2-Hydroxy-2-phenyl-nonanoic acid | 22986-75-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Hydroxy-2-phenyl-nonanoic acid
• 英文别名: 2-Hydroxy-2-phenylnonanoic acid
• CAS: 22986-75-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: KRXXHKSNTQTHSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙醇 、 2-Hydroxy-2-phenyl-nonanoic acid 在 硫酸 作用下， 反应 12.0h， 以86%的产率得到2-Hydroxy-2-phenyl-nonanoic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Studies for Hydantoins and Analogues as Voltage-Gated Sodium Channel Ligands

  摘要：

  We previously developed a preliminary 3-D QSAR model for the binding of 14 hydantoins to the neuronal voltage-gated sodium channel; this model was successful in designing,an effective non-hydantoin ligand. To further understand structural features that result in optimum binding. here we synthesized a variety of compound classes and evaluated their binding affinities to the neuronal voltage-gated sodium channel using the [H-3]-batrachotoxinin A 20-a-benzoate ([H-3]BTX-B) binding assay. In order to understand the importance of the hydantoin ring for good sodium channel binding, related non-hydantoins such as hydroxy amides, oxazolidinediones, hydroxy acids, and amino acids were included. Two major conclusions were drawn: (1) The hydantoin ring is not critical for compounds with long alkyl side chains, but it is important for compounds with shorter side chains. (2) Relative to Khodorov's pharmacophore. which contains two hydrophobic regions, a third hydrophobic region may enhance binding to provide nanomolar inhibitors.

  DOI：

  10.1021/jm040077o
• 作为产物：
  描述：

  2-Hydroxy-2-phenylnonanenitrile 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2-Hydroxy-2-phenyl-nonanoic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Studies for Hydantoins and Analogues as Voltage-Gated Sodium Channel Ligands

  摘要：

  We previously developed a preliminary 3-D QSAR model for the binding of 14 hydantoins to the neuronal voltage-gated sodium channel; this model was successful in designing,an effective non-hydantoin ligand. To further understand structural features that result in optimum binding. here we synthesized a variety of compound classes and evaluated their binding affinities to the neuronal voltage-gated sodium channel using the [H-3]-batrachotoxinin A 20-a-benzoate ([H-3]BTX-B) binding assay. In order to understand the importance of the hydantoin ring for good sodium channel binding, related non-hydantoins such as hydroxy amides, oxazolidinediones, hydroxy acids, and amino acids were included. Two major conclusions were drawn: (1) The hydantoin ring is not critical for compounds with long alkyl side chains, but it is important for compounds with shorter side chains. (2) Relative to Khodorov's pharmacophore. which contains two hydrophobic regions, a third hydrophobic region may enhance binding to provide nanomolar inhibitors.

  DOI：

  10.1021/jm040077o

文献信息

• NA CHANNELS, DISEASE, AND RELATED ASSAYS AND COMPOSITIONS
  申请人：Brown Milton L.

  公开号：US20110230442A1

  公开（公告）日：2011-09-22

  Disclosed are molecules and their synthesis, for use in blocking gated ion channels such as voltage-gated sodium channels (VGSCs) and prostate voltage sodium channels (PVSCs). These inhibitors have superior blocking efficacy, for instance in displacing the radioligand [ 3 H]-Batrachotoxin-B ([ 3 H]-BTX-B) that binds to site 2 of a VGSC. The molecules of the invention comprise a moiety which increases the binding affinity of molecules for the protein binding site in prostate cancer cells (PCs), and which is also fluorescent. In one embodiment the invention molecules are an inhibition system that can be used to target over-abundant or hyperactive VGSCs selectively in pain, epilepsy or prostate cancer, inhibiting the proliferation of PCs. The fluorescent moiety also facilitates screening, tracking, and pharmacodynamic studies of the drug in a biological system both in vitro and in vivo.

  本发明涉及分子及其合成，用于阻断门控离子通道，例如电压门控钠通道（VGSC）和前列腺电压钠通道（PVSC）。这些抑制剂具有卓越的阻断效力，例如在取代结合到VGSC的位点2的放射性配体[3H]-Batrachotoxin-B ([3H]-BTX-B)方面。本发明的分子包括一个基团，增加分子对前列腺癌细胞（PC）中蛋白质结合位点的结合亲和力，并且也是荧光的。在一种实施方式中，本发明的分子是一种抑制系统，可用于选择性地靶向过度丰富或过度活跃的VGSC，从而抑制疼痛、癫痫或前列腺癌的PC的增殖。荧光基团还有助于在体外和体内生物系统中筛选、跟踪和药效学研究药物。
• MASHEVSKAYA M. S.; VAXRIN M. I., IZV. VUZOV. XIMIYA I XIM. TEXNOL., 1979, 22, HO 11, 1323-1326
  作者：MASHEVSKAYA M. S.、 VAXRIN M. I.

  DOI：——

  日期：——
• KARAVANOV N. A.; PAVLOVA N. N.; LAPKIN I. I., ZH. ORGAN. XIMII, 1977, 13, HO 12, 2547-2549
  作者：KARAVANOV N. A.、 PAVLOVA N. N.、 LAPKIN I. I.

  DOI：——

  日期：——
• US8816095B2
  申请人：——

  公开号：US8816095B2

  公开（公告）日：2014-08-26
• Synthesis and Structure−Activity Relationship Studies for Hydantoins and Analogues as Voltage-Gated Sodium Channel Ligands
  作者：Congxiang Zha、George B. Brown、Wayne J. Brouillette

  DOI：10.1021/jm040077o

  日期：2004.12.1

  We previously developed a preliminary 3-D QSAR model for the binding of 14 hydantoins to the neuronal voltage-gated sodium channel; this model was successful in designing,an effective non-hydantoin ligand. To further understand structural features that result in optimum binding. here we synthesized a variety of compound classes and evaluated their binding affinities to the neuronal voltage-gated sodium channel using the [H-3]-batrachotoxinin A 20-a-benzoate ([H-3]BTX-B) binding assay. In order to understand the importance of the hydantoin ring for good sodium channel binding, related non-hydantoins such as hydroxy amides, oxazolidinediones, hydroxy acids, and amino acids were included. Two major conclusions were drawn: (1) The hydantoin ring is not critical for compounds with long alkyl side chains, but it is important for compounds with shorter side chains. (2) Relative to Khodorov's pharmacophore. which contains two hydrophobic regions, a third hydrophobic region may enhance binding to provide nanomolar inhibitors.