1,5-bis-(4-hydroxy-3,5-dimethylphenyl)penta-1,4-dien-3-one | 1020399-36-3

• 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: 1,5-bis-(4-hydroxy-3,5-dimethylphenyl)penta-1,4-dien-3-one
• 英文别名: 1,5-Bis(4-hydroxy-3,5-dimethylphenyl)penta-1,4-dien-3-one；(1E,4E)-1,5-bis(4-hydroxy-3,5-dimethylphenyl)penta-1,4-dien-3-one
• CAS: 1020399-36-3
• 化学式: C₂₁H₂₂O₃
• 分子量: 322.404
• InChiKey: FLMOTUCGPJDWCT-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴代环丙烷 、 1,5-bis-(4-hydroxy-3,5-dimethylphenyl)penta-1,4-dien-3-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以75%的产率得到
  参考文献：
  名称：

  In vivo growth inhibitory and anti-angiogenic effects of synthetic novel dienone cyclopropoxy curcumin analogs on mouse Ehrlich ascites tumor

  摘要：

  In the present study, four novel dienone cyclopropoxy curcumin analogs 1a- 4a were synthesized by nucleophillic substitution reaction with cyclopropyl bromide. The tumor inhibitory and anti-angiogenic e. ffects of the synthetic compounds were studied on mouse Ehrlich ascites tumor (EAT) in vivo. The compounds 1a-4a increased the life span (% ILS) of EAT bearing mice with corresponding signifi. cant reduction in ascites volume and cell number and induced apoptotic bodies in EAT cells. Anti-angiogenic studies of the compounds demonstrated signifi. cant reduction of microvessel density (MVD) in the peritoneum wall sections of mice and induced avascular zone in CAM model. Our. findings demonstrate that the tumor growth inhibitory e. ffects of synthetic dienone cyclopropoxy curcumin analogs 1a-4a could be mediated by promoting apoptosis and inhibiting tumor angiogenesis. However, the compounds need to be explored further to assess its clinical relevance. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.051
• 作为产物：
  描述：

  (1E,4E)-1,5-bis[4-(methoxymethoxy)-3,5-dimethylphenyl]penta-1,4-dien-3-one 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以91.6%的产率得到1,5-bis-(4-hydroxy-3,5-dimethylphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  表观遗传的多个配体：混合的组蛋白/蛋白质甲基转移酶，乙酰转移酶和III类脱乙酰酶（沉默调节蛋白）抑制剂。

  摘要：

  制备了许多带有两个通过饱和/不饱和，线性/（多）环间隔基连接的邻-溴和邻，邻-二溴苯酚部分的新化合物（化合物1-9），作为AMI-5（曙红）的简化类似物。是最近报道的精氨酸和组蛋白赖氨酸甲基转移酶（PRMT和HKMT）抑制剂。使用组蛋白和非组蛋白蛋白作为底物，针对一组PRMT（RmtA，PRMT1和CARM1）和人SET7（HKMT）对此类化合物进行了测试。还对它们进行了HAT和SIRT筛选，因为它们在结构上与某些HAT和/或SIRT调制器有关。根据抑制数据，某些测试化合物（1b，1c，4b，4f，4j，4l，7b和7f）能够以相似的效力抑制PRMT，HKMT，HAT和SIRT，因此表现为这些表观遗传靶标（epi-MLs）的多个配体。当在人类白血病U937细胞系上进行测试时，epi-MLs诱导高凋亡水平[即40.7％（4l）和42.6％（7b）]和/或大规模的剂量依赖性细胞分化[即95.2％（1c）]和96

  DOI：

  10.1021/jm701595q

文献信息

• Synthesis of Curcumin Analogues as Potential Antioxidant, Cancer Chemopreventive Agents
  作者：Khairia M. Youssef、Magda A. El-Sherbeny、Faiza S. El-Shafie、Hassan A. Farag、Omar A. Al-Deeb、Sit Albanat A. Awadalla

  DOI：10.1002/ardp.200300763

  日期：2004.1

  New series of 3, 5‐bis(substituted benzylidene)‐4‐piperidones, 2, 7‐bis(substituted benzylidene)cycloheptanones, 1, 5‐bis(substituted phenyl)‐1, 4‐pentadien‐3‐ones, 1, 7‐bis(substituted phenyl)‐1, 6‐heptadien‐3, 5‐diones, 1, 1‐bis(substituted cinnamoyl)‐cyclopentanes, and 1, 1‐bis(substituted cinnamoyl)cyclohexanes have been synthesized and tested for their antioxidant activity. Among the tested compounds

