((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid ethyl ester | 635313-77-8

• 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: ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid ethyl ester
• CAS: 635313-77-8
• 化学式: C₁₈H₂₆N₂O₇S
• 分子量: 414.48
• InChiKey: XIBXQASZMSRBPN-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  127.87
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid ethyl ester 在 palladium on activated charcoal sodium hydroxide 、 草酰氯 、 氢气 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 [(4aR,7S,7aS)-4-carbamoyl-2-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyridin-7-yl] 2-[[(2S,3S)-2-amino-3-methylpentanoyl]sulfamoyl]acetate
  参考文献：
  名称：

  Synthesis and activity of analogues of the isoleucyl tRNA synthetase inhibitor SB-203207

  摘要：

  Twenty two analogues of SB-203207 have been prepared by total synthesis, and evaluated as inhibitors of a range of tRNA synthetases. Changes to the bicyclic core, removing either the terminal amino substituent or the sulfonyl group from the side chain, and altering either the carbon skeleton or stereochemistry of the isoleucine residue, decreases the potency of inhibition of isoleucyl tRNA synthetase. Substituting the isoleucine residue with other amino acids produces inhibitors of the corresponding synthetases. In particular, a methionine derivative is 50-100 times more potent against methionyl tRNA synthetase than against any of the corresponding isoleucyl, leucyl, valyl, alanyl and prolyl synthetases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00237-2
• 作为产物：
  描述：

  2-氨磺酰基乙酸乙酯 、 N-苄氧羰基-L-异亮氨酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以94%的产率得到((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis and activity of analogues of the isoleucyl tRNA synthetase inhibitor SB-203207

  摘要：

  Twenty two analogues of SB-203207 have been prepared by total synthesis, and evaluated as inhibitors of a range of tRNA synthetases. Changes to the bicyclic core, removing either the terminal amino substituent or the sulfonyl group from the side chain, and altering either the carbon skeleton or stereochemistry of the isoleucine residue, decreases the potency of inhibition of isoleucyl tRNA synthetase. Substituting the isoleucine residue with other amino acids produces inhibitors of the corresponding synthetases. In particular, a methionine derivative is 50-100 times more potent against methionyl tRNA synthetase than against any of the corresponding isoleucyl, leucyl, valyl, alanyl and prolyl synthetases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00237-2