novel chemical compounds and pharmaceutical compositions thereof, useful in the treatment of various diseases and disease states. Also described are methods of synthesizing natural products and novel, structurally-related chemical compounds. More particularly, disclosed are new analogs of and processes for the preparation of compounds and pharmaceutical compositions thereof useful in the treatment of, for example, inflammation, cancer, multiple myeloma, cachexia, cardiovascular disease, anti-infectious, diabetes, otitis media, sinusitis and transplant rejection.

  本文描述了化学化合物和药物组合物，包括新型化学化合物和药物组合物，用于治疗各种疾病和疾病状态。还描述了合成天然产物和新的结构相关化学化合物的方法。更具体地，披露了用于治疗炎症、癌症、多发性骨髓瘤、消瘦、心血管疾病、抗感染、糖尿病、中耳炎、鼻窦炎和移植排斥等疾病的化合物和药物组合物的新类似物和制备方法。
• WO2007/15757
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and anti-inflammatory effects of novel pimarane diterpenoid analogs
  作者：Young-Ger Suh、Kwang-Ok Lee、Sung-Hyun Moon、Seung-Yong Seo、Yong-Sil Lee、Seok-Ho Kim、Seung-Mann Paek、Young-Ho Kim、Yun-Sang Lee、Jae Min Jeong、Seung Jin Lee、Sang Geon Kim

  DOI：10.1016/j.bmcl.2004.04.054

  日期：2004.7

  Syntheses and excellent anti-inflammatory effects of a series of novel acanthoic acid analogs are reported. In particular, the mechanistic basis for their anti-inflammatory effects is also described. (C) 2004 Elsevier Ltd. All rights reserved.
• Novel Interleukin-1 and Tumor Necrosis Factor-Alpha Modulators, Syntheses of Said Modulators and Their Enantiomers and Methods of Using Said Modulators
  申请人：Palladino Michael

  公开号：US20080188475A1

  公开（公告）日：2008-08-07

  Disclosed herein are novel tricyclic diterpene compounds. These compounds, including their prodrug esters and acid-addition salts, are useful as Interleukin-1 and Tumor Necrosis Factor-alpha modulators, and thus useful in the treatment of various diseases. Pharmaceutical compositions comprising, and uses of, theapeautically effective amounts of the above compounds and their prodrug esters, and pharmaceutically acceptable carrier, are also disclosed, and are useful as, for example, anti-inflamatory analgestics, treatments for immune disorders, anti-cancer and anti-tumor agents, and in the treatment of cardiovascular disease, skin redness, and viral infection, for example. Completley synthetic and semi-synthetic methods of making these compounds and their analogs are disclosed.