3-hydroxy-N-acetyl-4-aminostilbene | 23784-26-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-hydroxy-N-acetyl-4-aminostilbene
• 英文别名: (E)-N-(2-hydroxy-4-styrylphenyl)acetamide；N-[2-hydroxy-4-[(E)-2-phenylethenyl]phenyl]acetamide
• CAS: 23784-26-1
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: NEFFYAYMFWPCHZ-BQYQJAHWSA-N

物化性质

• 沸点：
  484.6±44.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-N-acetyl-4-aminostilbene 在 硫酸 、 N,N'-二环己基碳二亚胺 作用下， 反应 2.5h， 生成 3-(sulfonatooxy)-N-acetyl-4-aminostilbene
  参考文献：
  名称：

  Azide and Solvent Trapping of Electrophilic Intermediates Generated during the Hydrolysis of N-(Sulfonatooxy)-N-acetyl-4-aminostilbene

  摘要：

  Hydrolysis of the carcinogenic title compound 1a in 5 vol % CH3CN-H2O, mu = 0.5, 20 degrees C at pH 7.2 in 0.02 M phosphate buffer, yields the rearranged material 3-(sulfonatooxy)-N-acetyl-4-aminostilbene (4) (23 +/- 1%), threo-1,2-dihydroxy-1-phenyl-2-(4-acetamidophenyl)ethane (5) (57 +/- 2%), and erythro-1,2-dihydroxy-1-phenyl-2-(4-acetamidophenyl)ethane (6) (20 +/- 2%) in the absence of added nucleophiles. Addition of N-3(-) has no effect on the rate constant for decomposition of 1a (ca. 1.9 x 10(-2) s(-1)), but generates a number of adducts that result from trapping of three different electrophilic intermediates. The ortho-N-3 adduct 3-azido-N-acetyl-4-aminostilbene (7) is produced from trapping of the nitrenium ion 2. A fit of the product yield data as a function of [N-3(-)] provides the ratio k(az)/k(s) of 280 +/- 10 M-1 for competitive trapping of 2 by N-3(-) and H2O. The nucleophilic aromatic substitution product 7 is a minor reaction product. The predominant site of attack by N-3(-) On 2 (ca. 85%) is at the beta-vinyl carbon to produce the quinone imide methide 3b. Attack of H2O at the same site produces the analogous intermediate 3a. Both of these electrophilic species are competitively trapped by N-3(-) and H2O with trapping ratios k(az)'/k(s)' for 3b of 107 +/- 8 M-1 and k(az)"/ k(s)" for 3a of 39 +/- 2 M-1. The reactivity patterns of 2 are unlike those of other N-arylnitrenium ions that undergo predominant nucleophilic aromatic substitution with nucleophiles such as N-3(-). The quinone imide methides that are produced by nucleophilic attack on the beta-carbon of 2 react selectively enough with nonsolvent nucleophiles that they may be physiologically relevant.

  DOI：

  10.1021/jo980500z
• 作为产物：
  描述：

  sodium phenylacetate 在 镍 吡啶 、 喹啉 、 ammonium hydroxide 、 copper chromite 、 碘 、 乙酸酐 、 一水合肼 作用下， 以 乙醇 、 乙酸乙酯 、 硝基苯 为溶剂， 反应 2.0h， 生成 3-hydroxy-N-acetyl-4-aminostilbene
  参考文献：
  名称：

  祖尔bedeutung CHEMISCH-biologischer wechselwirkungen献给模具toxische UND krebserzeugende wirkung aromatischer胺-III：SYNTHESE UND ANALYTIK einiger stoffwechselprodukte冯反-dimethylaminostilben，顺-4-二甲基aminostilbenund 4- dimethylaminobibenzyl

  摘要：

  DOI：

  10.1016/s0040-4020(01)91622-9

文献信息

• [EN] COMPOUNDS AS MODULATORS OF TLR2 SIGNALING<br/>[FR] COMPOSÉS UTILISÉS EN TANT QUE MODULATEURS DE SIGNALISATION TLR2
  申请人：NEUROPORE THERAPIES INC

  公开号：WO2019191189A1

  公开（公告）日：2019-10-03

  The present disclosure relates to compounds, pharmaceutical compositions comprising such compounds, and use of such compounds in methods of treatment or in medicaments for treatment of inflammatory diseases and certain neurological disorders that are related to inflammatory signaling processes, including but not limited to misfolded proteins.

