3-cyano-3-dimethylamino-tetrahydrofurane | 176445-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 3-cyano-3-dimethylamino-tetrahydrofurane
• 英文别名: 3-(dimethylamino)tetrahydro-3-furancarbonitrile；(+/-)3-(Dimethylamino)tetrahydro-3-furancarbonitrile；3-(dimethylamino)oxolane-3-carbonitrile
• CAS: 176445-75-3
• 化学式: C₇H₁₂N₂O
• 分子量: 140.185
• InChiKey: FTSNUROASHTNGX-UHFFFAOYSA-N

物化性质

• 沸点：
  244.4±40.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cyano-3-dimethylamino-tetrahydrofurane 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R,S) 4-amino-5-chloro-N-<3-dimethylamino-3-tetrahydrofuranyl>methyl-2-methoxybenzamide
  参考文献：
  名称：

  Serotoninergic properties of new conformationally restricted benzamides

  摘要：

  A new series of benzamides derived from metoclopramide have been synthesized, in which the vicinal carbon of the basic nitrogen atom of the ethyl chain is situated on the C-3, C-4, C-5 and C-6 rings. The diamino derivatives were prepared through Strecker's reaction from the corresponding ketones except for the cyclopropyl derivatives where 1-ethoxy-1-trimethylsiloxy cyclopropane was used as the starting material. The benzamides were prepared using the mixed anhydride method. They were tested in binding assays for D-2, 5-HT3 and 5-HT4 receptors. The results show a marked increase in the selectivity and potency of these derivatives for 5-HT3 receptors with regard to metoclopramide (compound 1d: 5-HT3 K-i = 9.03 nM; 5-HT4 K-i > 5000; D-2 K-i > 5000). The influences of steric hindrance and hydrophobic properties on the affinity of benzamide derivatives for 5-HT3 receptors were also emphasized by these data. The X-ray crystal structure of compound 1d was compared with that of the minimal energy conformer of BRL 24682, a reference 5-HT3 receptor antagonist benzamide, determined using the Random Search program. Superimposition of the two structures showed a suitable fit between the pharmacophore groups previously determined to be important for 5-HT3 receptor antagonists. On the other hand, the hydrophobic parts of the basic moieties had different spatial occupancies.

  DOI：

  10.1016/0223-5234(96)89139-2
• 作为产物：
  描述：

  二氢-3(2H)-呋喃酮 、 盐酸二甲胺 、 氰化钾 以 水 为溶剂， 以88%的产率得到3-cyano-3-dimethylamino-tetrahydrofurane
  参考文献：
  名称：

  Serotoninergic properties of new conformationally restricted benzamides

  摘要：

  A new series of benzamides derived from metoclopramide have been synthesized, in which the vicinal carbon of the basic nitrogen atom of the ethyl chain is situated on the C-3, C-4, C-5 and C-6 rings. The diamino derivatives were prepared through Strecker's reaction from the corresponding ketones except for the cyclopropyl derivatives where 1-ethoxy-1-trimethylsiloxy cyclopropane was used as the starting material. The benzamides were prepared using the mixed anhydride method. They were tested in binding assays for D-2, 5-HT3 and 5-HT4 receptors. The results show a marked increase in the selectivity and potency of these derivatives for 5-HT3 receptors with regard to metoclopramide (compound 1d: 5-HT3 K-i = 9.03 nM; 5-HT4 K-i > 5000; D-2 K-i > 5000). The influences of steric hindrance and hydrophobic properties on the affinity of benzamide derivatives for 5-HT3 receptors were also emphasized by these data. The X-ray crystal structure of compound 1d was compared with that of the minimal energy conformer of BRL 24682, a reference 5-HT3 receptor antagonist benzamide, determined using the Random Search program. Superimposition of the two structures showed a suitable fit between the pharmacophore groups previously determined to be important for 5-HT3 receptor antagonists. On the other hand, the hydrophobic parts of the basic moieties had different spatial occupancies.

  DOI：

  10.1016/0223-5234(96)89139-2

文献信息

• 2-AMINO-1-PHENYLETHYLCARBOXAMIDE DERIVATIVES
  申请人：Bozzoli Andrea

  公开号：US20090286828A1

  公开（公告）日：2009-11-19

  The present invention relates to compounds of formula (I), or to salts or solvates thereof, their use in the manufacture of medicaments for treating neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof. wherein R 1 is a group selected from:

  本发明涉及公式（I）的化合物，或其盐或溶剂化物，它们在制造治疗神经和神经精神障碍的药物方面的用途，特别是治疗精神病、痴呆症或注意力缺陷障碍。该发明还包括制备这些化合物和它们的药物制剂的过程。 其中R1是从以下组中选择的：
• Glycine Transport Inhibitors
  申请人：Bradley Daniel Marcus

  公开号：US20080287547A1

  公开（公告）日：2008-11-20

  The present invention relates to compounds of formula (I), or to salts or solvates thereof, their use in the manufacture of medicaments for treating neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof.

  本发明涉及公式（I）的化合物，或其盐或溶剂化物，其用于制造治疗神经和神经精神障碍的药物，特别是精神病、痴呆或注意力缺陷障碍。该发明还包括制备这些化合物和制药配方的过程。
• Glycine transport inhibitors
  申请人：Glaxo Group Limited

  公开号：US07745642B2

  公开（公告）日：2010-06-29

  The present invention relates to compounds of formula (I), or to salts or solvates thereof, their use in the manufacture of medicaments for treating neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof.

  本发明涉及公式（I）的化合物，或其盐或溶剂化物，它们在制造用于治疗神经系统和神经精神障碍的药物中的使用，特别是用于治疗精神病、痴呆或注意力缺陷障碍。该发明还包括制备这些化合物和它们的药物制剂的过程。
• WO2006/67430
  申请人：——

  公开号：——

  公开（公告）日：——
• GLYCINE TRANSPORT INHIBITORS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1841727A1

  公开（公告）日：2007-10-10