(E)-1-bromo-4-(thiophen-2-yl)but-3-en-2-one | 923025-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-1-bromo-4-(thiophen-2-yl)but-3-en-2-one
• 英文别名: (E)-1-bromo-4-thiophen-2-ylbut-3-en-2-one
• CAS: 923025-56-3
• 化学式: C₈H₇BrOS
• 分子量: 231.113
• InChiKey: CPZKSDWEONFCLN-ONEGZZNKSA-N

物化性质

• 沸点：
  312.4±27.0 °C(Predicted)
• 密度：
  1.575±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-bromo-4-(thiophen-2-yl)but-3-en-2-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-(thiophen-2-yl)-1-(triphenylphosphoranylidene)-(3E)-buten-2-one
  参考文献：
  名称：

  Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues

  摘要：

  Coruscanone A, a plant-derived cyclopentenedione derivative, showed potent in vitro antifungal activity against Candida albicans and Cryptococcus neoformans comparable to amphotericin B and fluconazole. A series of analogues have been synthesized by modification of the cyclopentenedione ring, the enolic methoxy functionality, and the side chain styryl moiety of this natural product lead. A structurally close 1,4-benzoquinone analogue was also prepared. All the compounds were examined for their in vitro activity against major opportunistic fungal pathogens including C. albicans, C. neoformans, and Aspergillus fumigatus and fluconazole-resistant C. albicans strains, with several analogues demonstrating potent antifungal activity. Structure-activity relationship studies indicate that the 2-methoxymethylenecyclopent-4-ene-1,3-dione structural moiety is the pharmacophore responsible for the antifungal activity of this class of compounds while the side chain styryl-like moiety plays an important complementary role, presumably contributing to target binding.

  DOI：

  10.1021/jm061123i
• 作为产物：
  描述：

  4-(2-噻吩基)丁-3-烯-2-酮 在 pyrrolidone hydrotribromide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以59%的产率得到(E)-1-bromo-4-(thiophen-2-yl)but-3-en-2-one
  参考文献：
  名称：

  Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues

  摘要：

  Coruscanone A, a plant-derived cyclopentenedione derivative, showed potent in vitro antifungal activity against Candida albicans and Cryptococcus neoformans comparable to amphotericin B and fluconazole. A series of analogues have been synthesized by modification of the cyclopentenedione ring, the enolic methoxy functionality, and the side chain styryl moiety of this natural product lead. A structurally close 1,4-benzoquinone analogue was also prepared. All the compounds were examined for their in vitro activity against major opportunistic fungal pathogens including C. albicans, C. neoformans, and Aspergillus fumigatus and fluconazole-resistant C. albicans strains, with several analogues demonstrating potent antifungal activity. Structure-activity relationship studies indicate that the 2-methoxymethylenecyclopent-4-ene-1,3-dione structural moiety is the pharmacophore responsible for the antifungal activity of this class of compounds while the side chain styryl-like moiety plays an important complementary role, presumably contributing to target binding.

  DOI：

  10.1021/jm061123i

文献信息

• Synthesis and cytotoxic/antimicrobial screening of 2-alkenylimidazo[1,2-a]pyrimidines
  作者：Ángel Ramírez-Trinidad、Karol Carrillo-Jaimes、José A. Rivera-Chávez、Eduardo Hernández-Vázquez

  DOI：10.1007/s00044-022-02997-6

  日期：2023.1

  2-a]pyrimidines for exploring their cytotoxic and antimicrobial properties. After performing a preliminary screening, two compounds displayed good cytotoxicity against prostate, breast, and colon cancer types; either bulky or an extra phenyl attached at the styryl moiety seems to be a requirement for good activity. With respect to the antimicrobial effect, some compounds showed considerable inhibition

  多氮杂杂环化合物显示出过多的生物学特性，在临床使用的药物中占很大比例。然而，imizado[1,2- a ]嘧啶环系统在药物应用方面需要更多关注。在此，我们报告了一个涉及醛缩合/溴化/Hantzsch 反应的序列，以构建一系列 2-alkenylimidazo[1,2- a] 用于探索其细胞毒性和抗菌特性的嘧啶。经过初步筛选，两种化合物对前列腺癌、乳腺癌和结肠癌均表现出良好的细胞毒性；在苯乙烯基部分连接的庞大或额外的苯基似乎是良好活性的必要条件。关于抗菌作用，一些化合物对多重耐药性肺炎克雷伯菌表现出相当大的抑制作用，肺炎克雷伯菌是当今最具威胁性的细菌之一。因此，该系列可能成为设计更多活性化合物的基础。 图形概要
• Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues
  作者：K. Suresh Babu、Xing-Cong Li、Melissa R. Jacob、Qifeng Zhang、Shabana I. Khan、Daneel Ferreira、Alice M. Clark

  DOI：10.1021/jm061123i

  日期：2006.12.1

  Coruscanone A, a plant-derived cyclopentenedione derivative, showed potent in vitro antifungal activity against Candida albicans and Cryptococcus neoformans comparable to amphotericin B and fluconazole. A series of analogues have been synthesized by modification of the cyclopentenedione ring, the enolic methoxy functionality, and the side chain styryl moiety of this natural product lead. A structurally close 1,4-benzoquinone analogue was also prepared. All the compounds were examined for their in vitro activity against major opportunistic fungal pathogens including C. albicans, C. neoformans, and Aspergillus fumigatus and fluconazole-resistant C. albicans strains, with several analogues demonstrating potent antifungal activity. Structure-activity relationship studies indicate that the 2-methoxymethylenecyclopent-4-ene-1,3-dione structural moiety is the pharmacophore responsible for the antifungal activity of this class of compounds while the side chain styryl-like moiety plays an important complementary role, presumably contributing to target binding.