N-(1-乙基-2-吡咯烷基甲基)-2-甲氧基-5-硝基苯甲酰胺 | 23694-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(1-乙基-2-吡咯烷基甲基)-2-甲氧基-5-硝基苯甲酰胺
• 英文名称: N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-nitrobenzamide
• 英文别名: N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-methoxy-5-nitrobenzamide；N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-nitrobenzamide
• CAS: 23694-03-3
• 化学式: C₁₅H₂₁N₃O₄
• 分子量: 307.349
• InChiKey: DVRHYBYPKBFJKY-UHFFFAOYSA-N

物化性质

• 熔点：
  159.5-161 °C
• 沸点：
  467.2±35.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 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：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(1-乙基-2-吡咯烷基甲基)-2-甲氧基-5-硝基苯甲酰胺 在 盐酸 、 tin 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.25h， 生成 5-((N-(tert-butyl)sulfamoyl)(methyl)amino)-N-((1-ethylpyrrolidin-2-yl)methyl)-2-methoxybenzamide
  参考文献：
  名称：

  Synthesis and neuroleptic activity of N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-5-sulfonamidobenzamides

  摘要：

  A series of some novel N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamides involving replacement of the sulfamoyl group in sulpiride with a sulfonamido group was synthesized and tested for dopamine receptor blockade. In comparison with sulpiride, several compounds were considerably more potent than sulpiride as dopamine receptor blockers. The structure-activity relationships are discussed.

  DOI：

  10.1021/jm00375a009
• 作为产物：
  描述：

  2-甲氧基-5-硝基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 N-(1-乙基-2-吡咯烷基甲基)-2-甲氧基-5-硝基苯甲酰胺
  参考文献：
  名称：

  Synthesis and neuroleptic activity of N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-5-sulfonamidobenzamides

  摘要：

  A series of some novel N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamides involving replacement of the sulfamoyl group in sulpiride with a sulfonamido group was synthesized and tested for dopamine receptor blockade. In comparison with sulpiride, several compounds were considerably more potent than sulpiride as dopamine receptor blockers. The structure-activity relationships are discussed.

  DOI：

  10.1021/jm00375a009

文献信息

• Meta-sulfonamido-benzamides
  申请人：Shionogi & Co., Ltd.

  公开号：US04328155A1

  公开（公告）日：1982-05-04

  Meta-sulfonamido-benzamide derivatives of the formula: ##STR1## [wherein R is a hydrogen atom or a lower alkyl, cyano, or lower alkanesulfonyl group; R.sup.1 is a lower alkyl, phenyl, amino, lower alkylamino, di(lower)alkylamino, or C.sub.4 -C.sub.5 alkyleneamino group; R.sup.2 is a hydrogen or halogen atom or a lower alkyl, di(lower)alkylamino, or lower alkoxy group; R.sup.3 is a hydrogen atom or a methyl or methoxy group; R.sup.4 is a hydrogen or halogen atom; R.sup.5 is a lower alkyl, lower alkenyl, C.sub.3 -C.sub.6 cycloalkyl, benzyl, or halogenobenzyl group; and n is 1 or zero] or their acid addition salts, showing pharmacological activity such as anti-emetic or psychotropic activity, are provided via several routes.

  该公式的甲磺酰氨基苯甲酰衍生物：[其中R是氢原子或较低的烷基，氰基，或较低的烷磺基; R.sup.1是较低的烷基，苯基，氨基，较低的烷氨基，二(较低)烷氨基，或C.sub.4-C.sub.5烷基氨基; R.sup.2是氢原子或卤素原子或较低的烷基，二(较低)烷氨基，或较低的烷氧基; R.sup.3是氢原子或甲基或甲氧基; R.sup.4是氢原子或卤素原子; R.sup.5是较低的烷基，较低的烯基，C.sub.3-C.sub.6环烷基，苄基，或卤代苄基; n为1或零]或其酸盐，具有抗恶心或精神活性等药理活性，通过多种途径提供。
• Enantiometric iodobenzamides
  申请人：THE VANDERBILT UNIVERSITY

  公开号：EP0320630A1

  公开（公告）日：1989-06-21

  Novel iodine-substituted benzamide derivatives of formula I wherein R¹ is a hydrogen atom, a lower alkyl group consisting of 1 to 4 carbon atoms, a cycloalkyl group consisting of 3 to 7 carbon atoms, an alkenyl group consisting of 2 to 4 carbon atoms, an alkynyl group consisting of 2 to 4 carbon atoms, a phenyl group, a halogen substituted phenyl group, or an enantiomer or pharmaceutically suitable salt thereof, exhibit high blocking activity and specifity for the dopamine D-2 receptor.

  式I的新碘取代苯甲酰胺衍生物，其中R¹是氢原子，由1至4个碳原子组成的较低烷基基团，由3至7个碳原子组成的环烷基基团，由2至4个碳原子组成的烯基基团，由2至4个碳原子组成的炔基基团，苯基，卤素取代的苯基，或其对映体或药学上适用的盐，表现出对多巴胺D-2受体的高阻断活性和特异性。
• Valenta, Vladimir; Holubek, Jiri; Svatek, Emil, Collection of Czechoslovak Chemical Communications, 1990, vol. 55, p. 1297 - 1310
  作者：Valenta, Vladimir、Holubek, Jiri、Svatek, Emil、Matousova, Oluse、Metysova, Jirina、Protiva, Miroslav

  DOI：——

  日期：——
• VALENTA, VLADIMIR;HOLUBEK, JIRI;SVATEK, EMIL;MATOUSOVA, OLUSE;METYSOVA, J+, COLLECT. CZECHOSL. CHEM. COMMUN., 55,(1990) N, C. 1297-1298
  作者：VALENTA, VLADIMIR、HOLUBEK, JIRI、SVATEK, EMIL、MATOUSOVA, OLUSE、METYSOVA, J+

  DOI：——

  日期：——
• US4328155A
  申请人：——

  公开号：US4328155A

  公开（公告）日：1982-05-04