2-[[2-(3,4-二氯苯基)乙酰基]氨基]乙酸 | 153906-08-2

• 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
• 中文名称: 2-[[2-(3,4-二氯苯基)乙酰基]氨基]乙酸
• 英文名称: N-(3,4-dichlorophenylacetyl)glycine
• 英文别名: Glycine, N-[(3,4-dichlorophenyl)acetyl]-；2-[[2-(3,4-dichlorophenyl)acetyl]amino]acetic acid
• CAS: 153906-08-2
• 化学式: C₁₀H₉Cl₂NO₃
• mdl: MFCD11646711
• 分子量: 262.092
• InChiKey: DBGGEQBTIPZUAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[[2-(3,4-二氯苯基)乙酰基]氨基]乙酸 在 sodium acetate 作用下， 以 氯仿 、 水 、 乙酸酐 为溶剂， 反应 1.0h， 生成 (Z)-2-(3,4-dichlorophenylacetylamino)-3-(3,4-dimethoxyphenyl)-N-methyl-2-propenamide
  参考文献：
  名称：

  Electron Transfer-initiated and Highly Selective Photocyclization of N-Acyl-α-dehydroarylalaninamides to 3,4-Dihydroquinolinone Derivatives

  摘要：

  DOI：

  10.3987/com-04-10242
• 作为产物：
  描述：

  3,4-二氯苯乙酸 在 甲醇 、 氢氧化钾 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-[[2-(3,4-二氯苯基)乙酰基]氨基]乙酸
  参考文献：
  名称：

  A new approach to the design of .sigma.-2-selective ligands: synthesis and evaluation of N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine-related polyamines at .sigma.-1 and .sigma.-2 receptor subtypes

  摘要：

  A series of polyamines based on the high affinity sigma receptor ligand N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine (3) were developed and evaluated for their binding characteristics at sigma-1 and sigma-2 receptor subtypes. The data indicated that a considerable degree of structural variation is possible while still retaining nanomolar affinity at a receptors; As the structure of the polyamines was varied, their binding at sigma-1 and sigma-2 subtypes showed quite different and in some cases opposite trends, supporting the belief that these are pharmacologically distinct entities. Polyamines containing two nitrogen atoms showed optimal binding at both sigma-1 and sigma-2 receptor subtypes. Although additional nitrogen atoms resulted in decreased affinity at sigma-1 and sigma-2 subtypes, an increase in selectivity for sigma-2 subtypes was evident; the parent 3 showed greater selectivity for sigma-1 subtypes. Internitrogen spacings had a large effect on binding affinity and subtype selectivity. For example, the difference between N-[3-(1-pyrrolidinyl)propyl]-N'-(3,4-dichlorobenzyl)-N,N'-dimethylethylenediamine (8) [K-i = 29.9 nM at sigma-1 receptor and 18.3 nM at alpha-2 receptor] to N-[3-(1-pyrrolidinyl)propyl]-N'-(3,4-dichlorobenzyl)-N/N'-dimethylethylenedi- amine (10) [K-i = 1.49 nM at sigma-1 receptor and 12.1 nM at sigma-2 receptor] illustrates the importance of internitrogen spacing. Triamines 11 and 13 [K-i(sigma-2)/K-i(sigma-1) = 0.19 and 0.10, respectively] containing the N-N-N-Ar spacings 3-3-2 and 4-4-2, proved to be the most sigma-2 subtype selective of the 15 polyamines examined in this study. The N-N-N spacings appear to be an important factor in their sigma-2 subtype selectivity. These compounds will serve as templates in the design of still further sigma-2 subtype selective ligands. The pyrrolidine ring (present in most of the polyamines tested in this series) proved to be an important recognition site for a receptor binding activity. Furthermore, alkyl substitution also appears to be important since the stripped down polyamines N-[2-(3,4-dichlorophenyl)ethyl]ethylenediamine (15) and N-1-[2-(3,4-dichlorophenyl)ethyl] diethylenetriamine (16) exhibited relatively low binding affinity.

