(1,4)-1,5-双[3,5-双(甲氧基甲氧基)苯基]-1,4-戊二烯-3-酮 | 917813-62-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: (1,4)-1,5-双[3,5-双(甲氧基甲氧基)苯基]-1,4-戊二烯-3-酮
• 英文名称: GO-Y030
• 英文别名: (1E,4E)-1,5-bis-(3,5-bismethoxymethoxyphenyl)penta-1,4-dien-3-one；(1E,4E)-1,5-Bis[3,5-bis(methoxymethoxy)phenyl]-1,4-pentadiene-3-one；(1E,4E)-1,5-bis[3,5-bis(methoxymethoxy)phenyl]penta-1,4-dien-3-one
• CAS: 917813-62-8
• 化学式: C₂₅H₃₀O₉
• 分子量: 474.508
• InChiKey: WZNSZBNRYKYIQK-KQQUZDAGSA-N

物化性质

• 熔点：
  90.0 to 94.0 °C
• 沸点：
  632.5±55.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1,4)-1,5-双[3,5-双(甲氧基甲氧基)苯基]-1,4-戊二烯-3-酮 在 噻吩-2-甲酸亚铜(I) 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  [EN] NOVEL COMPOUND OR SALT THEREOF, AND ANTITUMOR ACTIVATOR CONTAINING SAME AS ACTIVE INGREDIENT
  [FR] NOUVEAU COMPOSÉ OU SON SEL, ET ACTIVATEUR ANTITUMORAL EN CONTENANT EN TANT QUE PRINCIPE ACTIF
  [JA] 新規化合物又はその塩及びこれらを有効成分とする抗腫瘍活性剤

  摘要：

  クルクミン誘導体の生体内有効性及び抗腫瘍活性を向上した新規化合物又はその塩及びこれらを有効成分とする抗腫瘍活性剤を提供する。次の一般式で表される化合物又はその塩である。Ｒ１～Ｒ４は水素原子、Ｃ１－４低級アルキル基、ヒドロキシＣ１－４低級アルキル基、Ｃ１－４低級アルコキシＣ１－４低級アルキル基、及びＣ１－４低級アルコキシＣ１－４低級アルコキシＣ１－４低級アルキル基から選ばれる置換基であり、Ｒ１～Ｒ４は同一であってもよく、異なっていてもよい。ｎは１～６である。Ｓｕｇａｒは単糖類又は二糖類である。

  公开号：

  WO2022190915A1
• 作为产物：
  描述：

  3,5-bis(methoxymethoxy)benzaldehyde 、 丙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (1,4)-1,5-双[3,5-双(甲氧基甲氧基)苯基]-1,4-戊二烯-3-酮
  参考文献：
  名称：

  Structure–activity relationship of C5-curcuminoids and synthesis of their molecular probes thereof

  摘要：

  A series of novel analogues of 1,5-bis(4-hydroxy-3-methoxyphenyl)-penta-(1E,4E)-1,4-dien-3-one (C-5-curcumin), which is a natural analogue of curcumin isolated from the rhizomes of Curcuma domestica Val. (Zingiberacea), were synthesized and evaluated for their cytotoxicities against human colon cancer cell line HCT-116 to conclude the SAR of C-5-curcuminoids for further development of their use in cancer chemotherapy: (1) Bis(arylmethylidene) acetone serves as a promising skeleton for eliciting cytotoxicity. (2) The 3-oxo-1,4-pentadiene structure is essential for eliciting cytotoxicity. (3) As for the extent of the aromatic substituents, hexasubstituted compounds exhibit strong activities, in which 3,4,5-hexasubstitution results in the highest potency. (5) The symmetry between two aryl rings is not an essential requirement for bis(arylmethylidene) acetones to elicit cytotoxicity. (6) para-Positions allows the installation of additional functional groups for use as molecular probes. By taking advantage of the SAR diagram, we have elaborated several advanced derivatives having GI(50) of single-digit micromolar potencies that will function as molecular probes to target and/or report key biomolecules interacting with curcumin and C-5-curcumin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.045

文献信息

• BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER
  申请人：Shibata Hiroyuki

