2-(4-(4-fluorophenyl)-2,2-dimethyltetrahydro-2H-pyran-4-yl)acetonitrile | 330998-24-8

• 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: 2-(4-(4-fluorophenyl)-2,2-dimethyltetrahydro-2H-pyran-4-yl)acetonitrile
• 英文别名: 2-[4-(4-fluorophenyl)-2,2-dimethyloxan-4-yl]acetonitrile
• CAS: 330998-24-8
• 化学式: C₁₅H₁₈FNO
• 分子量: 247.312
• InChiKey: DPDHQPZJMMVGIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-(4-fluorophenyl)-2,2-dimethyltetrahydro-2H-pyran-4-yl)acetonitrile 在 甲醇 、 sodium tetrahydroborate 、 cobalt(II) chloride 作用下， 反应 2.0h， 以179 mg的产率得到2-(4-(4-fluorophenyl)-2,2-dimethyltetrahydro-2H-pyran-4-yl)ethanamine
  参考文献：
  名称：

  [EN] TETRAHYDROPYRAN-4-YLETHYLAMINO- OR TETRAHYDROPYRANYL-4-ETHYLOXY-PYRIMIDINES OR -PYRIDAZINES AS ISOPRENYLCYSTEINCARBOXYMETHYL TRANSFERASE INHIBITORS
  [FR] PYRIMIDINES OU PYRIDAZINES TÉTRAHYDROPYRAN-4-YLÉTHYLAMINO- OU TÉTRAHYDROPYRANYL-4-ÉTHYLOXY UTILES COMME INHIBITEURS DE L'ISOPRÉNYL-CYSTÉINE-CARBOXY-MÉTHYL-TRANSFÉRASE

  摘要：

  化合物的结构式（I）：其中：R1选自：（i）苯基，可选择一个氟原子取代；（ii）噻吩基；（iii）呋喃基；（iv）C1-4烷基；和（v）氢；R2选自：（II），R3选自：（III），X选自NH和O；R4选自苯基，5-成员杂环基或6-成员杂环基，均可选择一个或多个取代基，所述取代基选自：甲基，甲氧基，三氟甲基，三氟甲氧基，氰基，氟原子，-OC2H4OMe和吡唑基。

  公开号：

  WO2014041349A1
• 作为产物：
  描述：

  ethyl 2-cyano-2-(2,2-dimethyl-tetrahydropyran-4-ylidene)acetate 在 copper(I) bromide dimethylsulfide complex 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 反应 1.5h， 生成 2-(4-(4-fluorophenyl)-2,2-dimethyltetrahydro-2H-pyran-4-yl)acetonitrile
  参考文献：
  名称：

  Discovery and SAR of Methylated Tetrahydropyranyl Derivatives as Inhibitors of Isoprenylcysteine Carboxyl Methyltransferase (ICMT)

  摘要：

  A series of tetrahydropyranyl (THP) derivatives has been developed as potent inhibitors of isoprenylcysteine carboxyl methyltransferase (ICMT) for use as anticancer agents. Structural modification of the submicromolar hit compound 3 led to the potent 3-methoxy substituted analogue 27. Further SAR development around the THP ring resulted in an additional 10-fold increase in potency, exemplified by analogue 75 with an IC50 of 1.3 nM. Active and potent compounds demonstrated a dose-dependent increase in Ras cytosolic protein. Potent ICMT inhibitors also reduced cell viability in several cancer cell lines with growth inhibition (GI(50)) values ranging from 0.3 to >100 mu M. However, none of the cellular effects observed using ICMT inhibitors were as pronounced as those resulting from a farnesyltransferase inhibitor.

  DOI：

  10.1021/jm200249a