5-(3-甲氧基苯基)-1H-吡唑-3-羧酸乙酯 | 723339-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(3-甲氧基苯基)-1H-吡唑-3-羧酸乙酯
• 英文名称: ethyl 3-(3-methoxyphenyl)-1H-pyrazole-5-carboxylate
• CAS: 723339-63-7
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: VBAFPHAPTHNKIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-甲氧基苯基)-1H-吡唑-3-羧酸乙酯 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 5-(3-甲氧基苯基)-1h-吡唑-3-羧酸
  参考文献：
  名称：

  某些新型3-苯基-N- [3-（4-苯基哌嗪-1基）丙基] -1 H-吡唑-5-羧酰胺衍生物的合成及抗炎活性

  摘要：

  合成了一系列新的3-苯基-N- [3-（4-苯基哌嗪-1基）丙基] -1H-吡唑-5-羧酰胺衍生物，并用角叉菜胶诱导的大鼠爪水肿模型研究了它们的抗炎活性。体内。发现所有合成的化合物都是有效的抗炎药。

  DOI：

  10.1016/j.bmcl.2011.05.105
• 作为产物：
  描述：

  ethyl 4-(3-methoxyphenyl)-2,4-dioxobutanoate 在 溶剂黄146 、 肼 作用下， 反应 12.0h， 生成 5-(3-甲氧基苯基)-1H-吡唑-3-羧酸乙酯
  参考文献：
  名称：

  某些新型3-苯基-N- [3-（4-苯基哌嗪-1基）丙基] -1 H-吡唑-5-羧酰胺衍生物的合成及抗炎活性

  摘要：

  合成了一系列新的3-苯基-N- [3-（4-苯基哌嗪-1基）丙基] -1H-吡唑-5-羧酰胺衍生物，并用角叉菜胶诱导的大鼠爪水肿模型研究了它们的抗炎活性。体内。发现所有合成的化合物都是有效的抗炎药。

  DOI：

  10.1016/j.bmcl.2011.05.105

文献信息

• “On water” synthesis of N-unsubstituted pyrazoles: semicarbazide hydrochloride as an alternative to hydrazine for preparation of pyrazole-3-carboxylate derivatives and 3,5-disubstituted pyrazoles
  作者：Violeta Marković、Milan D. Joksović

  DOI：10.1039/c4gc02028f

  日期：——

  A green, simple and highly efficient method for the synthesis of pyrazole-3-carboxylates and 3,5-disubstituted pyrazoles by cyclization of 4-aryl(hetaryl, alkyl)-2,4-diketoesters and 1,3-diketones with semicarbazide hydrochloride under “on water” conditions has been developed. This method also does not require toxic hydrazine and product purification, eliminating the use of toxic liquid chemicals.

  一种绿色，简单且高效的方法，通过用氨基脲盐酸盐将4-芳基（杂芳基，烷基）-2,4-二酮酸酯和1,3-二酮环化，合成吡唑-3-羧酸酯和3,5-二取代的吡唑在“水上”条件下已经开发出来。该方法也不需要毒性肼和产物纯化，从而消除了对有毒液体化学物质的使用。
• Acyclic pyrazole compounds for the inhibition of mitogen activated protein kinase-activated protein kinase-2
  申请人：Pharmacia Corporation

  公开号：US20040152739A1

  公开（公告）日：2004-08-05

  Compounds are described which inhibit mitogen activated protein kinase-activated protein kinase-2 (MK-2). Methods of making such compounds are described, as well as a method of using them for the inhibition of MK-2, and for the prevention or treatment of a disease or disorder that is mediated by TNF&agr;, where the method involves administering to the subject an MK-2 inhibiting compound of the present invention. Pharmaceutical compositions and kits which contain the present MK-2 inhibiting compounds are also described.

