α,β-bibromo-chalcone | 7020-20-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: α,β-bibromo-chalcone
• 英文别名: α,β-Bibrom-chalkon；α,β-Dibrom-chalkon；ω-Brom-ω-(α-brom-benzyliden)-acetophenon；Phenylbenzoylacetylen-dibromid；α.β-Dibrom-α-phenyl-β-benzoyl-aethylen；ω-Brom-ω-(α-brom-benzal)-acetophenon；Dibromochalcone；2,3-dibromo-1,3-diphenylprop-2-en-1-one
• CAS: 7020-20-4
• 化学式: C₁₅H₁₀Br₂O
• 分子量: 366.052
• InChiKey: MAOFQPQVGCBJTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α,β-bibromo-chalcone 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-azido-1,3-diphenylprop-2-en-1-one
  参考文献：
  名称：

  Rational Design and Synthesis of Isatin‐Chalcone Hybrids Integrated with 1H‐1,2,3‐Triazole: Anti‐Proliferative Profiling and Molecular Docking Insights

  摘要：

  In this study, a series of isatin‐chalcone linked triazoles were synthesized using Cu‐promoted Azide‐Alkyne Cycloaddition (CuAAC) reaction and evaluated for their cytotoxicity against various cancer cell lines. The most potent compound displayed approximately 2.5 times greater activity compared to both reference compounds against ovarian cancer cell lines. These findings were supported by caspase‐mediated apoptosis and molecular docking analyses. Docking revealed comparable VEGFR‐2 affinities for 5b and 5‐FU but highlighted stronger interaction of 5b with EGFR, evident from its lower docking score. Overall, these results signify the notable anti‐proliferative potential of most synthesized hybrids, notably emphasizing the efficacy of compound 5b in suppressing cancer cell growth.

  DOI：

  10.1002/cmdc.202400015
• 作为产物：
  描述：

  苯亚甲基苯乙酮 在 溴 作用下， 以 四氯化碳 为溶剂， 生成 α,β-bibromo-chalcone
  参考文献：
  名称：

  Rational Design and Synthesis of Isatin‐Chalcone Hybrids Integrated with 1H‐1,2,3‐Triazole: Anti‐Proliferative Profiling and Molecular Docking Insights

  摘要：

  In this study, a series of isatin‐chalcone linked triazoles were synthesized using Cu‐promoted Azide‐Alkyne Cycloaddition (CuAAC) reaction and evaluated for their cytotoxicity against various cancer cell lines. The most potent compound displayed approximately 2.5 times greater activity compared to both reference compounds against ovarian cancer cell lines. These findings were supported by caspase‐mediated apoptosis and molecular docking analyses. Docking revealed comparable VEGFR‐2 affinities for 5b and 5‐FU but highlighted stronger interaction of 5b with EGFR, evident from its lower docking score. Overall, these results signify the notable anti‐proliferative potential of most synthesized hybrids, notably emphasizing the efficacy of compound 5b in suppressing cancer cell growth.

  DOI：

  10.1002/cmdc.202400015

文献信息

• Chalcone and its analogs as agents for the inhibition of angiogenesis and related disease states
  申请人：——

  公开号：US20020040029A1

  公开（公告）日：2002-04-04

  The present invention relates to chalcone and chalcone derivatives and analogs which are useful as angiogenesis inhibitors. The present compounds, which are inexpensive to synthesize, exhibit unexpectedly good activity as angiogenesis inhibitors. The present invention also relates to the use of chalcone and its analogs as antitumor/anticancer agents and to treat a number of conditions or disease states in which angiogenesis is a factor, including angiongenic skin diseases such as psoriasis, acne, rosacea, warts, eczema, hemangiomas, lymphangiogenesis, among numerous others, as well as chronic inflammatory disease such as arthritis.

  本发明涉及香豆素和香豆素衍生物以及类似物，这些化合物可用作抗血管生成抑制剂。这些化合物的合成成本低廉，并表现出出乎意料的良好的抗血管生成活性。本发明还涉及使用香豆素及其类似物作为抗肿瘤/抗癌剂，以及治疗一些与血管生成有关的疾病或病态，包括血管生成性皮肤病如牛皮癣、痤疮、酒渣鼻、疣、湿疹、血管瘤、淋巴管生成等等，以及慢性炎症性疾病如关节炎。
• Thiabenzenes. III. Synthesis and properties of thiabenzene 1-oxides
  作者：Alfred G. Hortmann、Ronald L. Harris

  DOI：10.1021/ja00739a019

  日期：1971.5
• Dufraisse, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1914, vol. 158, p. 1692
  作者：Dufraisse

  DOI：——

  日期：——
• US6462075B1
  申请人：——

  公开号：US6462075B1

  公开（公告）日：2002-10-08
• US6906105B2
  申请人：——

  公开号：US6906105B2

  公开（公告）日：2005-06-14