1-(3-fluorophenyl)-3-(phenylamino)-but-2-en-1-one | 1411690-90-8

• 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: 1-(3-fluorophenyl)-3-(phenylamino)-but-2-en-1-one
• 英文别名: 3-Anilino-1-(3-fluorophenyl)but-2-en-1-one
• CAS: 1411690-90-8
• 化学式: C₁₆H₁₄FNO
• 分子量: 255.292
• InChiKey: JEADQMMQNDNAEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 1-(3-fluorophenyl)-3-(phenylamino)-but-2-en-1-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以75%的产率得到
  参考文献：
  名称：

  Synthesis of iridium and ruthenium complexes with (N,N), (N,O) and (O,O) coordinating bidentate ligands as potential anti-cancer agents

  摘要：

  已制备出几种含有 (N,N)、(N,O) 和 (O,O) 配位双齿配体的 Ru-arene 和 Ir-Cp* 复合物，并发现这些复合物对 HT-29 和 MCF-7 细胞系都有活性。通过在金属复合物中加入具有生物活性的配体，可以提高抗癌活性。

  DOI：

  10.1039/c2dt32104a
• 作为产物：
  描述：

  1-(3-氟苯基)丁烷-1,3-二酮 、 苯胺 在 盐酸 作用下， 以 水 、 甲苯 为溶剂， 反应 16.0h， 以83%的产率得到1-(3-fluorophenyl)-3-(phenylamino)-but-2-en-1-one
  参考文献：
  名称：

  Synthesis of iridium and ruthenium complexes with (N,N), (N,O) and (O,O) coordinating bidentate ligands as potential anti-cancer agents

  摘要：

  已制备出几种含有 (N,N)、(N,O) 和 (O,O) 配位双齿配体的 Ru-arene 和 Ir-Cp* 复合物，并发现这些复合物对 HT-29 和 MCF-7 细胞系都有活性。通过在金属复合物中加入具有生物活性的配体，可以提高抗癌活性。

  DOI：

  10.1039/c2dt32104a

文献信息

• Hypoxia-Sensitive Metal β-Ketoiminato Complexes Showing Induced Single-Strand DNA Breaks and Cancer Cell Death by Apoptosis
  作者：Rianne M. Lord、Andrew J. Hebden、Christopher M. Pask、Imogen R. Henderson、Simon J. Allison、Samantha L. Shepherd、Roger M. Phillips、Patrick C. McGowan

  DOI：10.1021/acs.jmedchem.5b00455

  日期：2015.6.25

  A series of ruthenium and iridium complexes have been synthesized and characterized with 20 novel crystal structures discussed. The library of beta-ketoiminato complexes has been shown to be active against MCF-7 (human breast carcinoma); HT-29 (human colon carcinoma), A2780 (hint-tan ovarian carcinoma), and A2780cis (cisplatin-resistant human ovarian carcinoma) cell lines, with selected complexes' being more than three tithes, as active as cisplatin against the A2780cis cell line. Selected complexes were also tested against the noncancerous ARPE-19 (retinal pigment epithelial cells) cell line, in Order to evaluate the complexes selectivity for cancer cells. Complexes have also been shown to be highly active under hypoxic,conditions, with the activities of some complexes increasing with a decrease in O-2 concentration. The enzyme thioredoxin reductase is overexpressed in cancer cells, and complexes reported herein have the advantage of inhibiting this enzyme, with IC50 values measured. in the nanomolar range. The anticancer activity of these complexes was further investigated to determine whether activity is due to effects on cellular growth or cell survival. The complexes were flail-id to induce significant levels of cancer cell,death by apoptosis with levels induced correlating closely with activity in chemosensitivity studies, As a possible cause of,cell death, the ability of the complexes to induce damage to cellular DNA was also assessed. The complexes failed to induce double-strand DNA breaks or DNA cross-linking but induced significant levels of single-strand DNA breaks, indicating a mechanism of action different from that of cisplatin.
• Anticancer, antifungal and antibacterial potential of bis(β-ketoiminato)ruthenium(II) carbonyl complexes
  作者：Cecilia R. Madzivire、Pablo Caramés-Méndez、Christopher M. Pask、Roger M. Phillips、Rianne M. Lord、Patrick C. McGowan

  DOI：10.1016/j.ica.2019.119025

  日期：2019.12