{(R)-6-[(Benzo[b]thiophene-2-carbonyl)-amino]-5-oxo-[1,4]thiazepan-4-yl}-acetic acid | 911304-66-0

• 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: {(R)-6-[(Benzo[b]thiophene-2-carbonyl)-amino]-5-oxo-[1,4]thiazepan-4-yl}-acetic acid
• CAS: 911304-66-0
• 化学式: C₁₆H₁₆N₂O₄S₂
• 分子量: 364.446
• InChiKey: USMIAVZXKMKLFI-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  86.71
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {(R)-6-[(Benzo[b]thiophene-2-carbonyl)-amino]-5-oxo-[1,4]thiazepan-4-yl}-acetic acid 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 碳酸氢钠 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 Benzo[b]thiophene-2-carboxylic acid {(R)-4-[((S)-2-hydroxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-1,1,5-trioxo-1λ⁶-[1,4]thiazepan-6-yl}-amide
  参考文献：
  名称：

  Synthesis and evaluation of thiazepines as interleukin-1β converting enzyme (ICE) inhibitors

  摘要：

  A series of monocyclic thiazepine inhibitors of interleukin-1 beta converting enzyme (ICE) were synthesized in eight steps from commercially available intermediates. In vitro biological evaluation showed the thiazepines to be moderately potent ICE inhibitors, with the most active compound exhibiting an IC50 value of 30 nM in an enzyme inhibition assay. Compounds of this class possessed good selectivity against the related enzymes caspase-3 and caspase-8. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.016
• 作为产物：
  描述：

  ((R)-6-amino-5-oxo-[1,4]thiazepa-4-yl)-acetic acid ethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 {(R)-6-[(Benzo[b]thiophene-2-carbonyl)-amino]-5-oxo-[1,4]thiazepan-4-yl}-acetic acid
  参考文献：
  名称：

  Synthesis and evaluation of thiazepines as interleukin-1β converting enzyme (ICE) inhibitors

  摘要：

  A series of monocyclic thiazepine inhibitors of interleukin-1 beta converting enzyme (ICE) were synthesized in eight steps from commercially available intermediates. In vitro biological evaluation showed the thiazepines to be moderately potent ICE inhibitors, with the most active compound exhibiting an IC50 value of 30 nM in an enzyme inhibition assay. Compounds of this class possessed good selectivity against the related enzymes caspase-3 and caspase-8. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.016