(R)-1-benzylpiperidin-3-yl 2-hydroxy-2,2-diphenylacetate | 315191-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-1-benzylpiperidin-3-yl 2-hydroxy-2,2-diphenylacetate
• 英文别名: ethyl benzilate；[(3R)-1-benzyl-3-piperidyl] 2-hydroxy-2,2-diphenyl-acetate；[(3R)-1-benzylpiperidin-3-yl] 2-hydroxy-2,2-diphenylacetate
• CAS: 315191-13-0
• 化学式: C₂₆H₂₇NO₃
• 分子量: 401.505
• InChiKey: DYTJZBGUAADDIX-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1-benzylpiperidin-3-yl 2-hydroxy-2,2-diphenylacetate 在 10percent Pd/C 高氯酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以83%的产率得到Hydroxy-diphenyl-acetic acid (R)-piperidin-3-yl ester
  参考文献：
  名称：

  Synthesis, ¹⁸F-Labeling, and Biological Evaluation of Piperidyl and Pyrrolidyl Benzilates as in Vivo Ligands for Muscarinic Acetylcholine Receptors

  摘要：

  A series of 31 compounds based on the piperidyl or pyrrolidyl benzilate scaffold were prepared from methyl benzilate and 4-piperidinol, (R)-(+)-3-piperidinol, or (R)-(+)-3-pyrrolidinol. Amine substituents included alkyl and aralkyl groups. In vitro K-i values ranged from 0.05 nM to > 100 nM. (R)-N-( 2-Fluoroethyl)-3-piperidyl benzilate (3-FEPB, 22, K-i = 12.1 nM) and N-(2-fluoroethyl)-4-piperidyl benzilate (4-FEPB, 8, K-i = 1.83 nM) were selected for radiolabeling with fluorine-18. Using alkylation with 2-[F-18]fluoroethyl triflate, 3-[F-18]FEPB (42) and 4-[F-18]-FEPB (43) were produced in 7-9% radiochemical yield and >97% radiochemical purity. For in vivo studies, retention was moderate in mouse brain for 42; however, blocking with scopolamine showed that uptake was not muscarinic cholinergic receptor-mediated. Conversely, 43 exhibited high, receptor-mediated retention in mouse brain, with significant; clearance after 1 h. These results suggest that 43 could have applications as an in vivo probe for measuring endogenous acetylcholine levels.

  DOI：

  10.1021/jm000305o
• 作为产物：
  描述：

  二苯乙醇酸甲酯 、 (R)-(-)-1-苄基-3-羟基哌啶 在 sodium 作用下， 以 苯 为溶剂， 反应 2.5h， 以46%的产率得到(R)-1-benzylpiperidin-3-yl 2-hydroxy-2,2-diphenylacetate
  参考文献：
  名称：

  Synthesis, ¹⁸F-Labeling, and Biological Evaluation of Piperidyl and Pyrrolidyl Benzilates as in Vivo Ligands for Muscarinic Acetylcholine Receptors

  摘要：

  A series of 31 compounds based on the piperidyl or pyrrolidyl benzilate scaffold were prepared from methyl benzilate and 4-piperidinol, (R)-(+)-3-piperidinol, or (R)-(+)-3-pyrrolidinol. Amine substituents included alkyl and aralkyl groups. In vitro K-i values ranged from 0.05 nM to > 100 nM. (R)-N-( 2-Fluoroethyl)-3-piperidyl benzilate (3-FEPB, 22, K-i = 12.1 nM) and N-(2-fluoroethyl)-4-piperidyl benzilate (4-FEPB, 8, K-i = 1.83 nM) were selected for radiolabeling with fluorine-18. Using alkylation with 2-[F-18]fluoroethyl triflate, 3-[F-18]FEPB (42) and 4-[F-18]-FEPB (43) were produced in 7-9% radiochemical yield and >97% radiochemical purity. For in vivo studies, retention was moderate in mouse brain for 42; however, blocking with scopolamine showed that uptake was not muscarinic cholinergic receptor-mediated. Conversely, 43 exhibited high, receptor-mediated retention in mouse brain, with significant; clearance after 1 h. These results suggest that 43 could have applications as an in vivo probe for measuring endogenous acetylcholine levels.

  DOI：

  10.1021/jm000305o

文献信息

• Compounds as anti-tubercular agents
  申请人：SPHAERA PHARMA PVT. LTD.

  公开号：US10100012B2

  公开（公告）日：2018-10-16

  The present invention relates to novel compounds of formula (1): The present invention also discloses compounds of formula (1) along with other pharmaceutical acceptable excipients and use of the compounds as anti-tubercular agents.

  本发明涉及式（1）的新型化合物：本发明还公开了式(1)化合物与其他药物可接受的赋形剂以及这些化合物作为抗结核剂的用途。
• NOVEL COMPOUNDS AS ANTI-TUBERCULAR AGENTS
  申请人：Sphaera Pharma Pvt. Ltd.

  公开号：EP3148518A2

  公开（公告）日：2017-04-05
• [EN] NOVEL COMPOUNDS AS ANTI-TUBERCULAR AGENTS<br/>[FR] NOUVEAUX COMPOSÉS UTILISÉS COMME AGENTS ANTI-TUBERCULEUX
  申请人：SPHAERA PHARMA PRIVATE LTD

  公开号：WO2015181837A2

  公开（公告）日：2015-12-03

  The present invention relates to novel compounds of formula (1): The present invention also discloses compounds of formula (1) along with other pharmaceutical acceptable excipients and use of the compounds as anti-tubercular agents.
• Synthesis, ¹⁸F-Labeling, and Biological Evaluation of Piperidyl and Pyrrolidyl Benzilates as in Vivo Ligands for Muscarinic Acetylcholine Receptors
  作者：Marc B. Skaddan、Michael R. Kilbourn、Scott E. Snyder、Phil S. Sherman、Tim J. Desmond、Kirk A. Frey

  DOI：10.1021/jm000305o

  日期：2000.11.1

  A series of 31 compounds based on the piperidyl or pyrrolidyl benzilate scaffold were prepared from methyl benzilate and 4-piperidinol, (R)-(+)-3-piperidinol, or (R)-(+)-3-pyrrolidinol. Amine substituents included alkyl and aralkyl groups. In vitro K-i values ranged from 0.05 nM to > 100 nM. (R)-N-( 2-Fluoroethyl)-3-piperidyl benzilate (3-FEPB, 22, K-i = 12.1 nM) and N-(2-fluoroethyl)-4-piperidyl benzilate (4-FEPB, 8, K-i = 1.83 nM) were selected for radiolabeling with fluorine-18. Using alkylation with 2-[F-18]fluoroethyl triflate, 3-[F-18]FEPB (42) and 4-[F-18]-FEPB (43) were produced in 7-9% radiochemical yield and >97% radiochemical purity. For in vivo studies, retention was moderate in mouse brain for 42; however, blocking with scopolamine showed that uptake was not muscarinic cholinergic receptor-mediated. Conversely, 43 exhibited high, receptor-mediated retention in mouse brain, with significant; clearance after 1 h. These results suggest that 43 could have applications as an in vivo probe for measuring endogenous acetylcholine levels.