  本公开涉及化合物、包含这种化合物的药物组合物，以及利用这些化合物进行治疗方法或用于治疗与炎症信号传导过程相关的炎症性疾病和某些神经系统疾病的药物。这些神经系统疾病与炎症信号传导过程有关，包括但不限于蛋白质错折。
• Compounds as modulators of TLR2 signaling
  申请人：Neuropore Therapies, inc.

  公开号：US11345713B2

  公开（公告）日：2022-05-31

  The present disclosure relates to compounds, pharmaceutical compositions comprising such compounds, and use of such compounds in methods of treatment or in medicaments for treatment of inflammatory diseases and certain neurological disorders that are related to inflammatory signaling processes, including but not limited to misfolded proteins.

  本公开涉及化合物、包含此类化合物的药物组合物，以及此类化合物在治疗炎症性疾病和某些神经系统疾病（包括但不限于折叠错误的蛋白质）的治疗方法或药物中的用途。
• COMPOUNDS AS MODULATORS OF TLR2 SIGNALING
  申请人：Neuropore Therapies, Inc.

  公开号：US20210024539A1

  公开（公告）日：2021-01-28

  The present disclosure relates to compounds, pharmaceutical compositions comprising such compounds, and use of such compounds in methods of treatment or in medicaments for treatment of inflammatory diseases and certain neurological disorders that are related to inflammatory signaling processes, including but not limited to misfolded proteins.
• Zur bedeutung chemisch-biologischer wechselwirkungen für die toxische und krebserzeugende wirkung aromatischer amine—III
  作者：M. Metzler、H.-G. Neumann

  DOI：10.1016/s0040-4020(01)91622-9

  日期：1971.1
• Azide and Solvent Trapping of Electrophilic Intermediates Generated during the Hydrolysis of <i>N</i>-(Sulfonatooxy)-<i>N</i>-acetyl-4-aminostilbene
  作者：Michael Novak、Kelly J. Kayser、Michael E. Brooks

  DOI：10.1021/jo980500z

  日期：1998.8.1

  Hydrolysis of the carcinogenic title compound 1a in 5 vol % CH3CN-H2O, mu = 0.5, 20 degrees C at pH 7.2 in 0.02 M phosphate buffer, yields the rearranged material 3-(sulfonatooxy)-N-acetyl-4-aminostilbene (4) (23 +/- 1%), threo-1,2-dihydroxy-1-phenyl-2-(4-acetamidophenyl)ethane (5) (57 +/- 2%), and erythro-1,2-dihydroxy-1-phenyl-2-(4-acetamidophenyl)ethane (6) (20 +/- 2%) in the absence of added nucleophiles. Addition of N-3(-) has no effect on the rate constant for decomposition of 1a (ca. 1.9 x 10(-2) s(-1)), but generates a number of adducts that result from trapping of three different electrophilic intermediates. The ortho-N-3 adduct 3-azido-N-acetyl-4-aminostilbene (7) is produced from trapping of the nitrenium ion 2. A fit of the product yield data as a function of [N-3(-)] provides the ratio k(az)/k(s) of 280 +/- 10 M-1 for competitive trapping of 2 by N-3(-) and H2O. The nucleophilic aromatic substitution product 7 is a minor reaction product. The predominant site of attack by N-3(-) On 2 (ca. 85%) is at the beta-vinyl carbon to produce the quinone imide methide 3b. Attack of H2O at the same site produces the analogous intermediate 3a. Both of these electrophilic species are competitively trapped by N-3(-) and H2O with trapping ratios k(az)'/k(s)' for 3b of 107 +/- 8 M-1 and k(az)"/ k(s)" for 3a of 39 +/- 2 M-1. The reactivity patterns of 2 are unlike those of other N-arylnitrenium ions that undergo predominant nucleophilic aromatic substitution with nucleophiles such as N-3(-). The quinone imide methides that are produced by nucleophilic attack on the beta-carbon of 2 react selectively enough with nonsolvent nucleophiles that they may be physiologically relevant.