3-(4-三氟甲基-1H-咪唑-2-基)吡啶 | 33468-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-(4-三氟甲基-1H-咪唑-2-基)吡啶
• 英文名称: MK 534
• 英文别名: 3-(4-trifluoromethyl-1(3)H-imidazol-2-yl)-pyridine；3-[5-(trifluoromethyl)-1H-imidazol-2-yl]pyridine
• CAS: 33468-84-7
• 化学式: C₉H₆F₃N₃
• mdl: MFCD11036238
• 分子量: 213.162
• InChiKey: BSIXIBWASJDSKW-UHFFFAOYSA-N

物化性质

• 熔点：
  228-229 °C
• 密度：
  1.393

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-三氟甲基-1H-咪唑-2-基)吡啶 生成 2-pyridin-3-yl-1H-imidazole-5-carboxylic acid
  参考文献：
  名称：

  BALDWIN J. J.; LUMMA P. K.; NOVELLO F. C.; PONTICELLO G. S.; SPRAGUE J. M+, J. MED. CHEM., 1977, 20, NO 9, 1189-1193

  摘要：

  DOI：
• 作为产物：
  描述：

  3-吡啶甲醛 、 1,1-二溴-3,3,3-三氟丙酮 在 ammonium hydroxide 、 sodium acetate 作用下， 生成 3-(4-三氟甲基-1H-咪唑-2-基)吡啶
  参考文献：
  名称：

  新型联咪唑的合成及其强心活性。

  摘要：

  合成了一系列取代的2,2'-bi-1H-咪唑和相关类似物，并评估了其正性肌力。基于非经典生物等位线方法的结构活性关系研究表明，咪唑环之一上的氰基必须具有所需的药理特性。4（5）-Cyano-2,2'-bi-1H-咪唑（15a）是该系列中最有效的正性肌力药。在麻醉狗中，0.16 mg / kg iv时左心室dP / dt增加25％（ED25％= 0.16 mg / kg），在1 mg / kg iv时左心室收缩力增加60％。化合物15a是分离自犬心的IV型环状核苷酸磷酸二酯酶的良好抑制剂，具有与氨力农相似的效力。5'-cyano-2,4'-bi-1H-咪唑（44）和4-cyano-2,4' -bi-1H-咪唑（48）具有正性肌力活性。另外，两种可能的1,1'-二甲基氰基-2,2'-bi-1H-咪唑（24和25）是不活泼的，表明酸性NH和氰基对于正性肌力活性至关重要。

  DOI：

  10.1021/jm00163a052

文献信息

• Trifluoromethylimidazoles and a method for their preparation
  申请人：Merck & Co., Inc.

  公开号：US04125530A1

  公开（公告）日：1978-11-14

  4(5)-Trifluoromethylimidazoles having optional substituents in the 1 and 2 positions are provided. The novel 4(5)-trifluoromethylimidazoles are prepared by reacting a 1,1-dihalo-3,3,3-trifluoroacetone compound with an appropriate carboxaldehyde and ammonia. The 4(5)-trifluoromethylimidazoles are useful as anti-gout and anti-hyperuricemic agents.

  提供了在1和2位置具有可选取代基的4(5)-三氟甲基咪唑。通过将1,1-二卤-3,3,3-三氟乙酮化合物与适当的醛和氨反应制备了新型的4(5)-三氟甲基咪唑。这些4(5)-三氟甲基咪唑可用作抗痛风和抗高尿酸血症药物。
• 2-Pyrazinyl-trifluoromethylimidazoles and a method for their preparation
  申请人：Merck & Co., Inc.

  公开号：US04032522A1

  公开（公告）日：1977-06-28

  4(5)-Trifluoromethylimidazoles having optional substituents in the 1 and 2 positions are provided. The novel 4(5)-trifluoromethylimidazoles are prepared by reacting a 1,1-dihalo-3,3,3-trifluoroacetone compound with an appropriate carboxaldehyde and ammonia. The 4(5)-trifluoromethylimidazoles are useful as anti-gout and anti-hyperuricemic agents.

  提供具有1和2位置可选取代基的4(5)-三氟甲基咪唑。通过将1,1-二卤-3,3,3-三氟丙酮化合物与适当的醛和氨反应制备新型的4(5)-三氟甲基咪唑。这些4(5)-三氟甲基咪唑可用作抗痛风和抗高尿酸血症药物。
• Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3
  申请人：Yao Wenqing

  公开号：US08754114B2

  公开（公告）日：2014-06-17

  The present invention relates to substituted imidazopyridazines and substituted benzimidazoles, as well as pharmaceutical compositions comprising the same, which are FGFR3 inhibitors useful in the treatment of cancer and other diseases.

  本发明涉及取代咪唑吡啶和取代苯并咪唑酮，以及包含它们的制药组合物，它们是FGFR3抑制剂，可用于治疗癌症和其他疾病。
• SUBSTITUTED IMIDAZOPYRIDAZINES AND BENZIMIDAZOLES AS INHIBITORS OF FGFR3
  申请人：Incyte Corporation

  公开号：US20140243308A1

  公开（公告）日：2014-08-28

  The present invention relates to substituted imidazopyridazines and substituted benzimidazoles, as well as pharmaceutical compositions comprising the same, which are FGFR3 inhibitors useful in the treatment of cancer and other diseases.

  本发明涉及取代咪唑吡啶和取代苯并咪唑的化合物，以及包含其的药物组合物，它们是FGFR3抑制剂，可用于癌症和其他疾病的治疗。
• Synthesis, Structure, and Neuroprotective Properties of Novel Imidazolyl Nitrones
  作者：Alain Dhainaut、André Tizot、Eric Raimbaud、Brian Lockhart、Pierre Lestage、Solo Goldstein

  DOI：10.1021/jm991154w

  日期：2000.6.1

  A new series of imidazolyl nitrones spin traps has been synthesized and evaluated pharmacologically. The salient structural feature of these molecules is the presence of an imidazole moiety substituted by aromatic or heteroaromatic cycles. This connectivity imparts to the nitrone superior neuroprotective properties in vivo and in parallel reduced side effects and toxicity. Thus compound 6a (a 2-phenylimidazolyl nitrone) administered intraperitoneally protects (80%) mice from lethality induced by an intracerebroventricular administration of tert-butyl hydroperoxide (t-BHP) an oxidant capable of inducing neurodegenerative processes. Administration of the archetypal nitrone phenyl-tert-butyl nitrone (PBN) at an equimolar dose also affords some protection (60%) in this test. However, this activity is accompanied by hypothermia, whereas no such effect is apparent for 6a. Moreover, previously prepared nonsubstituted or alkyl-substituted imidazolyl nitrones were shown to be extremely toxic to rats in contrast to the compounds prepared in this study. The observed activities in vivo correlate well with the calculated partition coefficients (ClogP) and HOMO energy level.