GO-Y031 | 917813-58-2

• 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
• 英文名称: GO-Y031
• 英文别名: (1E,4E)-1,5-bis-(3,5-dimethoxy-4-methoxymethoxyphenyl)penta-1,4-dien-3-one；(1e,4e)-1,5-Bis(3,5-dimethoxy-4-methoxymethoxyphenyl)pentadien-3-one；(1E,4E)-1,5-bis[3,5-dimethoxy-4-(methoxymethoxy)phenyl]penta-1,4-dien-3-one
• CAS: 917813-58-2
• 化学式: C₂₅H₃₀O₉
• 分子量: 474.508
• InChiKey: LZFKDHLOJFADBV-FIFLTTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  14
• 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

• 作为产物：
  描述：

  3,5-dimethoxy-4-(methoxymethoxy)benzaldehyde 、 丙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 GO-Y031
  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。
• US8178727B2
  申请人：——

  公开号：US8178727B2

  公开（公告）日：2012-05-15
• Structure–activity relationship of C5-curcuminoids and synthesis of their molecular probes thereof
  作者：Hiroyuki Yamakoshi、Hisatsugu Ohori、Chieko Kudo、Atsuko Sato、Naoki Kanoh、Chikashi Ishioka、Hiroyuki Shibata、Yoshiharu Iwabuchi

  DOI：10.1016/j.bmc.2009.12.045

  日期：2010.2

  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.