N-{[4-(but-2-ynyloxy)phenyl]sulfonyl}-5-fluorotryptophan

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-{[4-(but-2-ynyloxy)phenyl]sulfonyl}-5-fluorotryptophan
• 英文别名: rac-2-(4-(but-2-ynyloxy)phenylsulfonamido)-3-(5-fluoro-1H-indol-3-yl)propanoic acid；2-[(4-but-2-ynoxyphenyl)sulfonylamino]-3-(5-fluoro-1H-indol-3-yl)propanoic acid
• 化学式: C₂₁H₁₉FN₂O₅S
• 分子量: 430.457
• InChiKey: QOGALZKFHQFSHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-氟-DL-色氨酸 、 4-but-2-ynyloxybenzenesulfonyl chloride 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 生成 N-{[4-(but-2-ynyloxy)phenyl]sulfonyl}-5-fluorotryptophan
  参考文献：
  名称：

  Synthesis and activity of tryptophan sulfonamide derivatives as novel non-hydroxamate TNF-α converting enzyme (TACE) inhibitors

  摘要：

  A novel series of non-hydroxamate tryptophan sulfonamide derivatives containing a butynyloxy P1' moiety was identified as inhibitors of TNF-alpha converting enzyme (TACE). The structure-activity relationship of the series was examined via substitution on the tryptophan indole ring. Of the compounds investigated, 2-(4-(but-2-ynyloxy)phenylsulfonamido)-3-(1-(4-methoxybenzyl)-1H-indol-3-yl)propanoic acid (12p) has the best in vitro potency against isolated TACE enzyme with an IC(50) of 80 nM. Compound 12p also shows good selectivity over MMP-1, -13, -14.

  DOI：

  10.1016/j.bmc.2009.04.033

文献信息

• Alkynyl-containing tryptophan derivative inhibitors of tace/matrix metalloproteinase
  申请人：Park Kaapjoo

  公开号：US20060160884A1

  公开（公告）日：2006-07-20

  This invention provides compounds of Formula I, having the structure: that are useful in treating diseases or disorders mediated by TNF-α. The invention further provides methods for use of the compounds for treating such a disease or disorder or for alleviating symptoms thereof.

  这项发明提供了具有结构的化合物，可以用于治疗由TNF-α介导的疾病或紊乱。该发明还提供了使用这些化合物治疗这种疾病或紊乱，或缓解其症状的方法。
• US7576222B2
  申请人：——

  公开号：US7576222B2

  公开（公告）日：2009-08-18
• Synthesis and activity of tryptophan sulfonamide derivatives as novel non-hydroxamate TNF-α converting enzyme (TACE) inhibitors
  作者：Kaapjoo Park、Ariamala Gopalsamy、Alexis Aplasca、John W. Ellingboe、Weixin Xu、Yuhua Zhang、Jeremy I. Levin

  DOI：10.1016/j.bmc.2009.04.033

  日期：2009.6

  A novel series of non-hydroxamate tryptophan sulfonamide derivatives containing a butynyloxy P1' moiety was identified as inhibitors of TNF-alpha converting enzyme (TACE). The structure-activity relationship of the series was examined via substitution on the tryptophan indole ring. Of the compounds investigated, 2-(4-(but-2-ynyloxy)phenylsulfonamido)-3-(1-(4-methoxybenzyl)-1H-indol-3-yl)propanoic acid (12p) has the best in vitro potency against isolated TACE enzyme with an IC(50) of 80 nM. Compound 12p also shows good selectivity over MMP-1, -13, -14.