ethoxycarbonyl 4-acetamido-5-chloro-2-methoxybenzoate | 30574-72-2

• 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: ethoxycarbonyl 4-acetamido-5-chloro-2-methoxybenzoate
• CAS: 30574-72-2
• 化学式: C₁₃H₁₄ClNO₆
• 分子量: 315.71
• InChiKey: QEMSMEBPSYXVAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethoxycarbonyl 4-acetamido-5-chloro-2-methoxybenzoate 以63%的产率得到
  参考文献：
  名称：

  REGNIER G. L.; CANEVARI R. J.; DUHAULT J. L.; LAUBIE M. L., ARZNEIMITTELFORSCHUNG , 1974, 24, NO 12, 1964-1970

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲氧基-4-乙酰胺基-5-氯苯甲酸 、 氯甲酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 ethoxycarbonyl 4-acetamido-5-chloro-2-methoxybenzoate
  参考文献：
  名称：

  4-氨基-5-氯-2-甲氧基-N-[（2S，4S）-1-乙基-2-羟甲基-4-吡咯烷基]苯甲酰胺（TKS159）及其旋光异构体的合成及药理活性。

  摘要：

  4-氨基-5-氯-2-甲氧基-N-（1-乙基-2-羟甲基-4-吡咯烷基）苯甲酰胺中的四个旋光异构体（2S，4S）-1（TKS159），（2S，4R） -25，（2R，4S）-26和（2R，4R）-27由旋光的4-氨基-1-乙基-2-羟甲基吡咯烷二对甲苯磺酸酯[（2S，4S）-14，（ 2S，4R）-17，（2R，4S）-20和（2R，4R）-23]。（2S，4S）-14，（2S，4R）-17，（2R，4S）-20和（2R，4R）-23的必需品是从市售反式4-羟基-L-脯氨酸制备的。（2S，4S）-1（TKS159），（2S，4R）-25，（2R，4S）-26和（2R，4R）-27的绝对构型被确定。在苯甲酰胺衍生物中，四种旋光异构体（2S，4S）-1，（2S，4R）-25，（2R，4S）-26和（2R，4R）-27对5-羟色胺显示出相对强的亲和力放射性配体结合测定（[3H] GR113808

  DOI：

  10.1248/cpb.47.1650

文献信息

• Synthesis and neuroleptic activity of benzamides. cis-N-(1-Benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide and related compounds
  作者：Sumio Iwanami、Mutsuo Takashima、Yasufumi Hirata、Osamu Hasegawa、Shinji Usuda

  DOI：10.1021/jm00142a019

  日期：1981.10

  Three series of benzamides of N,N-disubstituted ethylenediamines (linear alkane-1,2-diamines), 1-substituted 2-(aminomethyl)pyrrolidines, and 1-substituted 3-aminopyrrolidines (cyclic alkane-1,2-diamines) were designed and synthesized as potential neuroleptics. All target compounds were evaluated for their inhibitory effects on apomorphine-induced stereotyped behavior in rats, and a good correlation between structure and activity was found throughout the series. In the linear series (analogues of metoclopramide), introduction of a benzyl group on the terminal nitrogen, rather than an ethyl group, and a methyl group on the p-amino group of metoclopramide both enhanced the activity. The resulting N-[2-(N-benzyl-N-methylamino)ethyl]-5-chloro-2-methoxy-4-(methylamino) benzamide(23) was about 15 times more active than metoclopramide. In the cyclic series, particularly among the benzamides of 1-benzyl-3-aminopyrrolidine, most of the compounds tested were more active than the corresponding linear benzamides. cis-N-(1-Benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino) benzamide (YM-09151-2, 55) was the most active among all of the compounds tested, being 13 and 408 times more potent than haloperidol and metoclopramide, respectively. Moreover, compound 55 exhibited a fairly high ratio of antistereotypic activity to cataleptogenicity compared with haloperidol and metoclopramide. It is expected that compound 55 may be used as a potent drug with few side effects in the treatment of psychosis.