tert-butyl 5-(2-bromo-5-fluorobenzyl)-6-{3-[(tert-butoxycarbonyl)amino]-3-ethylpiperidin-1-yl}-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylate | 1338930-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: tert-butyl 5-(2-bromo-5-fluorobenzyl)-6-{3-[(tert-butoxycarbonyl)amino]-3-ethylpiperidin-1-yl}-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylate
• CAS: 1338930-84-9
• 化学式: C₃₂H₄₃BrFN₅O₆
• 分子量: 692.626
• InChiKey: KCYHBPFXGOOWHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  45.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  116.8
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  zinc(II) cyanide 、 tert-butyl 5-(2-bromo-5-fluorobenzyl)-6-{3-[(tert-butoxycarbonyl)amino]-3-ethylpiperidin-1-yl}-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylate 在 二(三叔丁基膦)钯 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 1.0h， 以68%的产率得到tert-butyl 6-{3-[(tert-butoxycarbonyl)amino]-3-ethylpiperidin-1-yl}-5-(2-cyano-5-fluorobenzyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylate
  参考文献：
  名称：

  2-({6-[(3R)-3-amino-3-methylpiperidine-1-yl]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-5H-pyrrolo[3,2-d]pyrimidine-5-yl}methyl)-4-fluorobenzonitrile (DSR-12727): A potent, orally active dipeptidyl peptidase IV inhibitor without mechanism-based inactivation of CYP3A

  摘要：

  Wereport on the identification of 2-({6-[(3R)-3-amino-3-methylpiperidine-1-yl]-1,3-dimethyl-2,4-dioxo-1,2,3,4- tetrahydro-5H-pyrrolo[3,2-d] pyrimidine-5-yl}methyl)-4-fluorobenzonitrile (DSR-12727) (7a) as a potent and orally active DPP-4 inhibitor without mechanism-based inactivation of CYP3A. Compound 7a showed good DPP-4 inhibitory activity (IC50 = 1.1 nM), excellent selectivity against related peptidases and other off-targets, good pharmacokinetic and pharmacodynamic profile, great in vivo efficacy in Zucker-fatty rat, and no safety concerns both in vitro and in vivo. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.042
• 作为产物：
  描述：

  3-哌啶甲酸乙酯 在 lithium amide 、 叠氮磷酸二苯酯 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 、 sodium hexamethyldisilazane 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 107.0h， 生成 tert-butyl 5-(2-bromo-5-fluorobenzyl)-6-{3-[(tert-butoxycarbonyl)amino]-3-ethylpiperidin-1-yl}-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylate
  参考文献：
  名称：

  2-({6-[(3R)-3-amino-3-methylpiperidine-1-yl]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-5H-pyrrolo[3,2-d]pyrimidine-5-yl}methyl)-4-fluorobenzonitrile (DSR-12727): A potent, orally active dipeptidyl peptidase IV inhibitor without mechanism-based inactivation of CYP3A

  摘要：

  Wereport on the identification of 2-({6-[(3R)-3-amino-3-methylpiperidine-1-yl]-1,3-dimethyl-2,4-dioxo-1,2,3,4- tetrahydro-5H-pyrrolo[3,2-d] pyrimidine-5-yl}methyl)-4-fluorobenzonitrile (DSR-12727) (7a) as a potent and orally active DPP-4 inhibitor without mechanism-based inactivation of CYP3A. Compound 7a showed good DPP-4 inhibitory activity (IC50 = 1.1 nM), excellent selectivity against related peptidases and other off-targets, good pharmacokinetic and pharmacodynamic profile, great in vivo efficacy in Zucker-fatty rat, and no safety concerns both in vitro and in vivo. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.042