(E)-2-(3-oxoprop-1-en-1-yl)phenyl benzoate | 199934-50-4

• 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: (E)-2-(3-oxoprop-1-en-1-yl)phenyl benzoate
• 英文别名: 2'-benzoyloxycinnamaldehyde；2-benzoyloxycinnamaldehyde；2-(3-Oxoprop-1-en-1-yl)phenyl benzoate；[2-[(E)-3-oxoprop-1-enyl]phenyl] benzoate
• CAS: 199934-50-4
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: QRGLVSPIIXTSIE-UXBLZVDNSA-N

物化性质

• 沸点：
  471.1±28.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

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

安全信息

• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  甲氧基胺盐酸盐 、 (E)-2-(3-oxoprop-1-en-1-yl)phenyl benzoate 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 [2-[(E,3E)-3-methoxyiminoprop-1-enyl]phenyl] benzoate
  参考文献：
  名称：

  Synthesis and biological evaluation of cinnamyl compounds as potent antitumor agents

  摘要：

  A series of cinnamyl compounds related to 2'-hydroxycinnamaldehyde were synthesized and their antitumor effects against human cancer cells evaluated. Hydroxylamine derivative 6 inhibited the growth of human cancer cells and human colon tumor xenograft in nude mice. Its antitumor effects belong to the induction of apoptosis and arresting cell cycle at G(2)/M phase, which is confirmed by detection of apoptosis markers and cell cycle analysis. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.033
• 作为产物：
  描述：

  2-allylphenyl benzoate 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以75%的产率得到(E)-2-(3-oxoprop-1-en-1-yl)phenyl benzoate
  参考文献：
  名称：

  （模块化合成ë）直接从allylarenes -cinnamaldehydes经由无金属DDQ介导的氧化过程†

  摘要：

  通过无金属的DDQ介导的烯丙基芳烃的氧化转化，可以有效合成（E）-肉桂醛。该协议提供了一种实用的方法来制备具有宽泛的官能团耐受性的多种（E）-肉桂醛，并具有良好的优异收率，包括从植物提取物中容易获得天然产物蓝丹醛和香叶基氧基芥子醛。最后，提出了单电子转移过程的机理。

  DOI：

  10.1039/c8ob01469h

文献信息

• Inhibition of Human Tumor Growth by 2′-Hydroxy- and 2′-Benzoyl-oxycinnamaldehydes
  作者：Chang Lee、Dong Hong、Sang Han、Se Park、Hyae Kim、Byoung-Mog Kwon、Hwan Kim

  DOI：10.1055/s-2006-960772

  日期：1999.4

  2'-Hydroxycinnamaldehyde (HCA) was isolated from Cinnamomum cassia Blume (Lauraceae) and 2'-benzoyloxycinnamaldehyde (BCA) was prepared by the reaction of HCA and benzoyl chloride. HCA and BCA strongly inhibited in vitro growth of 29 kinds of human cancer cells and in vivo growth of SW-620 human tumor xenograft without the loss of body weight in nude mice. HCA prevented adherence of SW-620 cells to

  2'-羟基肉桂醛 (HCA) 是从肉桂 (Lauraceae) 中分离出来的，2'-苯甲酰氧基肉桂醛 (BCA) 是通过 HCA 和苯甲酰氯的反应制备的。HCA 和 BCA 强烈抑制 29 种人癌细胞的体外生长和 SW-620 人肿瘤异种移植物的体内生长，而不会降低裸鼠体重。HCA 阻止 SW-620 细胞粘附到培养物表面，但不抑制致癌 K-Ras 加工，暗示其在细胞水平上的抗肿瘤机制。
• Composition for preventing cancer comprising 2'-benzoyl-oxycinnamaldehyde
  申请人：Kwon Byoung-Mog

  公开号：US20060035968A1

  公开（公告）日：2006-02-16

  Disclosed is a composition for preventing cancer comprising a compound represented by Chemical Formula 1, 2′-benzoyloxycinnamaldehyde (BCA). BCA has the effects of delaying tumor incidence and increasing immune cells in a transgenic mouse overexpressing H-ras oncogene playing a critical role in tumor cell growth. Thus, BCA is useful as a cancer preventive drug.

