(Z)-3-(3,5-di-iso-propyl-2-hydroxyphenyl)but-2-en-1-ol | 566913-35-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (Z)-3-(3,5-di-iso-propyl-2-hydroxyphenyl)but-2-en-1-ol
• 英文别名: 2-(3-hydroxy-1-methyl-propenyl)-4,6-diisopropyl-phenol；2-[(Z)-4-hydroxybut-2-en-2-yl]-4,6-di(propan-2-yl)phenol
• CAS: 566913-35-7
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: RSIFPUSAJWAOJR-SDQBBNPISA-N

物化性质

• 沸点：
  373.5±31.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-(3,5-di-iso-propyl-2-hydroxyphenyl)but-2-en-1-ol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (Z)-3-[3,5-di-iso-propyl-2-(2,2,2-trifluoroethoxy)phenyl]but-2-en-1-al
  参考文献：
  名称：

  Novel (2E,4E,6Z)-7-(2-Alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic Acid Retinoid X Receptor Modulators Are Active in Models of Type 2 Diabetes

  摘要：

  Previous data have shown that RXR-selective agonists (e.g., 3 and 4) are insulin sensitizers in rodent models of non-insulin-dependent diabetes mellitus (NIDDM). Unfortunately, they also produce dramatic increases in triglycerides and profound suppression of the thyroid hormone axis. Here we describe the design and synthesis of new RXR modulators that retain the insulin-sensitizing activity of RXR agonists but produce substantially reduced side effects. These molecules bind selectively and with high affinity to RXR and, unlike RXR agonists, do not activate RXR homodimers. To further evaluate the antidiabetic activity of these RXR modulators, we have designed a concise and systematic structure-activity relationship around the 2E,4E,6Z-7-aryl-3-methylocta-2,4,6-trienoic acid scaffold. Selected compounds have been evaluated using insulin-resistant rodents (db/db mice) to characterize effects on glucose homeostasis. Our studies demonstrate the effectiveness of RXR modulators in lowering plasma glucose in the db/db mouse model.

  DOI：

  10.1021/jm020340q
• 作为产物：
  描述：

  4-methyl-6,8-di-iso-propylcoumarin 在 lithium aluminium tetrahydride 、 盐酸 、 水 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以70%的产率得到(Z)-3-(3,5-di-iso-propyl-2-hydroxyphenyl)but-2-en-1-ol
  参考文献：
  名称：

  3,5-di-iso-propyl-heptatrienoic acid derivatives having serum glucose reducing activity

  摘要：

  该式化合物具有降低糖尿病哺乳动物血清葡萄糖水平的能力，而不会出现降低血清甲状腺素水平的不良副作用。

  公开号：

  US06759546B1

文献信息

• 3,5-di-iso-propyl-heptatrienoic acid derivatives having serum glucose reducing activity
  申请人：Allergan, Inc.

  公开号：US06759546B1

  公开（公告）日：2004-07-06

  Compounds of the formula where the variables have the meaning defined in the specification are capable of reducing serum glucose levels in diabetic mammals without the undesirable side effect of reducing serum thyroxine levels.

  该式化合物具有降低糖尿病哺乳动物血清葡萄糖水平的能力，而不会出现降低血清甲状腺素水平的不良副作用。
• US6759546B1
  申请人：——

  公开号：US6759546B1

  公开（公告）日：2004-07-06
• [EN] 3,5-ISO- PROPYL- HEPTATRIENOIC ACID DERIVATIVES HAVING SERUM GLUCOSE REDUCING ACTIVITY<br/>[FR] DERIVES D'ACIDE 3,5-DI-ISO-PROPYL-HEPTATRIENOIQUE A ACTIVITE DE REDUCTION DE GLUCOSE SERIQUE
  申请人：ALLERGAN INC

  公开号：WO2004069781A2

  公开（公告）日：2004-08-19

  Compounds of formula (i) where the variables have the meaning defined in the specification are capable of reducing serum glucose levels in diabetic mammals without the undesirable side effect of reducing serum thyroxine levels.
• Novel (2<i>E</i>,4<i>E</i>,6<i>Z</i>)-7-(2-Alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic Acid Retinoid X Receptor Modulators Are Active in Models of Type 2 Diabetes
  作者：P. Y. Michellys、R. J. Ardecky、J. H. Chen、D. L. Crombie、G. J. Etgen、A. L. Faulkner、M. M. Faul、T. A. Grese、R. A. Heyman、D. S. Karanewsky、K. Klausing、M. D. Leibowitz、S. Liu、D. A. Mais、C. M. Mapes、K. B. Marschke、A. Reifel-Miller、K. M. Ogilvie、D. Rungta、A. W. Thompson、J. S. Tyhonas、M. F. Boehm

  DOI：10.1021/jm020340q

  日期：2003.6.1

  Previous data have shown that RXR-selective agonists (e.g., 3 and 4) are insulin sensitizers in rodent models of non-insulin-dependent diabetes mellitus (NIDDM). Unfortunately, they also produce dramatic increases in triglycerides and profound suppression of the thyroid hormone axis. Here we describe the design and synthesis of new RXR modulators that retain the insulin-sensitizing activity of RXR agonists but produce substantially reduced side effects. These molecules bind selectively and with high affinity to RXR and, unlike RXR agonists, do not activate RXR homodimers. To further evaluate the antidiabetic activity of these RXR modulators, we have designed a concise and systematic structure-activity relationship around the 2E,4E,6Z-7-aryl-3-methylocta-2,4,6-trienoic acid scaffold. Selected compounds have been evaluated using insulin-resistant rodents (db/db mice) to characterize effects on glucose homeostasis. Our studies demonstrate the effectiveness of RXR modulators in lowering plasma glucose in the db/db mouse model.