  DOI：

  10.1021/jm00028a016

文献信息

• A Convenient Synthesis of Papaverine Analogs via Photocyclization of N-Acyl-a-dehydroarylalaninamide Derivatives
  作者：Tadamitsu Sakurai、Hideki Hoshina、Kei Maekawa、Kaori Kobayashi、Tetsutaro Igarashi

  DOI：10.3987/com-06-10710

  日期：——
• A New Route to Papaverine Analogs via Photocyclization of Substituted N-Acyl-α-dehydrophenylalaninamides
  作者：Tadamitsu Sakurai、Hideki Hoshina、Kei Maekawa、Keisuke Taie、Tetsutaro Igarashi

  DOI：10.3987/com-03-9801

  日期：——
• A new approach to the design of .sigma.-2-selective ligands: synthesis and evaluation of N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine-related polyamines at .sigma.-1 and .sigma.-2 receptor subtypes
  作者：Brian R. de Costa、Xiao-shu He、Celia Dominguez、Janet Cutts、Wanda Williams、Wayne D. Bowen

  DOI：10.1021/jm00028a016

  日期：1994.1

  A series of polyamines based on the high affinity sigma receptor ligand N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine (3) were developed and evaluated for their binding characteristics at sigma-1 and sigma-2 receptor subtypes. The data indicated that a considerable degree of structural variation is possible while still retaining nanomolar affinity at a receptors; As the structure of the polyamines was varied, their binding at sigma-1 and sigma-2 subtypes showed quite different and in some cases opposite trends, supporting the belief that these are pharmacologically distinct entities. Polyamines containing two nitrogen atoms showed optimal binding at both sigma-1 and sigma-2 receptor subtypes. Although additional nitrogen atoms resulted in decreased affinity at sigma-1 and sigma-2 subtypes, an increase in selectivity for sigma-2 subtypes was evident; the parent 3 showed greater selectivity for sigma-1 subtypes. Internitrogen spacings had a large effect on binding affinity and subtype selectivity. For example, the difference between N-[3-(1-pyrrolidinyl)propyl]-N'-(3,4-dichlorobenzyl)-N,N'-dimethylethylenediamine (8) [K-i = 29.9 nM at sigma-1 receptor and 18.3 nM at alpha-2 receptor] to N-[3-(1-pyrrolidinyl)propyl]-N'-(3,4-dichlorobenzyl)-N/N'-dimethylethylenedi- amine (10) [K-i = 1.49 nM at sigma-1 receptor and 12.1 nM at sigma-2 receptor] illustrates the importance of internitrogen spacing. Triamines 11 and 13 [K-i(sigma-2)/K-i(sigma-1) = 0.19 and 0.10, respectively] containing the N-N-N-Ar spacings 3-3-2 and 4-4-2, proved to be the most sigma-2 subtype selective of the 15 polyamines examined in this study. The N-N-N spacings appear to be an important factor in their sigma-2 subtype selectivity. These compounds will serve as templates in the design of still further sigma-2 subtype selective ligands. The pyrrolidine ring (present in most of the polyamines tested in this series) proved to be an important recognition site for a receptor binding activity. Furthermore, alkyl substitution also appears to be important since the stripped down polyamines N-[2-(3,4-dichlorophenyl)ethyl]ethylenediamine (15) and N-1-[2-(3,4-dichlorophenyl)ethyl] diethylenetriamine (16) exhibited relatively low binding affinity.
• Electron Transfer-initiated and Highly Selective Photocyclization of N-Acyl-α-dehydroarylalaninamides to 3,4-Dihydroquinolinone Derivatives
  作者：Tadamitsu Sakurai、Kei Maekawa、Kunio Fujita、Katsuyuki Iizuka、Tetsutaro Igarashi

  DOI：10.3987/com-04-10242

  日期：——