tert-butyl N-[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-fluorosulfonyl-4-methylpentan-2-yl]amino]-1-oxo-3-phenylmethoxybutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamate | 1415548-63-8

• 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: tert-butyl N-[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-fluorosulfonyl-4-methylpentan-2-yl]amino]-1-oxo-3-phenylmethoxybutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamate
• CAS: 1415548-63-8
• 化学式: C₂₈H₄₆FN₃O₇S
• 分子量: 587.754
• InChiKey: BAVGWCCDFLWGNO-IOXZRWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-fluorosulfonyl-4-methylpentan-2-yl]amino]-1-oxo-3-phenylmethoxybutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 AJ32
  参考文献：
  名称：

  Peptido Sulfonyl Fluorides as New Powerful Proteasome Inhibitors

  摘要：

  A new class of potent proteasome inhibitors is described, of which the members contain an amino acid inspired sulfonyl fluoride as the electrophilic trap. In total, 24 peptido sulfonyl fluoride inhibitors have been designed and synthesized, which were inspired by the backbone sequences of the proteasome inhibitors bortezomib, epoxomicin, and Cbz-Leu(3)-aldehyde. Nine of them were very potent proteasome inhibitors, the best of which had an IC50 of 7 nM. A number of the peptido sulfonyl fluoride inhibitors were found to be highly selective for the beta 5 proteasome subunit.

  DOI：

  10.1021/jm301443r
• 作为产物：
  描述：

  (2S)-2-Amino-4-methylpentane-1-sulfonyl fluoride 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 tert-butyl N-[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-fluorosulfonyl-4-methylpentan-2-yl]amino]-1-oxo-3-phenylmethoxybutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamate
  参考文献：
  名称：

  Peptido Sulfonyl Fluorides as New Powerful Proteasome Inhibitors

  摘要：

  A new class of potent proteasome inhibitors is described, of which the members contain an amino acid inspired sulfonyl fluoride as the electrophilic trap. In total, 24 peptido sulfonyl fluoride inhibitors have been designed and synthesized, which were inspired by the backbone sequences of the proteasome inhibitors bortezomib, epoxomicin, and Cbz-Leu(3)-aldehyde. Nine of them were very potent proteasome inhibitors, the best of which had an IC50 of 7 nM. A number of the peptido sulfonyl fluoride inhibitors were found to be highly selective for the beta 5 proteasome subunit.

  DOI：

  10.1021/jm301443r

文献信息

• Peptido Sulfonyl Fluorides as New Powerful Proteasome Inhibitors
  作者：Arwin J. Brouwer、Anika Jonker、Paul Werkhoven、Ethan Kuo、Nan Li、Nerea Gallastegui、Johan Kemmink、Bogdan I. Florea、Michael Groll、Herman S. Overkleeft、Rob M. J. Liskamp

  DOI：10.1021/jm301443r

  日期：2012.12.27

  A new class of potent proteasome inhibitors is described, of which the members contain an amino acid inspired sulfonyl fluoride as the electrophilic trap. In total, 24 peptido sulfonyl fluoride inhibitors have been designed and synthesized, which were inspired by the backbone sequences of the proteasome inhibitors bortezomib, epoxomicin, and Cbz-Leu(3)-aldehyde. Nine of them were very potent proteasome inhibitors, the best of which had an IC50 of 7 nM. A number of the peptido sulfonyl fluoride inhibitors were found to be highly selective for the beta 5 proteasome subunit.