4-(methoxycarbonyl)-N-[(2,2-dimethylcyclopentyl)methyl]benzamide | 212380-02-4

• 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-(methoxycarbonyl)-N-[(2,2-dimethylcyclopentyl)methyl]benzamide
• 英文别名: 4-[[[(2,2-Dimethylcyclopentyl)Methyl]Amino]-carbonyl]Benzoic Acid Methyl Ester；methyl 4-[(2,2-dimethylcyclopentyl)methylcarbamoyl]benzoate
• CAS: 212380-02-4
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: CGFTVWBVIACEGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(methoxycarbonyl)-N-[(2,2-dimethylcyclopentyl)methyl]benzamide 在 一水合肼 作用下， 反应 5.5h， 生成 (-)-4-(5-butyl-1,3,4-oxadiazol-2-yl)-N-[(2,2-dimethylcyclopentyl)]-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：

  (2,2-dimethylcyclopentyl)methylamine hydrochloride 、 对苯二甲酸单甲酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到4-(methoxycarbonyl)-N-[(2,2-dimethylcyclopentyl)methyl]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

• Benzoic acid derivatives and related compounds as antiarrhythmic agents
  申请人：——

  公开号：US20020137968A1

  公开（公告）日：2002-09-26

  Benzoic acid derivatives of the formula I 1 where X is oxygen, sulfur, —NH, —NR 1 , —N—CN, —N—OR 1 or —N—NO 2 ; Y is a single bond, —C═C—, or —NH; R 1 is alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocyclo, or (heterocyclo)alkyl; and R 2 is aryl or heterocyclo. The compounds of formula I are useful in the treatment of arrhythmia.

  公式I的苯甲酸衍生物 其中X为氧、硫、—NH、—NR 1 、—N—CN、—N—OR 1 或—N—NO 2 ； Y为单键、—C═C—或—NH； R 1 为烷基、烯基、炔基、芳基、环烷基、杂环烷基或(杂环烷基)；和 R 2 为芳基或杂环烷基。公式I的化合物在心律失常的治疗中很有用。
• US6624309B1
  申请人：——

  公开号：US6624309B1

  公开（公告）日：2003-09-23
• 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.