6-(1,2,2-三氯乙烯基)咪唑并(1,2-a)吡啶-2-氨基甲酸甲酯 | 71820-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 6-(1,2,2-三氯乙烯基)咪唑并(1,2-a)吡啶-2-氨基甲酸甲酯
• 中文别名: α.-D-核-六二醛-1,5-吡喃糖苷,甲基3-脱氧-4-O-甲基-2-O-(苯基甲基)-
• 英文名称: 2-methoxycarbonylamino-6-trichlorovinyl imidazo [1,2-a] pyridine
• 英文别名: Methyl 6-(1,2,2-trichloroethenyl)imidazo(1,2-a)pyridine-2-carbamate；methyl N-[6-(1,2,2-trichloroethenyl)imidazo[1,2-a]pyridin-2-yl]carbamate
• CAS: 71820-94-5
• 化学式: C₁₁H₈Cl₃N₃O₂
• 分子量: 320.562
• InChiKey: OXGVNSTXIHAKHB-UHFFFAOYSA-N

物化性质

• 熔点：
  225-226 °C(Solv: ethanol (64-17-5))
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-5-乙炔基吡啶 在 六甲基磷酰三胺 、 selenium(IV) oxide 、 氯化亚砜 、 sodium azide 、 氯 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 四氯化碳 、 水 、 丙酮 为溶剂， 反应 14.58h， 生成 6-(1,2,2-三氯乙烯基)咪唑并(1,2-a)吡啶-2-氨基甲酸甲酯
  参考文献：
  名称：

  Substituted imidazo[1,2-a]pyridine-2-carbamate anthelmintics

  摘要：

  Anthelmintic efficacies of a series of 6-substituted methyl imidazo[1,2-alpha]pyridine-2-carbamates were compared to similarly substituted benzimidazole-2-carbamates. With only one exception, methyl 6-benzoylimidazo[1,2-alpha]pyridine-2-carbamate, both classes of compounds exhibited similar activity vs. Nematospiroides dubius in mice. Preliminary screening indicated methyl 6-(1,2,2-trichloroethenyl)imidazo[1,2-alpha]pyridine-2-carbamate to be the most potent derivative in the series. However, evaluation in sheep indicated that its anthelmintic spectrum was inferior to methyl 6-(phenylsulfinyl)imidazo[1,2-alpha]pyridine-2-carbamate.

  DOI：

  10.1021/jm00144a030

文献信息

• Anthelmintic imidazo [1,2-a] pyridines
  申请人：Merck & Co., Inc.

  公开号：US04154835A1

  公开（公告）日：1979-05-15

  Novel substituted imidazo [1,2-a] pyridine compounds are disclosed which have a high degree of anthelmintic activity. The compounds are substituted with a carbamate and a halogenated alkene group. Processes for the preparation of such compounds are also disclosed as well as compositions which use the described compounds as active ingredients for the treatment of helminthiasis.

  本发明揭示了一种替代咪唑[1,2-a]吡啶化合物，其具有高度的驱虫活性。该化合物被取代为一种氨基甲酸酯和一种卤代烯烃基团。本发明还揭示了制备这种化合物的方法，以及使用所述化合物作为活性成分治疗蠕虫病的组合物。
• BOCHIS, R. J.;OLEN, L. E.;WAKSMUNSKI, F. S.;MROZIK, H.;ESKOLA, P.;KULSA, +, J. MED. CHEM., 1981, 24, N 12, 1518-1521
  作者：BOCHIS, R. J.、OLEN, L. E.、WAKSMUNSKI, F. S.、MROZIK, H.、ESKOLA, P.、KULSA, +

  DOI：——

  日期：——
• Substituted imidazo[1,2-a]pyridine-2-carbamate anthelmintics
  作者：Richard J. Bochis、Leonard E. Olen、Frank S. Waksmunski、Helmut Mrozik、Philip Eskola、Peter Kulsa、George Wilks、Joyce E. Taylor、John R. Egerton

  DOI：10.1021/jm00144a030

  日期：1981.12

  Anthelmintic efficacies of a series of 6-substituted methyl imidazo[1,2-alpha]pyridine-2-carbamates were compared to similarly substituted benzimidazole-2-carbamates. With only one exception, methyl 6-benzoylimidazo[1,2-alpha]pyridine-2-carbamate, both classes of compounds exhibited similar activity vs. Nematospiroides dubius in mice. Preliminary screening indicated methyl 6-(1,2,2-trichloroethenyl)imidazo[1,2-alpha]pyridine-2-carbamate to be the most potent derivative in the series. However, evaluation in sheep indicated that its anthelmintic spectrum was inferior to methyl 6-(phenylsulfinyl)imidazo[1,2-alpha]pyridine-2-carbamate.