(E)-6-(2,6,6-trimethylcyclohex-1-enyl)hex-5-ene-2,4-dione | 95470-30-7

• 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: (E)-6-(2,6,6-trimethylcyclohex-1-enyl)hex-5-ene-2,4-dione
• 英文别名: (E)-6-(2,6,6-trimethylcyclohexen-1-yl)hex-5-ene-2,4-dione
• CAS: 95470-30-7
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: OXKITSFINKCFKE-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  异香兰素 、 (E)-6-(2,6,6-trimethylcyclohex-1-enyl)hex-5-ene-2,4-dione 在 boron trioxide 、 硼酸三丁酯 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以30%的产率得到(1E,4Z,6E)-5-hydroxy-7-(3-hydroxy-4-methoxyphenyl)-1-(2,6,6-trimethylcyclohexen-1-yl)hepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Design and Synthesis of Androgen Receptor Antagonists with Bulky Side Chains for Overcoming Antiandrogen Resistance

  摘要：

  Incorporation of curcumin and beta-ionone into one chemical entity led to identification of a novel antiandrogen with two bulky side chains, 6, which is a pure antagonist of the wild-type and the T877A, W741C, and H874Y mutated androgen receptors (AR), showing no cross-reactivity with progesterone receptor and low micromolar cytotoxicity in LNCaP, PCa-2b, 22Rv1, and C4-2B prostate cancer cells. Molecular modeling indicates 6 adopts a "Y"-shape conformation and forms multiple hydrogen bonds with AR backbone.

  DOI：

  10.1021/jm801218k
• 作为产物：
  描述：

  beta-紫罗酮 、 乙酸乙酯 在 甲醇 、 sodium 、 水 作用下， 反应 7.0h， 以26%的产率得到(E)-6-(2,6,6-trimethylcyclohex-1-enyl)hex-5-ene-2,4-dione
  参考文献：
  名称：

  [EN] HYBRID -IONONE AND CURCUMIN MOLECULES AS ANTICANCER AGENTS
  [FR] MOLÉCULES HYBRIDES D'IONONE ET DE CURCUMINE EN TANT QU'AGENTS ANTICANCÉREUX

  摘要：

  本发明涉及合成一系列离子酮和姜黄素衍生物，作为对激素敏感和非激素敏感癌症有效的多靶点药物。具体而言，本发明涉及一种独特的双功能抗雄激素剂，既抑制雄激素受体（AR），又抑制IKB激酶（IKK）。合成了一系列基于离子酮的查尔酮，并展示了它们对前列腺癌细胞系的体外细胞毒性。通过反应基于离子酮的查尔酮和肼形成的一系列衍生物，在前列腺癌、乳腺癌和肺癌细胞系中展示了显著的抗增殖活性。公式（I），（II）。

  公开号：

  WO2010060214A1

文献信息

• HYBRID -IONONE AND CURCUMIN MOLECULES AS ANTICANCER AGENTS
  申请人：TRT Pharma Inc .

  公开号：EP2361245A1

  公开（公告）日：2011-08-31
• HYBRID-IONONE AND CURCUMIN MOLECULES AS ANTICANCER AGENTS
  申请人：Wu Jian Hui

  公开号：US20110230488A1

  公开（公告）日：2011-09-22

  The present invention relates to the synthesis of a series of ionone and curcumin derivatives as multi-targeting agents effective against both hormone-sensitive and hormone-independent cancers. In particular, the present invention is directed to a distinct class of bifunctional antiandrogens, which inhibit both AR and IKBkinases (IKK). A series of ionone-based chalcones were synthesised and their in vitro cytotoxicity against prostate cancer cell lines were demonstrated. A series of derivatives formed by reacting ionone-based chalcones and hydrazines demonstrate substantial antiproliferative activities in prostate cancer, breast cancer and lung cancer cell lines.
• US8470889B2
  申请人：——

  公开号：US8470889B2

  公开（公告）日：2013-06-25
• Design and Synthesis of Androgen Receptor Antagonists with Bulky Side Chains for Overcoming Antiandrogen Resistance
  作者：Jinming Zhou、Guoyan Geng、Qingwen Shi、Francoise Sauriol、Jian Hui Wu

  DOI：10.1021/jm801218k

  日期：2009.9.10

  Incorporation of curcumin and beta-ionone into one chemical entity led to identification of a novel antiandrogen with two bulky side chains, 6, which is a pure antagonist of the wild-type and the T877A, W741C, and H874Y mutated androgen receptors (AR), showing no cross-reactivity with progesterone receptor and low micromolar cytotoxicity in LNCaP, PCa-2b, 22Rv1, and C4-2B prostate cancer cells. Molecular modeling indicates 6 adopts a "Y"-shape conformation and forms multiple hydrogen bonds with AR backbone.
• [EN] HYBRID -IONONE AND CURCUMIN MOLECULES AS ANTICANCER AGENTS<br/>[FR] MOLÉCULES HYBRIDES D'IONONE ET DE CURCUMINE EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：TRT PHARMA INC

  公开号：WO2010060214A1

  公开（公告）日：2010-06-03

  The present invention relates to the synthesis of a series of ionone and curcumin derivatives as multi-targeting agents effective against both hormone-sensitive and hormone-independent cancers. In particular, the present invention is directed to a distinct class of bifunctional antiandrogens, which inhibit both AR and IKBkinases (IKK). A series of ionone-based chalcones were synthesised and their in vitro cytotoxicity against prostate cancer cell lines were demonstrated. A series of derivatives formed by reacting ionone-based chalcones and hydrazines demonstrate substantial antiproliferative activities in prostate cancer, breats cancer and lung cancer cell lines. Formulae (I), (II)

  本发明涉及合成一系列离子酮和姜黄素衍生物，作为对激素敏感和非激素敏感癌症有效的多靶点药物。具体而言，本发明涉及一种独特的双功能抗雄激素剂，既抑制雄激素受体（AR），又抑制IKB激酶（IKK）。合成了一系列基于离子酮的查尔酮，并展示了它们对前列腺癌细胞系的体外细胞毒性。通过反应基于离子酮的查尔酮和肼形成的一系列衍生物，在前列腺癌、乳腺癌和肺癌细胞系中展示了显著的抗增殖活性。公式（I），（II）。