2'-benzoyloxycinnamaldehyde | 208118-56-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2'-benzoyloxycinnamaldehyde
• 英文别名: BCA；2-Benzoyloxycinnamaldehyde；[2-(3-oxoprop-1-enyl)phenyl] benzoate
• CAS: 208118-56-3
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: QRGLVSPIIXTSIE-UHFFFAOYSA-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：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-benzoyloxycinnamaldehyde 、 丙烯酸羟乙酯 在 对苯二酚 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 (3-(2-benzoyloxy)phenylprop-2-ene-1,1-diyl)bis(oxy)bis(ethane-2,1-diyl)diacrylate
  参考文献：
  名称：

  하이드록시 라디칼 생성유도 고분자 항암제 및 그의 제조방법

  摘要：

  本发明涉及一种含有新奈醛衍生物和氨基金属罗芬衍生物的羟基自由基诱导高分子，通过将新奈醛衍生物和氨基金属罗芬衍生物替代的聚（β-氨基酯）、新奈醛衍生物和氨基金属罗芬衍生物替代的聚（氨基氨基）或它们的共聚物，以及与亲水性聚乙二醇类化合物共聚合，从而形成微胶束。微胶束的结构对pH变化敏感，当在弱酸性肿瘤组织周围环境下，缩醛键断裂，导致微胶束崩解，并释放在高分子链中结合的新奈醛衍生物和氨基金属罗芬衍生物。在酸性条件下，新奈醛衍生物产生过氧化氢，而氨基金属罗芬衍生物与过氧化氢反应，生成具有高毒性的羟基自由基，使癌细胞自溶。因此，与使用传统生物降解高分子作为药物传递体不同，本研究中高分子本身可用作治疗药物，并且通过微胶束结构可以包含其他药物，并具有特异积累在癌症部位的能力。因此，通过减少对正常细胞的毒性，同时通过新奈醛衍生物诱导过氧化氢生成和氨基金属罗芬衍生物生成羟基自由基的协同作用，可以获得增强的抗癌氧化治疗效果。通过这种机制，polyCAFE不仅具有高分子本身的优良生物活性，在生理条件下分解并发挥强大的抗癌效果，而且当吸收传统抗癌药物时，可以用作癌组织敏感性药物传递体的优点。

  公开号：

  KR20160093807A
• 作为产物：
  描述：

  Benzoic acid 2-((E)-3-hydroxy-propenyl)-phenyl ester 在 manganese(IV) oxide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 2'-benzoyloxycinnamaldehyde
  参考文献：
  名称：

  Synthesis and biological activity of cinnamaldehydes as angiogenesis inhibitors

  摘要：

  A series of 2-hydroxycinnamaldehyde derivatives was synthesized for examing a structure-activity relationship for inhibition of angiogenesis. The anti-angiogenic effects of 2'-substituted cinnamaldehdes and related analogs were determined in a chick embryo chorioallantoic membrane assay system. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10008-7

文献信息

• Rhodanine-based PRL-3 inhibitors blocked the migration and invasion of metastatic cancer cells
  作者：Garam Min、Su-Kyung Lee、Hye-Nan Kim、Young-Min Han、Rhan-Hee Lee、Dae Gwin Jeong、Dong Cho Han、Byoung-Mog Kwon

  DOI：10.1016/j.bmcl.2013.04.092

  日期：2013.7

  PRL-3, phosphatase of regenerating liver-3, plays a role in cancer progression through its involvement in invasion, migration, metastasis, and angiogenesis. We synthesized rhodanine derivatives, CG-707 and BR-1, which inhibited PRL-3 enzymatic activity with IC50 values of 0.8 mu M and 1.1 mu M, respectively. CG-707 and BR-1 strongly inhibited the migration and invasion of PRL-3 overexpressing colon cancer cells without exhibiting cytotoxicity. The specificity of the inhibitors on PRL-3 phosphatase activity was confirmed by the phosphorylation recovery of known PRL-3 substrates such as ezrin and cytokeratin 8. The compounds selectively inhibited PRL-3 in comparison with other phosphatases, and CG-707 regulated epithelial-to-mesenchymal transition (EMT) marker proteins. The results of the present study reveal that rhodanine is a specific PRL-3 inhibitor and a good lead molecule for obtaining a selective PRL-3 inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.
• Dual pH-sensitive oxidative stress generating micellar nanoparticles as a novel anticancer therapeutic agent
  作者：Sanga Park、Byeongsu Kwon、Wonseok Yang、Eunji Han、Wooyoung Yoo、Byoung-Mog Kwon、Dongwon Lee

  DOI：10.1016/j.jconrel.2014.09.017

  日期：2014.12

  Cancer cells are under oxidative stress due to a large production of reactive oxygen species (ROS), which involve in cell proliferation and cancer promotion and progression. On the other hand, ROS promotes cell death, depending on the rate of ROS production and the activity of antioxidant systems. Recently, "oxidation therapy" has arisen as a promising anticancer strategy, which can be achieved by inducing the generation of cytotoxic level of ROS or inhibiting the antioxidant systems in tumor cells. Here, we report oxidative stress amplifying nanoplatforms as novel anticancer therapeutics, which are able not only to suppress antioxidant but also to generate ROS simultaneously in acidic tumor microenvironments. The oxidative stress amplifying nanoplatforms are composed of dual pH-sensitive PBCAE copolymer, polymeric prodrug of BCA (benzoyloxycinnamaldehyde) and heme oxygenase-1 (HO-1) inhibiting zinc protoporphyrin (ZnPP). PBCAE was designed to incorporate ROS-generating BCA in its backbone via acid-cleavable acetal linkages and self-assemble to form micelles that encapsulate ZnPP. In vitro proof-of-concept studies revealed that ZnPP encapsulated in PBCAE micelles suppressed HO-1 to make cancer cells more vulnerable to BCA-induced ROS, leading to enhanced apoptotic cell death. In addition, ZnPP-loaded PBCAE micelles significantly suppressed the tumor growth in human cancer xenograft mouse models. We believe that oxidative stress amplifying micellar nanoparticles have a great potential as novel redox anticancer therapeutics. (C) 2014 Elsevier B.V. All rights reserved.