3-Anilino-1-(4-chlorophenyl)but-2-en-1-one

• 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: 3-Anilino-1-(4-chlorophenyl)but-2-en-1-one
• 化学式: C₁₆H₁₄ClNO
• 分子量: 271.746
• InChiKey: LAQDMCUFYQFRQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 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：
  2

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 3-Anilino-1-(4-chlorophenyl)but-2-en-1-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  Hypoxia-Sensitive Metal β-Ketoiminato Complexes Showing Induced Single-Strand DNA Breaks and Cancer Cell Death by Apoptosis

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.5b00455
• 作为产物：
  描述：

  对氯苯乙酮 在 盐酸 、 sodium ethanolate 作用下， 以 水 、 甲苯 为溶剂， 生成 3-Anilino-1-(4-chlorophenyl)but-2-en-1-one
  参考文献：
  名称：

  Hypoxia-Sensitive Metal β-Ketoiminato Complexes Showing Induced Single-Strand DNA Breaks and Cancer Cell Death by Apoptosis

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.5b00455

文献信息

• β-Ketoiminato Iridium(III) Organometallic Complexes: Selective Cytotoxicity towards Colorectal Cancer Cells HCT116 <i>p53</i> -/-
  作者：Rianne M. Lord、Markus Zegke、Imogen R. Henderson、Christopher M. Pask、Helena J. Shepherd、Patrick C. McGowan

  DOI：10.1002/chem.201804901

  日期：2019.1.7

  library of organometallic iridium(III) compounds of the type [Cp*IrCl(L)] (Cp*=pentamethylcyclopentadienyl and L=a functionalized β‐ketoiminato ligand) showing moderate to high cytotoxicity against a range of cancer cell lines. All compounds show increased activity towards colorectal cancer, with preferential activity observed against the immortalized p53‐null colorectal cell line, HCT116 p53‐/‐, with

  该报告提出了一种新的[Cp * IrCl（L）]类型的有机金属铱（III）化合物库（Cp * =五甲基环戊二烯基和L =功能化的β-酮亚胺基配体），对一系列癌细胞具有中等至高细胞毒性线。所有化合物均显示出对结肠直肠癌的增强活性，并观察到对永生化的p53无效结肠直肠癌细胞系HCT116 p53- /的优先活性‐，灵敏度因子（SF）最高为26.7。此外，当针对正常细胞类型进行测试时，该化合物对癌细胞具有极好的选择性，选择性比（SR）高达35.6，与顺铂相反，顺铂既对癌细胞也不具有选择性，也不具有特异性（SF = 0.43和SR = 0.7 –2.3）。这项工作提供了对不存在p53的铱化合物的细胞毒性的初步了解，并且在治疗缺少p53基因或突变基因的癌症中具有潜在的应用前景。
• 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
• 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.