(2E,4E)-5-phenyl-1-(1H-pyrrol-2-yl)penta-2,4-dien-1-one | 111260-60-7

• 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,4E)-5-phenyl-1-(1H-pyrrol-2-yl)penta-2,4-dien-1-one
• CAS: 111260-60-7
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: UFNVFMUJEGROII-HINBXAKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 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：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-乙酰基吡咯 、 肉桂醛 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以72 %的产率得到(2E,4E)-5-phenyl-1-(1H-pyrrol-2-yl)penta-2,4-dien-1-one
  参考文献：
  名称：

  Synthesis, Characterization, Antioxidant, and Anticancer Activity against Colon Cancer Cells of Some Cinnamaldehyde-Based Chalcone Derivatives

  摘要：

  The purpose of the current investigation was to produce cinammaldehyde-based chalcone derivatives (3a–k) to evaluate their potential effectiveness as antioxidant and inhibitory agents versus human Caco-2 cancer cells. The findings obtained using the DPPH assay showed that compound 3e had the highest effective antioxidant activity with the best IC50 value compared with the other compounds. Moreover, the cytotoxic findings revealed that compound 3e was the best compound for inhibiting Caco-2 development in contrast to all other produced derivatives, with the lowest IC50 concentration (32.19 ± 3.92 µM), and it also had no detrimental effects on healthy human lung cells (wi38 cells). Exposure of Caco-2 cells with this IC50 value of compound 3e resulted in a substantial rise in the number of early and late cells that are apoptotic with a significant comet nucleus when compared with control cells employing the annexin V/PI and comet evaluations, respectively. Furthermore, qRT-PCR and ELISA examinations indicated that compound 3e significantly altered the expression of genes and their relative proteins related to apoptosis in the treated Caco-2 cells, thus significantly inhibiting Caco-2 growth through activating Caspase-3 via an intrinsic apoptotic pathway. As a result, compound 3e could serve as an effective therapy for human colon cancer.

  DOI：

  10.3390/biom14020216

文献信息

• Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance
  作者：Ibidapo S. Williams、Prashant Joshi、Linda Gatchie、Mohit Sharma、Naresh K. Satti、Ram A. Vishwakarma、Bhabatosh Chaudhuri、Sandip B. Bharate

  DOI：10.1016/j.bmcl.2017.07.010

  日期：2017.8

  Inhibitors of CYP1 enzymes may play vital roles in the prevention of cancer and overcoming chemo-resistance to anticancer drugs. In this letter, we report synthesis of twenty-three pyrrole based heterocyclic chalcones which were screened for inhibition of CYP1 isoforms. Compound 3n potently inhibited CYP1B1 with an IC50 of ∼0.2 μM in Sacchrosomes™ and CYP1B1-expressing live human cells. However, compound

  CYP1酶的抑制剂可能在预防癌症和克服对抗癌药物的化学耐药性中起着至关重要的作用。在这封信中，我们报告了二十三种基于吡咯的杂环查耳酮的合成，这些化合物经筛选可抑制CYP1同工型。在Sacchrosomes™和CYP1B1表达的活人细胞中，化合物3n抑制CYP1B1的IC 50约为0.2μM。然而，化合物3J其既抑制CYP1A1和CYP1B1，其IC 50 ~0.9μM的，使用相同的系统中，也有效地拮抗B [一个的的AhR在酵母信令（IC] P-介导的诱导50，1.5μM），完全保护的B [ a的人类细胞通过恢复顺铂的细胞毒性，在过度表达CYP1B1的人细胞中，] P毒性和完全逆转顺铂耐药性。进行分子建模研究，以合理地观察到化合物3j和3n对酶抑制作用的潜力和选择性。
• Riccomanni, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1924, vol. <5> 33 I, p. 146
  作者：Riccomanni

  DOI：——

  日期：——