2'-氯-5'-(三氟甲基)-琥珀酰苯胺酸 | 199803-99-1

• 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: 2'-氯-5'-(三氟甲基)-琥珀酰苯胺酸
• 英文名称: 2'-chloro-5'-(trifluoromethyl)-succinanilic acid
• 英文别名: 4-[2-Chloro-5-(trifluoromethyl)anilino]-4-oxobutanoic acid
• CAS: 199803-99-1
• 化学式: C₁₁H₉ClF₃NO₃
• mdl: MFCD00157413
• 分子量: 295.646
• InChiKey: HSXZNNQNKDOXGY-UHFFFAOYSA-N

物化性质

• 沸点：
  451.4±45.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  紫朱牛舌草(ALKANNATINCTORIA)根提取物 、 2'-氯-5'-(三氟甲基)-琥珀酰苯胺酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.25h， 以75.2%的产率得到1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(2-chloro-5-(trifluoromethyl)phenylamino)-4-oxobutanoate
  参考文献：
  名称：

  Novel naphthalene-enoates: Design and anticancer activity through regulation cell autophagy

  摘要：

  Eleven dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl) naphthalene derivatives as anticancer agents through regulating cell autophagy were designed and synthesized. The anticancer activity results indicated that most compounds manifested obvious un-toxic effect on GES-1 and L-02 with IC50 from 0.58 to 1.41 mM. Among them, (S, Z)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(3,4-dihydroisoquinolin- 2(1 H)-yl)-4-oxobut-2-enoate (compound 4i) could induce cancer cells apoptosis. Further experiments showed that autophagy played an important role in the pro-apoptotic effect of this compound. Preliminary mechanism indicated that this compound could inhibit phosphoinositide 3-kinase/protein kinase B and the mammalian target of rapamycin (PI3K/AKT/mTOR) pathway by mediating apoptosis in an autophagy-dependent manner.

  DOI：

  10.1016/j.biopha.2019.108747
• 作为产物：
  描述：

  丁二酸酐 、 3-氨基-4-氯三氟甲苯 以 甲苯 为溶剂， 反应 2.5h， 生成 2'-氯-5'-(三氟甲基)-琥珀酰苯胺酸
  参考文献：
  名称：

  Novel naphthalene-enoates: Design and anticancer activity through regulation cell autophagy

  摘要：

  Eleven dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl) naphthalene derivatives as anticancer agents through regulating cell autophagy were designed and synthesized. The anticancer activity results indicated that most compounds manifested obvious un-toxic effect on GES-1 and L-02 with IC50 from 0.58 to 1.41 mM. Among them, (S, Z)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(3,4-dihydroisoquinolin- 2(1 H)-yl)-4-oxobut-2-enoate (compound 4i) could induce cancer cells apoptosis. Further experiments showed that autophagy played an important role in the pro-apoptotic effect of this compound. Preliminary mechanism indicated that this compound could inhibit phosphoinositide 3-kinase/protein kinase B and the mammalian target of rapamycin (PI3K/AKT/mTOR) pathway by mediating apoptosis in an autophagy-dependent manner.

  DOI：

  10.1016/j.biopha.2019.108747

文献信息

• SALTS OF PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1091958A1

  公开（公告）日：2001-04-18
• [EN] SALTS OF PAROXETINE<br/>[FR] SELS DE PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2000001692A1

  公开（公告）日：2000-01-13

  Piperidine compounds, processes for preparing them, pharmaceutical compositions comprising them and their use in therapy are disclosed.
• Novel naphthalene-enoates: Design and anticancer activity through regulation cell autophagy
  作者：Meng Di Yang、Xiao Bao Shen、Yang Sheng Hu、Yan Yan Chen、Xin Hua Liu

  DOI：10.1016/j.biopha.2019.108747

  日期：2019.5

  Eleven dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl) naphthalene derivatives as anticancer agents through regulating cell autophagy were designed and synthesized. The anticancer activity results indicated that most compounds manifested obvious un-toxic effect on GES-1 and L-02 with IC50 from 0.58 to 1.41 mM. Among them, (S, Z)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(3,4-dihydroisoquinolin- 2(1 H)-yl)-4-oxobut-2-enoate (compound 4i) could induce cancer cells apoptosis. Further experiments showed that autophagy played an important role in the pro-apoptotic effect of this compound. Preliminary mechanism indicated that this compound could inhibit phosphoinositide 3-kinase/protein kinase B and the mammalian target of rapamycin (PI3K/AKT/mTOR) pathway by mediating apoptosis in an autophagy-dependent manner.