3-(二甲基氨基)-4-甲氧基苯甲酸甲酯 | 344332-16-7

• 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: 3-(二甲基氨基)-4-甲氧基苯甲酸甲酯
• 英文名称: methyl 3-N,N-dimethylamino-4-methoxybenzoate
• 英文别名: methyl 3-dimethylamino-4-methoxybenzoate；3-dimethylamino-4-methoxy-benzoic acid methyl ester；3-Dimethylamino-4-methoxy-benzoesaeure-methylester；3-Dimethylamino-anissaeure-methylester；Methyl 3-(dimethylamino)-4-methoxybenzoate
• CAS: 344332-16-7
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: GHXNUPBZXUAPNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  3-(二甲基氨基)-4-甲氧基苯甲酸甲酯 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 以82%的产率得到3-dimethylamino-4-methoxybenzyl alcohol
  参考文献：
  名称：

  Antitumor agents 222. † †For Part 221, see ref 1. Synthesis and anti-androgen activity of new diarylheptanoids

  摘要：

  Fifteen new diarylheptanoids were synthesized and evaluated for antagonistic activity against androgen receptor (AR)-mediated reporter gene transcription using DU145, PC-3, and LNCaP prostate cancer cell lines. Most compounds showed activity in a 5alpha-dihydrotestosterone (DHT)-induced reporter gene expression assay in DU145 cells transfected with wild-type AR. Ten compounds (5, 8, 10, 14-15, and 18-22) were equipotent with hydroxyflutamide (HF), the anti-androgen currently available for the treatment of prostate cancer. However, except for compounds 5 and 10, none of the tested compounds was significantly effective in attenuating DHT-induced reporter gene expression in LNCaP cells, which contain endogenous mutant AR. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.029
• 作为产物：
  描述：

  5-carboxy-2-methoxy-tri-N-methyl-anilinium betaine 生成 3-(二甲基氨基)-4-甲氧基苯甲酸甲酯
  参考文献：
  名称：

  Einhorn; Ruppert, Justus Liebigs Annalen der Chemie, 1902, vol. 325, p. 320

  摘要：

  DOI：

文献信息

• Calas; Barbier; Giral, European Journal of Medicinal Chemistry, 1982, vol. 17, # 6, p. 497 - 504
  作者：Calas、Barbier、Giral、et al.

  DOI：——

  日期：——
• Synthesis of Aryl-Substituted 1,3-Butadiones
  作者：Burkhard König

  DOI：10.1081/scc-120016361

  日期：2003.1.4

  The synthesis of several electron donor substituted 1-aryl-1,3-butadiones and their use as ligands in the formation of scandium(III) complexes is reported.
• Griess, Chemische Berichte, 1872, vol. 5, p. 588
  作者：Griess

  DOI：——

  日期：——
• CALAS, M.;BARBIER, A.;GIRAL, L.;BALMAYER, B.;DESPAUX, E., EUR. J. MED. CHEM.-CHIM. THER., 1982, 17, N 6, 457-504
  作者：CALAS, M.、BARBIER, A.、GIRAL, L.、BALMAYER, B.、DESPAUX, E.

  DOI：——

  日期：——
• Antitumor agents 222. † †For Part 221, see ref 1. Synthesis and anti-androgen activity of new diarylheptanoids
  作者：Hironori Ohtsu、Hideji Itokawa、Zhiyan Xiao、Ching-Yuan Su、Charles C.-Y Shih、Tzuying Chiang、Eugene Chang、YiFen Lee、Shang-Yi Chiu、Chawnshang Chang、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2003.08.029

  日期：2003.11

  Fifteen new diarylheptanoids were synthesized and evaluated for antagonistic activity against androgen receptor (AR)-mediated reporter gene transcription using DU145, PC-3, and LNCaP prostate cancer cell lines. Most compounds showed activity in a 5alpha-dihydrotestosterone (DHT)-induced reporter gene expression assay in DU145 cells transfected with wild-type AR. Ten compounds (5, 8, 10, 14-15, and 18-22) were equipotent with hydroxyflutamide (HF), the anti-androgen currently available for the treatment of prostate cancer. However, except for compounds 5 and 10, none of the tested compounds was significantly effective in attenuating DHT-induced reporter gene expression in LNCaP cells, which contain endogenous mutant AR. (C) 2003 Elsevier Ltd. All rights reserved.