phomamide | 74347-50-5

• 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: phomamide
• 英文别名: c[Tyr(O-Dal)-Ser]；2,5-Piperazinedione, 3-(hydroxymethyl)-6-((4-((3-methyl-2-butenyl)oxy)phenyl)methyl)-, (3S,6S)-；(3S,6S)-3-(hydroxymethyl)-6-[[4-(3-methylbut-2-enoxy)phenyl]methyl]piperazine-2,5-dione
• CAS: 74347-50-5
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: KRLKPTMEUFJHKD-GJZGRUSLSA-N

物化性质

• 沸点：
  634.9±50.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Boc-Tyr-Ser-OMe 在 N-甲基吗啉 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 仲丁醇 为溶剂， 反应 4.0h， 生成 phomamide
  参考文献：
  名称：

  Synthesis and anti-cancer activity of naturally occurring 2,5-diketopiperazines

  摘要：

  Three naturally occurring oxyprenylated diketopiperazines were synthesized and preliminarily tested as growth inhibitory agents in vitro against various cancer cell lines. The compounds were tested on six human cancer cell lines with different sensitivity to proapoptotic stimuli using the MTT colorimetric assay. The data revealed that of the chemicals under study only deoxymicelianamide (11) displayed the highest activity, recording mean IC50 growth inhibitory values ranging from 2 to 23 mu M. A comparative study with the non-geranylated saturated derivative of (11) revealed the importance of the presence of the geranyloxy side chain and the exocyclic 2,5-DPK double bond moiety for the observed activity. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2014.07.010

文献信息

• Concise Synthesis of 2,5-Diketopiperazines via Catalytic Hydroxy-Directed Peptide Bond Formations
  作者：Masayoshi Koshizuka、Kaito Shinoda、Kazuishi Makino、Naoyuki Shimada

  DOI：10.1021/acs.joc.3c00195

  日期：2023.6.2

  concise synthesis of this type of DKPs through diboronic acid anhydride-catalyzed hydroxy-directed peptide bond formations. The sequential reactions in this report, which consist of three steps, an intermolecular catalytic condensation reaction in which water is the only byproduct, a simple deprotection of the nitrogen-protecting group, and an intramolecular cyclization, enabled the synthesis of functionalized

  具有羟甲基官能团的 2,5-二酮哌嗪 (DKP) 是许多生物活性分子和功能材料中的必需结构。我们已经建立了一个简单的协议，用于通过二硼酸酐催化的羟基定向肽键形成简明合成此类 DKP。本报告中的连续反应由三个步骤组成，其中水是唯一的副产物的分子间催化缩合反应、氮保护基团的简单脱保护和分子内环化，使功能化 DKPs 的合成成为可能。无需任何中间纯化即可获得优异的产量。该协议的效用已通过合成天然产物、phomamide 和 Cyclo(Deala- l -Leu) 得到证明。
• Ferezou, Jean-Pierre; Quesneau-Thierry, Annik; Barbier, Michel, Journal of the Chemical Society. Perkin transactions I, 1980, p. 113 - 115
  作者：Ferezou, Jean-Pierre、Quesneau-Thierry, Annik、Barbier, Michel、Kollmann, Albert、Bousquet, Jean-Francois

  DOI：——

  日期：——
• Synthesis and anti-cancer activity of naturally occurring 2,5-diketopiperazines
  作者：Adriano Mollica、Roberto Costante、Serena Fiorito、Salvatore Genovese、Azzurra Stefanucci、Veronique Mathieu、Robert Kiss、Francesco Epifano

  DOI：10.1016/j.fitote.2014.07.010

  日期：2014.10

  Three naturally occurring oxyprenylated diketopiperazines were synthesized and preliminarily tested as growth inhibitory agents in vitro against various cancer cell lines. The compounds were tested on six human cancer cell lines with different sensitivity to proapoptotic stimuli using the MTT colorimetric assay. The data revealed that of the chemicals under study only deoxymicelianamide (11) displayed the highest activity, recording mean IC50 growth inhibitory values ranging from 2 to 23 mu M. A comparative study with the non-geranylated saturated derivative of (11) revealed the importance of the presence of the geranyloxy side chain and the exocyclic 2,5-DPK double bond moiety for the observed activity. (C) 2014 Elsevier B.V. All rights reserved.