3,4-二羟基-5-(3-甲基丁基)-2-(3-甲基-1-氧代丁基)-4-(4-甲基-1-氧代戊基)环戊-2-烯-1-酮 | 28815-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,4-二羟基-5-(3-甲基丁基)-2-(3-甲基-1-氧代丁基)-4-(4-甲基-1-氧代戊基)环戊-2-烯-1-酮
• 英文名称: tetrahydroisohumulone
• 英文别名: 3,4-Dihydroxy-5-(3-methylbutyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopentyl)cyclopent-2-en-1-one；3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one
• CAS: 28815-20-5；22748-57-8
• 化学式: C₂₁H₃₄O₅
• 分子量: 366.498
• InChiKey: JIZQRWKUYFNSDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二羟基-5-(3-甲基丁-2-烯基)-2-(3-甲基-1-氧代丁基)-4-(4-甲基-1-氧代戊-3-烯基)环戊-2-烯-1-酮 在 5% Pd(II)/C(eggshell) 氢气 作用下， 以 甲醇 、 水 为溶剂， 35.0 ℃ 、446.08 kPa 条件下， 反应 2.0h， 以94.2%的产率得到3,4-二羟基-5-(3-甲基丁基)-2-(3-甲基-1-氧代丁基)-4-(4-甲基-1-氧代戊基)环戊-2-烯-1-酮
  参考文献：
  名称：

  WO2011/59486

  摘要：

  公开号：

文献信息

• METHODS OF SYNTHESIZING ALPHA ACIDS AND SUBSTANTIALLY ENANTIOMERICALLY PURE COMPOSITIONS THEREOF
  申请人：KINDEX PHARMACEUTICALS, INC.

  公开号：US20150197472A1

  公开（公告）日：2015-07-16

  Methods of synthesizing a cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one (“KDT500”) derivative are provided. Such methods may be used to synthesize any desired KDT derivative. In one embodiment, the KDT500 derivative is KDT501.

  提供了合成顺式3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮（“KDT500”）衍生物的方法。这些方法可用于合成任何所需的KDT衍生物。在一个实施例中，KDT500衍生物是KDT501。
• CIS 3,4-DIHYDROXY-2-(3-METHYLBUTANOYL)-5-(3-METHYLBUTYL)-4-(4-METHYLPENTANOYL)CYCLOPENT-2-EN-1-ONE DERIVATIVES, SUBSTANTIALLY ENANTIOMERICALLY PURE COMPOSITIONS AND METHODS
  申请人：Carroll Brian J.

  公开号：US20120108671A1

  公开（公告）日：2012-05-03

  The present application provides cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives and substantially enantiomerically pure compositions thereof. These derivatives include (+)-(4S,5R)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, (−)-(4R,5S)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, and salts and crystals thereof. The application further provides methods of using the disclosed compounds and compositions to activate PPARγ, activate GPR120, inhibit inflammation, and treat conditions responsive to PPARγ modulation, conditions responsive to GPR120 modulation, and metabolic disturbances such as diabetes.

  本申请提供了顺式3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮衍生物及其基本对映纯组合物。这些衍生物包括(+)-(4S,5R)-3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮，(-)-(4R,5S)-3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮，以及它们的盐和晶体。该申请还提供了使用所披露的化合物和组合物来激活PPARγ、激活GPR120、抑制炎症，并治疗对PPARγ调节敏感的病症、对GPR120调节敏感的病症以及代谢紊乱如糖尿病的方法。
• CIS, 3,4-DIHYDROXY-2-(3-METHYLBUTANOYL)-5-(3-METHYLBUTYL)-4-(4-METHYLPENTANOYL)CYCLOPENT-2-EN-1-ONE DERIVATIVES, SUBSTANTIALLY ENANTIOMERICALLY PURE COMPOSITIONS AND METHODS
  申请人：CARROLL Brian J.

  公开号：US20130018105A1

  公开（公告）日：2013-01-17

  The present application provides cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives and substantially enantiomerically pure compositions thereof. These derivatives include (+)-(4S,5R)—3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, (−)-(4R,5S)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, and salts and crystals thereof. The application further provides methods of using the disclosed compounds and compositions to activate PPARγ, activate GPR120, inhibit inflammation, and treat conditions responsive to PPARγ modulation, conditions responsive to GPR120 modulation, and metabolic disturbances such as diabetes.

  本申请提供了cis 3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮衍生物及其相当对映纯的组合物。这些衍生物包括(+)-(4S,5R)-3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮，(-)-(4R,5S)-3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮，以及它们的盐和晶体。该申请进一步提供了使用所述化合物和组合物激活PPARγ，激活GPR120，抑制炎症，以及治疗对PPARγ调节敏感的疾病，对GPR120调节敏感的疾病和代谢紊乱，如糖尿病的方法。
• [EN] CIS 3,4-DIHYDROXY-2-(3-METHYLBUTANOYL)-5-(-3-METHYLBUTYL)-4-(4-METHYLPENTANOYL)CYCLOPENT-2-EN-1-ONE DERIVATIVES, SUBSTANTIALLY ENANTIOMERICALLY PURE COMPOSITIONS AND METHODS<br/>[FR] DÉRIVÉS DE CIS 3,4-DIHYDROXY-2-(3-MÉTHYLBUTANOYL)-5-(3-MÉTHYLBUTYL)-4-(4-MÉTHYLPENTANOYL)CYCLOPENT-2-ÈN-1-ONE, COMPOSITIONS SENSIBLEMENT ÉNANTIOMÉRIQUEMENT PURES ET PROCÉDÉS
  申请人：KINDEX THERAPEUTICS LLC

  公开号：WO2012058649A1

  公开（公告）日：2012-05-03

  The present application provides cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3- methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives and substantially enantiomerically pure compositions thereof. These derivatives include (+)-(4S,5R)- 3,4- dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, (-)-(4R,5S)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4- methylpentanoyl)cyclopent-2-en-1-one, and salts and crystals thereof. The application further provides methods of using the disclosed compounds and compositions to activate PPARƳ, activate GPR120, inhibit inflammation, and treat conditions responsive to PPARƳ modulation, conditions responsive to GPR120 modulation, and metabolic disturbances such as diabetes.

  本申请提供cis 3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮衍生物及其基本对映体纯组合物。这些衍生物包括(+)-(4S,5R)-3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮，(-)-(4R,5S)-3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮，以及其盐和晶体。该申请进一步提供了使用所述化合物和组合物激活PPARƳ，激活GPR120，抑制炎症，并治疗对PPARƳ调节敏感的疾病，对GPR120调节敏感的疾病以及代谢紊乱，如糖尿病的方法。
• TETRAHYDRO-ISOHUMULONE DERIVATIVES, METHODS OF MAKING AND USING
  申请人：KINDEX PHARMACEUTICALS, INC.

  公开号：US20150119461A1

  公开（公告）日：2015-04-30

  The present application provides novel tetrahydro-isohumulone (THIAA) derivatives and substantially enantiomerically pure compositions and pharmaceutical formulations thereof. The application further provides methods of using the disclosed compounds and compositions to activate PPARγ, inhibit inflammation, and treat conditions associated with inflammation and conditions responsive to PPARγ modulation such as diabetes.

  本申请提供了新型四氢异葎草酮（THIAA）衍生物以及其在对映体纯度上的组成和制药配方。该申请还提供了使用所述化合物和组合物激活PPARγ、抑制炎症以及治疗与炎症相关的疾病和对PPARγ调节敏感的疾病（如糖尿病）的方法。