(4R,5R)-1-benzyl-4,5-dihydro-2,4,5-triphenyl-1H-imidazole-4-carboxylic acid | 905913-84-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4R,5R)-1-benzyl-4,5-dihydro-2,4,5-triphenyl-1H-imidazole-4-carboxylic acid
• 英文别名: (4R,5R)-3-benzyl-2,4,5-triphenyl-1,4-dihydroimidazol-3-ium-5-carboxylate
• CAS: 905913-84-0
• 化学式: C₂₉H₂₄N₂O₂
• 分子量: 432.522
• InChiKey: SHAVOCVWHNDNMP-GGXMVOPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-1-benzyl-4,5-dihydro-2,4,5-triphenyl-1H-imidazole-4-carboxylic acid 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以100%的产率得到(4R,5R)-1-benzyl-4,5-dihydro-2,4,5-triphenyl-1H-imidazole-4-carboxylic acid hydrochloride
  参考文献：
  名称：

  [EN] SUBSTITUTED IMIDAZOLINE COMPOUNDS
  [FR] COMPOSÉS D'IMIDAZOLINE SUBSTITUÉS

  摘要：

  本发明涉及包括前药和其盐的取代咪唑啉化合物组合物。在某些实施例中，本发明涉及将这些组合物用作治疗剂，优选用于治疗关节炎或癌症。在进一步的实施例中，本发明涉及含有有效量的上述取代咪唑啉化合物的制药组合物，其作为遗传表达或与转录因子NF-ϰB相互作用的激动剂或拮抗剂发挥作用。

  公开号：

  WO2009048586A1
• 作为产物：
  描述：

  N-苄烯丁胺 在 4-二甲氨基吡啶 、 三甲基氯硅烷 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (4R,5R)-1-benzyl-4,5-dihydro-2,4,5-triphenyl-1H-imidazole-4-carboxylic acid
  参考文献：
  名称：

  Sensitization of Cancer Cells to DNA Damaging Agents by Imidazolines

  摘要：

  Apoptosis, or programmed cell death, is a cellular mechanism used to regulate cell number and eliminate damaged or mutated cells. Concomitant with the initiation of the apoptotic cell signal, chemotherapeutic agents also induce anti-apoptotic factors, such as NF-kappa B, which compromise the overall efficacy of chemotherapeutic anticancer treatment. Here we describe an adjuvant therapy in which a small molecule is used to sensitize cancer cells toward apoptosis induced by chemotherapeutics. Our results indicate that the imidazoline 1d modulates the pro-survival NF-kappa B pathway and selectively sensitizes cancer cells toward DNA damaging agents, thus enhancing the overall efficacy of the treatment. Pretreatment of cancer cells with the noncytotoxic imidazoline 1d (10 nM) resulted in a significant increase in apoptosis and anticancer efficacy of the clinically significant DNA damaging agents camptothecin and cisplatin. Noncancerous cells remained unaffected during this regimen.

  DOI：

  10.1021/ja060273f

文献信息

• NF-kB inhibitors and uses thereof
  申请人：Tepe Jetze J.

  公开号：US20080114015A1

  公开（公告）日：2008-05-15

  A diastereomers of imidazolines as 4-position acids are described. The imidazoline diastereomers potentiate the activity of antitumor drugs and are potent inhibitors of the transcription factor NF-κB.
• Substituted Imidazoline Compounds
  申请人：Tepe Jetze

  公开号：US20090156830A1

  公开（公告）日：2009-06-18

  The invention relates to compositions comprising substituted imidazoline compounds including prodrugs, and salts thereof. In some embodiments, the invention relates to the use of these compositions as therapeutic agents, preferably for the treatment of arthritis or cancer. In further embodiments, The invention relates to the pharmaceutical compositions with effective amounts of substituted imidazoline compounds disclosed herein that function as agonist or antagonists of the genetic expression or interactions with transcription factor NF-κB.
• US8252942B2
  申请人：——

  公开号：US8252942B2

  公开（公告）日：2012-08-28
• Sensitization of Cancer Cells to DNA Damaging Agents by Imidazolines
  作者：Vasudha Sharma、Satyamaheshwar Peddibhotla、Jetze J. Tepe

  DOI：10.1021/ja060273f

  日期：2006.7.19

  Apoptosis, or programmed cell death, is a cellular mechanism used to regulate cell number and eliminate damaged or mutated cells. Concomitant with the initiation of the apoptotic cell signal, chemotherapeutic agents also induce anti-apoptotic factors, such as NF-kappa B, which compromise the overall efficacy of chemotherapeutic anticancer treatment. Here we describe an adjuvant therapy in which a small molecule is used to sensitize cancer cells toward apoptosis induced by chemotherapeutics. Our results indicate that the imidazoline 1d modulates the pro-survival NF-kappa B pathway and selectively sensitizes cancer cells toward DNA damaging agents, thus enhancing the overall efficacy of the treatment. Pretreatment of cancer cells with the noncytotoxic imidazoline 1d (10 nM) resulted in a significant increase in apoptosis and anticancer efficacy of the clinically significant DNA damaging agents camptothecin and cisplatin. Noncancerous cells remained unaffected during this regimen.
• [EN] SUBSTITUTED IMIDAZOLINE COMPOUNDS<br/>[FR] COMPOSÉS D'IMIDAZOLINE SUBSTITUÉS
  申请人：UNIV MICHIGAN STATE

  公开号：WO2009048586A1

  公开（公告）日：2009-04-16

  The invention relates to compositions comprising substituted imidazoline compounds including prodrugs, and salts thereof. In some embodiments, the invention relates to the use of these compositions as therapeutic agents, preferably for the treatment of arthritis or cancer. In further embodiments, The invention relates to the pharmaceutical compositions with effective amounts of substituted imidazoline compounds disclosed herein that function as agonist or antagonists of the genetic expression or interactions with transcription factor NF-ϰB.

  本发明涉及包括前药和其盐的取代咪唑啉化合物组合物。在某些实施例中，本发明涉及将这些组合物用作治疗剂，优选用于治疗关节炎或癌症。在进一步的实施例中，本发明涉及含有有效量的上述取代咪唑啉化合物的制药组合物，其作为遗传表达或与转录因子NF-ϰB相互作用的激动剂或拮抗剂发挥作用。