amantamide

• 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: amantamide
• 英文别名: amantamide A；Amantamide；methyl (2S)-1-[(2R)-2-[[2-[[(2S,3S)-2-[[(2R)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-(butanoylamino)-3-methylbutanoyl]-methylamino]-4-methylpentanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]-methylamino]-3-methylbutanoyl]amino]-3-methylpentanoyl]amino]acetyl]-methylamino]-3-phenylpropanoyl]pyrrolidine-2-carboxylate
• 化学式: C₅₇H₉₃N₉O₁₁
• 分子量: 1080.42
• InChiKey: ZPZNPEATKLIUKY-SFHKMCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  77
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  244
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  amantamide 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.25h， 生成
  参考文献：
  名称：

  Discovery of Amantamide, a Selective CXCR7 Agonist from Marine Cyanobacteria

  摘要：

  CXCR7 plays an emerging role in several physiological processes. A linear peptide, amantamide (1), was isolated from marine cyanobacteria, and the structure was determined by NMR and mass spectrometry. The total synthesis was achieved by solid-phase method. After screening two biological target libraries, 1 was identified as a selective CXCR7 agonist. The selective activation of CXCR7 by 1 could provide the basis for developing CXCR7-targeted therapeutics and deciphering the role of CXCR7 in different diseases.

  DOI：

  10.1021/acs.orglett.9b00163
• 作为产物：
  描述：

  、 碘甲烷 在 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以4 mg的产率得到amantamide
  参考文献：
  名称：

  Discovery of Amantamide, a Selective CXCR7 Agonist from Marine Cyanobacteria

  摘要：

  CXCR7 plays an emerging role in several physiological processes. A linear peptide, amantamide (1), was isolated from marine cyanobacteria, and the structure was determined by NMR and mass spectrometry. The total synthesis was achieved by solid-phase method. After screening two biological target libraries, 1 was identified as a selective CXCR7 agonist. The selective activation of CXCR7 by 1 could provide the basis for developing CXCR7-targeted therapeutics and deciphering the role of CXCR7 in different diseases.

  DOI：

  10.1021/acs.orglett.9b00163

文献信息

• Discovery of Amantamide, a Selective CXCR7 Agonist from Marine Cyanobacteria
  作者：Xiao Liang、Danmeng Luo、Jia-Lei Yan、Mohammad A. Rezaei、Lilibeth A. Salvador-Reyes、Sarath P. Gunasekera、Chenglong Li、Tao Ye、Valerie J. Paul、Hendrik Luesch

  DOI：10.1021/acs.orglett.9b00163

  日期：2019.3.15

  CXCR7 plays an emerging role in several physiological processes. A linear peptide, amantamide (1), was isolated from marine cyanobacteria, and the structure was determined by NMR and mass spectrometry. The total synthesis was achieved by solid-phase method. After screening two biological target libraries, 1 was identified as a selective CXCR7 agonist. The selective activation of CXCR7 by 1 could provide the basis for developing CXCR7-targeted therapeutics and deciphering the role of CXCR7 in different diseases.