((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester | 681293-19-6

• 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 (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester
• CAS: 681293-19-6
• 化学式: C₂₆H₃₆N₄O₈S
• 分子量: 564.66
• InChiKey: FPXXBJISPUMWER-XNRHKNHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  174.2
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 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：

  (5-氧代环戊烯-1-基)乙酸甲酯 在 三乙烯二胺 、 4-二甲氨基吡啶 、 L-Selectride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， -17.0~18.0 ℃ 、101.33 kPa 条件下， 反应 21.0h， 生成 ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid (4aR,7S,7aS)-4-carbamoyl-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindin-7-yl ester
  参考文献：
  名称：

  摘要：

  The ketone (+/-)- 5, which embodies the bicyclic core associated with the title tRNA synthetase inhibitors 1 and 2, has been prepared via a three-component coupling reaction involving 2-( hydroxymethyl) cyclopent-2-enone (15), methylamine (6) and propiolamide (10); straightforward elaboration of the readily derived acetates ()- 21 and (+)- 21 has provided the biologically active analogues 23 and 24, respectively, of the title compounds.

  DOI：

  10.1039/b104890m