1,7-bis(3,4-dimethoxyphenyl)-4-methylhepta-1,6-diene-3,5-dione | 187930-43-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,7-bis(3,4-dimethoxyphenyl)-4-methylhepta-1,6-diene-3,5-dione
• 英文别名: trimethylcurcumin；1,7-di(3,4-dimethoxyphenyl)-4-methyl-1,6-heptadiene-3,5-dione；(1E,6E)-1,7-bis(3,4-dimethoxyphenyl)-4-methylheptan-1,6-diene-3,5-dione；trimethyl curcumin-I；(1E,6E)-1,7-bis(3,4-dimethoxyphenyl)-4-methylhepta-1,6-diene-3,5-dione；4-Methyl-Dimethylcurcumarin
• CAS: 187930-43-4
• 化学式: C₂₄H₂₆O₆
• 分子量: 410.467
• InChiKey: PHWBSWZXLDMWQC-JMQWPVDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,7-bis(3,4-dimethoxyphenyl)-4-methylhepta-1,6-diene-3,5-dione 在 tert-butoxyl radical 作用下， 以 水 、 乙腈 为溶剂， 生成 trimethylcurcumin β-oxo-alkyl radical
  参考文献：
  名称：

  姜黄素如何优先与水溶性抗氧化剂一起使用

  摘要：

  在这项研究中，我们通过脉冲辐射分解和激光闪光光解研究了姜黄素自由基的理化特性。合成了两种甲基化姜黄素衍生物甲基姜黄素和三甲基姜黄素，以探索苯酚羟基和 β-二酮部分在姜黄素自由基化学中的作用。我们的结果表明，最初生成的 β-氧代-烷基可能通过分子内 H 原子转移迅速转化为苯氧基型姜黄素自由基。这种苯氧基不与氧反应，k < 10(5) M(-1) s(-1)，并且可以被任何具有适当氧化还原电位的水溶性抗氧化剂修复，例如 E(6) < 0.83 V ，含维生素 C，k = (6 +/- 1) x 10(6) M(-1) s(-1)。提出了姜黄素化学预防癌症的分子机制，

  DOI：

  10.1021/ja003823x
• 作为产物：
  描述：

  姜黄素 、 碘甲烷 反应 24.0h， 生成 1,7-bis(3,4-dimethoxyphenyl)-4-methylhepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  一种双取代芳基类化合物及其应用

  摘要：

  本发明涉及一种双取代芳基类化合物及其应用，所述的双取代芳基类化合物结构如式I、II或III所示，通过实验验证发现该类双取代芳基类化合物可以与唑类抗真菌药物共同使用，可提高耐药菌对唑类药物的敏感性，实现逆转耐药，因此本发明为临床耐药真菌的治疗提供了一种新途径。

  公开号：

  CN106800547B

文献信息

• Novel curcumin analogues and uses thereof
  申请人：Lee Kuo-Hsiung

  公开号：US20050187255A1

  公开（公告）日：2005-08-25

  The present invention relates to compounds capable of acting as androgen receptor antagonists, pharmaceutical formulations containing the same, and methods of use thereof. Such uses include, but are not limited to, use as antitumor agents, particularly for the treatment of cancers such as colon, skin and prostate cancer and to induce androgen receptor antagonist activity in a subject afflicted with an androgen-related affliction. Examples of androgen-related afflictions include, but are not limited to, baldness, hirsutism, behavioral disorders, acne, and uninhibited spermatogenesis wherein inhibition of spermatogenesis is so desired.

