(3E)-4-(3,5-dimethoxy-4-prop-2-ynyloxy-phenyl)-but-3-en-2-one | 918340-11-1

• 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: (3E)-4-(3,5-dimethoxy-4-prop-2-ynyloxy-phenyl)-but-3-en-2-one
• 英文别名: (E)-4-(3,5-dimethoxy-4-prop-2-ynoxyphenyl)but-3-en-2-one
• CAS: 918340-11-1
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: BWQVKQTYTPLQNL-VOTSOKGWSA-N

物化性质

• 沸点：
  420.6±45.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E)-4-(3,5-dimethoxy-4-prop-2-ynyloxy-phenyl)-but-3-en-2-one 、 3,5-dimethoxy-4-(methoxymethoxy)benzaldehyde 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以30%的产率得到(1E,4E)-1-(3,5-dimethoxy-4-(methoxymethoxy)phenyl)-5-(3,5-dimethoxy-4-(prop-2-ynyloxy)phenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  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

  摘要：

  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。

  公开号：

  US20100152493A1
• 作为产物：
  描述：

  丙酮 、 3,5-dimethoxy-4-propargyloxybenzaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以54%的产率得到(3E)-4-(3,5-dimethoxy-4-prop-2-ynyloxy-phenyl)-but-3-en-2-one
  参考文献：
  名称：

  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

  摘要：

  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。

  公开号：

  US20100152493A1

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, β-catenin-degrading agent, and p53 expression enhancer
  申请人：National University Corporation Tohoku University

  公开号：US08178727B2

  公开（公告）日：2012-05-15

  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.

  要求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，即双(芳基甲基亚乙酮)，它既具有优异的抗肿瘤活性，又具有预防化学治疗的活性。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，具有预防化学治疗的活性。可以合成具有增强抗肿瘤活性和预防化学治疗活性的衍生物。
• 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.
• US8178727B2
  申请人：——

  公开号：US8178727B2

  公开（公告）日：2012-05-15