benzyl 4-<(ethoxycarbonyl)methyl>-3-<2-(methoxycarbonyl)ethyl>-5-methylpyrrole-2-carboxylate | 220720-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 4-<(ethoxycarbonyl)methyl>-3-<2-(methoxycarbonyl)ethyl>-5-methylpyrrole-2-carboxylate
• 英文别名: benzyl 4-(2-ethoxy-2-oxoethyl)-3-(3-methoxy-3-oxopropyl)-5-methyl-1H-pyrrole-2-carboxylate
• CAS: 220720-48-9
• 化学式: C₂₁H₂₅NO₆
• 分子量: 387.433
• InChiKey: WJGFCGNXKFJMGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 4-<(ethoxycarbonyl)methyl>-3-<2-(methoxycarbonyl)ethyl>-5-methylpyrrole-2-carboxylate 在 palladium on activated charcoal lead(IV) acetate 、 Montmorillonite clay K₁₀ 、 硫酸 、 氢溴酸 、 氢气 、 溶剂黄146 、 三乙胺 、 三氟乙酸 、 copper dichloride 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 21.25h， 生成 3,8,13,17-tetrakis<2-(methoxycarbonyl)ethyl>-7-<(methoxycarbonyl)methyl>-2,12,18-trimethylporphyrin
  参考文献：
  名称：

  Normal and Abnormal Heme Biosynthesis. 2.¹ Synthesis and Metabolism of Type-III Pentacarboxylic Porphyrinogens:  Further Experimental Evidence for the Enzymic Clockwise Decarboxylation of Uroporphyrinogen-III

  摘要：

  Uroporphyrinogen decarboxylase catalyses the sequential decarboxylation of uroporphyrinogen-III (1) to-give coproporphyrinogen-III (2), a precursor to the hemes and chlorophylls. This involves the decarboxylation of four nonequivalent acetate side chains to produce methyl units and in principle could take place by 24 different pathways involving up to 14 intermediary porphyrinogens. In the past, seemingly contradictory data have been presented that either support an ordered "clockwise" decarboxylation pathway or a random decarboxylation process. Four pentacarboxylate porphyrinogens might be involved immediately before the formation of 2, and these compounds have been synthesized as the corresponding porphyrin pentamethyl esters via tripyrrene and a,c-biladiene intermediates. Hydrolysis of the methyl esters and reduction with 3% sodium amalgam gave the required porphyrinogens, and these were incubated with crude enzyme preparations derived from chicken red cell hemolysates. One of these pentacarboxylate porphyrinogens (5dab) consistently proved to be a much better substrate than the other three, providing new support for the "clockwise" pathway for coproporphyrinogen-III formation.

  DOI：

  10.1021/jo9814748
• 作为产物：
  描述：

  methyl 4,6-dioxoheptanoate, keto-tautomer 在 sodium acetate 、 potassium carbonate 、 锌 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 反应 6.0h， 生成 benzyl 4-<(ethoxycarbonyl)methyl>-3-<2-(methoxycarbonyl)ethyl>-5-methylpyrrole-2-carboxylate
  参考文献：
  名称：

  Investigations regarding the utility of prodigiosenes to treat leukemia

  摘要：

  灵菌烯具有 4-甲氧基吡咯基二吡林骨架，以其抗癌活性而闻名。 C 环的结构修饰产生了一系列灵菌烯，在针对 NCI 60 癌细胞系组的体外分析中，这些灵菌烯显示出针对白血病细胞系的有希望的活性。使用斑马鱼模型对这些化合物进行的进一步体内研究表明，在人类 K562 慢性粒细胞白血病细胞中具有持久的抗白血病特性。

  DOI：

  10.1039/c2ob26535d

文献信息

• Normal and Abnormal Heme Biosynthesis. 2.¹ Synthesis and Metabolism of Type-III Pentacarboxylic Porphyrinogens:  Further Experimental Evidence for the Enzymic Clockwise Decarboxylation of Uroporphyrinogen-III
  作者：Timothy D. Lash、Ukti N. Mani、Elizabeth A. Lyons、Pornlert Thientanavanich、Marjorie A. Jones

  DOI：10.1021/jo9814748

  日期：1999.1.1

  Uroporphyrinogen decarboxylase catalyses the sequential decarboxylation of uroporphyrinogen-III (1) to-give coproporphyrinogen-III (2), a precursor to the hemes and chlorophylls. This involves the decarboxylation of four nonequivalent acetate side chains to produce methyl units and in principle could take place by 24 different pathways involving up to 14 intermediary porphyrinogens. In the past, seemingly contradictory data have been presented that either support an ordered "clockwise" decarboxylation pathway or a random decarboxylation process. Four pentacarboxylate porphyrinogens might be involved immediately before the formation of 2, and these compounds have been synthesized as the corresponding porphyrin pentamethyl esters via tripyrrene and a,c-biladiene intermediates. Hydrolysis of the methyl esters and reduction with 3% sodium amalgam gave the required porphyrinogens, and these were incubated with crude enzyme preparations derived from chicken red cell hemolysates. One of these pentacarboxylate porphyrinogens (5dab) consistently proved to be a much better substrate than the other three, providing new support for the "clockwise" pathway for coproporphyrinogen-III formation.
• Investigations regarding the utility of prodigiosenes to treat leukemia
  作者：Deborah A. Smithen、A. Michael Forrester、Dale P. Corkery、Graham Dellaire、Julie Colpitts、Sherri A. McFarland、Jason N. Berman、Alison Thompson

  DOI：10.1039/c2ob26535d

  日期：——

  Prodigiosenes, possessing a 4-methoxypyrrolyldipyrrin skeleton, are known for their anti-cancer activity. Structural modification of the C-ring resulted in a series of prodigiosenes that displayed promising activity against leukemia cell lines during in vitro analysis against the NCI 60 cancer cell line panel. Further in vivo studies of these compounds using the zebrafish model showed persistence of anti-leukemia properties in human K562 chronic myelogenous leukemia cells.

  灵菌烯具有 4-甲氧基吡咯基二吡林骨架，以其抗癌活性而闻名。 C 环的结构修饰产生了一系列灵菌烯，在针对 NCI 60 癌细胞系组的体外分析中，这些灵菌烯显示出针对白血病细胞系的有希望的活性。使用斑马鱼模型对这些化合物进行的进一步体内研究表明，在人类 K562 慢性粒细胞白血病细胞中具有持久的抗白血病特性。