(3-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-yl)methanol | 1015869-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-yl)methanol
• 英文别名: 3-[(4-fluorophenyl)-1-methyl-1H-5-pyrazolyl]methanol；[3-(4-fluorophenyl)-1-methyl-1H-pyrazol-5-yl]methanol；[5-(4-Fluorophenyl)-2-methylpyrazol-3-yl]methanol
• CAS: 1015869-25-6
• 化学式: C₁₁H₁₁FN₂O
• 分子量: 206.22
• InChiKey: WBYHVKPHXICEOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-yl)methanol 在 氯化亚砜 、 potassium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 生成 3-bromo-N-((3-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-yl)methyl)aniline
  参考文献：
  名称：

  二芳基吡唑类化合物及其制备方法与应用

  摘要：

  本发明公开了二芳基吡唑类化合物及其制备方法与应用，结构如通式(I)所示：其中，R1为氢、卤素或甲基；R2为氢、氰基、三氟甲基或卤素；R3为氢、卤素或腈基；X如上式为氨甲酰基、硫脲基、甲胺基或氨甲基。本发明的二芳基吡唑类化合物，尤其是11aM01，11aM02，11M04，13aM01,16aM01，16aM02，16aM10，16aM11，16aM12，16aM15对前列腺癌细胞LNCaP和PC‑3均有较强的细胞生长抑制活性，11aM03，12aM01，12aM02，16aM05，16aM06，16aM07，16aM08，16aM13，16aM16对前列腺癌细胞LNCaP细胞有较强的选择性，这些化合物都可以用于制备抗肿瘤药物。

  公开号：

  CN104844514B
• 作为产物：
  描述：

  3-(4-fluorophenyl)-1-methyl-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1H-pyrazole 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以64%的产率得到(3-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-yl)methanol
  参考文献：
  名称：

  Synthesis and Structure−activity Relationships of Antitubercular 2-Nitroimidazooxazines Bearing Heterocyclic Side Chains

  摘要：

  Recently described biphenyl analogues Of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility.

  DOI：

  10.1021/jm901378u

文献信息

• Synthesis and biological evaluation of 3-(4-fluorophenyl)-1H-pyrazole derivatives as androgen receptor antagonists
  作者：Guangzhu Guo、Jianzhen Liu、Guanjie Wang、Daoguang Zhang、Jinjie Lu、Guisen Zhao

  DOI：10.1097/cad.0000000000000322

  日期：2016.4

  A novel series of 3-(4-fluorophenyl)-1H-pyrazole derivatives were synthesized and evaluated for their antiproliferative activity against two prostate cancer cell lines (LNCaP and PC-3) and androgen receptor target gene prostate-specific antigen (PSA) inhibitory activity in LNCaP cells. Several compounds showed potent antiproliferative activity against LNCaP cells and showed a promising PSA downregulation rate. Among these, compound 10e selectively inhibited LNCaP cell growth with an IC50 value of 18 mu mol/l and showed a PSA downregulation rate of 46%, which was better than the lead compound T3.
• 二芳基吡唑类化合物及其制备方法与应用
  申请人：山东大学

  公开号：CN104844514B

  公开（公告）日：2017-11-10

  本发明公开了二芳基吡唑类化合物及其制备方法与应用，结构如通式(I)所示：其中，R1为氢、卤素或甲基；R2为氢、氰基、三氟甲基或卤素；R3为氢、卤素或腈基；X如上式为氨甲酰基、硫脲基、甲胺基或氨甲基。本发明的二芳基吡唑类化合物，尤其是11aM01，11aM02，11M04，13aM01,16aM01，16aM02，16aM10，16aM11，16aM12，16aM15对前列腺癌细胞LNCaP和PC‑3均有较强的细胞生长抑制活性，11aM03，12aM01，12aM02，16aM05，16aM06，16aM07，16aM08，16aM13，16aM16对前列腺癌细胞LNCaP细胞有较强的选择性，这些化合物都可以用于制备抗肿瘤药物。
• Synthesis and Structure−activity Relationships of Antitubercular 2-Nitroimidazooxazines Bearing Heterocyclic Side Chains
  作者：Hamish S. Sutherland、Adrian Blaser、Iveta Kmentova、Scott G. Franzblau、Baojie Wan、Yuehong Wang、Zhenkun Ma、Brian D. Palmer、William A. Denny、Andrew M. Thompson

  DOI：10.1021/jm901378u

  日期：2010.1.28

  Recently described biphenyl analogues Of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility.