6-chloro-2-methyl-7-nitro-4H-3,1-benzoxazin-4-one | 405911-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6-chloro-2-methyl-7-nitro-4H-3,1-benzoxazin-4-one
• 英文别名: 6-Chloro-2-methyl-7-nitro-3,1-benzoxazin-4-one
• CAS: 405911-56-0
• 化学式: C₉H₅ClN₂O₄
• 分子量: 240.603
• InChiKey: VGGZNHXPQIQNEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  guanidinoethane sulfate 、 6-chloro-2-methyl-7-nitro-4H-3,1-benzoxazin-4-one 在 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.25h， 生成 N-[4-Chloro-2-(N'-ethyl-guanidinocarbonyl)-5-nitro-phenyl]-acetamide
  参考文献：
  名称：

  Novel inhibitors of the sodium–calcium exchanger: benzene ring analogues of N-guanidino substituted amiloride derivatives

  摘要：

  A series of N-guanidino substituted 2,4-diamino-5-carbonylguanidine molecules related to amiloride were synthesised and, evaluated for their ability to inhibit the sodium-calcium exchanger in rat insulinoma cells (RINm5F) and human platelets. Specific chemical pathways were used to prepare the benzene derivatives designed as bioisosteric analogues of the pyrazine derivatives of amiloride. Several so-called 'simplified analogues', where some substituents of amiloride were omitted or replaced, were also prepared and included in the biological evaluation. The inhibitory potency of the sodium-calcium exchanger was screened on both cell types by measuring their effect on Ca-45(2+) uptake. Among the most active compounds, N-(2 -amino-5-chloro-4-nitrobenzoyl)-N'-(1-naphtylmethyl)guanidine (IC50 = 3.4 muM) was found more active than amiloride (IC50 = 690 muM) and 3,4-dichlorobenzamil (IC50 = 15.2 muM), the reference inhibitor. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01247-8
• 作为产物：
  描述：

  2-乙酰氨基-5-氯-4-硝基苯甲酸 在 乙酸酐 作用下， 以 乙酸乙酯 为溶剂， 以70%的产率得到6-chloro-2-methyl-7-nitro-4H-3,1-benzoxazin-4-one
  参考文献：
  名称：

  Novel inhibitors of the sodium–calcium exchanger: benzene ring analogues of N-guanidino substituted amiloride derivatives

  摘要：

  A series of N-guanidino substituted 2,4-diamino-5-carbonylguanidine molecules related to amiloride were synthesised and, evaluated for their ability to inhibit the sodium-calcium exchanger in rat insulinoma cells (RINm5F) and human platelets. Specific chemical pathways were used to prepare the benzene derivatives designed as bioisosteric analogues of the pyrazine derivatives of amiloride. Several so-called 'simplified analogues', where some substituents of amiloride were omitted or replaced, were also prepared and included in the biological evaluation. The inhibitory potency of the sodium-calcium exchanger was screened on both cell types by measuring their effect on Ca-45(2+) uptake. Among the most active compounds, N-(2 -amino-5-chloro-4-nitrobenzoyl)-N'-(1-naphtylmethyl)guanidine (IC50 = 3.4 muM) was found more active than amiloride (IC50 = 690 muM) and 3,4-dichlorobenzamil (IC50 = 15.2 muM), the reference inhibitor. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01247-8

文献信息

• US7339057B2
  申请人：——

  公开号：US7339057B2

  公开（公告）日：2008-03-04
• Novel inhibitors of the sodium–calcium exchanger: benzene ring analogues of N-guanidino substituted amiloride derivatives
  作者：Françoise Rogister、Didier Laeckmann、Pierre-Olivier Plasman、Françoise Van Eylen、Marianne Ghyoot、Carine Maggetto、Jean-François Liégeois、Joseph Géczy、André Herchuelz、Jacques Delarge

  DOI：10.1016/s0223-5234(01)01247-8

  日期：2001.8

  A series of N-guanidino substituted 2,4-diamino-5-carbonylguanidine molecules related to amiloride were synthesised and, evaluated for their ability to inhibit the sodium-calcium exchanger in rat insulinoma cells (RINm5F) and human platelets. Specific chemical pathways were used to prepare the benzene derivatives designed as bioisosteric analogues of the pyrazine derivatives of amiloride. Several so-called 'simplified analogues', where some substituents of amiloride were omitted or replaced, were also prepared and included in the biological evaluation. The inhibitory potency of the sodium-calcium exchanger was screened on both cell types by measuring their effect on Ca-45(2+) uptake. Among the most active compounds, N-(2 -amino-5-chloro-4-nitrobenzoyl)-N'-(1-naphtylmethyl)guanidine (IC50 = 3.4 muM) was found more active than amiloride (IC50 = 690 muM) and 3,4-dichlorobenzamil (IC50 = 15.2 muM), the reference inhibitor. (C) 2001 Editions scientifiques et medicales Elsevier SAS.