ethyl 4-amino-5-propyl-1H-pyrazole-3-carboxylate | 76424-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-amino-5-propyl-1H-pyrazole-3-carboxylate
• CAS: 76424-50-5
• 化学式: C₉H₁₅N₃O₂
• 分子量: 197.237
• InChiKey: UWDSTWOEADSODH-UHFFFAOYSA-N

物化性质

• 沸点：
  383.1±42.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  81
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-amino-5-propyl-1H-pyrazole-3-carboxylate 在 氨 、 sodium ethanolate 、 三乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 72.5h， 生成 5-(2-乙氧基苯基)-3-丙基-1,6-二氢-7H-吡唑并[4,3-d]嘧啶-7-酮
  参考文献：
  名称：

  Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 1. Sildenafil analogs

  摘要：

  Parasitic diseases, such as African sleeping sickness, have a significant impact on the health and wellbeing in the poorest regions of the world. Pragmatic drug discovery efforts are needed to find new therapeutic agents. In this Letter we describe target repurposing efforts focused on trypanosomal phosphodiesterases. We outline the synthesis and biological evaluation of analogs of sildenafil (1), a human PDE5 inhibitor, for activities against trypanosomal PDEB1 (TbrPDEB1). We find that, while low potency analogs can be prepared, this chemical class is a sub-optimal starting point for further development of TbrPDE inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.119
• 作为产物：
  描述：

  在 盐酸 、 indium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 ethyl 4-amino-5-propyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Novel 6-N-arylcarboxamidopyrazolo[4,3-d]pyrimidin-7-one derivatives as potential anti-cancer agents

  摘要：

  A novel series of 3,5,6-trisubstituted pyrazolo[4,3-d] pyrimidin-7-one derivatives, especially 6-N-arylcarboxamidopyrazolo[4,3-d]pyrimidin-7-ones were synthesized and evaluated for their in vitro anticancer activities against various human cancer cell lines. The inhibitory activities for several kinases have also been tested. The prepared compounds library exhibited significant anticancer activity towards HT-29 colon and DU-145 prostate cancer cell lines. The structure-activity relationships of the 6-N-arylcarboxamidopyrazolo[4,3-d] pyrimidin-7-one scaffold at R-1, R-2 and R-3 have been elucidated. Among the synthesized compounds, 12b was the most active compound with GI(50) value of 0.44 mu M and 1.07 mu M against HT-29 and DU-145 cell lines, respectively, and 13a was the most selective compound towards colon cancer cell line. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.01.029

文献信息

• 一种胺基吡唑化合物的制备方法及用途
  申请人：山东特珐曼药业有限公司

  公开号：CN117777023A

  公开（公告）日：2024-03-29

  本发明公开了一种胺基吡唑化合物的制备方法及使用其制备西地那非的方法。所述胺基吡唑化合物如式I所示。式I化合物是以工业化学品2‑戊酮为原料制备得到，可用于合成5型磷酸二酯酶(PDE5)的选择性抑制剂西地那非。本发明方法具有原材料易得、操作简便，而且避免了硝化反应，从技术源头上避免了硝化反应所伴有的安全隐患以及大量硝化废液造成的环保压力，适合于开发为绿色可持续性的西地那非原料药生产工艺。#imgabs0#
• Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 1. Sildenafil analogs
  作者：Cuihua Wang、Trent D. Ashton、Alden Gustafson、Nicholas D. Bland、Stefan O. Ochiana、Robert K. Campbell、Michael P. Pollastri

  DOI：10.1016/j.bmcl.2012.01.119

  日期：2012.4

  Parasitic diseases, such as African sleeping sickness, have a significant impact on the health and wellbeing in the poorest regions of the world. Pragmatic drug discovery efforts are needed to find new therapeutic agents. In this Letter we describe target repurposing efforts focused on trypanosomal phosphodiesterases. We outline the synthesis and biological evaluation of analogs of sildenafil (1), a human PDE5 inhibitor, for activities against trypanosomal PDEB1 (TbrPDEB1). We find that, while low potency analogs can be prepared, this chemical class is a sub-optimal starting point for further development of TbrPDE inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.
• Novel 6-N-arylcarboxamidopyrazolo[4,3-d]pyrimidin-7-one derivatives as potential anti-cancer agents
  作者：Vani N. Devegowda、Jung Hyun Kim、Ki-Cheol Han、Eun Gyeong Yang、Hyunah Choo、Ae Nim Pae、Ghilsoo Nam、Kyung Il Choi

  DOI：10.1016/j.bmcl.2010.01.029

  日期：2010.3

  A novel series of 3,5,6-trisubstituted pyrazolo[4,3-d] pyrimidin-7-one derivatives, especially 6-N-arylcarboxamidopyrazolo[4,3-d]pyrimidin-7-ones were synthesized and evaluated for their in vitro anticancer activities against various human cancer cell lines. The inhibitory activities for several kinases have also been tested. The prepared compounds library exhibited significant anticancer activity towards HT-29 colon and DU-145 prostate cancer cell lines. The structure-activity relationships of the 6-N-arylcarboxamidopyrazolo[4,3-d] pyrimidin-7-one scaffold at R-1, R-2 and R-3 have been elucidated. Among the synthesized compounds, 12b was the most active compound with GI(50) value of 0.44 mu M and 1.07 mu M against HT-29 and DU-145 cell lines, respectively, and 13a was the most selective compound towards colon cancer cell line. (C) 2010 Published by Elsevier Ltd.