N-methyl-N-(3-dimethylaminopropyl)-2,2-diphenylacetamide

• 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: N-methyl-N-(3-dimethylaminopropyl)-2,2-diphenylacetamide
• 英文别名: N-(3-Dimethylamino-propyl)-N-methyl-2,2-diphenyl-acetamide；N-[3-(dimethylamino)propyl]-N-methyl-2,2-diphenylacetamide
• 化学式: C₂₀H₂₆N₂O
• 分子量: 310.439
• InChiKey: SMPSGJVWPMQUMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-二苯基乙酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 N-methyl-N-(3-dimethylaminopropyl)-2,2-diphenylacetamide
  参考文献：
  名称：

  A Structure−Activity Relationship Study of Novel Phenylacetamides Which Are Sodium Channel Blockers

  摘要：

  A structure-activity relationship study of a series of novel Na+ channel blockers, structurally related to N-[3-(2,6-dimethyl-1-piperidinyl)propyl]-alpha-phenylbenzeneacetamide (1, PD85639) is described. The diphenylacetic acid portion of the molecule was left unchanged throughout the study, while structural features in the amine portion and the amide alkyl linkage of the molecule were modified. The compounds were tested for inhibition of veratridine-stimulated Na+ influx in CHO cells expressing type IIA Na+ channels. Several derivatives show a trend toward more potent Na+ channel blockade activity with increasing lipophilicity of the amine portion of the molecule. The presence of a phenyl ring near the amine increases inhibitory potency. A three-carbon spacer between the amide and amine is optimal, and a secondary amide linkage is preferred.

  DOI：

  10.1021/jm950467y

文献信息

• Compounds for the treatment of urinary incontinence
  申请人：Kabi Pharmacia AB

  公开号：EP0367040A1

  公开（公告）日：1990-05-09

  The invention concerns compounds having the formula I wherein Ar is a phenyl or benzyl group which is optionally substituted with hydroxy or alkoxy; R¹ is hydrogen, lower alkyl, lower alkoxy, hydroxy; R² is hydrogen, lower alkyl; R³ is NR⁴R⁵, wherein R⁴ and R⁵ which can be the same or different, are lower al­kyl, or wherein R⁴ and R⁵, when taken together, form a ring with the nitrogen atom, whereby said ring optionally is sub­stituted with lower alkyl; n is 0 or 1; m is 2 or 3 and their salts with physiologically acceptable acids and when the compounds can be in form of optical isomers, the racemic mixture and the individual isomers, for the treatment of dis­orders of the urinary bladder.

  本发明涉及具有式 I 的化合物 其中 Ar 是苯基或苄基，可选择被羟基或烷氧基取代； R¹ 是氢、低级烷基、低级烷氧基、羟基； R² 是氢、低级烷基 R³ 是 NR⁴R⁵，其中 R⁴ 和 R⁵ 可以相同或不同，均为低级烷基，或其中 R⁴ 和 R⁵ 合在一起时与氮原子形成一个环，其中所述环可选择被低级烷基取代； n 为 0 或 1； m 为 2 或 3，以及 它们与生理上可接受的酸的盐，以及当化合物可以光学异构体、外消旋混合物和单个异构体的形式存在时，用于治疗膀胱疾病。
• US5236956A
  申请人：——

  公开号：US5236956A

  公开（公告）日：1993-08-17
• A Structure−Activity Relationship Study of Novel Phenylacetamides Which Are Sodium Channel Blockers
  作者：Ioannis Roufos、Sheryl Hays、Roy D. Schwarz

  DOI：10.1021/jm950467y

  日期：1996.1.1

  A structure-activity relationship study of a series of novel Na+ channel blockers, structurally related to N-[3-(2,6-dimethyl-1-piperidinyl)propyl]-alpha-phenylbenzeneacetamide (1, PD85639) is described. The diphenylacetic acid portion of the molecule was left unchanged throughout the study, while structural features in the amine portion and the amide alkyl linkage of the molecule were modified. The compounds were tested for inhibition of veratridine-stimulated Na+ influx in CHO cells expressing type IIA Na+ channels. Several derivatives show a trend toward more potent Na+ channel blockade activity with increasing lipophilicity of the amine portion of the molecule. The presence of a phenyl ring near the amine increases inhibitory potency. A three-carbon spacer between the amide and amine is optimal, and a secondary amide linkage is preferred.