N1-(2-phenylethyl)-(2R)-2-{[(4-benzylpiperidino)methyl]carboxamido}-3-[1-(tert-butoxycarbonyl)-3-indolyl]propanamide | 540483-73-6

• 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: N1-(2-phenylethyl)-(2R)-2-{[(4-benzylpiperidino)methyl]carboxamido}-3-[1-(tert-butoxycarbonyl)-3-indolyl]propanamide
• 英文别名: N1-phenethyl-(2R)-2-[(4-benzylpiperidino)-methyl]-carboxamido-3-(1-(tert-butoxycarbonyl)-3-indolyl)-propanamide；tert-butyl 3-[(2R)-2-[[2-(4-benzylpiperidin-1-yl)acetyl]amino]-3-oxo-3-(2-phenylethylamino)propyl]indole-1-carboxylate
• CAS: 540483-73-6
• 化学式: C₃₈H₄₆N₄O₄
• 分子量: 622.808
• InChiKey: RZZVINWZTOOALW-MGBGTMOVSA-N

物化性质

• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N1-(2-phenylethyl)-(2R)-2-{[(4-benzylpiperidino)methyl]carboxamido}-3-[1-(tert-butoxycarbonyl)-3-indolyl]propanamide 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.1h， 生成 N1-(2-phenylethyl)-(2R)-2-{[(4-benzylpiperidino)methyl]carboxamido}-3-(1H-3-indolyl)propanamide
  参考文献：
  名称：

  [DE] NICHT-PEPTIDISCHE BRS-3-AGONISTEN
  [EN] NON-PEPTIDIC BRS-3 AGONISTS
  [FR] AGONISTES DU RECEPTEUR BRS-3 NON PEPTIDIQUES

  摘要：

  新的、选择性的BRS-3激动剂有效化合物已被描述，其具有通用式(I)，其中A<1>、A<2>、A<3>、R<1>、R<2>、R<3>、Ar<1>、Ar<2>、Ar<3>、m和n具有描述中指定的含义，以及包含这些化合物的药物和制备式(I)化合物的方法。

  公开号：

  WO2003104196A1
• 作为产物：
  描述：

  4-苄基哌啶 在 sodium hydroxide 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 N1-(2-phenylethyl)-(2R)-2-{[(4-benzylpiperidino)methyl]carboxamido}-3-[1-(tert-butoxycarbonyl)-3-indolyl]propanamide
  参考文献：
  名称：

  Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3

  摘要：

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.

  DOI：

  10.1021/jm0210921

文献信息

• [DE] NICHT-PEPTIDISCHE BRS-3-AGONISTEN<br/>[EN] NON-PEPTIDIC BRS-3 AGONISTS<br/>[FR] AGONISTES DU RECEPTEUR BRS-3 NON PEPTIDIQUES
  申请人：SOLVAY PHARM GMBH

  公开号：WO2003104196A1

  公开（公告）日：2003-12-18

  Es werden neue, selektiv BRS-3 agonistisch wirksame Verbindungen der allgemeinen Formel (I), worin A<1>, A<2 >, A<3 >, R<1>, R<2> , R<3 >, Ar<1> , Ar<2> , Ar<3> , m und n die in der Beschreibung angegebenen Bedeutungen besitzen, sowie diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung von Verbindungen der Formel (I) beschrieben.

  新的、选择性的BRS-3激动剂有效化合物已被描述，其具有通用式(I)，其中A<1>、A<2>、A<3>、R<1>、R<2>、R<3>、Ar<1>、Ar<2>、Ar<3>、m和n具有描述中指定的含义，以及包含这些化合物的药物和制备式(I)化合物的方法。
• Non-peptidic BRS-3 agonists
  申请人：Weber Dirk

  公开号：US20050171146A1

  公开（公告）日：2005-08-04

  Selectively BRS-3-agonistic compounds of formula I wherein A 1 , A 2 , A 3 , R 1 , R 2 , R 3 , Ar 1 , Ar 2 , Ar 3 , m and n have the meanings given in the description, and also pharmaceutical compositions containing these compounds and a process for the preparation of compounds of Formula I are described.

  本文描述了式I的选择性BRS-3激动剂化合物，其中A1、A2、A3、R1、R2、R3、Ar1、Ar2、Ar3、m和n具有描述中给出的含义，以及包含这些化合物的制药组合物和制备式I化合物的过程。
• US7244743B2
  申请人：——

  公开号：US7244743B2

  公开（公告）日：2007-07-17
• Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3
  作者：Dirk Weber、Claudia Berger、Peter Eickelmann、Jochen Antel、Horst Kessler

  DOI：10.1021/jm0210921

  日期：2003.5.1

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.