Trimethylcurcumin | 52552-50-8

• 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: Trimethylcurcumin
• 英文别名: (1E,4Z,6E)-1,7-bis(3,4-dimethoxyphenyl)-5-hydroxy-4-methylhepta-1,4,6-trien-3-one
• CAS: 52552-50-8
• 化学式: C₂₄H₂₆O₆
• 分子量: 410.467
• InChiKey: CQBXDAPYUFNDGT-QDUGDBSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Trimethylcurcumin 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 以7%的产率得到1,7-bis-(3,4-dimethoxy-phenyl)-4-methyl-heptane-3,5-diol
  参考文献：
  名称：

  Antitumor Agents. Part 214:††For paper 213, see ref 1. Synthesis and Evaluation of Curcumin Analogues as Cytotoxic Agents

  摘要：

  Fifty-eight curcumin analogues were prepared and evaluated for in vitro cytotoxicity against a panel of human tumor cell lines. Compound 50 was the most potent analogue against several cell lines, including HOS (bone cancer) and 1A9 (breast cancer), with ED50 values of 0.97 and <0.63 mug/mL, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00249-3
• 作为产物：
  描述：

  乙酰丙酮 在 boron trioxide 、 硼酸三丁酯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 12.5h， 生成 Trimethylcurcumin
  参考文献：
  名称：

  中央亚甲基碳上的乙酰氧基取代基赋予姜黄素类自由基清除活性的显着增强

  摘要：

  为了使化合物成为捕获自由基的抗氧化剂，抗氧化剂衍生的自由基必须对分子氧足够惰性，因为这会产生有害的链增长性过氧自由基。姜黄素具有独特的结构，在同一分子中具有酚羟基以及β-二酮部分，两者都能够将电子提供给自由基。然而，由于对分子氧的反应性，源自β-二酮部分的以碳为中心的自由基不能用作捕获自由基的抗氧化剂。在这项研究中，我们认为通过用吸电子基团取代来稳定以碳为中心的自由基会增强所得姜黄素清除自由基的抗氧化活性。因此，各种取代基（甲基，烯丙基，甲氧基，黄原酸酯，包括广谱的极性取代基作用的乙酰氧基和乙酰氧基）被引入到酚类和非酚类姜黄素的中心亚甲基位置。在存在游离酚羟基的情况下，亚甲基取代基对姜黄素的抗氧化活性没有显着影响（欧洲共同体50  = 23.2-30.3μM）与异常的乙酰氧基取代的衍生物（EC 50  = 8.7μM），其显示出比姜黄素更有效的活性（EC 50  = 22.6μM）。但是，

  DOI：

  10.1016/j.bmc.2011.04.055

文献信息

• Compounds with (1E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof
  申请人：SHIH Charles

  公开号：US20150190351A1

  公开（公告）日：2015-07-09

  The present invention includes compounds, pharmaceuticals and cosmetics having at least one (substituted phenyl)-propenal moiety. The compounds and compositions of the present invention are useful in the treatment or prevention of medical conditions including androgen associated conditions, androgen associated inflammation, a wound (the compounds assist with wound healing), acne, rheumatoid arthritis, psoriasis, rosacea, and alopecia; Kennedy's disease (spinal and bulbar muscular atrophy, or SBMA), polyglutamine-mediated motor neuron degeneration; cancers such as prostate cancer, bladder cancer, breast cancer, ovarian cancer, hepatocellular (liver) cancer, and pancreatic cancer; and other medical conditions described herein. Treatment of such medical conditions includes administering to an individual suffering from a medical condition describe herein, a therapeutically effective amount of any of the disclosed compounds, their derivatives, or pharmaceutical compositions thereof.

  本发明涉及具有至少一个（取代苯基）丙烯醛基团的化合物、药物和化妆品。本发明的化合物和组合物可用于治疗或预防医学状况，包括雄激素相关状况、雄激素相关炎症、创伤（该化合物有助于创伤愈合）、痤疮、类风湿性关节炎、银屑病、酒渣鼻和脱发；肯尼迪病（脊髓和延髓肌肉萎缩症，或SBMA）、多谷氨酸介导的运动神经元退化；癌症，如前列腺癌、膀胱癌、乳腺癌、卵巢癌、肝细胞癌和胰腺癌；以及本文所述的其他医学状况。治疗此类医学状况包括向患有本文所述医学状况的个体施用所述化合物、其衍生物或其药物组成物的治疗有效量。
• COMPOUNDS WITH (1E, 6E)-1,7-BIS-(3,4-DIMETHOXYPHENYL)-4-4-DISUBSTITUTED-HEPTA-1,6-DIENE-3,5-DIONE STRUCTURAL SCAFFOLD, THEIR BIOLOGICAL ACTIVITY, AND USES THEREOF
  申请人：Allianz Pharmascience Ltd.

  公开号：US20160264539A1

  公开（公告）日：2016-09-15

  The present invention relates to compounds having at least one (substituted phenyl)-propenal moiety. The compounds are useful in treating a subject suffering from an androgen receptor-associated medical condition, e.g., inflammation, acne, alopecia, hirsutism, wound, Spinal and Bulbar Muscular Atrophy (SBMA, Kennedy's Disease), unwanted immune response, immune disorder, or cancer.

