2,2,2-trichloro-1-(4,5-diiodo-1-methyl-1H-pyrrol-2-yl)ethanone | 57975-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-trichloro-1-(4,5-diiodo-1-methyl-1H-pyrrol-2-yl)ethanone
• 英文别名: 4,5-Diiod-1-methylpyrrol-2-yl-trichlormethylketon；4,5-diiodo-1-methylpyrrol-2-yl trichloromethyl ketone；2,2,2-Trichloro-1-(4,5-diiodo-1-methylpyrrol-2-yl)ethanone
• CAS: 57975-83-4
• 化学式: C₇H₄Cl₃I₂NO
• 分子量: 478.283
• InChiKey: BYEOGXPGGYNVIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(2,5-dioxoimidazolidin-4-ylidene)propylcarbamate 、 2,2,2-trichloro-1-(4,5-diiodo-1-methyl-1H-pyrrol-2-yl)ethanone 在 三氟乙酸 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以81.818%的产率得到
  参考文献：
  名称：

  Investigation Into Novel Mukanadin B, Mukanadin D and Mukanadin F Derivatives as Antagonists of 5‐HT1A Signalling

  摘要：

  Marine bromopyrrole alkaloids are a diverse family of natural products with a large array of biological applications. The mukanadin family is a group of molecules consisting of seven members (mukanadin A ‐ G) that possess a range of biological activities. Inhibition of serotonergic signaling has been demonstrated by mukanadin B derivatives, presenting this chemical scaffold as a candidate for further SAR exploration. A library of thirteen novel mukanadin B and D derivatives with structural variation targeted at the pyrrole ring, central linker and hydantoin ring, were synthesized. These analogues were subsequently assessed for serotonergic antagonism, in addition to natural products, mukanadin B, D, F and 9‐hydroxy mukanadin B. A collection of compounds exhibited significant 5‐HT1A signaling, including five of the novel derivatives and two of the naturally occurring bromopyrroles, mukanadin B and F. Particular SAR information could be determined from these results, such as modification of the pyrrole ring being a well‐tolerated strategy for improving serotonergic inhibition. Other changes to the pharmacophore led to significant reduction in activity such as saturation of the linker region, or no conclusive improvement in inhibitory activity such as a 9‐OH group or replacement of the hydantoin ring with a triazole moiety.

  DOI：

  10.1002/cmdc.202400102
• 作为产物：
  描述：

  2,2,2-三氯-1-(1-甲基-1H-吡咯-2-基)-乙酮 在 碘 、 silver trifluoroacetate 作用下， 以 二氯甲烷 为溶剂， 以78 %的产率得到2,2,2-trichloro-1-(4,5-diiodo-1-methyl-1H-pyrrol-2-yl)ethanone
  参考文献：
  名称：

  Investigation Into Novel Mukanadin B, Mukanadin D and Mukanadin F Derivatives as Antagonists of 5‐HT1A Signalling

  摘要：

  Marine bromopyrrole alkaloids are a diverse family of natural products with a large array of biological applications. The mukanadin family is a group of molecules consisting of seven members (mukanadin A ‐ G) that possess a range of biological activities. Inhibition of serotonergic signaling has been demonstrated by mukanadin B derivatives, presenting this chemical scaffold as a candidate for further SAR exploration. A library of thirteen novel mukanadin B and D derivatives with structural variation targeted at the pyrrole ring, central linker and hydantoin ring, were synthesized. These analogues were subsequently assessed for serotonergic antagonism, in addition to natural products, mukanadin B, D, F and 9‐hydroxy mukanadin B. A collection of compounds exhibited significant 5‐HT1A signaling, including five of the novel derivatives and two of the naturally occurring bromopyrroles, mukanadin B and F. Particular SAR information could be determined from these results, such as modification of the pyrrole ring being a well‐tolerated strategy for improving serotonergic inhibition. Other changes to the pharmacophore led to significant reduction in activity such as saturation of the linker region, or no conclusive improvement in inhibitory activity such as a 9‐OH group or replacement of the hydantoin ring with a triazole moiety.

  DOI：

  10.1002/cmdc.202400102

文献信息

• 4,5 Dihalopyrrol 2-yl di and tri halomethyl ketones
  申请人：Sterling Drug Inc.

  公开号：US03963746A1

  公开（公告）日：1976-06-15

  4,5-Dihalopyrrol-2-yl di- and trihalomethyl ketones, prepared by reaction of pyrrole with a di- or trihaloacetyl halide or with a di- or trihaloacetic anhydride and halogenation of the resulting pyrrol-2-yl di- or trihalomethyl ketone, useful as antibacterial, herbicidal and insecticidal agents.

  通过将吡咯与二卤代乙酰卤或三卤代乙酰卤反应，或与二卤代乙酸酐反应并卤代生成的吡咯-2-基二或三卤代甲基酮进行卤代反应制备的4,5-二卤代吡咯-2-基二或三卤代甲基酮，可用作抗菌、除草和杀虫剂。
• US3963746A
  申请人：——

  公开号：US3963746A

  公开（公告）日：1976-06-15