2-phenyl-3-(3,4,5-trimethoxyphenyl)acrylic acid | 121189-90-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-phenyl-3-(3,4,5-trimethoxyphenyl)acrylic acid
• 英文别名: (E)-2-phenyl-3-(3,4,5-trimethoxyphenyl)acrylic acid；2-phenyl-3t-(3.4.5-trimethoxy-phenyl)-acrylic acid；2-Phenyl-3t-(3.4.5-trimethoxy-phenyl)-acrylsaeure；(E)-2-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid
• CAS: 121189-90-0
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: YITBDTHDPPLHMZ-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-phenyl-3-(3,4,5-trimethoxyphenyl)acrylic acid 生成 2-phenyl-3t-(3.4.5-trimethoxy-phenyl)-acrylic acid-(4-phenyl-phenacyl ester)
  参考文献：
  名称：

  36.秋水仙碱和相关化合物。第二部分 N-乙酰基胆甾醇甲基醚的简单类似物的合成

  摘要：

  DOI：

  10.1039/jr9400000198
• 作为产物：
  描述：

  苯乙酸 、 3,4,5-三甲氧基苯甲醛 在 三乙胺 作用下， 以 乙酸酐 为溶剂， 反应 5.0h， 以54%的产率得到2-phenyl-3-(3,4,5-trimethoxyphenyl)acrylic acid
  参考文献：
  名称：

  Novel stilbene scaffolds efficiently target Mycobacterium tuberculosis nucleoid-associated protein, HU

  摘要：

  通过分子对接，识别出新型的stilbene支架，作为靶向核酸结合蛋白HU的抑制剂，用于抑制结核分枝杆菌。

  DOI：

  10.1039/d0nj05947a

文献信息

• Structural requirements for substrate in highly enantioselective hydrogenation over the cinchonidine-modified Pd/C
  作者：Takashi Sugimura、Takayuki Uchida、Junya Watanabe、Takeshi Kubota、Yasuaki Okamoto、Tomonori Misaki、Tadashi Okuyama

  DOI：10.1016/j.jcat.2008.11.022

  日期：2009.2.15

  Relationship between substrate Structure and enantioselectivity is studied for the asymmetric hydrogenation of 42 different (E)-alpha, beta-disubstituted acrylic acids (propenoic acids) over cinchonidine-modified Pd/C. The beta-phenyl group is indispensable for high enantioselectivity of alpha-phenylcinnamic acid (2,3-diphenylpropenoic acid, 81% ee), and substitution on this group affects markedly the selectivity. The high ee up to 92% was achieved by the beta-p-alkoxyphenyl substitution, and the selectivity is ascribed mainly to stronger interaction of the substrate with the chiral modifier on the catalyst surface. In contrast, substitution on the alpha-phenyl group does not affect notably the enantioselectivity (80-82% ee) or even the alpha-phenyl group itself is not indispensable but replaceable with a properly bulky group for the high enantioselectivity, (C) 2008 Elsevier Inc. All rights reserved.
• Design and synthesis of a C7-aryl piperlongumine derivative with potent antimicrotubule and mutant p53-reactivating properties
  作者：Surendra R. Punganuru、Hanumantha Rao Madala、Sanjay N. Venugopal、Ramakrishna Samala、Constantinos Mikelis、Kalkunte S. Srivenugopal

  DOI：10.1016/j.ejmech.2015.10.052

  日期：2016.1

  Small molecules that can restore biological function to the p53 mutants found in human cancers have been highly sought to increase the anticancer efficacy. In efforts to generate hybrid anticancer drugs that can impact two or more targets simultaneously, we designed and developed piperlongumine (PL) derivatives with an aryl group inserted at the C-7 position. This insertion bestowed a combretastatin A4 (CA4, an established microtubule disruptor) like structure while retaining the piperlongumine configuration. The new compounds exhibited potent antiproliferative activities against eight cancer cell lines, in particular, were more cytotoxic against the SKBR-3 breast cancer cells which harbor a R175H mutation in p53 suppressor. KSS-9, a representative aryl PL chosen for further studies induced abundant ROS generation and protein glutathionylation. KSS-9 strongly disrupted the tubulin polymerization in vitro, destabilized the microtubules in cells and induced a potent G2/M cell cycle block. More interestingly, KSS-9 showed the ability to reactivate the p53 mutation and restore biological activity to the R175H mutant protein present in SKBR3 cells. Several procedures, including immunocytochemistry using conformation-specific antibodies for p53, immunoprecipitation combined with western blotting, electrophoretic shift mobility shift assays showed a reciprocal loss of mutant protein and generation of wildtype like protein. p53 reactivation was accompanied by the induction of the target genes, MDM2, p21cip1 and PUMA. Mechanistically, the redox-perturbation in cancer cells by the hybrid drug appears to underlie the p53 reactivation process. This anticancer drug approach merits further development. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological evaluation of 1,1-Dichloro-2,3-diarylcyclopropanes as antitubulin and anti-breast cancer agents
  作者：Sastry S. Jonnalagadda、Ernst ter Haar、Ernest Hamel、Chii M. Lin、Robert A. Magarian、Billy W. Day

  DOI：10.1016/s0968-0896(97)00014-x

  日期：1997.4

  Z-1,1-Dichloro-2,3-diphenylcyclopropane (1) is an effective 'anti-breast cancer agent in rodents and in cell culture. We recently determined that 1 inhibits tubulin assembly in vitro. and causes microtubule loss in breast cancer cells, leading to accumulation in the G2/M portion of the cell cycle. Aryl ring-halogenated, methoxylated and benzyloxylated derivatives of 1, as well as its E-isomer and the dichlorocyclopropyl derivative of diethylstilbestrol (DES), were synthesized and tested for their ability to inhibit the assembly of tubulin into micro tubules. Including 1, 17 cyclopropyl compounds were tested. One (Z-1,1-dichloro-2-(4-methoxyphenyl)-3-phenylcyclopropane (12)) was found to be more active than 1. In addition, E-1,1-dichlorocyclopropylDES (17) was more potent than DES. The E-isomer of 1 (16) was inactive. The cytostatic activities of the compounds against MCF-7 and MDA-MB231 human breast cancer cells, and their abilities to perturb microtubules in MCF-7 cells were also evaluated. Z-Dichloro-2-(4-fluorophenyl)-3-phenylcyclo (5), Z-1,1-dichloro-2-(4-fluorophenyl)-3-(4-methoxyphenyl)cyclopropane (11), and Z-1,1-dichloro-2-(4-methoxyphenyl) -3-phenylcyclopropane (12) were more potent than 1 against the breast cancer cells. (C) 1997 Elsevier Science Ltd.