((R)-6-benzoylamino-5-oxo-[1,4]thiazepa-4-yl)-acetic acid | 635706-27-3

• 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-benzoylamino-5-oxo-[1,4]thiazepa-4-yl)-acetic acid
• 英文别名: 2-[(6R)-6-benzamido-5-oxo-1,4-thiazepan-4-yl]acetic acid
• CAS: 635706-27-3
• 化学式: C₁₄H₁₆N₂O₄S
• 分子量: 308.358
• InChiKey: KXSBAMIULQRISA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((R)-6-benzoylamino-5-oxo-[1,4]thiazepa-4-yl)-acetic acid 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 N-{(R)-4-[((S)-2-hydroxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-5-oxo-1-[1,4]thiazepan-6-yl}-benzamide
  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-tert-butoxycarbonylamino-5-oxo-[1,4]thiazepa-4-yl)-acetic acid ethyl ester 在 lithium hydroxide 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ((R)-6-benzoylamino-5-oxo-[1,4]thiazepa-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

文献信息

• [EN] DERIVATIVES OF AZEPINE AND THIAZERAN AS INTERLEUKIN CONVERTING ENZYME INHIBITORS<br/>[FR] DERIVES D'AZEPINE ET DE THIAZERAN UTILISES COMME INHIBITEURS DE ENZYME DE CONVERSION DE L'INTERLEUKINE
  申请人：PROCTER & GAMBLE

  公开号：WO2003103677A1

  公开（公告）日：2003-12-18

  The present invention relates to interleukin - Iβ converting enzyme inhibitors of formula I: wherein each X is independently selected from: i) -C(W)2-; ii) -C(O)-; iii) -NR2-; iv) -S-; v) -S(O)-; vi) -S(O)2-; vii) two units, one from each adjacent X unit, can be taken together to form a substituted or unsubstituted double bond having the formula -CW=CW-; wherein each W is hydrogen of a unit having the formula -(L2)j-R2, the index j is 0 or 1;R is a carbocyclic or heterocyclic aryl ring; R1 is a cysteine trap; each R2 is independently a suitable substituent; and L, L1, and L2 are linking units.

  本发明涉及公式I的白细胞介素-Iβ转化酶抑制剂，其中每个X独立地从以下选项中选择：i) -C(W)2-；ii) -C(O)-；iii) -NR2-；iv) -S-；v) -S(O)-；vi) -S(O)2-；vii) 两个单位，每个单位来自相邻的X单位，可以结合在一起形成具有公式 -CW=WC- 的取代或未取代的双键；其中每个W是具有公式 -(L2)j-R2 的单位的氢，指数j为0或1；R是一个碳环或杂环芳基环；R1是一个半胱氨酸陷阱；每个R2独立地是一个合适的取代基；L、L1和L2是连接单元。