(S)-N-benzylglutamine

• 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: (S)-N-benzylglutamine
• 英文别名: α-N-Benzyl-L-glutamin；N-benzylglutamine；(2S)-5-amino-2-(benzylamino)-5-oxopentanoic acid
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: BBUJGGQUSKNINS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-benzylglutamine 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (4S)-4-[benzyl(propyl)amino]-5-hydroxypentanamide
  参考文献：
  名称：

  Molecular Determinants of Biased Agonism at the Dopamine D₂Receptor

  摘要：

  The development of biased (functionally selective) ligands Provides a formidable challenge in medicinal chemistry. In an effort to learn to design functionally selective molecular tools for the highly therapeutically relevant dopamine D-2 receptor, we synthesized a collection of agonists based on structurally distinct head groups derived from canonical or atypical dopaminergic pharmacophores. The test compounds feature a long lipophilic appendage that was shown to mediate biased signaling. By employing functional assays and molecular dynamics simulations, we could show that atypical dopamine surrogates of type 1 and 2 promote biased signaling, while ligands built from classical dopaminergic head groups (type 3 and 4) typically elicit more balanced signaling profiles. Besides this, we found a strong influence of the stereochemistry of type 4 aminotetraline-derived agonists on functional selectivity at D-2 receptors. Whereas the (S)-enantiomer behaved as a full agonist, the biased ligand (R)-4 induced poor G protein coupling but substantial beta-arrestin recruitment.

  DOI：

  10.1021/jm501889t
• 作为产物：
  描述：

  L-谷氨酰胺 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 (S)-N-benzylglutamine
  参考文献：
  名称：

  Molecular Determinants of Biased Agonism at the Dopamine D₂Receptor

  摘要：

  The development of biased (functionally selective) ligands Provides a formidable challenge in medicinal chemistry. In an effort to learn to design functionally selective molecular tools for the highly therapeutically relevant dopamine D-2 receptor, we synthesized a collection of agonists based on structurally distinct head groups derived from canonical or atypical dopaminergic pharmacophores. The test compounds feature a long lipophilic appendage that was shown to mediate biased signaling. By employing functional assays and molecular dynamics simulations, we could show that atypical dopamine surrogates of type 1 and 2 promote biased signaling, while ligands built from classical dopaminergic head groups (type 3 and 4) typically elicit more balanced signaling profiles. Besides this, we found a strong influence of the stereochemistry of type 4 aminotetraline-derived agonists on functional selectivity at D-2 receptors. Whereas the (S)-enantiomer behaved as a full agonist, the biased ligand (R)-4 induced poor G protein coupling but substantial beta-arrestin recruitment.

  DOI：

  10.1021/jm501889t

文献信息

• Glutamate aggrecanase inhibitors
  申请人：Sum Phaik-Eng

  公开号：US20070043066A1

  公开（公告）日：2007-02-22

  The present invention relates to modulators of metalloproteinase activity.

  本发明涉及金属蛋白酶活性调节剂。
• Substituted glutarimides and their use as inhibitors of IL-12 production
  申请人：GRUENENTHAL GmbH

  公开号：US20030064987A1

  公开（公告）日：2003-04-03

  Substituted glutarimides of formula I 1 and their method of making. Also disclosed are pharmaceutical compositions comprising the glutarimidie, particularly as immunomodulators and as inhibitors of angiopathies, or haematological or oncological diseases, as well as a method for treating various diseases using the glutarimides.

  公式I1的替代戊二酰亚胺及其制备方法。还披露了包含戊二酰亚胺的药物组合物，特别是作为免疫调节剂和血管病、血液学疾病或肿瘤学疾病的抑制剂，以及使用戊二酰亚胺治疗各种疾病的方法。
• Urea derivative, process for producing the same, and use
  申请人：Kubo Keiji

  公开号：US20070093501A1

  公开（公告）日：2007-04-26

  The present invention provides a urea derivative or a salt thereof, which is useful as a therapeutic agent for thrombosis. The derivative is represented by Formula (I): wherein Cy is an aromatic hydrocarbon group which may be substituted or an aromatic heterocyclic group which may be substituted; R 1 is a hydrogen atom or a hydrocarbon group which may be substituted; V is —C(O)—, —S(O)—, or —S(O) 2 —; W is —N(R 2 )—, —O—, or a bond (wherein R 2 is a hydrogen atom or a hydrocarbon group which may be substituted); X is alkylene which may be substituted; Y is —C(O)—, —S(O)—, or —S(O) 2 —; Z is a bond, a chain hydrocarbon group which may be substituted, or —N═; ring A is a non-aromatic nitrogen-containing heterocyclic ring which may be substituted; ring B is a nitrogen-containing heterocyclic ring which may be substituted; and [Chemical formula 2] , are each independently a single bond or a double bond; provided that R 1 may be bonded to R 2 to form a non-aromatic nitrogen-containing heterocyclic ring and that R 2 may be bonded to a substituent of X to form a non-aromatic nitrogen-containing heterocyclic ring which may be substituted.

  本发明提供一种尿素衍生物或其盐，其作为治疗血栓症的治疗剂是有用的。该衍生物由公式（I）表示：其中，Cy是芳香族羟基烃基或芳香族杂环基，可以被取代；R1是氢原子或可以被取代的碳氢基团；V是-C（O）-，-S（O）-或-S（O）2-；W是-N（R2）-，-O-或键（其中R2是氢原子或可以被取代的碳氢基团）；X是可以被取代的烷基；Y是-C（O）-，-S（O）-或-S（O）2-；Z是键，可以被取代的链烃基团或-N═；环A是非芳香族含氮杂环环，可以被取代；环B是含氮杂环环，可以被取代；而[化学式2]都是单键或双键；但是，R1可以与R2连接形成非芳香族含氮杂环环，而R2可以与X的取代基连接形成可以被取代的非芳香族含氮杂环环。
• COMPOUNDS AND METHODS TO INHIBIT OR AUGMENT AN INFLAMMATORY RESPONSE
  申请人：Grainger J. David

  公开号：US20080045557A1

  公开（公告）日：2008-02-21

  Isolated and purified chemokine peptides, variants, and derivatives thereof, as well as chemokine peptide analogs, are provided.

  提供了分离和纯化的趋化因子肽、变体及其衍生物，以及趋化因子肽类似物。
• GLUTAMATE AGGRECANASE INHIBITORS
  申请人：Sum Phaik-Eng

  公开号：US20100010012A1

  公开（公告）日：2010-01-14

  The present invention relates to modulators of metalloproteinase activity.

  本发明涉及金属蛋白酶活性调节剂。