ethyl 3-phenyl-1-(2-bromoethyl)-1H-pyrazole-5-carboxylate | 1101861-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-phenyl-1-(2-bromoethyl)-1H-pyrazole-5-carboxylate
• 英文别名: ethyl 1-(2-bromoethyl)-3-phenyl-1H-pyrazole-5-carboxylate；2-(2-Bromo-ethyl)-5-phenyl-2H-pyraZole-3-carboxylic acid ethyl ester；ethyl 2-(2-bromoethyl)-5-phenylpyrazole-3-carboxylate
• CAS: 1101861-35-1
• 化学式: C₁₄H₁₅BrN₂O₂
• 分子量: 323.189
• InChiKey: FORHYIJNYPSQGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-phenyl-1-(2-bromoethyl)-1H-pyrazole-5-carboxylate 在 lithium aluminium tetrahydride 、 sodium hydride 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 9.34h， 生成 ethyl 2-((1-(2-(diethylamino)ethyl)-3-phenyl-1H-pyrazol-5-yl)methoxy)acetate
  参考文献：
  名称：

  Design and Synthesis of Novel Pyrazole-based Lp-PLA2 Inhibitors

  摘要：

  AbstractA series of novel pyrazole‐based lipoprotein‐associated phospholipase A2 (Lp‐PLA2) inhibitors have been designed and synthetized by a variety of acetophenones via a 10‐step convergent approach. The synthetic approach is carefully optimized, and an unsuccessful alternative route is also discussed. The in vitro biological activity reveals that all the synthesized compounds are potent Lp‐PLA2 inhibitors with compound 13b being the most potent one (Lp‐PLA2, IC50=1.5 nmol/L).

  DOI：

  10.1002/cjoc.201180354
• 作为产物：
  描述：

  4-苯基-2,4-二氧丁酸乙酯 在 potassium carbonate 、 一水合肼 、 溶剂黄146 、 potassium iodide 作用下， 以 水 、 乙腈 为溶剂， 反应 3.17h， 生成 ethyl 3-phenyl-1-(2-bromoethyl)-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  Design and Synthesis of Novel Pyrazole-based Lp-PLA2 Inhibitors

  摘要：

  AbstractA series of novel pyrazole‐based lipoprotein‐associated phospholipase A2 (Lp‐PLA2) inhibitors have been designed and synthetized by a variety of acetophenones via a 10‐step convergent approach. The synthetic approach is carefully optimized, and an unsuccessful alternative route is also discussed. The in vitro biological activity reveals that all the synthesized compounds are potent Lp‐PLA2 inhibitors with compound 13b being the most potent one (Lp‐PLA2, IC50=1.5 nmol/L).

  DOI：

  10.1002/cjoc.201180354

文献信息

• Synthesis and preliminary biological evaluation of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives as potential agents against A549 lung cancer cells
  作者：Jin-Hua Zhang、Chuan-Dong Fan、Bao-Xiang Zhao、Dong-Soo Shin、Wen-Liang Dong、Yong-Sheng Xie、Jun-Ying Miao

  DOI：10.1016/j.bmc.2008.10.066

  日期：2008.12.15

  determined by IR, (1)H NMR and mass spectroscopy, in addition, representative single-crystal structures were characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that the compounds could inhibit the growth of A549 cells in dosage- and time-dependent manners. The study on structure-activity relationships showed that compounds with 4-chlorophenyl group at pyrazole moiety

  通过3-芳基-1-（2-溴乙基）-1H-吡唑-5-羧酸乙酯与胺的反应，合成了一系列新颖的吡唑并[1,5-a]吡嗪-4（5H）-衍生物。一般加热条件和微波辅助条件。通过IR，（1）H NMR和质谱确定化合物的结构，此外，通过使用X射线衍射分析表征代表性的单晶结构。初步生物学评估表明，该化合物可以剂量和时间依赖性抑制A549细胞的生长。结构-活性关系的研究表明，吡唑部分具有4-氯苯基的化合物，例如5-苄基-2-（4-氯苯基）-6,7-二氢吡唑并[1,5-a]吡嗪-4（5H） ）-1（3o）具有更大的抑制作用。
• Microwave-assisted synthesis, crystal structure of pyrazolo[1,5-a]pyrazin-4(5H)-ones and their selective effects on lung cancer cells
  作者：Ning Liu、Jin-Hua Zhang、Bao-Xiang Zhao、Jing Zhao、Le Su、Wen-Liang Dong、Shang-Li Zhang、Jun-Ying Miao

  DOI：10.1016/j.ejmech.2011.03.018

  日期：2011.6

  A series of novel pyrazolo[1,5-a[pyrazin-4(5H)-one derivatives with hydrophilic group was synthesized under general heating condition and microwave-assisted condition. The structures of compounds were determined by IR, (1)H NMR and HRMS, moreover, representative crystal structures were characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that some compounds could inhibit the growth of A549, H322 and H1299 cells in dosage dependent manners. The compounds could inhibit growth of A549, H322 and H1299 cells in different mechanism. Compounds 3e-h inhibited growth of A549 cells by inducing a strong G1-phase arrest. Whereas these compounds inhibited growth of H1299 and H322 cells by inducing apoptosis. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Design and Synthesis of Novel Pyrazole-based Lp-PLA2 Inhibitors
  作者：Yi Wang、Weiren Xu、Hua Shao、Yafei Xie、Jianwu Wang

  DOI：10.1002/cjoc.201180354

  日期：2011.10

  AbstractA series of novel pyrazole‐based lipoprotein‐associated phospholipase A2 (Lp‐PLA2) inhibitors have been designed and synthetized by a variety of acetophenones via a 10‐step convergent approach. The synthetic approach is carefully optimized, and an unsuccessful alternative route is also discussed. The in vitro biological activity reveals that all the synthesized compounds are potent Lp‐PLA2 inhibitors with compound 13b being the most potent one (Lp‐PLA2, IC50=1.5 nmol/L).