  本发明涉及至少具有一个（取代苯基）-丙烯醛基团的化合物。这些化合物可用于治疗患有雄激素受体相关医疗状况的受试者，例如炎症、痤疮、脱发、多毛症、创伤、脊髓和延髓肌肉萎缩症（SBMA，肯尼迪病）、不需要的免疫反应、免疫障碍或癌症。
• COMPOUNDS WITH (1E,6E)-1,7-BIS-(3,4- DIMETHOXYPHENYL)-4,4-DISSTITUTED-HEPA-1,6-DIENE-3,5-DI-ONE STRUCTURAL SCAFFOLD,THEIR BIOLOGICAL ACTIVITY, AND USES THEREOF
  申请人：Allianz Pharmascience Ltd

  公开号：EP3150203A1

  公开（公告）日：2017-04-05

  The present invention includes compounds, pharmaceuticals and cosmetics having at least one (substituted phenyl)-propenal moiety. The compounds and compositions of the present invention are useful in the treatment or prevention of medical conditions including androgen associated conditions, androgen associated inflammation, a wound (the compounds assist with wound healing), acne, rheumatoid arthritis, psoriasis, rosacea, and alopecia; Kennedy's disease (spinal and bulbar muscular atrophy, or SBMA), polyglutamine-mediated motor neuron degeneration; cancer such as prostate cancer, bladder cancer, breast cancer, ovarian cancer, hepatocellular (liver) cancer, and pancreatic cancer; and other medical conditions described herein. Treatment of such medical condition includes administering to an individual suffering from a medical condition describe herein, a therapeutically effective amount of any of the disclosed compounds, their derivatives, or pharmaceutical compositions thereof.

  本发明包括至少具有一个（取代苯基）-丙烯醛分子的化合物、药品和化妆品。本发明的化合物和组合物可用于治疗或预防医学病症，包括雄激素相关病症、雄激素相关炎症、伤口（化合物有助于伤口愈合）、痤疮、类风湿性关节炎、牛皮癣、酒渣鼻和脱发；肯尼迪病（脊髓和球部肌肉萎缩症，或 SBMA）、多聚谷氨酰胺介导的运动神经元变性；癌症，如前列腺癌、膀胱癌、乳腺癌、卵巢癌、肝癌和胰腺癌；以及本文所述的其他病症。对此类病症的治疗包括向患有本文所述病症的个体施用治疗有效量的任何已公开化合物、其衍生物或其药物组合物。
• Antitumor Agents. 217. Curcumin Analogues as Novel Androgen Receptor Antagonists with Potential as Anti-Prostate Cancer Agents
  作者：Hironori Ohtsu、Zhiyan Xiao、Junko Ishida、Masahiro Nagai、Hui-Kang Wang、Hideji Itokawa、Ching-Yuan Su、Charles Shih、Tzuying Chiang、Eugene Chang、Lee、Meng-Yin Tsai、Chawnshang Chang、Kuo-Hsiung Lee

  DOI：10.1021/jm020200g

  日期：2002.11.1

  A number of curcumin analogues were prepared and evaluated as potential androgen receptor antagonists against two human prostate cancer cell lines, PC-3 and DU-145, in the presence of androgen receptor (AR) and androgen receptor coactivator, ARA70. Compounds 4 [5-hydroxy-1,7-bis(3,4-dimethoxyphenyl)-1,4,6-heptatrien-3-one], 20 [5-hydroxy-1,7-bis[3-methoxy-4-(meth-oxycarbonylmethoxy)phenyl]-1,4,6-heptatrien-3-one], 22 [7-(4-hydroxy-3-methoxyphenyl)-4-[3(4-hydroxy-3-methoxyphenyl)acryloyl]-5-oxohepta-4,6-dienoic acid ethyl ester], 23 [7-(4-hydroxy-3-methoxyphenyl)-4-[3-(4-hydroxy-3-methoxyphenyl)acryloyl]5-oxohepta-4,6-dienoic acid], and 39 [bis(3,4-dimethoxyphenyl)-1,3-propanedione] showed potent antiandrogenic activities and were superior to hydroxyflutamide, which is the currently available antiandrogen for the treatment of prostate cancer. Structure-activity relationship (SAR) studies indicated that the bis(3,4-dimethoxyphenyl) moieties, the conjugated beta-diketone moiety, and the intramolecular symmetry of the molecules seem to be important factors related to antiandrogenic activity. The data further suggest that the coplanarity of the beta-diketone moiety and the presence of a strong hydrogen bond donor group were also crucial for the antiandrogenic activity, which is consistent with previous SAR results for hydroxyflutamide analogues. When the pharmacophoric elements of dihydrotestosterone (DHT) and compound 4 are superposed, the resulting construct implies that the curcumin analogues may function as a 17alpha-substituted DHT. Compounds 4, 20, 22, 23, and 39 have been identified as a new class of antiandrogen agents, and these compounds or their new synthetic analogues could be developed into clinical trial candidates to control androgen receptor-mediated prostate cancer growth.
• US9000222B2
  申请人：——

  公开号：US9000222B2

  公开（公告）日：2015-04-07