(Z)-N-(3-(2,5-dioxoimidazolidin-4-ylidene)propyl)-1H-pyrrole-2-carboxamide | 1548272-72-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-N-(3-(2,5-dioxoimidazolidin-4-ylidene)propyl)-1H-pyrrole-2-carboxamide
• 英文别名: N-[(3Z)-3-(2,5-dioxoimidazolidin-4-ylidene)propyl]-1H-pyrrole-2-carboxamide
• CAS: 1548272-72-5
• 化学式: C₁₁H₁₂N₄O₃
• 分子量: 248.241
• InChiKey: AAMTVHUXELSOLY-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-debromo-dehydroxymukanadin F 以 氘代甲醇 为溶剂， 生成 (Z)-N-(3-(2,5-dioxoimidazolidin-4-ylidene)propyl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Mukanadin F的合成和绝对立体化学重排：溴吡咯生物碱的异构化研究对海洋天然产物的分离

  摘要：

  合成的，对映体纯的，溴吡咯烷生物碱mukanadin F的光谱分析确定，所报道的天然产物的绝对立体化学是错误分配的。此外，穆卡纳丁F和类似化合物在诸如阳光和溶剂的良性条件下进行消旋和链烯异构化。

  DOI：

  10.1002/ejoc.201800422

文献信息

• Concise synthesis of Didebromohamacanthin A and Demethylaplysinopsine: Addition of Ethylenediamine and Guanidine Derivatives to the Pyrrole-Amino Acid Diketopiperazines in Oxidative Conditions
  作者：Ludmila Ermolenko、Hu Zhaoyu、Clarisse Lejeune、Carine Vergne、Céline Ratinaud、Thanh Binh Nguyen、Ali Al-Mourabit

  DOI：10.1021/ol4036177

  日期：2014.2.7

  Oxidative nucleophilic addition of ethylenediamine and guanidine derivatives to pyrrole-amino acid diketopiperazines was shown to provide substituted 5,6-dihydro-2(1H)-piperazinones, quinoxalinones, and 2-aminoimidazolones. On the basis of this methodology, a concise approach to natural products didebromohamacanthin A and demethylaplysinopsine has been demonstrated.

  乙二胺和胍衍生物的氧化亲核加成到吡咯-氨基酸二酮哌嗪中，显示提供取代的5，6-二氢-2（1 H）-哌嗪酮，喹喔啉酮和2-氨基咪唑啉酮。在这种方法的基础上，已经证明了对天然产物双溴金刚烷菌素A和去甲基aplysinopsine的一种简明方法。
• Investigation Into Novel Mukanadin B, Mukanadin D and Mukanadin F Derivatives as Antagonists of 5‐HT1A Signalling
  作者：Shaun W. P. Rees、Tayla A. Rees、Michelle van Rensburg、Christopher S. Walker、Lisa I. Pilkington、David Barker

  DOI：10.1002/cmdc.202400102

  日期：2024.8

  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.