3-chloro-N-[4-(N,N-dimethylamino)phenyl]thiophene-2-carboxamide

• 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: 3-chloro-N-[4-(N,N-dimethylamino)phenyl]thiophene-2-carboxamide
• 英文别名: 3-chloro-N-[4-(dimethylamino)phenyl]thiophene-2-carboxamide
• 化学式: C₁₃H₁₃ClN₂OS
• 分子量: 280.778
• InChiKey: LORYFMZQUUHFPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-N-[4-(N,N-dimethylamino)phenyl]thiophene-2-carboxamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以70%的产率得到4-(3-chlorothiophene-2-carboxamido)-N,N-dimethylbenzenamine hydrochloride
  参考文献：
  名称：

  Exploring antiproliferative activity of heteroaromatic amides and their fused derivatives using 3D-QSAR, synthesis, and biological tests

  摘要：

  In this manuscript the synthesis, antiproliferative activity, and 3D-QSAR study of novel heteroaromatic benzamides and their cyclic products, quinolones and naphthyridones were described. The in vitro antiproliferative screening on three tumor cell lines showed in general moderate antiproliferative effect, except 2-benzimidazolyl and 2-benzothiazolyl substituted heteroaromatic amides, which showed prominent antiproliferative effect with GI(50) concentration at micromolar range. Cyclic quinolones and naphthyridones demonstrated similar activity as their acyclic precursors. Using measured anticancer activities, 3D-QSAR models were obtained. Their prediction abilities were tested by internal and external prediction. Molecular properties with the highest positive or negative influence on compound's anticancer activities have been identified. It was found that possibility of compound to accept H-bond (WN1), sum of hydrophobic surface areas, possibility of weak hydrophobic interactions (D1), and complete molecular surface of compound (S) should be increased, while possibility of weak hydrophilic interactions (W1) should be decreased in order to enhance anticancer activity of investigated compounds.

  DOI：

  10.1007/s00706-015-1478-8
• 作为产物：
  描述：

  N,N-二甲基-对苯二胺 、 3-氯噻吩-2-甲酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以29%的产率得到3-chloro-N-[4-(N,N-dimethylamino)phenyl]thiophene-2-carboxamide
  参考文献：
  名称：

  Exploring antiproliferative activity of heteroaromatic amides and their fused derivatives using 3D-QSAR, synthesis, and biological tests

  摘要：

  In this manuscript the synthesis, antiproliferative activity, and 3D-QSAR study of novel heteroaromatic benzamides and their cyclic products, quinolones and naphthyridones were described. The in vitro antiproliferative screening on three tumor cell lines showed in general moderate antiproliferative effect, except 2-benzimidazolyl and 2-benzothiazolyl substituted heteroaromatic amides, which showed prominent antiproliferative effect with GI(50) concentration at micromolar range. Cyclic quinolones and naphthyridones demonstrated similar activity as their acyclic precursors. Using measured anticancer activities, 3D-QSAR models were obtained. Their prediction abilities were tested by internal and external prediction. Molecular properties with the highest positive or negative influence on compound's anticancer activities have been identified. It was found that possibility of compound to accept H-bond (WN1), sum of hydrophobic surface areas, possibility of weak hydrophobic interactions (D1), and complete molecular surface of compound (S) should be increased, while possibility of weak hydrophilic interactions (W1) should be decreased in order to enhance anticancer activity of investigated compounds.

  DOI：

  10.1007/s00706-015-1478-8

文献信息

• Exploring antiproliferative activity of heteroaromatic amides and their fused derivatives using 3D-QSAR, synthesis, and biological tests
  作者：Irena Sović、Marko Viskić、Branimir Bertoša、Katja Ester、Marijeta Kralj、Marijana Hranjec、Grace Karminski-Zamola

  DOI：10.1007/s00706-015-1478-8

  日期：2015.9

  In this manuscript the synthesis, antiproliferative activity, and 3D-QSAR study of novel heteroaromatic benzamides and their cyclic products, quinolones and naphthyridones were described. The in vitro antiproliferative screening on three tumor cell lines showed in general moderate antiproliferative effect, except 2-benzimidazolyl and 2-benzothiazolyl substituted heteroaromatic amides, which showed prominent antiproliferative effect with GI(50) concentration at micromolar range. Cyclic quinolones and naphthyridones demonstrated similar activity as their acyclic precursors. Using measured anticancer activities, 3D-QSAR models were obtained. Their prediction abilities were tested by internal and external prediction. Molecular properties with the highest positive or negative influence on compound's anticancer activities have been identified. It was found that possibility of compound to accept H-bond (WN1), sum of hydrophobic surface areas, possibility of weak hydrophobic interactions (D1), and complete molecular surface of compound (S) should be increased, while possibility of weak hydrophilic interactions (W1) should be decreased in order to enhance anticancer activity of investigated compounds.