苯酚,3-氟-,单酯和硼酸(H3BO3)(9CI) | 279250-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 苯酚,3-氟-,单酯和硼酸(H3BO3)(9CI)
• 中文别名: 2-(1,3-噻唑-2-基)-1H-咪唑-5-甲腈
• 英文名称: 2-(2-thiazolyl)-4-cyano-1H-imidazole
• 英文别名: 2-thiazol-2-yl-1H-imidazole-4-carbonitrile；2-(Thiazol-2-yl)-1H-imidazole-5-carbonitrile；2-(1,3-thiazol-2-yl)-1H-imidazole-5-carbonitrile
• CAS: 279250-90-7
• 化学式: C₇H₄N₄S
• 分子量: 176.202
• InChiKey: XZBOZGVRHYXHAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.6
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-(2-thiazolyl)-4-trifluoromethyl-1H-imidazole	279250-86-1	C7H4F3N3S	219.19

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2-(1,3-噻唑-2-基)-1H-咪唑-5-甲醛	2-thiazol-2-yl-1H-imidazole-4-carbaldehyde	279251-07-9	C7H5N3OS	179.202
  ——	1-methyl-2-thiazol-2-yl-1H-imidazole-4-carbonitrile	1312325-03-3	C8H6N4S	190.228
  ——	(Z)-α-[2-(thiazol-2-yl)imidazol-4-yl]-N-tert-butylnitrone	——	C11H14N4OS	250.324
  1-甲基-2-噻唑-2-基-1H-咪唑-4-甲醛	1-methyl-2-thiazol-2-yl-1H-imidazole-4-carbaldehyde	623906-10-5	C8H7N3OS	193.229

反应信息

• 作为反应物：
  描述：

  苯酚,3-氟-,单酯和硼酸(H3BO3)(9CI) 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以45%的产率得到2-(1,3-噻唑-2-基)-1H-咪唑-5-甲醛
  参考文献：
  名称：

  Synthesis, Structure, and Neuroprotective Properties of Novel Imidazolyl Nitrones

  摘要：

  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.

  DOI：

  10.1021/jm991154w
• 作为产物：
  描述：

  2-(2-thiazolyl)-4-trifluoromethyl-1H-imidazole 在 氨 作用下， 以 甲醇 、 水 为溶剂， 生成 苯酚,3-氟-,单酯和硼酸(H3BO3)(9CI)
  参考文献：
  名称：

  [EN] 2-ARYLIMIDAZOLE DERIVATIVES AS PDE10A ENZYME INHIBITORS
  [FR] DÉRIVÉS DE 2-ARYLIMIDAZOLE EN TANT QU'INHIBITEURS DE L'ENZYME PDE10A

  摘要：

  这项发明涉及一类PDE10A酶抑制剂化合物。该发明提供了一种包含本发明化合物的治疗有效量和药学可接受载体的药物组合物。本发明还提供了制备式(I)化合物的方法。本发明进一步提供了一种治疗神经退行性疾病的方法，包括向患有神经退行性疾病的对象施用式(I)化合物的治疗有效量。本发明还提供了一种治疗药物成瘾的方法，包括向患有药物成瘾的对象施用式(I)化合物的治疗有效量。本发明还提供了一种治疗精神障碍的方法，包括向患有精神障碍的对象施用式(I)化合物的治疗有效量。

  公开号：

  WO2011072696A1

文献信息

• [EN] 2-ARYLIMIDAZOLE DERIVATIVES AS PDE10A ENZYME INHIBITORS<br/>[FR] DÉRIVÉS DE 2-ARYLIMIDAZOLE EN TANT QU'INHIBITEURS DE L'ENZYME PDE10A
  申请人：LUNDBECK & CO AS H

  公开号：WO2011072696A1

  公开（公告）日：2011-06-23

  This invention is directed to compounds, which are PDE10A enzyme inhibitors. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. The present invention also provides processes for the preparation of the compounds of formula (I). The present invention further provides a method of treating a subject suffering from a neurodegenerative disorder comprising administering to the subject a therapeutically effective amount of a compound of formula (I). The present invention also provides a method of treating a subject suffering from a drug addiction comprising administering to the subject a therapeutically effective amount of a compound of formula (I). The present invention further provides a method of treating a subject suffering from a psychiatric disorder comprising administering to the subject a therapeutically effective amount of a compound of formula (I).

  这项发明涉及一类PDE10A酶抑制剂化合物。该发明提供了一种包含本发明化合物的治疗有效量和药学可接受载体的药物组合物。本发明还提供了制备式(I)化合物的方法。本发明进一步提供了一种治疗神经退行性疾病的方法，包括向患有神经退行性疾病的对象施用式(I)化合物的治疗有效量。本发明还提供了一种治疗药物成瘾的方法，包括向患有药物成瘾的对象施用式(I)化合物的治疗有效量。本发明还提供了一种治疗精神障碍的方法，包括向患有精神障碍的对象施用式(I)化合物的治疗有效量。
• 2-ARYLIMIDAZOLE DERIVATIVES AS PDE10A ENZYME INHIBITORS
  申请人：Püschl Ask

  公开号：US20120302548A1

  公开（公告）日：2012-11-29

  This invention is directed to compounds, which are PDE10A enzyme inhibitors. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. The present invention also provides processes for the preparation of the compounds of formula I. The present invention further provides a method of treating a subject suffering from a neurodegenerative disorder comprising administering to the subject a therapeutically effective amount of a compound of formula I. The present invention also provides a method of treating a subject suffering from a drug addiction comprising administering to the subject a therapeutically effective amount of a compound of formula I. The present invention further provides a method of treating a subject suffering from a psychiatric disorder comprising administering to the subject a therapeutically effective amount of a compound of formula I.

  本发明涉及一种PDE10A酶抑制剂化合物。本发明提供一种药物组合物，该药物组合物包括本发明的化合物的治疗有效量和药学上可接受的载体。本发明还提供了制备式I化合物的方法。本发明还提供了一种治疗神经退行性疾病的方法，包括向患者施用式I化合物的治疗有效量。本发明还提供了一种治疗药物成瘾的方法，包括向患者施用式I化合物的治疗有效量。本发明还提供了一种治疗精神障碍的方法，包括向患者施用式I化合物的治疗有效量。
• US8501797B2
  申请人：——

  公开号：US8501797B2

  公开（公告）日：2013-08-06
• US8927738B2
  申请人：——

  公开号：US8927738B2

  公开（公告）日：2015-01-06
• 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.