4-[4-(2-methyl-quinolin-4-ylmethyl)-benzoylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester | 936491-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-[4-(2-methyl-quinolin-4-ylmethyl)-benzoylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester
• CAS: 936491-30-4
• 化学式: C₂₅H₂₆N₂O₄
• 分子量: 418.492
• InChiKey: DCFXSXLCKMRZDX-JTHBVZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.52
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[4-(2-methyl-quinolin-4-ylmethyl)-benzoylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 以55%的产率得到(3R,4R)-N-hydroxy-4-({4-[(2-methyl-4-quinolinyl)methyl]benzoyl}amino)tetrahydro-2H-pyran-3-carboxamide
  参考文献：
  名称：

  A new 4-(2-methylquinolin-4-ylmethyl)phenyl P1′ group for the β-amino hydroxamic acid derived TACE inhibitors

  摘要：

  A new P1' group for TACE inhibitors was identified by eliminating the oxygen atom in the linker of the original 4-(2methylquinolin-4-ylmethoxy)phenyl P1' group. Incorporation of this 4-(2-methylquinolin-4-ylmethyl)phenyl group onto different beta-aminohydroxamic acid cores provided compound 18, which demonstrated potent porcine TACE (p-TACE) and human whole blood activity, excellent PK properties, and good selectivity against a variety of MMPs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.041
• 作为产物：
  描述：

  methyl 4-{(2-methyl-4-quinolinyl)[(methylsulfonyl)oxy]methyl}benzoate 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 生成 4-[4-(2-methyl-quinolin-4-ylmethyl)-benzoylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A new 4-(2-methylquinolin-4-ylmethyl)phenyl P1′ group for the β-amino hydroxamic acid derived TACE inhibitors

  摘要：

  A new P1' group for TACE inhibitors was identified by eliminating the oxygen atom in the linker of the original 4-(2methylquinolin-4-ylmethoxy)phenyl P1' group. Incorporation of this 4-(2-methylquinolin-4-ylmethyl)phenyl group onto different beta-aminohydroxamic acid cores provided compound 18, which demonstrated potent porcine TACE (p-TACE) and human whole blood activity, excellent PK properties, and good selectivity against a variety of MMPs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.041