(1E,4E)-1,5-bis(2,3,4-trimethoxyphenyl)penta-1,4-dien-3-one | 917813-57-1

• 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: (1E,4E)-1,5-bis(2,3,4-trimethoxyphenyl)penta-1,4-dien-3-one
• 英文别名: GO-Y020；(1E,4E)-1,5-bis(2,3,4-trimethoxyphenyl)-1,4-pentadiene-3-one；(1E,4E)-1,5-bis-(2,3,4-trimethoxyphenyl)penta-1,4-dien-3-one
• CAS: 917813-57-1
• 化学式: C₂₃H₂₆O₇
• 分子量: 414.455
• InChiKey: VPOIVFUDDKCPQY-MKICQXMISA-N

物化性质

• 熔点：
  85-87 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  573.1±50.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1,5-bis(2,3,4-trimethoxyphenyl)penta-1,4-dien-3-one 、 巯基乙胺 以 甲醇 、 aq. phosphate buffer 为溶剂， 生成
  参考文献：
  名称：

  姜黄素的单羰基类似物具有治疗结直肠癌的潜力

  摘要：

  姜黄素具有多种生物学特性，使得这种化合物可以有效治疗包括癌症在内的多种疾病。然而，姜黄素的临床应用因其较差的药代动力学而受到影响，因此寻找具有更好药代动力学和药理学特性的新型类似物至关重要。在这里，我们的目的是评估姜黄素单羰基类似物的稳定性、生物利用度和药代动力学特征。合成了姜黄素1a–q的单羰基类似物的小型文库。生理条件下的亲脂性和稳定性均通过 HPLC-UV 进行评估，同时通过 NMR 和 UV 光谱监测两种不同的方法评估每种化合物的亲电特性。在人结肠癌细胞中评估了类似物1a–q的潜在治疗效果以及在永生化肝细胞中的毒性。我们的结果表明，姜黄素类似物1e是一种有前景的抗结直肠癌药物，具有更高的稳定性和功效/安全性。

  DOI：

  10.1002/cbdv.202300222
• 作为产物：
  描述：

  丙酮 、 2,3,4-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 (1E,4E)-1,5-bis(2,3,4-trimethoxyphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors

  摘要：

  对47种合成的姜黄素样二芳基戊烷类类似物进行了抗黑色素生成筛选，结果显示其中一些对B16黑色素瘤细胞的黑色素生成具有强抑制作用。这些作用主要被认为是通过抑制酪氨酸酶活性、抑制酪氨酸酶表达和降解黑色素色素实现的。还讨论了那些抑制黑色素生成和酪氨酸酶活性的姜黄素样二芳基戊烷类类似物的结构-活性关系。在测试的化合物中，（2E,6E）-2,6-双（2,5-二甲氧基苄叉）环己酮显示了最强的抗黑色素生成效果，其机制被认为是在B16黑色素瘤细胞中降解黑色素色素，既不影响酪氨酸酶活性也不影响酪氨酸酶表达。

  DOI：

  10.1007/s11418-011-0568-0

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。
• THERAPEUTIC CURCUMIN DERIVATIVES
  申请人：STC.UNM

  公开号：US20150011494A1

  公开（公告）日：2015-01-08

  Curcumin analogues and methods are provided for treatment of disease.

  提供了类姜黄素及其方法，用于治疗疾病。
• 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.
• Synthesis and evaluation of curcumin-related compounds for anticancer activity
  作者：Xingchuan Wei、Zhi-Yun Du、Xi Zheng、Xiao-Xing Cui、Allan H. Conney、Kun Zhang

  DOI：10.1016/j.ejmech.2012.04.005

  日期：2012.7

  Sixty-one curcumin-related compounds were synthesized and evaluated for their anticancer activity toward cultured prostate cancer PC-3 cells, pancreas cancer Panc-1 cells and colon cancer HT-29 cells. Inhibitory effects of these compounds on the growth of PC-3. Panc-1 and HT-29 cells were determined by the MTT assay. Compounds E10, F10, FN1 and FN2 exhibited exceptionally potent inhibitory effects on the growth of cultured PC-3, Panc-1 and HT-29 cells. The IC50 for these compounds was lower than 1 mu M in all three cell lines. E10 was 72-, 46- and 117-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. F10 was 69-, 34- and 72-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. FN1 and FN2 had about the same inhibitory effect as E10 and F10 toward Panc-1 cells but were less active than E10 and F10 toward PC-3 and HT-29 cells. The active compounds were potent stimulators of apoptosis. The present study indicates that E10, F10, FN1 and FN2 may have useful anticancer activity. (C) 2012 Elsevier Masson SAS. All rights reserved.
• US8178727B2
  申请人：——

  公开号：US8178727B2

  公开（公告）日：2012-05-15