4-benzoylcinnamic acid

• 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: 4-benzoylcinnamic acid
• 英文别名: (E)-3-(4-benzoylphenyl)acrylic acid；(E)-3-(4-benzoylphenyl)prop-2-enoic acid
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: MSHKPYYDASUVTE-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzoylcinnamic acid 在 RhCl(PPh₃)3 氢气 作用下， 生成 3-(4-苯甲酰基苯基)丙酸
  参考文献：
  名称：

  New taxanes as highly efficient reversal agents for multi-drug resistance in cancer cells

  摘要：

  New non-cytotoxic taxanes synthesized from 10-deacetylbaccatin III and special hydrophobic acylating agents show remarkable MDR reversal activity (less than or equal to 99.8%) against drug-resistant human breast cancer cells when co-administered with paclitaxel or doxorubicin. This activity is ascribed to the highly efficient blocking of P-glycoprotein efflux by these new taxanes. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10218-9
• 作为产物：
  描述：

  4-溴苯甲酰苯 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 4-benzoylcinnamic acid
  参考文献：
  名称：

  肉桂酸异羟肟酸衍生的基于活性的蛋白谱探针的设计与合成

  摘要：

  在我们不断努力寻找新的抗丙型肝炎病毒（HCV）剂的过程中，我们验证了化合物1的抗复制子活性，化合物1是我们最近报道的一种有效且选择性的抗HCV异羟肟酸。1表现出的良好的理化和体外吸收，分布，代谢和排泄（ADME）性能使其成为理想的母体化合物，由此可以设计和合成基于活性的蛋白质谱（ABPP）探针3。探针3的评估表明，它具有必要的抗HCV活性和选择性。因此，我们已成功获得化合物3作为合适的ABPP探针来鉴定化合物1的潜在分子靶标。有望将探针3及其改良的类似物加入到越来越多的ABPP探针中，这些探针不仅对生物化学和细胞功能的研究，而且对蛋白质靶标选择性抑制剂的发现都做出了重要贡献。

  DOI：

  10.1016/j.bmc.2015.12.035

文献信息

• New Sugar‐Based Permeant Analogs of D‐ Myo ‐Inositol 1,4,5‐Trisphosphate Mimicking the Effect of Vasopressin: Synthesis and Biologic Evaluation*
  作者：Françoise Chrétien、Fabien Roussel、Mauricette Hilly、Jean‐Pierre Mauger、Yves Chapleur

  DOI：10.1081/car-200068070

  日期：2005.8.1

  of the xylose‐inositol analogy, a series of permeant analogs of D‐myo‐inositol 1,4,5‐trisphosphate (InsP3) have been synthesized by various esterifications of the phosphate groups. Their ability to cross the cell membrane has been tested on vasopressin cells. Very fast liberation of calcium occurs when active analogs are introduced in the extracellular medium on intact cells. Membrane crossing as well

  根据木糖-肌醇的类似物，已通过磷酸酯基团的各种酯化反应合成了一系列D-肌醇1,4,5-三磷酸酯（InsP3）的渗透性类似物。在血管加压素细胞上已经测试了它们穿过细胞膜的能力。当将活性类似物引入完整细胞的细胞外培养基中时，钙会非常快速地释放出来。使用所有磷酸酯基团的酰氧基甲基酯化，膜的转运以及磷酸酯的水解都非常快。游离化合物在细胞中的行为类似于InsP3。对于表达血管加压素受体的大鼠肝细胞，以这种方式制备的一种类似物的行为类似于血管加压素。*致敬Jacques H. van Boom及其在该领域的杰出贡献。
• General Synthesis of Alkenyl Sulfides by Palladium-Catalyzed Thioetherification of Alkenyl Halides and Tosylates
  作者：Noelia Velasco、Cintia Virumbrales、Roberto Sanz、Samuel Suárez-Pantiga、Manuel A. Fernández-Rodríguez

  DOI：10.1021/acs.orglett.8b00854

  日期：2018.5.18

  ligand is reported. These reactions occur under low catalyst loading and in high yields and display wide scope, including the coupling of bulky thiols and trisubstituted bromoolefins, and functional group tolerance. In addition, the thioetherification of less reactive chloroalkenes and, for the first time, alkenyl tosylates was accomplished using a catalyst generated from CyPFtBu alkylbisphosphine ligand

  据报道，链烯基溴化物与硫醇的交联反应是由廉价dppf配体衍生的钯配合物催化的。这些反应在低催化剂负载和高收率下发生，并显示出较宽的范围，包括大体积硫醇和三取代溴代烯烃的偶联以及官能团的耐受性。另外，使用由CyPF t Bu烷基双膦配体产生的催化剂实现了反应性较低的氯代烯烃的硫醚化以及首次甲苯基甲苯磺酸酯的硫醚化。
• Design, Synthesis and Structure−Activity Relationships of Novel Taxane-Based Multidrug Resistance Reversal Agents
  作者：Iwao Ojima、Christopher P. Borella、Xinyuan Wu、Pierre-Yves Bounaud、Cecilia Fumero Oderda、Matthew Sturm、Michael L. Miller、Subrata Chakravarty、Jin Chen、Qing Huang、Paula Pera、Tracy A. Brooks、Maria R. Baer、Ralph J. Bernacki

  DOI：10.1021/jm049483y

  日期：2005.3.1

  A series of novel taxane-based multidrug resistance (MDR) reversal agents (TRAs) has been designed and synthesized. Structure-activity relationship (SAR) study clearly indicates that modification of the C-7 position with hydrophobic arenecarbonyleinnamoyl groups brings about high potency against drug efflux mediated by P-glycoprotein (P-gp). Six TRAs exhibit ability to modulate a wide range of ATP-binding cassette (ABC) transporters, such as P-gp, multidrug resistance-associated protein 1 (MRP1), and breast cancer resistance protein (BCRP), which may serve as novel broad-spectrum modulators of ABC transporters.
• Targeting FtsZ for Antituberculosis Drug Discovery:  Noncytotoxic Taxanes as Novel Antituberculosis Agents
  作者：Qing Huang、Fumiko Kirikae、Teruo Kirikae、Antonella Pepe、Amol Amin、Laurel Respicio、Richard A. Slayden、Peter J. Tonge、Iwao Ojima

  DOI：10.1021/jm050920y

  日期：2006.1.1

  Screening of 120 taxanes identified a number of compounds that exhibited significant antituberculosis activity. Rational optimization of selected compounds led to the discovery that the C-seco-taxane-multidrug-resistance (MDR) reversal agents (C-seco-TRAs) are non-cytotoxic at the upper limit of solubility and detection (> 80 mu M), while maintaining MIC99 values of 1.25-2.5 mu M against drug-resistant and drug-sensitive strains of Mycobacterium tuberculosis (MTB). Treatment of MTB cells with TRA 3aa and 10a at the MIC caused filamentation and prolongation of the cells, a phenotypic response to FtsZ inactivation.
• New photoaffinity analogs of paclitaxel
  作者：Iwao Ojima、Pierre-Yves Bounaud、David G. Ahern

  DOI：10.1016/s0960-894x(99)00161-4

  日期：1999.4

  Two new photoreactive paclitaxel analogs bearing [H-3(2)]-3-(4-benzoyl)phenylpropanoyl group as the photophore as well as radiolabeling unit at the 7 and 10 positions, respectively, are developed. These new photoreactive analogs showed excellent preliminary results on the photoaffinity labeling of tubulin and P-glycoprotein. (C) 1999 Elsevier Science Ltd. All rights reserved.