ethyl 5-amino-1-(4-methylphenylsulfonyl)-1H-pyrazole-4-carboxylate | 52793-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-amino-1-(4-methylphenylsulfonyl)-1H-pyrazole-4-carboxylate
• 英文别名: ethyl 5-amino-1-tosyl-1H-pyrazole-4-carboxylate；ethyl 5-amino-1-p-toluenesulfonylpyrazole-4-carboxylate；ethyl 5-amino-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carboxylate；ethyl 5-amino-1-(4-methylphenyl)sulfonylpyrazole-4-carboxylate
• CAS: 52793-45-0
• 化学式: C₁₃H₁₅N₃O₄S
• 分子量: 309.346
• InChiKey: JUHMHPOXZAYYJP-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  510.3±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 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：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-1-(4-methylphenylsulfonyl)-1H-pyrazole-4-carboxylate 在 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 4-(4-Methylphenyl)sulfonyl-2,4,5,11,12-pentazatricyclo[7.4.0.03,7]trideca-1(9),3(7),5-triene-8,10,13-trione
  参考文献：
  名称：

  Synthesis and Chemiluminescence of 1,3-Disubstituted 4-Hydroxypyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones

  摘要：

  Reactions of 1,3-disubstituted 5-aminopyrazole-4-carboxylate derivatives (la-c) with dimethyl acetylenedicarboxylate gave the corresponding dimethyl 1,3-disubstituted 4-hydroxypyrazolo[3,4-b]pyridine-5,6-dicarboxylates (2a-c) which reacted with hydrazine hydrate to give 1,3-disubstituted 4-hydroxy-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones (3a-d). These tricyclic pyridazine derivatives were alternatively synthesized from 4-hydroxypyrrolo[3,4-e] pyrazolo[3,4-b]pyridine-5,7-diones (7a-c) prepared by reactions of 5-aminopyrazoles (1e-g) with 1-methyl-3-methylthio-4-methoxycarbonylmaleimide (5) followed by Gould-Jacacobs reaction. These tricyclic pyridazine derivatives were evaluated for chemiluminescence. 4-Hydroxy-3-methylthio-1-phenyl-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-dione (3d) showed the greatest chemiluminescence intensity in the presence of H2O2 and peroxidase in a solution of phosphate buffer at pH 10.

  DOI：

  10.3987/com-96-s17
• 作为产物：
  描述：

  对甲苯磺酰肼 、 2-氰基-3-乙氧基丙烯酸乙酯 以 乙腈 为溶剂， 反应 6.0h， 以90%的产率得到ethyl 5-amino-1-(4-methylphenylsulfonyl)-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro cytotoxic activity of novel pyrazolo[3,4-d]pyrimidines and related pyrazole hydrazones toward breast adenocarcinoma MCF-7 cell line

  摘要：

  New series of pyrazolo[3,4-d]pyrimidines (7a-e and 13a-d) and pyrazole hydrazones 17a-d were synthesized and evaluated for their antiproliferative activity against human breast adenocarcinoma MCF-7 cell line. Most of the tested compounds exploited potent to moderate growth inhibitory activity, in particular compound 7e exhibited superior potency to the reference drug cisplatin (IC50 = 7.60 and 13.29 mu M, respectively). The antitumor activity of the new compounds was accompanied by significant increase in the activity of superoxide dismutase with concomitant decrease in the activities of catalase and glutathione peroxidase and reduced glutathione level. Accordingly, the overproduction of hydrogen peroxide, nitric oxide and other free radicals allowed reactive oxygen species (ROS)-mediated tumor cells death, as monitored by reduction in the synthesis of protein and nucleic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.036

文献信息

• A CLEAN AND RAPID SYNTHESIS OF 5-AMINOPYRAZOLE-4-CARBOXYLIC ACID ESTERS AND NITRILES USING MONTMORILLONITE K10
  作者：G. Jagath Reddy、S. Sailaja、D. Manjula、K. Srinivasa Rao

  DOI：10.1515/hc.2005.11.5.385

  日期：2005.1

  phosphodiesterase inhibitors, C N S agents, benzodiazepine receptor antagonists. Pyrazole ortho amino esters and nitriles are of immense use in the synthesis of these compounds. They also serve as intermediates in agrochemicals pesticides and in the synthesis o f desamino pyrazole carboxylates and nitriles. V C N R,NHNH 2 + M K 1 0 , I P A

  使用蒙脱石在非均相催化条件下合成了一系列 5-氨基吡唑-4-羧酸酯（4a-0 和腈（5a-f））。引言 吡唑以其解热、镇痛和抗炎等药理特性而闻名。许多据报道，吡唑稠合的双环和三环杂环具有潜在的生物活性，如磷酸二酯酶抑制剂、中枢神经系统药物、苯二氮卓受体拮抗剂。吡唑邻氨基酯和腈在这些化合物的合成中具有巨大的用途。它们也可作为农用化学品的中间体用于合成脱氨基吡唑羧酸盐和腈类 VCNR,NHNH 2 + MK 1 0 , IPA
• A convenient synthesis and molecular modeling study of novel pyrazolo[3,4-<i>d</i>]pyrimidine and pyrazole derivatives as anti-tumor agents
  作者：Ibrahim F. Nassar、Saad R. Atta-Allah、Abdel-Sattar S. Hamad Elgazwy

  DOI：10.3109/14756366.2014.940936

  日期：2015.5.4

  An efficient method to obtain ethyl 5-amino-1-tosyl-1H-pyrazole-4-carboxylate (3) was outlined using condensation reactions of 4-methylbenzenesulfonylhydrazide with (E)-ethyl 2-cyano-3-ethoxyacrylate. The cyclocondensation reaction of this substrate and its hydrazide derivative with urea, thiourea, formamide, formic acid, d-glucose, o-phenylenediamine, 4-dimethylaminobenzaldehyde, anthracene-9-carbaldehyde

  利用4-甲基苯磺酰肼与（E）-2-氰基-3-乙氧基丙烯酸乙酯的缩合反应，概述了获得5-氨基-1-甲苯基-1H-吡唑-4-羧酸乙酯（3）的有效方法。该底物及其酰肼衍生物与尿素，硫脲，甲酰胺，甲酸，d-葡萄糖，邻苯二胺，4-二甲基氨基苯甲醛，蒽-9-甲醛，巯基乙酸和二硫化碳的环缩合反应再与肼的水合物类似物提供系列的吡唑并[3,4-d]嘧啶，吡唑并[3,4-d]恶嗪-4-酮，吡唑-4-葡萄糖苷，4-苯并[d]咪唑，1,3-噻唑烷酮，1,3， 4-恶二唑-2（3H）-硫酮和1,2,4-三唑-5（4H）-硫酮衍生物。化合物3的结构由X射线晶体学数据支持。口服，