N-((3,4-dihydro-2H-benzo[h]chromen-2-yl)methyl)-3-methylbutanamide | 1609235-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: N-((3,4-dihydro-2H-benzo[h]chromen-2-yl)methyl)-3-methylbutanamide
• 英文别名: N-(3,4-dihydro-2H-benzo[h]chromen-2-ylmethyl)-3-methylbutanamide
• CAS: 1609235-62-2
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: XFGDRXHMGNHMTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((3,4-dihydro-2H-benzo[h]chromen-2-yl)methyl)-3-methylbutanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 N-((3,4-dihydro-2H-benzo[h]chromen-2-yl)methyl)-3-methylbutan-1-amine
  参考文献：
  名称：

  Design and synthesis of 3,4-dihydro-2H-benzo[h]chromene derivatives as potential NF-κB inhibitors

  摘要：

  A novel class of NF-kappa B inhibitors were designed and synthesized based on KL-1156 (6-hydroxy-7-methoxychroman-2-carboxylic acid phenyl amide) which is unambiguously considered to be a promising inhibitor for the translocation step of NF-kappa B. Especially in this study we focused on the modifying the chroman moiety of KL-1156 into four parts for exploring the SAR studies linked with physical properties of substituents resulted the development of novel 1a-k, 2a-f, 3a-d and 4a-d derivatives of 3,4-dihydro-2H-benzo[h] chromene. From the SAR studies we were very delightfully identified that several new N-aryl-3,4-dihydro-2H-benzo[h] chromene-2-carboxamide derivatives (1a-k) exhibited good inhibitory activity and anti-proliferative activity than parent lead compound KL-1156, among them 1i exhibited outstanding inhibitory effect on LPS-induced NF-kappa B transcriptional activity and anti-proliferative activity on NCI-H23 lung cancer cell lines than KL-1156. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.053
• 作为产物：
  描述：

  2-carbethoxy-3,4-dihydro-2H-naphtho[1,2-b]pyran 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 三乙胺 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 13.0h， 生成 N-((3,4-dihydro-2H-benzo[h]chromen-2-yl)methyl)-3-methylbutanamide
  参考文献：
  名称：

  Design and synthesis of 3,4-dihydro-2H-benzo[h]chromene derivatives as potential NF-κB inhibitors

  摘要：

  A novel class of NF-kappa B inhibitors were designed and synthesized based on KL-1156 (6-hydroxy-7-methoxychroman-2-carboxylic acid phenyl amide) which is unambiguously considered to be a promising inhibitor for the translocation step of NF-kappa B. Especially in this study we focused on the modifying the chroman moiety of KL-1156 into four parts for exploring the SAR studies linked with physical properties of substituents resulted the development of novel 1a-k, 2a-f, 3a-d and 4a-d derivatives of 3,4-dihydro-2H-benzo[h] chromene. From the SAR studies we were very delightfully identified that several new N-aryl-3,4-dihydro-2H-benzo[h] chromene-2-carboxamide derivatives (1a-k) exhibited good inhibitory activity and anti-proliferative activity than parent lead compound KL-1156, among them 1i exhibited outstanding inhibitory effect on LPS-induced NF-kappa B transcriptional activity and anti-proliferative activity on NCI-H23 lung cancer cell lines than KL-1156. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.053