D-237 | 1003565-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: D-237
• 英文别名: (S)-6-((2-(4-phenylpiperazin-1-yl)ethyl)(propyl)amino)-5,6,7,8-tetrahydronaphthalen-1-ol；(6S)-6-[2-(4-phenylpiperazin-1-yl)ethyl-propylamino]-5,6,7,8-tetrahydronaphthalen-1-ol
• CAS: 1003565-52-3
• 化学式: C₂₅H₃₅N₃O
• 分子量: 393.572
• InChiKey: ACDYFMOSSUKHJD-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  30
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  D-237 、 对甲氧基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到[(6S)-6-[2-(4-phenylpiperazin-1-yl)ethyl-propylamino]-5,6,7,8-tetrahydronaphthalen-1-yl] 4-methoxybenzenesulfonate
  参考文献：
  名称：

  Modification of agonist binding moiety in hybrid derivative 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-1-ol/-2-amino versions: Impact on functional activity and selectivity for dopamine D2/D3 receptors

  摘要：

  The goal of the present study was to explore, in our previously developed hybrid template, the effect of introduction of additional heterocyclic rings (mimicking catechol hydroxyl groups as bioisosteric replacement) on selectivity and affinity for the D-3 versus D-2 receptor. In addition, we wanted to explore the effect of derivatization of functional groups of the agonist binding moiety in compounds developed by us earlier from the hybrid template. Binding affinity (K-i) of the new compounds was measured with tritiated spiperone as the radioligand and HEK-293 cells expressing either D-2 or D-3 receptors. Functional activity of selected compounds was assessed in the GTP gamma S binding assay. In the imidazole series, compound 10a exhibited the highest D-3 affinity whereas the indole derivative 13 exhibited similar high D-3 affinity. Functionalization of the amino group in agonist (+)-9d with different sulfonamides derivatives improved the D-3 affinity significantly with (+)-14f exhibiting the highest affinity. However, functionalization of the hydroxyl and amino groups of 15 and (+)-9d, known agonist and partial agonist, to sulfonate ester and amide in general modulated the affinity. In both cases loss of agonist potency resulted from such derivatization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.059

文献信息

• BIFUNCTIONAL/POLYFUNCTIONAL DOPAMINE D2/D3 AGONIST AS NEUROPROTECTIVE AGENTS FOR TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：Dutta Aloke K.

  公开号：US20120108815A1

  公开（公告）日：2012-05-03

  A precursor for the deposition of a thin film by atomic layer deposition is provided. The compound has the formula M x L y where M is a metal and L is an amidrazone-derived ligand or an amidate-derived ligand. A process of forming a thin film using the precursors is also provided.

  提供了一种用于原子层沉积薄膜的前体。该化合物具有MxLy的公式，其中M是金属，L是来自酰胺肼衍生的配体或酰胺酸衍生的配体。还提供了使用前体形成薄膜的过程。
• US9034877B2
  申请人：——

  公开号：US9034877B2

  公开（公告）日：2015-05-19
• Modification of agonist binding moiety in hybrid derivative 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-1-ol/-2-amino versions: Impact on functional activity and selectivity for dopamine D2/D3 receptors
  作者：Bhaskar Gopishetty、Suhong Zhang、Prashant S. Kharkar、Tamara Antonio、Maarten Reith、Aloke K. Dutta

  DOI：10.1016/j.bmc.2013.03.059

  日期：2013.6

  The goal of the present study was to explore, in our previously developed hybrid template, the effect of introduction of additional heterocyclic rings (mimicking catechol hydroxyl groups as bioisosteric replacement) on selectivity and affinity for the D-3 versus D-2 receptor. In addition, we wanted to explore the effect of derivatization of functional groups of the agonist binding moiety in compounds developed by us earlier from the hybrid template. Binding affinity (K-i) of the new compounds was measured with tritiated spiperone as the radioligand and HEK-293 cells expressing either D-2 or D-3 receptors. Functional activity of selected compounds was assessed in the GTP gamma S binding assay. In the imidazole series, compound 10a exhibited the highest D-3 affinity whereas the indole derivative 13 exhibited similar high D-3 affinity. Functionalization of the amino group in agonist (+)-9d with different sulfonamides derivatives improved the D-3 affinity significantly with (+)-14f exhibiting the highest affinity. However, functionalization of the hydroxyl and amino groups of 15 and (+)-9d, known agonist and partial agonist, to sulfonate ester and amide in general modulated the affinity. In both cases loss of agonist potency resulted from such derivatization. (C) 2013 Elsevier Ltd. All rights reserved.