  本文描述了一些抑制有丝分裂原活化蛋白激酶激活蛋白激酶-2（MK-2）的化合物。文中还描述了制备这些化合物的方法，以及使用它们抑制MK-2，预防或治疗由TNFα介导的疾病或障碍的方法，其中该方法涉及向受试者注射本发明的MK-2抑制化合物。文中还描述了包含本MK-2抑制化合物的制药组合物和试剂盒。
• PYRAZOLE COMPOUNDS AS PROTEIN KINASE INHIBITORS
  申请人：Hanau E. Cathleen

  公开号：US20080113971A1

  公开（公告）日：2008-05-15

  Compounds are described which inhibit mitogen activated protein kinase-activated protein kinase-2 (MK-2). Methods of making such compounds are described, as well as a method of using them for the inhibition of MK-2, and for the prevention or treatment of a disease or disorder that is mediated by TNFα, where the method involves administering to the subject an MK-2 inhibiting compound of the present invention. Pharmaceutical compositions and kits which contain the present MK-2 inhibiting compounds are also described.

  本发明描述了一种抑制有丝分裂原活化蛋白激酶激活蛋白激酶-2（MK-2）的化合物。本发明还描述了制备这种化合物的方法，以及一种使用它们来抑制MK-2并预防或治疗由TNFα介导的疾病或障碍的方法，其中该方法涉及向受试者注射本发明的MK-2抑制化合物。本发明还描述了含有本MK-2抑制化合物的药物组合物和试剂盒。
• Synthesis and cytotoxicity evaluation of 1-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-3-aryl-1H-pyrazole-5-carboxylic acid derivatives
  作者：Lingaiah Nagarapu、Hanmant K. Gaikwad、Kartheeka Sarikonda、Jhansi Mateti、Rajashaker Bantu、P.S. Raghu、Krishna Madhuri Manda、Shasi Vardhan Kalvendi

  DOI：10.1016/j.ejmech.2010.07.004

  日期：2010.11

  Several novel molecules, 1-(3'-(9H-carbazol-4-yloxy)-2'-hydroxypropyl)-3-aryl-1H-pyrazole-5-carboxylic acid derivatives 3a-g were synthesized and screened to evaluate their cytotoxicity against cancer cells in vitro. The compounds 3a-g has been prepared by the reaction of ethyl 3-aryl-1H-pyrazole-5-carboxylate with 4-oxiranylmethoxy-9H-carbazole in moderate to excellent yields. The cytotoxicity of synthesized compounds was evaluated by a SRB (sulforhodamine B) assay against cancer cell such as SK-N-SH human neuroblastoma (NB), human A549 lung carcinoma, human breast cancer MCF-7 cell lines. The results showed that seven compounds can suppress SK-N-SH tumor cancer cell growth. Among them, compound 3d was the most effective small molecule in inhibiting SK-N-SH cell growth. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis, Structure-Activity Relationship, and Pharmacophore Modeling Studies of Pyrazole-3-Carbohydrazone Derivatives as Dipeptidyl Peptidase IV Inhibitors
  作者：Deyan Wu、Fangfang Jin、Weiqiang Lu、Jin Zhu、Cui Li、Wei Wang、Yun Tang、Hualiang Jiang、Jin Huang、Guixia Liu、Jian Li

  DOI：10.1111/j.1747-0285.2012.01365.x

  日期：2012.6

  Type 2 diabetes mellitus (T2DM) is a metabolic disease and a major challenge to healthcare systems around the world. Dipeptidyl peptidase IV (DPP‐4), a serine protease, has been rapidly emerging as an effective therapeutic target for the treatment for T2DM. In this study, a series of novel DPP‐4 inhibitors, featuring the pyrazole‐3‐carbohydrazone scaffold, have been discovered using an integrated approach of structure‐based virtual screening, chemical synthesis, and bioassay. Virtual screening of SPECS Database, followed by enzymatic activity assay, resulted in five micromolar or low‐to‐mid‐micromolar inhibitory level compounds (1–5) with different scaffold. Compound 1 was selected for the further structure modifications in considering inhibitory activity, structural variability, and synthetic accessibility. Seventeen new compounds were synthesized and tested with biological assays. Nine compounds (6e, 6g, 6k–l, and 7a–e) were found to show inhibitory effects against DPP‐4. Molecular docking models give rational explanation about structure–activity relationships. Based on eight DPP‐4 inhibitors (1–5, 6e, 6k, and 7d), the best pharmacophore model hypo1 was obtained, consisting of one hydrogen bond donor (HBD), one hydrogen bond acceptor (HBA), and two hydrophobic (HY) features. Both docking models and pharmacophore mapping results are in agreement with pharmacological results. The present studies give some guiding information for further structural optimization and are helpful for future DPP‐4 inhibitors design.