  新系列 3, 5-双（取代苯亚甲基）-4-哌啶酮，2, 7-双（取代苯亚甲基）环庚酮，1, 5-双（取代苯基）-1，4-戊二烯-3-，1， 7-双（取代苯基）-1, 6-庚二烯-3, 5-二酮，1, 1-双（取代肉桂酰基）-环戊烷和1, 1-双（取代肉桂酰基）环己烷已合成并测试其性能抗氧化活性。在被测化合物中，化合物II4、II9、II10、II11、V1和V4表现出较高的自由基清除活性，%抑制率分别为90.71、91.24、96.91、94.26、99.23和99.85%。此外，化合物 V1 是外周多核中性粒细胞 (PMN) 的安全成员，存活率为 91%。报告了详细的合成、光谱和生物学数据。
• 1,5-Diphenyl-1,4-pentadiene-3-ones and cyclic analogues as antioxidative agents. Synthesis and structure-activity relationship
  作者：S.S. Sardjiman、M.S. Reksohadiprodjo、L Hakim、H van der Goot、H Timmerman

  DOI：10.1016/s0223-5234(97)83288-6

  日期：1997.7

  A series of 1,5-diphenyl-1,4-pentadiene-3-ones and cyclic analogues with OH-groups in the pam position of the phenyl rings and various meta substituents were prepared and their antioxidant activity compared with that of curcumin. Most of them exhibited potent antioxidative activity, especially when all the meta positions were substituted by methoxy groups.
• Epigenetic Multiple Ligands: Mixed Histone/Protein Methyltransferase, Acetyltransferase, and Class III Deacetylase (Sirtuin) Inhibitors
  作者：Antonello Mai、Donghang Cheng、Mark T. Bedford、Sergio Valente、Angela Nebbioso、Andrea Perrone、Gerald Brosch、Gianluca Sbardella、Floriana De Bellis、Marco Miceli、Lucia Altucci

  DOI：10.1021/jm701595q

  日期：2008.4.1

  A number of new compounds bearing two ortho-bromo- and ortho, ortho-dibromophenol moieties linked through a saturated/unsaturated, linear/(poly)cyclic spacer (compounds 1- 9) were prepared as simplified analogues of AMI-5 (eosin), a recently reported inhibitor of both protein arginine and histone lysine methyltransferases (PRMTs and HKMTs). Such compounds were tested against a panel of PRMTs (RmtA

  制备了许多带有两个通过饱和/不饱和，线性/（多）环间隔基连接的邻-溴和邻，邻-二溴苯酚部分的新化合物（化合物1-9），作为AMI-5（曙红）的简化类似物。是最近报道的精氨酸和组蛋白赖氨酸甲基转移酶（PRMT和HKMT）抑制剂。使用组蛋白和非组蛋白蛋白作为底物，针对一组PRMT（RmtA，PRMT1和CARM1）和人SET7（HKMT）对此类化合物进行了测试。还对它们进行了HAT和SIRT筛选，因为它们在结构上与某些HAT和/或SIRT调制器有关。根据抑制数据，某些测试化合物（1b，1c，4b，4f，4j，4l，7b和7f）能够以相似的效力抑制PRMT，HKMT，HAT和SIRT，因此表现为这些表观遗传靶标（epi-MLs）的多个配体。当在人类白血病U937细胞系上进行测试时，epi-MLs诱导高凋亡水平[即40.7％（4l）和42.6％（7b）]和/或大规模的剂量依赖性细胞分化[即95.2％（1c）]和96
• In vivo growth inhibitory and anti-angiogenic effects of synthetic novel dienone cyclopropoxy curcumin analogs on mouse Ehrlich ascites tumor
  作者：H. Chandru、A.C. Sharada、B.K. Bettadaiah、C.S. Ananda Kumar、K.S. Rangappa、Sunila、K. Jayashree

  DOI：10.1016/j.bmc.2007.08.051

  日期：2007.12

  In the present study, four novel dienone cyclopropoxy curcumin analogs 1a- 4a were synthesized by nucleophillic substitution reaction with cyclopropyl bromide. The tumor inhibitory and anti-angiogenic e. ffects of the synthetic compounds were studied on mouse Ehrlich ascites tumor (EAT) in vivo. The compounds 1a-4a increased the life span (% ILS) of EAT bearing mice with corresponding signifi. cant reduction in ascites volume and cell number and induced apoptotic bodies in EAT cells. Anti-angiogenic studies of the compounds demonstrated signifi. cant reduction of microvessel density (MVD) in the peritoneum wall sections of mice and induced avascular zone in CAM model. Our. findings demonstrate that the tumor growth inhibitory e. ffects of synthetic dienone cyclopropoxy curcumin analogs 1a-4a could be mediated by promoting apoptosis and inhibiting tumor angiogenesis. However, the compounds need to be explored further to assess its clinical relevance. (c) 2007 Elsevier Ltd. All rights reserved.