  公开了一种预防癌症的组合物，包括一种由化学式1表示的化合物，2'-苯甲酰氧基肉桂醛（BCA）。BCA具有延迟转基因小鼠中H-ras癌基因过度表达所致的肿瘤发生和增加免疫细胞的作用，这些免疫细胞在肿瘤细胞生长中发挥关键作用。因此，BCA可用作预防癌症的药物。
• [EN] COMPOSITION FOR PREVENTING CANCER COMPRISING 2'-BENZOYL-OXYCINNAMALDEHYDE<br/>[FR] COMPOSITION POUR LA PREVENTION DU CANCER COMPRENANT LE 2'-BENZOYLOXYCINNAMALDEHYDE
  申请人：KOREA RES INST OF BIOSCIENCE

  公开号：WO2006016741A1

  公开（公告）日：2006-02-16

  Disclosed is a composition for preventing cancer comprising a compound represented by Chemical Formula 1, 2¡Ë-benzoyloxycinnamaldehyde (BCA). BCA has the effects of delaying tumor incidence and increasing immune cells in a transgenic mouse overexpressing H-ras oncogene playing a critical role in tumor cell growth. Thus, BCA is useful as a cancer preventive drug.

  公开了一种用于预防癌症的组合物，该组合物包括一种化合物，其化学式为1,2-苯甲酰氧基肉桂醛(BCA)。BCA具有延缓肿瘤发生和增加免疫细胞的作用，在过度表达H-ras癌基因的转基因小鼠中发挥了关键作用，该基因对肿瘤细胞生长具有重要作用。因此，BCA可用作预防癌症的药物。
• PHARMACEUTICAL COMPOSITION FOR TREATING ORAL PRECANCER AND METHOD FOR PREDICTING OR DIAGNOSING ORAL PRECANCER OR ORAL CANCER
  申请人：Met Life Sciences Co., Ltd.

  公开号：EP3567119A1

  公开（公告）日：2019-11-13

  The present invention relates to: a method for providing information for the prediction or diagnosis of oral precancer or oral cancer characterized by confirming expression of the Axin2 gene or the Snail gene in an oral leukoplakia tissue sample or an oral submucous fibrosis tissue sample; and a use of a compound capable of delaying or inhibiting the progression of a precancerous lesion and recurrent oral cancer using the compound capable of effectively inhibiting the expression of the Axin2 gene or the Snail gene. According to the present invention, the possibility of oral leukoplakia or submucous fibrosis which causes white lesions to appear inside the oral cavity can be predicted and diagnosed, thereby being useful in eliminating the potential risks of oral cancer by early prediction of progression into oral precancer or oral cancer for which effective treatment does not currently exist.

  本发明涉及：一种为预测或诊断口腔癌前病变或口腔癌提供信息的方法，其特征在于确认口腔白斑病组织样本或口腔黏膜下纤维化组织样本中Axin2基因或Snail基因的表达；以及使用能够有效抑制Axin2基因或Snail基因表达的化合物，延缓或抑制癌前病变和复发性口腔癌的进展。根据本发明，可以预测和诊断导致口腔内出现白色病变的口腔白斑病或粘膜下纤维化的可能性，从而通过早期预测口腔癌前病变或目前尚无有效治疗方法的口腔癌的进展，有助于消除口腔癌的潜在风险。
• Cinnamaldehydes inhibit cyclin dependent kinase 4/cyclin D1
  作者：Ha-Won Jeong、Mi-Ran Kim、Kwang-Hee Son、Mi Young Han、Ji-Hong Ha、Matthieu Garnier、Laurent Meijer、Byoung-Mog Kwon

  DOI：10.1016/s0960-894x(00)00357-7

  日期：2000.8

  A series of cinnamaldehydes was synthesized for the study of inhibitory activity against cyclin dependent kinases (CDKs). A couple of compounds selectively inhibited cyclin D1-CDK4 with an IC50 value of 7-18 mu M. (C) 2000 Elsevier Science Ltd. All rights reserved.