  公开号：US20100152493A1

  公开（公告）日：2010-06-17

  It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

  要改善姜黄素的溶解度，以开发一种能够在低浓度下抑制各种癌细胞生长的抗肿瘤化合物。因此，披露了一种新型合成化合物，双(芳基甲基亚乙酮)，具有优异的抗肿瘤活性和化学预防活性。合成并筛选了一种双(芳基甲基亚乙酮)（即具有姜黄素骨架的衍生物），它是一种抗肿瘤化合物并具有化学预防活性。可以合成具有增强抗肿瘤活性和化学预防活性的衍生物。
• Design, Synthesis, and Biological Evaluation of Water-Soluble Prodrugs of C5-Curcuminoid GO-Y030 Based on Reversible Thia-Michael Reaction
  作者：Hiroyuki Yamakoshi、Michihiro Fukuda、Hiro Ikeda、Shogo Fujiki、Aki Kohyama、Shota Nagasawa、Hanae Shinozaki、Hiroyuki Shibata、Yoshiharu Iwabuchi

  DOI：10.1248/cpb.c23-00775

  日期：2024.1.30

  Although curcumin and its analogs exhibit anticancer activity, they are still not used as anticancer drugs because of their water insolubility and extremely poor bioavailability. This study describes the development of water-soluble prodrugs of GO-Y030, a potent antitumor C5-curcuminoid, in an attempt to enhance its bioavailability. These prodrugs release the parent compound via a retro-thia-Michael

  尽管姜黄素及其类似物表现出抗癌活性，但由于其不溶于水且生物利用度极差，仍然没有被用作抗癌药物。本研究描述了 GO-Y030（一种有效的抗肿瘤 C5-姜黄素）的水溶性前药的开发，试图提高其生物利用度。这些前药通过逆硫-迈克尔反应释放母体化合物。为了通过水性实体的单一硫杂-迈克尔反应赋予 GO-Y030 足够的亲水性，我们使用了带有硫醇基团的修饰糖缀合物。通过炔丙基-聚乙二醇 (PEG)-硫醇的硫杂-迈克尔反应以及随后与 1-糖基叠氮化物的点击化学 (CuAAC) 反应，将水溶性基序安装在 GO-Y030 上。浊度测量显示前药的水溶性显着提高，表明二糖缀合物在 100 µM 时完全溶解在水中。它们的细胞毒性与母体化合物 GO-Y030 相当，表明 GO-Y030 是逐渐原位释放的。通过水中的降解研究证明了通过逆硫基-迈克尔反应从 GO-Y199 中释放 GO-Y030。我们基于逆硫基迈克尔反应的前药系统可用于靶向癌细胞。
• Therapeutic compositions containing curcumin, harmine, and isovanillin components, and methods of use thereof
  申请人：Ions Pharmaceutical S.à r.l.

  公开号：US10092550B2

  公开（公告）日：2018-10-09

  Human therapeutic treatment compositions comprise at least two of a curcumin component, a harmine component, and an isovanillin component, and preferably all three in combination. The agents are effective for the treatment of human conditions, especially human cancers.

  人类治疗组合物包含姜黄素成分、禾本科成分和异香兰素成分中的至少两种，最好是三种成分的组合。 这些制剂可有效治疗人类疾病，尤其是人类癌症。
• Human therapeutic agents
  申请人：Ankh Life Sciences Limited

  公开号：US10751330B2

  公开（公告）日：2020-08-25

  Human therapeutic treatment compositions comprise at least two of a curcumin component, a harmine component, and an isovanillin component, and preferably all three in combination. The agents are effective for the treatment of human conditions, especially human cancers.

  人类治疗组合物包含姜黄素成分、禾本科成分和异香兰素成分中的至少两种，最好是三种成分的组合。这些制剂可有效治疗人类疾病，尤其是人类癌症。
• THERAPEUTIC COMPOSITIONS CONTAINING CURCUMIN, HARMINE, AND ISOVANILLIN COMPONENTS, AND METHODS OF USE THEREOF
  申请人：Ions Pharmaceutical S.à r.l.

  公开号：US20170042865A1

  公开（公告）日：2017-02-16

  Human therapeutic treatment compositions comprise at least two of a curcumin component, a harmine component, and an isovanillin component, and preferably all three in combination. The agents are effective for the treatment of human conditions, especially human cancers.