  本发明涉及能够作为雄激素受体拮抗剂的化合物、含有该化合物的制药配方以及使用方法。此类使用包括但不限于用作抗肿瘤剂，特别是用于治疗结肠、皮肤和前列腺癌等癌症，并在患有与雄激素相关的疾病的受试者中诱导雄激素受体拮抗活性。雄激素相关疾病的例子包括但不限于脱发、多毛症、行为障碍、痤疮以及无抑制的精子生成，其中希望抑制精子生成。
• NOVEL CURCUMIN ANALOGUES AND USES THEREOF
  申请人：Lee Kuo-Hsiung

  公开号：US20080161391A1

  公开（公告）日：2008-07-03

  The present invention relates to compounds capable of acting as androgen receptor antagonists, pharmaceutical formulations containing the same, and methods of use thereof. Such uses include, but are not limited to, use as antitumor agents, particularly for the treatment of cancers such as colon, skin and prostate cancer and to induce androgen receptor antagonist activity in a subject afflicted with an androgen-related affliction. Examples of androgen-related afflictions include, but are not limited to, baldness, hirsutism, behavioral disorders, acne, and uninhibited spermatogenesis wherein inhibition of spermatogenesis is so desired.

  本发明涉及能够作为雄激素受体拮抗剂的化合物、含有该化合物的制药配方以及其使用方法。这些用途包括但不限于作为抗肿瘤剂，特别是用于治疗结肠癌、皮肤癌和前列腺癌等癌症，以及在患有雄激素相关疾病的人体内诱导雄激素受体拮抗活性。雄激素相关疾病的例子包括但不限于脱发、多毛症、行为障碍、痤疮以及需要抑制精子生成的不受抑制的精子生成。
• Synthesis and evaluation of electron-rich curcumin analogues
  作者：Michael W. Amolins、Laura B. Peterson、Brian S.J. Blagg

  DOI：10.1016/j.bmc.2008.10.057

  日期：2009.1

  The natural product curcumin has long been recognized for its medicinal properties and is utilized for the treatment of many diseases. However, it remains unknown whether this activity is based on its presumably promiscuous scaffold, or if it results from the Michael acceptor properties of the alpha,beta-unsaturated 1,3-diketone moiety central to its structure. To probe this issue, electron-rich pyrazole and isoxazole analogues were prepared and evaluated against two breast cancer cell lines, which resulted in the identification of several compounds that exhibit low micromolar to mid nanomolar anti-proliferative activity. A conjugate addition study was also performed to compare the relative electrophilicity of the diketone, pyrazole and isoxazole analogues. (C) 2008 Elsevier Ltd. All rights reserved.
• Antitumor Agents. 250. Design and Synthesis of New Curcumin Analogues as Potential Anti-Prostate Cancer Agents
  作者：Li Lin、Qian Shi、Alexander K. Nyarko、Kenneth F. Bastow、Chin-Chung Wu、Ching-Yuan Su、Charles C.-Y Shih、Kuo-Hsiung Lee

  DOI：10.1021/jm051043z

  日期：2006.6.1

  In a continuing study of curcumin analogues as potential drug candidates to treat prostate cancer at both androgen-dependent and androgen-refractory stages, we designed and synthesized over 40 new analogues classified into four series: monophenyl analogues ( series A), heterocycle-containing analogues ( series B), analogues bearing various substituents on the phenyl rings ( series C), and analogues with various linkers ( series D). These new compounds were tested for cytotoxicity against two human prostate cancer cell lines, androgen-dependent LNCaP and androgen-independent PC-3. Antiandrogenic activity was also evaluated in LNCaP cells and PC-3 cells transfected with wild-type androgen receptor. Ten compounds possessed potent cytotoxicity against both LNCaP and PC-3 cells, seven only against LNCaP, and one solely against PC-3. This study established an advanced structure-activity relationship ( SAR), and these correlations will guide the further design of new curcumin analogues with better anti-prostate cancer activity.
• Isolation, characterization and insect growth inhibitory activity of major turmeric constituents and their derivatives againstSchistocerca gregaria (Forsk) andDysdercus koenigii (Walk)
  作者：Hemanta Chowdhury、Suresh Walia、Vinod S Saxena

  DOI：10.1002/1526-4998(200012)56:12<1086::aid-ps250>3.0.co;2-x

  日期：2000.12