2-(3,4,5-trimethoxybenzoyl)-4-phenyl-1H-imidazole | 1429621-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3,4,5-trimethoxybenzoyl)-4-phenyl-1H-imidazole
• 英文别名: (3,4,5-Trimethoxyphenyl)(5-phenyl-1h-imidazol-2-yl)methanone；(5-phenyl-1H-imidazol-2-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1429621-76-0
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: IHGQAKVCJDAQEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  溴代环戊烷 、 2-(3,4,5-trimethoxybenzoyl)-4-phenyl-1H-imidazole 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以98.3%的产率得到(1-Cyclopentyl-4-phenyl-1H-imidazol-2-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Discovery of 4-Aryl-2-benzoyl-imidazoles as Tubulin Polymerization Inhibitor with Potent Antiproliferative Properties

  摘要：

  A series of 4-aryl-2-benzoyl-imidazoles were designed and synthesized based on our previously reported 2-aryl-4-benzoyl-imidazole (ABI) derivatives. The new structures reversed the aryl group and the benzoyl group of previous ABI structures and were named as reverse ABI (RABI) analogues. RABIs were evaluated for biological activity against eight cancer cell lines including multidrug-resistant cancer cell lines. In vitro assays indicated that several RABI compounds had excellent antiproliferative properties, with IC50 values in the low, nanomolar range. The average IC50 of the most active compound 12a is 14 nM. In addition, the mechanism of action of these new analogues was investigated by cell cycle analysis, tubulin polymerization assay, competitive mass spectrometry binding assay, and molecular docking studies. These studies confirmed that these new RABI analogues maintain their mechanisms of action by disrupting tubulin polymerization, similar to their parental ABI analogues.

  DOI：

  10.1021/jm4001117
• 作为产物：
  描述：

  2-(3,4,5-trimethoxybenzoyl)-5-phenyl-1H-imidazol-1-ol 在 三甲氧基磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以88%的产率得到2-(3,4,5-trimethoxybenzoyl)-4-phenyl-1H-imidazole
  参考文献：
  名称：

  Synthesis of 2-(3,4,5-trimethoxybenzoyl)-4(5)-phenyl-1H-imidazole

  摘要：

  The condensation of (2E)-N-hydroxy-2-hydroxyimino-2-phenylethanamine with 3,4,5-trimethoxy-phenylglyoxal afforded (1-hydroxy-5-phenyl-1H-imidazol-2-yl)phenylmethanone which reacted with trimethyl phosphite or chloroacetone to give 2-(3,4,5-trimethoxybenzoyl)-4(5)-phenyl-1H-imidazole.

  DOI：

  10.1134/s1070428017120193

文献信息

• COMPOUNDS FOR TREATMENT OF CANCER
  申请人：GTx, Inc.

  公开号：US20130197049A1

  公开（公告）日：2013-08-01

  The present invention relates to novel compounds having anti-cancer activity, methods of making these compounds, and their use for treating cancer and drug-resistant tumors, e.g. melanoma, metastatic melanoma, drug resistant melanoma, prostate cancer and drug resistant prostate cancer.

  本发明涉及具有抗癌活性的新化合物，制备这些化合物的方法，以及它们用于治疗癌症和耐药肿瘤的用途，例如黑色素瘤、转移性黑色素瘤、耐药性黑色素瘤、前列腺癌和耐药性前列腺癌。
• Compounds for treatment of cancer
  申请人：ONCTERNAL THERAPEUTICS, INC.

  公开号：US11084811B2

  公开（公告）日：2021-08-10

  The present invention relates to novel compounds having anti-cancer activity, methods of making these compounds, and their use for treating cancer and drug-resistant tumors, e.g. melanoma, metastatic melanoma, drug resistant melanoma, prostate cancer and drug resistant prostate cancer.

  本发明涉及具有抗癌活性的新型化合物、制造这些化合物的方法及其用于治疗癌症和耐药性肿瘤（如黑色素瘤、转移性黑色素瘤、耐药性黑色素瘤、前列腺癌和耐药性前列腺癌）的用途。
• US9447049B2
  申请人：——

  公开号：US9447049B2

  公开（公告）日：2016-09-20
• Discovery of 4-Aryl-2-benzoyl-imidazoles as Tubulin Polymerization Inhibitor with Potent Antiproliferative Properties
  作者：Min Xiao、Sunjoo Ahn、Jin Wang、Jianjun Chen、Duane. D. Miller、James T Dalton、Wei Li

  DOI：10.1021/jm4001117

  日期：2013.4.25

  A series of 4-aryl-2-benzoyl-imidazoles were designed and synthesized based on our previously reported 2-aryl-4-benzoyl-imidazole (ABI) derivatives. The new structures reversed the aryl group and the benzoyl group of previous ABI structures and were named as reverse ABI (RABI) analogues. RABIs were evaluated for biological activity against eight cancer cell lines including multidrug-resistant cancer cell lines. In vitro assays indicated that several RABI compounds had excellent antiproliferative properties, with IC50 values in the low, nanomolar range. The average IC50 of the most active compound 12a is 14 nM. In addition, the mechanism of action of these new analogues was investigated by cell cycle analysis, tubulin polymerization assay, competitive mass spectrometry binding assay, and molecular docking studies. These studies confirmed that these new RABI analogues maintain their mechanisms of action by disrupting tubulin polymerization, similar to their parental ABI analogues.
• Synthesis of 2-(3,4,5-trimethoxybenzoyl)-4(5)-phenyl-1H-imidazole
  作者：E. B. Nikolaenkova、I. A. Os’kina、A. Ya. Tikhonov

  DOI：10.1134/s1070428017120193

  日期：2017.12

  The condensation of (2E)-N-hydroxy-2-hydroxyimino-2-phenylethanamine with 3,4,5-trimethoxy-phenylglyoxal afforded (1-hydroxy-5-phenyl-1H-imidazol-2-yl)phenylmethanone which reacted with trimethyl phosphite or chloroacetone to give 2-(3,4,5-trimethoxybenzoyl)-4(5)-phenyl-1H-imidazole.