Biphenyl-4-sulfonic acid (2-amino-ethyl)-amide

• 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: Biphenyl-4-sulfonic acid (2-amino-ethyl)-amide
• 英文别名: N-(2-aminoethyl)-4-phenylbenzenesulfonamide
• 化学式: C₁₄H₁₆N₂O₂S
• 分子量: 276.359
• InChiKey: DLWLTTMLXUEPPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯-4-氨基-6,7-二甲氧基喹唑啉 、 Biphenyl-4-sulfonic acid (2-amino-ethyl)-amide 以 正丁醇 为溶剂， 生成 N-[2-(4-amino-6,7-dimethoxyquinazolin-2-ylamino)-ethyl]-4-biphenylsulfonamide
  参考文献：
  名称：

  Pharmacological Exploitation of the α1-Adrenoreceptor Antagonist Doxazosin to Develop a Novel Class of Antitumor Agents That Block Intracellular Protein Kinase B/Akt Activation

  摘要：

  The alpha1-adrenoreceptor antagonist doxazosin induces apoptosis in malignant cells with moderate potency via an alpha1-adrenoreceptor-independent mechanism. Here, we demonstrate that the ability of doxazosin to induce apoptosis in PC-3 prostate cancer cells was, in part, attributable to the inhibition of protein kinase B (PKB)/Akt activation. The separation of the effect of doxazosin on apoptosis from its original pharmacological activity provides molecular underpinnings to develop novel antitumor agents. Replacement of the (2,3-dihydro-benzo[1,4]dioxane)-carbonyl moiety of doxazosin with aryl-sulfonyl functions dramatically improves the potency in facilitating Akt deactivation and inducing apoptosis. The optimal compounds, 33 and 44, were effective in apoptosis induction at low micromolar concentrations irrespective of androgen dependency and p53 functional status. Both agents were active in suppressing the growth of a panel of 60 cancer-cell lines with IC50 values of 2.2 and 1.5 muM, respectively. Together, these in vitro efficacy data suggest the translational potential of these agents in prostate cancer treatment.

  DOI：

  10.1021/jm049752k
• 作为产物：
  描述：

  对联苯磺酰氯 、 乙二胺 以 甲醇 为溶剂， 反应 3.0h， 生成 Biphenyl-4-sulfonic acid (2-amino-ethyl)-amide
  参考文献：
  名称：

  Pharmacological Exploitation of the α1-Adrenoreceptor Antagonist Doxazosin to Develop a Novel Class of Antitumor Agents That Block Intracellular Protein Kinase B/Akt Activation

  摘要：

  The alpha1-adrenoreceptor antagonist doxazosin induces apoptosis in malignant cells with moderate potency via an alpha1-adrenoreceptor-independent mechanism. Here, we demonstrate that the ability of doxazosin to induce apoptosis in PC-3 prostate cancer cells was, in part, attributable to the inhibition of protein kinase B (PKB)/Akt activation. The separation of the effect of doxazosin on apoptosis from its original pharmacological activity provides molecular underpinnings to develop novel antitumor agents. Replacement of the (2,3-dihydro-benzo[1,4]dioxane)-carbonyl moiety of doxazosin with aryl-sulfonyl functions dramatically improves the potency in facilitating Akt deactivation and inducing apoptosis. The optimal compounds, 33 and 44, were effective in apoptosis induction at low micromolar concentrations irrespective of androgen dependency and p53 functional status. Both agents were active in suppressing the growth of a panel of 60 cancer-cell lines with IC50 values of 2.2 and 1.5 muM, respectively. Together, these in vitro efficacy data suggest the translational potential of these agents in prostate cancer treatment.

  DOI：

  10.1021/jm049752k

文献信息

• FIVE-MEMBERED HETEROCYCLIC DERIVATIVE, METHOD FOR PRODUCING SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  申请人：Industry Academic Cooperation Foundation, Hallym University

  公开号：EP3470404A1

  公开（公告）日：2019-04-17

  The present invention relates to a five-membered heterocyclic compound having an analgesic effect and a pharmaceutical composition comprising a derivative of the five-membered heterocyclic compound. More specifically, the present invention relates to a method for producing a five-membered heterocyclic compound having few side-effects and a broad analgesic effect, including pain relief for neuropathy, and to a pharmaceutical composition comprising the five-membered heterocyclic compound.

  本发明涉及一种具有镇痛效果的五元杂环化合物，以及包含该五元杂环化合物衍生物的药物组合物。更具体地，本发明涉及一种用于生产具有少量副作用和广泛镇痛效果的五元杂环化合物的方法，包括用于神经病症疼痛缓解的方法，以及包含该五元杂环化合物的药物组合物。