[4-(3-chlorobenzyloxy)benzyl]amino acetic acid, ethyl ester | 743392-72-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [4-(3-chlorobenzyloxy)benzyl]amino acetic acid, ethyl ester
• 英文别名: ethyl 2-[[4-[(3-chlorophenyl)methoxy]phenyl]methylamino]acetate
• CAS: 743392-72-5
• 化学式: C₁₈H₂₀ClNO₃
• 分子量: 333.815
• InChiKey: KKOFDFHYMWHLEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-(3-chlorobenzyloxy)benzyl]amino acetic acid, ethyl ester 在 NH₄OH 作用下， 以 二甲胺 为溶剂， 以0.7 g (23%)的产率得到[4-(3-chlorobenzyloxy)benzyl]amino-N,N-dimethylacetamide, hydrochloride
  参考文献：
  名称：

  N-phenylalkyl substituted .alpha.-amino carboxamide derivatives and

  摘要：

  式(I)中的N-苯基烷基取代的α-氨基羧酰胺衍生物，其中R是C1-C8烷基，C3-C8环烷基，呋喃基，噻吩基，吡啶基或未取代或取代的苯基；A是--（CH2）m--或--（CH2）p--X--（CH2）q--基团，其中X是--O--，--S--或--NR4--；R1、R2、R3、R'3、R4、n、m、p和q如上所定义；R5和R6各自独立地是氢或C1-C6烷基，以及其药学上可接受的盐，在哺乳动物中对中枢神经系统具有活性，并可用作抗癫痫、抗帕金森、神经保护、抗抑郁、抗痉挛和/或催眠剂。

  公开号：

  US05236957A1
• 作为产物：
  描述：

  4-[(3-氯苄基)氧基]苯甲枉醛 、 甘氨酸乙酯盐酸盐 在 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 生成 [4-(3-chlorobenzyloxy)benzyl]amino acetic acid, ethyl ester
  参考文献：
  名称：

  Synthesis and Anticonvulsant Activity of a New Class of 2-[(Arylalkyl)amino]alkanamide Derivatives

  摘要：

  Although most epilepsies are adequately treated by conventional antiepileptic therapy, there remains an unfulfilled need for safer and more effective anticonvulsant agents. Starting from milacemide, a weak anticonvulsant, and trying to elucidate its mechanism of action, we discovered a structurally novel class of potent and preclinically safe anticonvulsants. Here we report the structure-activity relationship (SAR) study within this series of compounds. Different parts of the structural lead 2-[[4-(3-chlorobenzoxy)benzyl]amino] acetamide (6) were thus varied (Figure 1), and many potent anticonvulsants were found. As an outcome of this study, 57 ((S)-2-[[4-(3-fluorobenzoxy)benzyl]amino]propanamide methanesulfonate, PNU-151774E) emerged as a promising candidate for further development for its potent anticonvulsant activity and outstanding therapeutic indexes (TIs) in different animal tests.

  DOI：

  10.1021/jm970599m

文献信息

• Synthesis and Anticonvulsant Activity of a New Class of 2-[(Arylalkyl)amino]alkanamide Derivatives
  作者：Paolo Pevarello、Alberto Bonsignori、Philippe Dostert、Franco Heidempergher、Vittorio Pinciroli、Maristella Colombo、Robert A. McArthur、Patricia Salvati、Claes Post、Ruggero G. Fariello、Mario Varasi

  DOI：10.1021/jm970599m

  日期：1998.2.1

  Although most epilepsies are adequately treated by conventional antiepileptic therapy, there remains an unfulfilled need for safer and more effective anticonvulsant agents. Starting from milacemide, a weak anticonvulsant, and trying to elucidate its mechanism of action, we discovered a structurally novel class of potent and preclinically safe anticonvulsants. Here we report the structure-activity relationship (SAR) study within this series of compounds. Different parts of the structural lead 2-[[4-(3-chlorobenzoxy)benzyl]amino] acetamide (6) were thus varied (Figure 1), and many potent anticonvulsants were found. As an outcome of this study, 57 ((S)-2-[[4-(3-fluorobenzoxy)benzyl]amino]propanamide methanesulfonate, PNU-151774E) emerged as a promising candidate for further development for its potent anticonvulsant activity and outstanding therapeutic indexes (TIs) in different animal tests.
• N-phenylalkyl substituted .alpha.-amino carboxamide derivatives and
  申请人：Farmitalia Carlo Erba Srl

  公开号：US05236957A1

  公开（公告）日：1993-08-17

  N-phenylalkyl substituted .alpha.-amino carboxamide derivatives of formula (I) ##STR1## wherein R is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, furyl, thienyl, pyridyl or unsubstituted or substituted phenyl; A is a --(CH.sub.2).sub.m -- or --(CH.sub.2).sub.p --X--(CH.sub.2).sub.q -- group wherein X is --O--, --S-- or --NR.sub.4 --; R.sub.1, R.sub.2, R.sub.3, R'.sub.3, R.sub.4, n, m, p and q are as herein defined; and each of R.sub.5 and R.sub.6 is independently hydrogen or C.sub.1 -C.sub.6 alkyl, and the pharmaceutically acceptable salts thereof, are active on the central nervous system and can be used as anti-epileptic, anti-Parkinson, neuroprotective, antidepressant, antispastic and/or hypnotic agents in mammals.

  式(I)中的N-苯基烷基取代的α-氨基羧酰胺衍生物，其中R是C1-C8烷基，C3-C8环烷基，呋喃基，噻吩基，吡啶基或未取代或取代的苯基；A是--（CH2）m--或--（CH2）p--X--（CH2）q--基团，其中X是--O--，--S--或--NR4--；R1、R2、R3、R'3、R4、n、m、p和q如上所定义；R5和R6各自独立地是氢或C1-C6烷基，以及其药学上可接受的盐，在哺乳动物中对中枢神经系统具有活性，并可用作抗癫痫、抗帕金森、神经保护、抗抑郁、抗痉挛和/或催眠剂。