((R)-5-oxo-[1,4]thiazepan-6-yl)-carbamic acid tert-butyl ester | 85591-15-7

• 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: ((R)-5-oxo-[1,4]thiazepan-6-yl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(6R)-5-oxo-1,4-thiazepan-6-yl]carbamate
• CAS: 85591-15-7
• 化学式: C₁₀H₁₈N₂O₃S
• 分子量: 246.331
• InChiKey: WZRSMKIBVJZKKT-ZETCQYMHSA-N

物化性质

• 沸点：
  466.8±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((R)-5-oxo-[1,4]thiazepan-6-yl)-carbamic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 RU 79181
  参考文献：
  名称：

  Discovery of highly potent Src SH2 binders: Structure–activity studies and X-ray structures

  摘要：

  Optimization of the hydrophobic moiety of caprolactam/thiazepinone based compounds led to the identification of potent Src SH2 binders in two different series incorporating a phosphotyrosine group (RU 81843) or a phosphobenzoic group (RU 79181). The X-ray co-structures with the Src SH2 domain revealed different binding modes for RU 81843 and RU 79181, and an excellent fit between RU81843 and the Src SH2 protein thus explaining its high potency (9 nM, 15-fold more potent than pYEE1 reference peptide). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00139-7
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (R)-6-氨基-1,4-THIAZEPAN-5-酮 在 三乙胺 作用下， 以 甲醇 为溶剂， 以70%的产率得到((R)-5-oxo-[1,4]thiazepan-6-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  [EN] DERIVATIVES OF AZEPINE AND THIAZERAN AS INTERLEUKIN CONVERTING ENZYME INHIBITORS
  [FR] DERIVES D'AZEPINE ET DE THIAZERAN UTILISES COMME INHIBITEURS DE ENZYME DE CONVERSION DE L'INTERLEUKINE

  摘要：

  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。

  公开号：

  WO2003103677A1

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。
• Discovery of highly potent Src SH2 binders: Structure–activity studies and X-ray structures
  作者：Pierre Deprez、Isabelle Baholet、Stéphane Burlet、Gudrun Lange、Remi Amengual、Bernard Schoot、Annie Vermond、Eliane Mandine、Dominique Lesuisse

  DOI：10.1016/s0960-894x(02)00139-7

  日期：2002.5

  Optimization of the hydrophobic moiety of caprolactam/thiazepinone based compounds led to the identification of potent Src SH2 binders in two different series incorporating a phosphotyrosine group (RU 81843) or a phosphobenzoic group (RU 79181). The X-ray co-structures with the Src SH2 domain revealed different binding modes for RU 81843 and RU 79181, and an excellent fit between RU81843 and the Src SH2 protein thus explaining its high potency (9 nM, 15-fold more potent than pYEE1 reference peptide). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and evaluation of thiazepines as interleukin-1β converting enzyme (ICE) inhibitors
  作者：Christopher D. Ellis、Kofi A. Oppong、Michael C. Laufersweiler、Steven V. O’Neil、David L. Soper、Yili Wang、John A. Wos、Amy N. Fancher、Wei Lu、Maureen K. Suchanek、Richard L. Wang、Biswanath De、Thomas P. Demuth

  DOI：10.1016/j.bmcl.2006.07.016

  日期：2006.9

  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.