5-萘-2-基-1H-吡唑-3-羧酸 | 164295-94-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-萘-2-基-1H-吡唑-3-羧酸
• 中文别名: 3-(2-萘基)-1H-吡唑-5-羧酸；5-萘-2-基-2H-吡唑-3-甲酸；5-(2-萘基)-2H-吡唑-3-甲酸
• 英文名称: 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylic acid
• 英文别名: 5-naphthalen-2-yl-1H-pyrazole-3-carboxylic acid；3-naphthalen-2-yl-1H-pyrazole-5-carboxylic acid
• CAS: 164295-94-7
• 化学式: C₁₄H₁₀N₂O₂
• mdl: MFCD03030348
• 分子量: 238.246
• InChiKey: JQMUXXNJOLCBJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  558.8±38.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  5-萘-2-基-1H-吡唑-3-羧酸 在 肼 作用下， 以 乙醇 、 水 为溶剂， 生成 5-naphthalen-2-yl-1H-pyrazol-3-carboxylic acid hydrazide
  参考文献：
  名称：

  [EN] SPHINGOSINE KINASE INHIBITORS
  [FR] INHIBITEURS DE SPHINGOSINE KINASE

  摘要：

  公开号：

  WO2003105840A3
• 作为产物：
  描述：

  4-(naphthalen-2-yl)-2,4-dioxobutanoic acid 在 一水合肼 、 溶剂黄146 作用下， 以82%的产率得到5-萘-2-基-1H-吡唑-3-羧酸
  参考文献：
  名称：

  5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII

  摘要：

  Inhibitory activity of a congeneric set of 23 phenyl-substituted 5-phenyl-pyrazole-3-carboxylic acids toward human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II, IX and XII was evaluated by a stopped-flow CO2 hydrase assay. These compounds exerted a clear, selective inhibition of hCA IX and XII over hCAI and II, with Ki in two to one digit micromolar concentrations (4-50 mu M). Derivatives bearing bulkier substituents in para-position of the phenyl ring inhibited hCA XII at one-digit micromolar concentrations, while derivatives having alkyl substituents in both ortho-and meta-positions inhibited hCA IX with Kis ranging between 5 and 25 mu M. Results of docking experiments offered a rational explanation on the selectivity of these compounds toward CA IX and XII, as well as on the substitution patterns leading to best CA IX or CA XII inhibitors. By examining the active sites of these four isoforms with GRID generated molecular-interaction fields, striking differences between hCA XII and the other three isoforms were observed. The field of hydrophobic probe (DRY) appeared significantly different in CA XII active site, comparing to other three isoforms studied. To the best of our knowledge such an observation was not reported in literature so far. Considering the selectivity of these carboxylates towards membrane-associated over cytosolic CA isoforms, the title compounds could be useful for the development of isoform-specific non-sulfonamide CA inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.052

文献信息

• (1,4-Diaza-bicyclo[3.2.2]non-6-en-4-yl)-heterocyclyl-methanone Ligands for Nicotinic Acetylcholine Receptors, Useful for the Treatment of Disease
  申请人：Herbert Brian

  公开号：US20100298306A1

  公开（公告）日：2010-11-25

  The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds, which act as ligands for the α7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof. The novel compounds include compounds of formula I: wherein X, R 1 , and R 2 are as herein defined.

  本发明一般涉及尼古丁乙酰胆碱受体（nACh受体）配体领域，nACh受体的激活以及与缺陷或功能障碍的尼古丁乙酰胆碱受体相关的疾病状况的治疗，特别是大脑的疾病状况。此外，本发明涉及新型化合物，其作为α7 nACh受体亚型的配体，制备这种化合物的方法，含有这种化合物的组合物以及其使用方法。这些新型化合物包括I式化合物，其中X，R1和R2的定义如本文所述。
• Sphingosine kinase inhibitors
  申请人：The Pennsylvania State University Research Foundation

  公开号：US20040034075A1

  公开（公告）日：2004-02-19

  The invention relates to compounds, compositions and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, autoimmune disease, inflammatory disease, or allergy.

  本发明涉及用于抑制鞘氨醇激酶和治疗或预防过度增殖性疾病、自身免疫性疾病、炎症性疾病或过敏症的化合物、组合物和方法。
• [EN] (1,4-DIAZA-BICYCLO[3.2.2]NON-6-EN-4-YL)-HETEROCYCLYL-METHANONE LIGANDS FOR NICOTINIC ACETYLCHOLINE RECEPTORS, USEFUL FOR THE TREATMENT OF DISEASE<br/>[FR] LIGANDS (1,4-DIAZA-BICYCLO[3.2.2]NON-6-ÈN-4-YL)-HÉTÉROCYCLYL-MÉTHANONE POUR LES RÉCEPTEURS NICOTINIQUES D'ACÉTYLCHOLINE, UTILES POUR LE TRAITEMENT D'UNE MALADIE
  申请人：MEMORY PHARM CORP

  公开号：WO2009055437A9

  公开（公告）日：2009-07-23
• Synthesis and bioactivity of sphingosine kinase inhibitors and their novel aspirinyl conjugated analogs
  作者：Arun K. Sharma、Ugir Hossain Sk、Melissa A. Gimbor、Jeremy A. Hengst、Xujun Wang、Jong Yun、Shantu Amin

  DOI：10.1016/j.ejmech.2010.06.005

  日期：2010.9

  Sphingosine kinase (SphK) is a lipid kinase with oncogenic activity, and SphK inhibitors (SKIS) are known for their anti-cancer activity. Here, we report highly efficient syntheses of SKIs and their aspirinyl (Asp) analogs. Both SKIs and their Asp analogs were highly cytotoxic towards multiple human cancer cell lines: in several cases the Asp analogs were up to three times more effective. Furthermore, they were equally potent inhibitors of SphK. The pharmacokinetic study indicated that SKI-I-Asp cleaved efficiently to form SKI-I and the half-life of SKI-I was increased from similar to 7 h in SKI-I to similar to 10 h in SKI-I-Asp injected mice, thereby prolonging its effect. In summary, the Asp-conjugated SKIs seem to be promising prodrugs of SKIs where delivery in vivo remains a problem. (C) 2010 Elsevier Masson SAS. All rights reserved.
• (1,4-DIAZA-BICYCLO[3.2.2]NON-6-EN-4-YL)-HETEROCYCLYL-METHANONE LIGANDS FOR NICOTINIC ACETYLCHOLINE RECEPTORS, USEFUL FOR THE TREATMENT OF DISEASE
  申请人：Memory Pharmaceuticals Corporation

  公开号：EP2212321A2

  公开（公告）日：2010-08-04