N-(4-bromophenyl)-6-bromo-2-oxochromene-3-carboxamide | 301818-11-1

• 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: N-(4-bromophenyl)-6-bromo-2-oxochromene-3-carboxamide
• 英文别名: 6-bromo-N-(4-bromophenyl)-2-oxo-2H-chromene-3-carboxamide；6-bromo-N-(4-bromophenyl)-2-oxochromene-3-carboxamide
• CAS: 301818-11-1
• 化学式: C₁₆H₉Br₂NO₃
• 分子量: 423.06
• InChiKey: PQWSZVGJWUTMRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-6-bromo-2-oxochromene-3-carboxamide 、 1-溴环戊烷羧酸甲酯 在 六甲基磷酰三胺 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 4.0h， 以88%的产率得到9-bromo-3-(4-bromophenyl)-1,1-tetramethylene-2,3,4,4a,5,10b-hexahydro-1H-chromeno[3,4-c]pyridine-2,4,5-trione
  参考文献：
  名称：

  Study of reaction of reformatsky reagent prepared from methyl bromocyclopentanecarboxylate and zinc with 2-oxochromen-and 6-bromo-2-oxochromen-3-carboxylic acids N-arylamides

  摘要：

  Reformatsky reagent prepared from methyl 1-bromocyclopentanecarboxylate and zinc reacted with 2-oxochromen- and 6-bromo-2-oxochromen-3-carboxylic acids N-arylamides yielding 3-aryl-1,1-tetramethylene and 3-aryl-9-bromo-1,1-tetramethylene-2,3,4,4a,5,10b-hexahydro-1H-chromeno[3,4-c]pyridine-2,4,5-triones as single diastereomers.

  DOI：

  10.1134/s1070428007100235
• 作为产物：
  描述：

  3-(4-溴苯胺基)-3-氧代丙酸甲酯 在 氢氧化钾 、 溶剂黄146 、 苄胺 作用下， 以 水 为溶剂， 生成 N-(4-bromophenyl)-6-bromo-2-oxochromene-3-carboxamide
  参考文献：
  名称：

  Novel coumarin-3-(N-aryl)carboxamides arrest breast cancer cell growth by inhibiting ErbB-2 and ERK1

  摘要：

  A series of novel coumarin carboxamides were synthesized, and their tumor cell cytotoxic activity was investigated. These compounds specifically inhibited the growth of cancer cells that have a high level of ErbB-2 expression. Immunoprecipitation analysis of the cell lysates prepared from carboxamide treated cancer cells showed the inhibition of ErbB-2 phosphorylation suggesting the interaction of these compounds with ErbB-2 receptor. The down regulation of the kinase activity was further confirmed by performing in vitro kinase assay with recombinant ErbB-2 incubated with carboxamides. The inhibition of ErbB-2 phosphorylation correlated with down-regulation of ERK1 MAP kinase activation that is involved in proliferative signaling pathway. Furthermore, the cell-killing activity of many of these inhibitors is restricted to tumor cells with no demonstrable cytotoxicity against normal human fibroblasts suggesting that these compounds are tumor-specific. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.051

文献信息

• Reformatsky reaction of methyl 1-bromocyclohexane-1-carboxylate with N-aryl-2-oxochromene-3-carboxamides
  作者：V. V. Shchepin、N. F. Kirillov、M. I. Vakhrin、O. B. Bayanova、S. N. Shurov、P. S. Silaichev

  DOI：10.1134/s1070363206070255

  日期：2006.7

  Reformatsky reagent generated from methyl 1-bromocyclohexane-1-carboxylate reacted with N-aryl-2-oxochromene-3-carboxamides and N-aryl-6-bromo-2-oxochromene-3-carboxan- des to give, depending on the conditions, the corresponding N-aryl-(6-bromo)-4-(1-methoxycarbonylcyclohexyl)-2-oxochroman-3-carboxamides or 3-aryl-(9-bromo)-1,1-pentamethylene-2,3,4,4a,5,10b-hexahydro-1H-chromeno[3,4-c]pyridine-2,4,5-triones. The products were isolated as a single diastereoisomer.
• Novel coumarin-3-(N-aryl)carboxamides arrest breast cancer cell growth by inhibiting ErbB-2 and ERK1
  作者：Natala Srinivasa Reddy、Kiranmai Gumireddy、Muralidhar R. Mallireddigari、Stephen C. Cosenza、Padmavathi Venkatapuram、Stanley C. Bell、E. Premkumar Reddy、M.V. Ramana Reddy

  DOI：10.1016/j.bmc.2005.02.051

  日期：2005.5

  A series of novel coumarin carboxamides were synthesized, and their tumor cell cytotoxic activity was investigated. These compounds specifically inhibited the growth of cancer cells that have a high level of ErbB-2 expression. Immunoprecipitation analysis of the cell lysates prepared from carboxamide treated cancer cells showed the inhibition of ErbB-2 phosphorylation suggesting the interaction of these compounds with ErbB-2 receptor. The down regulation of the kinase activity was further confirmed by performing in vitro kinase assay with recombinant ErbB-2 incubated with carboxamides. The inhibition of ErbB-2 phosphorylation correlated with down-regulation of ERK1 MAP kinase activation that is involved in proliferative signaling pathway. Furthermore, the cell-killing activity of many of these inhibitors is restricted to tumor cells with no demonstrable cytotoxicity against normal human fibroblasts suggesting that these compounds are tumor-specific. (c) 2005 Elsevier Ltd. All rights reserved.
• Study of reaction of reformatsky reagent prepared from methyl bromocyclopentanecarboxylate and zinc with 2-oxochromen-and 6-bromo-2-oxochromen-3-carboxylic acids N-arylamides
  作者：V. V. Shchepin、N. F. Kirillov、M. I. Vakhrin、O. B. Bayanova、S. N. Shurov

  DOI：10.1134/s1070428007100235

  日期：2007.10

  Reformatsky reagent prepared from methyl 1-bromocyclopentanecarboxylate and zinc reacted with 2-oxochromen- and 6-bromo-2-oxochromen-3-carboxylic acids N-arylamides yielding 3-aryl-1,1-tetramethylene and 3-aryl-9-bromo-1,1-tetramethylene-2,3,4,4a,5,10b-hexahydro-1H-chromeno[3,4-c]pyridine-2,4,5-triones as single diastereomers.