[(2R,3S)-4-oxo-3-(phenylmethoxycarbonylamino)-4-[[(7S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]butan-2-yl] methanesulfonate | 920760-24-3

• 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: [(2R,3S)-4-oxo-3-(phenylmethoxycarbonylamino)-4-[[(7S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]butan-2-yl] methanesulfonate
• CAS: 920760-24-3
• 化学式: C₃₃H₃₈N₂O₁₀S₂
• 分子量: 686.804
• InChiKey: LSWSSPVZOHMWRA-CHNYNYQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  189
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-4-oxo-3-(phenylmethoxycarbonylamino)-4-[[(7S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]butan-2-yl] methanesulfonate 在 potassium tert-butylate 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 以38%的产率得到benzyl 2-methyl-3-[[(7S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]carbamoyl]aziridine-1-carboxylate
  参考文献：
  名称：

  Part II. Development of novel colchicine-derived immunosuppressants with improved pharmacokinetic properties

  摘要：

  We have developed a new series of immunosuppressant with improved pharmacokinetic properties as the second-generation of colchicine analogs, which were designed based on the privileged structure derived from our previous work. In particular, we identified an analog (14), which exhibited a potent in vitro activity (IC50: 5 nM) in MLR and excellent in vivo efficacy in the Zymosan A-induced arthritis model, in the Carrageenan-induced edema model and in the local lymph node assay (LLNA). Analog 14 also revealed a good oral bioavailability (F: 67.3%) in BALB/c mice. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.068
• 作为产物：
  描述：

  N-苄氧羰基-L-苏氨酸 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 [(2R,3S)-4-oxo-3-(phenylmethoxycarbonylamino)-4-[[(7S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]butan-2-yl] methanesulfonate
  参考文献：
  名称：

  Part II. Development of novel colchicine-derived immunosuppressants with improved pharmacokinetic properties

  摘要：

  We have developed a new series of immunosuppressant with improved pharmacokinetic properties as the second-generation of colchicine analogs, which were designed based on the privileged structure derived from our previous work. In particular, we identified an analog (14), which exhibited a potent in vitro activity (IC50: 5 nM) in MLR and excellent in vivo efficacy in the Zymosan A-induced arthritis model, in the Carrageenan-induced edema model and in the local lymph node assay (LLNA). Analog 14 also revealed a good oral bioavailability (F: 67.3%) in BALB/c mice. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.068