ethyl 2-[(2S,4S)-4-amino-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1,3-thiazole-4-carboxylate | 1207593-50-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-[(2S,4S)-4-amino-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1,3-thiazole-4-carboxylate
• 英文别名: ethyl 2-[(2S,4S)-4-amino-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]-1,3-thiazole-4-carboxylate
• CAS: 1207593-50-7
• 化学式: C₁₅H₂₃N₃O₄S
• 分子量: 341.431
• InChiKey: RVKBWVJIKPHNKH-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(2S,4S)-4-amino-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1,3-thiazole-4-carboxylate 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 (4S)-1-methyl-N-{(3S,5S)-5-[4-(methylcarbamoyl)-1,3-thiazol-2-yl]pyrrolidin-3-yl}-2,6-dioxo-1,3-diazinane-4-carboxamide trifluoroacetate
  参考文献：
  名称：

  Characterization of Specific N-α-Acetyltransferase 50 (Naa50) Inhibitors Identified Using a DNA Encoded Library

  摘要：

  Two novel compounds were identified as Naa50 binders/inhibitors using DNA-encoded technology screening. Biophysical and biochemical data as well as cocrystal structures were obtained for both compounds (3a and 4a) to understand their mechanism of action. These data were also used to rationalize the binding affinity differences observed between the two compounds and a MLGP peptide-containing substrate. Cellular target engagement experiments further confirm the Naa50 binding of 4a and demonstrate its selectivity toward related enzymes (Naa10 and Naa60). Additional analogs of inhibitor 4a were also evaluated to study the binding mode observed in the cocrystal structures.

  DOI：

  10.1021/acsmedchemlett.0c00029
• 作为产物：
  描述：

  N-Boc-顺式-4-Fmoc-氨基-L-脯氨酸 在 劳森试剂 、 碳酸氢钠 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.34h， 生成 ethyl 2-[(2S,4S)-4-amino-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  FUNCTIONALIZED PYRROLIDINES AND USE THEREOF AS IAP INHIBITORS

  摘要：

  一种化合物的化学式1，或其盐，以及其使用方法，特别是作为IAP抑制剂的方法，以及相关的化合物、组合物和方法。

  公开号：

  US20120009141A1

文献信息

• FUNCTIONALIZED PYRROLIDINES AND USE THEREOF AS IAP INHIBITORS
  申请人：Laurent Alain

  公开号：US20120009141A1

  公开（公告）日：2012-01-12

  A compound of Formula 1: or a salt thereof, and methods for the use thereof, especially as an IAP inhibitor, as well as related compounds, compositions, and methods.

  一种化合物的化学式1，或其盐，以及其使用方法，特别是作为IAP抑制剂的方法，以及相关的化合物、组合物和方法。
• Characterization of Specific <i>N</i>-α-Acetyltransferase 50 (Naa50) Inhibitors Identified Using a DNA Encoded Library
  作者：Pei-Pei Kung、Patrick Bingham、Benjamin J. Burke、Qiuxia Chen、Xuemin Cheng、Ya-Li Deng、Dengfeng Dou、Junli Feng、Gary M. Gallego、Michael R. Gehring、Stephan K. Grant、Samantha Greasley、Anthony R. Harris、Karen A. Maegley、Jordan Meier、Xiaoyun Meng、Jose L. Montano、Barry A. Morgan、Brigitte S. Naughton、Prakash B. Palde、Thomas A. Paul、Paul Richardson、Sylvie Sakata、Alex Shaginian、William K. Sonnenburg、Chakrapani Subramanyam、Sergei Timofeevski、Jinqiao Wan、Wen Yan、Albert E. Stewart

  DOI：10.1021/acsmedchemlett.0c00029

  日期：2020.6.11

  Two novel compounds were identified as Naa50 binders/inhibitors using DNA-encoded technology screening. Biophysical and biochemical data as well as cocrystal structures were obtained for both compounds (3a and 4a) to understand their mechanism of action. These data were also used to rationalize the binding affinity differences observed between the two compounds and a MLGP peptide-containing substrate. Cellular target engagement experiments further confirm the Naa50 binding of 4a and demonstrate its selectivity toward related enzymes (Naa10 and Naa60). Additional analogs of inhibitor 4a were also evaluated to study the binding mode observed in the cocrystal structures.