(2'R,5R)-2',5-dibenzyl-4-hydroxy-1H,1'H-[3,3'-bipyrrole]-2,5'(2'H,5H)-dione | 1282523-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (2'R,5R)-2',5-dibenzyl-4-hydroxy-1H,1'H-[3,3'-bipyrrole]-2,5'(2'H,5H)-dione
• 英文别名: (2R)-2-benzyl-4-[(2R)-2-benzyl-5-oxo-1,2-dihydropyrrol-3-yl]-3-hydroxy-1,2-dihydropyrrol-5-one
• CAS: 1282523-18-5
• 化学式: C₂₂H₂₀N₂O₃
• 分子量: 360.412
• InChiKey: XUGKANINACIVSS-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5R)-5-Benzyl-1-tert-butyloxycarbonyl-4-hydroxy-1,5-dihydropyrrol-2-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以12%的产率得到(2'R,5R)-2',5-dibenzyl-4-hydroxy-1H,1'H-[3,3'-bipyrrole]-2,5'(2'H,5H)-dione
  参考文献：
  名称：

  Cytotoxic Tetramic Acid Derivative Produced by a Plant Type-III Polyketide Synthase

  摘要：

  The tetramic acid (2,4-pyrrolidinedione) scaffold has been recognized as an important structural feature because of its mycotoxic, antibacterial, antiviral, and antioxidant activities. This important class of natural products is reportedly produced by the type-I polyketide synthase/nonribosomal peptide synthetase (PKS/NRPS) hybrid megaenzyme systems. In contrast, the benzalacetone synthase (BAS) from Rheum palmatum is a structurally simple, plant-specific type-III PKS that catalyzes the one-step decarboxylative condensation of malonyl-CoA with 4-coumaroyl-CoA. The type-III PKS exhibits unusually broad substrate specificity and notable catalytic versatility. Here we report that R. palmatum BAS efficiently produces a series of unnatural, novel tetramic acid derivatives by the condensation of malonyl-CoA with aminoacyl-CoA thioesters chemically synthesized from L- and D-amino acids. Remarkably, the novel tetramic acid dimer ID-S formed from D-phenylalanoyl-CoA showed moderate antiproliferative activity against murine leukemia P388 cells.

  DOI：

  10.1021/ja2006737