(2-phenyl-1H-imidazol-4-yl)(m-tolyl)methanone | 1253697-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-phenyl-1H-imidazol-4-yl)(m-tolyl)methanone
• 英文别名: (3-Methylphenyl)(2-phenyl-1H-imidazol-5-yl)methanone；(3-methylphenyl)-(2-phenyl-1H-imidazol-5-yl)methanone
• CAS: 1253697-92-5
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: QNODZJMZDKBXNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3-Methylphenyl)[2-phenyl-1-(phenylsulfonyl)-1H-imidazol-4-yl]methanone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以20.5%的产率得到(2-phenyl-1H-imidazol-4-yl)(m-tolyl)methanone
  参考文献：
  名称：

  Discovery of Novel 2-Aryl-4-benzoyl-imidazoles Targeting the Colchicines Binding Site in Tubulin As Potential Anticancer Agents

  摘要：

  A series of 2-aryl-4-benzoyl-imidazoles (ABI) was synthesized as a result of structural modifications based on the previous set of 2-aryl-imidazole-4-carboxylic amide (AICA) derivatives and 4-substituted methoxylbenzoyl-aryl-thiazoles (SMART). The average IC50 of the most active compound (5da) was 15.7 nM. ABI analogues have substantially improved aqueous solubility (48.9 mu g/mL for 5ga vs 0.909 mu g/mL for SMART-I, 0.137 mu g/mL for paclitaxel, and 1.04 mu g/mL for combretastatin A4). Mechanism of action studies indicate that the anticancer activity of ABI analogues is through inhibition of tubulin polymerization by interacting with the colchicine binding site. Unlike paclitaxel and colchicine, the ABI compounds were equally potent against multidrug resistant cancer cells and the sensitive parental melanoma cancer cells. In vivo results indicated that 5cb was more effective than DTIC in inhibiting melanoma xenograph tumor growth. Our results suggest that the novel ABI compounds may be developed to effectively treat drug-resistant tumors.

  DOI：

  10.1021/jm100884b

文献信息

• [EN] COMPOUNDS FOR TREATMENT OF CANCER<br/>[FR] COMPOSÉS DESTINÉS AU TRAITEMENT DU CANCER
  申请人：GTX INC

  公开号：WO2011109059A1

  公开（公告）日：2011-09-09

  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、耐药黑色素瘤、前列腺癌和耐药前列腺癌。
• COMPOUNDS FOR TREATMENT OF CANCER
  申请人：Lu Yan

  公开号：US20120071524A1

  公开（公告）日：2012-03-22

  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应用，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。
• COMPOUNDS FOR TREATMENT OF PANCREATIC CANCER
  申请人：University of Tennessee Research Foundation

  公开号：EP3793548A1

  公开（公告）日：2021-03-24
• METHODS OF TREATING CORONAVIRUS
  申请人：VERU INC.

  公开号：US20210308105A1

  公开（公告）日：2021-10-07

  The present invention relates to methods of treating coronavirus infections using compounds having anti-tubulin or tubulin disruption activity.