N-(benzotriazol-1-ylmethyl)-3-methoxy-2-methylaniline | 156267-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: N-(benzotriazol-1-ylmethyl)-3-methoxy-2-methylaniline
• CAS: 156267-25-3
• 化学式: C₁₅H₁₆N₄O
• 分子量: 268.318
• InChiKey: KFCCZQXDRCZQFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.97
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(benzotriazol-1-ylmethyl)-3-methoxy-2-methylaniline 在 盐酸 、 sodium tetrahydroborate 、 正丁基锂 作用下， 生成 4-methoxy-1-methyloxindole
  参考文献：
  名称：

  Rewcastle, Gordon W.; Denny, William A., Heterocycles, 1994, vol. 37, # 2, p. 701 - 708

  摘要：

  DOI：
• 作为产物：
  描述：

  T406石油添加剂 、 聚合甲醛 、 2-甲基-3-甲氧基苯胺 以 乙醇 、 水 为溶剂， 以77%的产率得到N-(benzotriazol-1-ylmethyl)-3-methoxy-2-methylaniline
  参考文献：
  名称：

  Tyrosine Kinase Inhibitors. 3. Structure-Activity Relationships for Inhibition of Protein Tyrosine Kinases by Nuclear-Substituted Derivatives of 2,2'-Dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)

  摘要：

  A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3-dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity, While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20-fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC(50)s in the range 2-25 mu M, the most active being 4-substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF-mediated phosphorylation.

  DOI：

  10.1021/jm00039a016

文献信息

• Rewcastle Gordon W., Palmer Brian D., Dobrusin Ellen M., Fry David W., Kr+, J. Med. Chem, 37 (1994) N 13, S 2033-2042
  作者：Rewcastle Gordon W., Palmer Brian D., Dobrusin Ellen M., Fry David W., Kr+

  DOI：——

  日期：——