N-[(2R)-1-[[(2S)-6-amino-1-oxo-1-(4-pyridin-4-ylpiperazin-1-yl)hexan-2-yl]amino]-3-(1-benzothiophen-2-yl)-1-oxopropan-2-yl]-4-(2-oxo-1,4-dihydroquinazolin-3-yl)piperidine-1-carboxamide | 1610413-84-7

• 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: N-[(2R)-1-[[(2S)-6-amino-1-oxo-1-(4-pyridin-4-ylpiperazin-1-yl)hexan-2-yl]amino]-3-(1-benzothiophen-2-yl)-1-oxopropan-2-yl]-4-(2-oxo-1,4-dihydroquinazolin-3-yl)piperidine-1-carboxamide
• CAS: 1610413-84-7
• 化学式: C₄₀H₄₉N₉O₄S
• 分子量: 751.953
• InChiKey: ABEOUDUTXXUZON-OIDHKYIRSA-N

物化性质

• 沸点：
  1094.714±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.311±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  185
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-(哌啶-4-基)-3,4-二氢喹唑啉-2(1H)-酮 在 1H-1,2,4-三唑 、 盐酸 、 lithium hydroxide monohydrate 、 水 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(2R)-1-[[(2S)-6-amino-1-oxo-1-(4-pyridin-4-ylpiperazin-1-yl)hexan-2-yl]amino]-3-(1-benzothiophen-2-yl)-1-oxopropan-2-yl]-4-(2-oxo-1,4-dihydroquinazolin-3-yl)piperidine-1-carboxamide 、 N-[(2R)-1-[[(2S)-6-amino-1-oxo-1-(4-pyridin-4-ylpiperazin-1-yl)hexan-2-yl]amino]-3-(1-benzothiophen-2-yl)-1-oxopropan-2-yl]-4-(2,4-dioxo-1H-quinazolin-3-yl)piperidine-1-carboxamide
  参考文献：
  名称：

  Serendipitous oxidation product of BIBN4096BS: A potent CGRP receptor antagonist

  摘要：

  An oxidation product (5) formed during the synthesis of BIBN-4096BS (1) was found to be a potent CGRP antagonist (IC50 = 0.11 nM). While 5 was found to be ten-fold less potent than 1, another analog 8 with lower molecular weight containing the oxidized fragment demonstrated twenty-fold higher activity than its parent 7. Alternative conditions which preclude the formation of the oxidation product are described. The activities of 1, 5, 7 and 8 in functional cAMP assay are also discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.033

文献信息

• Serendipitous oxidation product of BIBN4096BS: A potent CGRP receptor antagonist
  作者：Bireshwar Dasgupta、Edward Kozlowski、Daniel R. Schroeder、John R. Torrente、Cen Xu、Sokhom Pin、Charlie M. Conway、Gene M. Dubowchik、John E. Macor、Vivekananda M. Vrudhula

  DOI：10.1016/j.bmcl.2014.04.033

  日期：2014.6

  An oxidation product (5) formed during the synthesis of BIBN-4096BS (1) was found to be a potent CGRP antagonist (IC50 = 0.11 nM). While 5 was found to be ten-fold less potent than 1, another analog 8 with lower molecular weight containing the oxidized fragment demonstrated twenty-fold higher activity than its parent 7. Alternative conditions which preclude the formation of the oxidation product are described. The activities of 1, 5, 7 and 8 in functional cAMP assay are also discussed. (C) 2014 Elsevier Ltd. All rights reserved.