nobilamide F | 1310050-79-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: nobilamide F
• 英文别名: H-Phe-D-aThr(1)-Val-Ala-Abu(2,3-dehydro)-(1)；(2S)-2-amino-N-[(3Z,6S,9S,12R,13R)-3-ethylidene-6,13-dimethyl-2,5,8,11-tetraoxo-9-propan-2-yl-1-oxa-4,7,10-triazacyclotridec-12-yl]-3-phenylpropanamide
• CAS: 1310050-79-3
• 化学式: C₂₅H₃₅N₅O₆
• 分子量: 501.583
• InChiKey: SJSVZSPSNORISU-QUXXMPFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  169
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  nobilamide F 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 盐酸 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 (S)-2-(5-((S)-1-amino-1-oxopropan-2-ylamino)-2,4-dinitrophenylamino)propanoic acid 、 DAA-allo-Thr 、 L-Phe-L-FDAA 、 (S)-2-(5-((S)-1-amino-1-oxopropan-2-ylamino)-2,4-dinitrophenylamino)-3-methylbutanoic acid
  参考文献：
  名称：

  Nobilamides A–H, Long-Acting Transient Receptor Potential Vanilloid-1 (TRPV1) Antagonists from Mollusk-Associated Bacteria

  摘要：

  New compounds nobilamides A-H and related known compounds A-3302-A and A-3302-B were isolated based upon their suppression of capsaicin-induced calcium uptake in a mouse dorsal root ganglion primary cell culture assay. Two of these compounds, nobilamide B and A-3302-A, were shown to be long-acting antagonists of mouse and human TRPV1 channels, abolishing activity for >1 h after removal of drug presumably via a covalent attachment. Other derivatives also inhibited the TRPV1 channel, albeit with low potency, affording a structure-activity profile to support the proposed mechanism of action. While the activities were modest, we propose a new mechanism of action and a new site of binding for these inhibitors that may spur development of related analogues for treatment of pain.

  DOI：

  10.1021/jm101621u

文献信息

• Nobilamides A–H, Long-Acting Transient Receptor Potential Vanilloid-1 (TRPV1) Antagonists from Mollusk-Associated Bacteria
  作者：Zhenjian Lin、Christopher A. Reilly、Rowena Antemano、Ronald W. Hughen、Lenny Marett、Gisela P. Concepcion、Margo G. Haygood、Baldomero M. Olivera、Alan Light、Eric W. Schmidt

  DOI：10.1021/jm101621u

  日期：2011.6.9

  New compounds nobilamides A-H and related known compounds A-3302-A and A-3302-B were isolated based upon their suppression of capsaicin-induced calcium uptake in a mouse dorsal root ganglion primary cell culture assay. Two of these compounds, nobilamide B and A-3302-A, were shown to be long-acting antagonists of mouse and human TRPV1 channels, abolishing activity for >1 h after removal of drug presumably via a covalent attachment. Other derivatives also inhibited the TRPV1 channel, albeit with low potency, affording a structure-activity profile to support the proposed mechanism of action. While the activities were modest, we propose a new mechanism of action and a new site of binding for these inhibitors that may spur development of related analogues for treatment of pain.