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
• Structure−Activity Relationships for 1-Phenylbenzimidazoles as Selective ATP Site Inhibitors of the Platelet-Derived Growth Factor Receptor
  作者：Brian D. Palmer、Jeff B. Smaill、Maruta Boyd、Diane H. Boschelli、Annette M. Doherty、James M. Hamby、Sonya S. Khatana、James B. Kramer、Alan J. Kraker、Robert L. Panek、Gina H. Lu、Tawny K. Dahring、R. Thomas Winters、H. D. Hollis Showalter、William A. Denny

  DOI：10.1021/jm9804681

  日期：1998.12.1

  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.