1-Cbz-3-乙基哌啶-3-羧酸 | 1245808-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-Cbz-3-乙基哌啶-3-羧酸
• 中文别名: 1-CBZ-3-乙基哌啶-3-甲酸
• 英文名称: 1-Cbz-3-ethylpiperidine-3-carboxylic Acid
• 英文别名: 3-ethyl-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid
• CAS: 1245808-57-4
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: UMJDUZFRWNBBGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  1-Cbz-3-乙基哌啶-3-羧酸 在 lithium amide 、 叠氮磷酸二苯酯 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 34.0h， 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
• 作为产物：
  描述：

  3-哌啶甲酸乙酯 在 sodium hexamethyldisilazane 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 73.0h， 生成 1-Cbz-3-乙基哌啶-3-羧酸
  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

文献信息

• SPIROCYCLES AS INHIBITORS OF 11-BETA HYDROXYL STEROID DEHYDROGENASE TYPE 1
  申请人：Yao Wenqing

  公开号：US20080318991A1

  公开（公告）日：2008-12-25

  The present invention relates to certain spirocyclic compounds that are inhibitors of 11-β hydroxyl steroid dehydrogenase type 1 (11βHSD1), compositions containing the same, and methods of using the same for the treatment of diabetes, obesity and other diseases.

  本发明涉及某些螺环化合物，这些化合物是11-β羟基类固醇脱氢酶1型（11βHSD1）的抑制剂，包含这些化合物的组合物，以及利用这些化合物治疗糖尿病、肥胖和其他疾病的方法。
• US8278318B2
  申请人：——

  公开号：US8278318B2

  公开（公告）日：2012-10-02
• 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
  作者：Yukihiro Nishio、Hidenori Kimura、Naoyuki Sawada、Eiji Sugaru、Masakuni Horiguchi、Michiko Ono、Yudai Furuta、Mutsuko Sakai、Yumi Masui、Misato Otani、Takahiko Hashizuka、Yayoi Honda、Jiro Deguchi、Tsutomu Nakagawa、Hiroyuki Nakahira

  DOI：10.1016/j.bmc.2011.07.042

  日期：2011.9

  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.