3-methoxy-N,2-dimethylaniline | 156267-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxy-N,2-dimethylaniline
• CAS: 156267-10-6
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: CQZYVBMGQFYAGU-UHFFFAOYSA-N

物化性质

• 沸点：
  250.1±28.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-N,2-dimethylaniline 在 盐酸 、 正丁基锂 、 氢溴酸 作用下， 生成 1-methyl-4-hydroxyoxindole
  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
• 作为产物：
  描述：

  N-(benzotriazol-1-ylmethyl)-3-methoxy-2-methylaniline 在 sodium tetrahydroborate 作用下， 生成 3-methoxy-N,2-dimethylaniline
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Macrocylic inhibitors of hepatitis c virus
  申请人：Janssen Sciences Ireland UC

  公开号：EP2937339A1

  公开（公告）日：2015-10-28

  Combinations comprising inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers, wherein each dashed line represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl; R4 is aryl or Het; n is 3, 4, 5, or 6; R5 is halo, C1-6alkyl, hydroxy, C1-6alkoxy, phenyl, or Het; R6 is C1-6alkoxy, or dimethylamino; R7 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R8 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl optionally substituted with one, two or three substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents.

  由式(I)的HCV复制抑制剂组成的组合物 及其 N-氧化物、盐和立体异构体的组合物，其中每条虚线代表一个任选双键； X 是 N、CH，如果 X 含有双键，则是 C； R1 是-OR7、-NH-SO2R8； R2 是氢，当 X 是 C 或 CH 时，R2 也可以是 C1-6 烷基； R3 是氢、C1-6烷基、C1-6烷氧基 C1-6烷基、C3-7 环烷基； R4 是芳基或 Het；n 是 3、4、5 或 6； R5 是卤素、C1-6烷基、羟基、C1-6烷氧基、苯基或 Het； R6 是 C1-6 烷氧基或二甲基氨基； R7 是氢；芳基；Het；被 C1-6 烷基任选取代的 C3-7 环烷基；或被 C3-7 环烷基、芳基或 Het 任选取代的 C1-6 烷基； R8 是芳基；Het；被 C1-6 烷基任选取代的 C3-7 环烷基；或被 C3-7 环烷基、芳基或 Het 任选取代的 C1-6 烷基； 芳基 是任选被一个、两个或三个取代基取代的苯基； Het 是 5 或 6 个成员的饱和、部分不饱和或完全不饱和杂环，含有 1 至 4 个选自氮、氧和硫的杂原子，并可任选被 1、2 或 3 个取代基取代。
• Hepatitis B antiviral agents
  申请人：Novira Therapeutics, Inc.

  公开号：US10196376B2

  公开（公告）日：2019-02-05

  The present invention includes a method of inhibiting, suppressing or preventing HBV infection in an individual in need thereof, comprising administering to the individual a therapeutically effective amount of at least one compound of the invention.

  本发明包括一种在有需要的个体中抑制、抑制或预防 HBV 感染的方法，包括向该个体施用治疗有效量的至少一种本发明化合物。
• 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：——
• Intermediates for the preparation of Macrocyclic inhibitors of hepatitis c virus
  申请人：Janssen Sciences Ireland UC

  公开号：EP2322516B1

  公开（公告）日：2015-09-23
• HEPATITIS B ANTIVIRAL AGENTS
  申请人：Novira Therapeutics Inc.

  公开号：EP2794565B1

  公开（公告）日：2017-07-26