(2E,5E)-2,5-bis(2,3-dimethoxybenzylidene)-cyclopentanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,5E)-2,5-bis(2,3-dimethoxybenzylidene)-cyclopentanone
• 英文别名: (2E,5E)-2,5-bis(2,3-dimethoxybenzylidene)cyclopentanone；2,5-bis((E)-2,3-dimethoxybenzylidene)cyclopentan-1-one；(2E,5E)-2,5-bis[(2,3-dimethoxyphenyl)methylidene]cyclopentan-1-one
• 化学式: C₂₃H₂₄O₅
• 分子量: 380.441
• InChiKey: VNKCZJKGJAEOCW-WXUKJITCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,5E)-2,5-bis(2,3-dimethoxybenzylidene)-cyclopentanone 在 氢气 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  螺环基磷配体用于末端和内部烯烃的高度区域选择性加氢甲酰化

  摘要：

  基于螺环骨架的新型二齿亚磷酰胺配体已被开发用于铑催化的加氢甲酰化反应。发现了一系列适合该方案的短链和长链烯烃，它们对线性醛具有很高的催化活性和极好的区域选择性。在优化的反应条件下，在Rh I催化的末端烯烃加氢甲酰化反应中，其周转数（TON）高达2.3×10 4，线性与支化比（l / b）高达174.4 。值得注意的是，还发现催化剂是在一些内部烯烃的异构化-加氢甲酰化高效，区域选择性得到用向上的TON值线性醛〜2.0×10 4和l / b比在23.4-30.6之间。X射线晶体学分析揭示了前催化剂[Rh（3 d）（acac）]中配体的顺式配位，而对催化活性的氢化物络合物[HRh（CO）2（3 d）]的NMR和IR研究表明，物种中配体的eq-eq配位。

  DOI：

  10.1002/chem.201203042
• 作为产物：
  描述：

  环戊酮 、 2,3-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 (2E,5E)-2,5-bis(2,3-dimethoxybenzylidene)-cyclopentanone
  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

• Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors
  作者：Takahiro Hosoya、Asami Nakata、Fumie Yamasaki、Faridah Abas、Khozirah Shaari、Nordin Hj Lajis、Hiroshi Morita

  DOI：10.1007/s11418-011-0568-0

  日期：2012.1

  Anti-melanogenesis screening of 47 synthesized curcumin-like diarylpentanoid analogues was performed to show that some had a potent inhibitory effect on the melanogenesis in B16 melanoma cells. Their actions were considered to be mostly due to tyrosinase inhibition, tyrosinase expression inhibition, and melanin pigment degradation. The structure–activity relationships of those curcumin-like diarylpentanoid analogues which inhibited the melanogenesis and tyrosinase activity were also discussed. Of those compounds assayed, (2E,6E)-2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone showed the most potent anti-melanogenesis effect, the mechanism of which is considered to be the degradation of the melanin pigment in B16 melanoma cells, affecting neither the tyrosinase activity nor tyrosinase expression.

  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。
• Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents
  作者：Guang Liang、Lili Shao、Yi Wang、Chengguang Zhao、Yanhui Chu、Jian Xiao、Yu Zhao、Xiaokun Li、Shulin Yang

  DOI：10.1016/j.bmc.2008.10.044

  日期：2009.3

  Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modi. cations of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically. (C) 2009 Published by Elsevier Ltd.
• Spiroketal-Based Phosphorus Ligands for Highly Regioselective Hydroformylation of Terminal and Internal Olefins
  作者：Xiaofei Jia、Zheng Wang、Chungu Xia、Kuiling Ding

  DOI：10.1002/chem.201203042

  日期：2012.11.26

  hydroformylation of terminal olefins. Remarkably, the catalysts were also found to be efficient in the isomerization–hydroformylation of some internal olefins, to regioselectively afford the linear aldehydes with TON values of up to 2.0×104 and l/b ratios in the range of 23.4–30.6. X‐ray crystallographic analysis revealed the cis coordination of the ligand in the precatalyst [Rh(3 d)(acac)], whereas

  基于螺环骨架的新型二齿亚磷酰胺配体已被开发用于铑催化的加氢甲酰化反应。发现了一系列适合该方案的短链和长链烯烃，它们对线性醛具有很高的催化活性和极好的区域选择性。在优化的反应条件下，在Rh I催化的末端烯烃加氢甲酰化反应中，其周转数（TON）高达2.3×10 4，线性与支化比（l / b）高达174.4 。值得注意的是，还发现催化剂是在一些内部烯烃的异构化-加氢甲酰化高效，区域选择性得到用向上的TON值线性醛〜2.0×10 4和l / b比在23.4-30.6之间。X射线晶体学分析揭示了前催化剂[Rh（3 d）（acac）]中配体的顺式配位，而对催化活性的氢化物络合物[HRh（CO）2（3 d）]的NMR和IR研究表明，物种中配体的eq-eq配位。
• Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant Candida spp.
  作者：Fei Zhao、Huai-Huai Dong、Yuan-Hua Wang、Tian-Yi Wang、Ze-Hao Yan、Fang Yan、Da-Zhi Zhang、Ying-Ying Cao、Yong-Sheng Jin

  DOI：10.1039/c6md00649c

  日期：——

  monoketone derivatives of curcumin were synthesized to investigate the synergy with fluconazole against fluconazole-resistant Candida spp. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant C. albicans, C. tropicalis and C. krusei in vitro. Most of these compounds showed

  合成了二十三种姜黄素单酮衍生物，以研究与氟康唑对耐氟康唑的念珠菌的协同作用。在体外测定了抗真菌增效剂氟康唑的最低抑菌浓度（MIC 80）和分数抑菌浓度指数（FICI）对耐氟康唑的白色念珠菌，热带念珠菌和克鲁氏梭菌的抑制作用。这些化合物中的大多数对热带念珠菌表现出良好的协同活性。其中，化合物9显示出对念珠菌的显着协同活性。spp。特区也进行了讨论。特别地，细胞生长测试显示，1μgml -1氟康唑和64μgml -1或128μgml -1化合物9的组合显示出对热带假丝酵母最有效的杀真菌作用。协同作用可能与细胞内ATP含量和细胞膜通透性的变化有关。我们的结果为这些化合物作为氟康唑耐药念珠菌病的治疗方法的潜在线​​索提供了未来评估和开发的基础。