4-methoxy-2-nitro-N-(2-thienyl)aniline | 220495-99-8

• 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: 4-methoxy-2-nitro-N-(2-thienyl)aniline
• 英文别名: 4-methoxy-2-nitro-N-(thien-2-yl)aniline；N-(4-methoxy-2-nitrophenyl)thiophen-2-amine
• CAS: 220495-99-8
• 化学式: C₁₁H₁₀N₂O₃S
• 分子量: 250.278
• InChiKey: BXNOBPXGZHQARO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-2-nitro-N-(2-thienyl)aniline 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醚 、 乙二醇甲醚 为溶剂， 反应 6.0h， 生成 5-Methoxy-1-(thien-2-yl)benzimidazole
  参考文献：
  名称：

  Structure−Activity Relationships for 1-Phenylbenzimidazoles as Selective ATP Site Inhibitors of the Platelet-Derived Growth Factor Receptor

  摘要：

  1-Phenylbenzimidazoles are shown to be a new class of ATP-site inhibitors of the platelet-derived growth factor receptor (PDGFR). Structure-activity relationships (SARs) are narrow, with closely related heterocycles being inactive. A systematic study of substituted 1-phenyl-benzimidazoles showed clear SARs. Substituents at the 4'- and 3'-positions of the phenyl ring are tolerated but do not significantly improve activity, while substituents at the 2'-position abolish it. Substituents in the 2-, 4-, and 7-positions of the benzimidazole ring (with the exception of 4-OH) also abolish activity. Most substituents at the 5- and B-positions maintain or increase activity, with the 5-OH, 5-OMe, 5-COMe, and 5-CO2Me analogues being >10-fold more potent than the parent 1-phenylbenzimidazole. The 5-OMe analogue was both the most potent inhibitor, and showed the highest selectivity (50-fold) between PDGFR and FGFR isolated enzymes, and also a moderately effective inhibitor (IC50 = 1.9 mu M) of PDGF-stimulated PDGFR autophosphorylation in rat aorta smooth muscle cells.

  DOI：

  10.1021/jm9804681
• 作为产物：
  描述：

  2-溴噻吩 、 2-硝基-4-甲氧基苯胺 在 copper(l) iodide 、 K₂O₃ 作用下， 反应 18.0h， 以25%的产率得到4-methoxy-2-nitro-N-(2-thienyl)aniline
  参考文献：
  名称：

  Structure−Activity Relationships for 1-Phenylbenzimidazoles as Selective ATP Site Inhibitors of the Platelet-Derived Growth Factor Receptor

  摘要：

  1-Phenylbenzimidazoles are shown to be a new class of ATP-site inhibitors of the platelet-derived growth factor receptor (PDGFR). Structure-activity relationships (SARs) are narrow, with closely related heterocycles being inactive. A systematic study of substituted 1-phenyl-benzimidazoles showed clear SARs. Substituents at the 4'- and 3'-positions of the phenyl ring are tolerated but do not significantly improve activity, while substituents at the 2'-position abolish it. Substituents in the 2-, 4-, and 7-positions of the benzimidazole ring (with the exception of 4-OH) also abolish activity. Most substituents at the 5- and B-positions maintain or increase activity, with the 5-OH, 5-OMe, 5-COMe, and 5-CO2Me analogues being >10-fold more potent than the parent 1-phenylbenzimidazole. The 5-OMe analogue was both the most potent inhibitor, and showed the highest selectivity (50-fold) between PDGFR and FGFR isolated enzymes, and also a moderately effective inhibitor (IC50 = 1.9 mu M) of PDGF-stimulated PDGFR autophosphorylation in rat aorta smooth muscle cells.

  DOI：

  10.1021/jm9804681

文献信息

• Benzimidazoles for inhibiting protein tyrosine kinase mediated cellular
  申请人：Warner-Lambert Company

  公开号：US05990146A1

  公开（公告）日：1999-11-23

  Benzimidazoles of Formula I below are inhibitors of protein tyrosine kinases, and are useful in treating cellular proliferation. ##STR1## The compounds are especially useful in treating cancer, atherosclerosis, restenosis, and psoriasis.

  下面的I式苯并咪唑是蛋白酪氨酸激酶的抑制剂，对治疗细胞增殖很有用。这些化合物在治疗癌症、动脉粥样硬化、再狭窄和牛皮癣方面特别有效。
• US6218388B1
  申请人：——

  公开号：US6218388B1

  公开（公告）日：2001-04-17