[4-amino(hydroxyimino)methyl]-N-(2,2-dimethylcyclopentylmethyl)benzamide | 381665-70-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4-amino(hydroxyimino)methyl]-N-(2,2-dimethylcyclopentylmethyl)benzamide
• 英文别名: (4-N-hydroxyamidinyl)-2,2-dimethylcyclopentylmethyl benzamide；N-[(2,2-Dimethylcyclopentyl)methyl]-4-[(hydroxyamino)iminomethyl]benzamide；N-[(2,2-dimethylcyclopentyl)methyl]-4-(N'-hydroxycarbamimidoyl)benzamide
• CAS: 381665-70-9
• 化学式: C₁₆H₂₃N₃O₂
• 分子量: 289.378
• InChiKey: IKSOUTINZJYOPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [4-amino(hydroxyimino)methyl]-N-(2,2-dimethylcyclopentylmethyl)benzamide 在 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 (-)-N-[(2,2-dimethylcyclopentyl)methyl]-4-[5-(3,3,3-trifluoropropyl)-1,2,4-oxadiazole-3-yl]benzamide
  参考文献：
  名称：

  Design and Synthesis of 4-Substituted Benzamides as Potent, Selective, and Orally Bioavailable I_Ks Blockers

  摘要：

  Multiple delayed rectifier potassium currents, including I-Ks are responsible for the repolarization and termination of the cardiac action potential, and blockers of these currents may be useful as antiarrhythmic agents. Modification of compound 5 produced 19(S) that is the most potent IF, blocker reported to date with > 5000-fold selectivity over other cardiac ion channels. Further modification produced 24A with 23% oral bioavailability.

  DOI：

  10.1021/jm015505u
• 作为产物：
  描述：

  对氰基苯甲酸 在 盐酸羟胺 、 sodium ethanolate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 [4-amino(hydroxyimino)methyl]-N-(2,2-dimethylcyclopentylmethyl)benzamide
  参考文献：
  名称：

  Design and Synthesis of 4-Substituted Benzamides as Potent, Selective, and Orally Bioavailable I_Ks Blockers

  摘要：

  Multiple delayed rectifier potassium currents, including I-Ks are responsible for the repolarization and termination of the cardiac action potential, and blockers of these currents may be useful as antiarrhythmic agents. Modification of compound 5 produced 19(S) that is the most potent IF, blocker reported to date with > 5000-fold selectivity over other cardiac ion channels. Further modification produced 24A with 23% oral bioavailability.

  DOI：

  10.1021/jm015505u

文献信息

• Design and Synthesis of 4-Substituted Benzamides as Potent, Selective, and Orally Bioavailable <i>I</i>_Ks Blockers
  作者：John Lloyd、Joan B. Schmidt、George Rovnyak、Saleem Ahmad、Karnail S. Atwal、Sharon N. Bisaha、Lidia M. Doweyko、Philip D. Stein、Sarah C. Traeger、Arvind Mathur、Mary Lee Conder、John DiMarco、Timothy W. Harper、Tonya Jenkins-West、Paul C. Levesque、Diane E. Normandin、Anita D. Russell、Randolph P. Serafino、Mark A. Smith、Nicholas J. Lodge

  DOI：10.1021/jm015505u

  日期：2001.11.1

  Multiple delayed rectifier potassium currents, including I-Ks are responsible for the repolarization and termination of the cardiac action potential, and blockers of these currents may be useful as antiarrhythmic agents. Modification of compound 5 produced 19(S) that is the most potent IF, blocker reported to date with > 5000-fold selectivity over other cardiac ion channels. Further modification produced 24A with 23% oral bioavailability.