ethyl 1-ethyl-4-nitro-1H-pyrazole-5-carboxylate | 1352200-79-3

• 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 1-ethyl-4-nitro-1H-pyrazole-5-carboxylate
• 英文别名: Ethyl 2-ethyl-4-nitropyrazole-3-carboxylate
• CAS: 1352200-79-3
• 化学式: C₈H₁₁N₃O₄
• 分子量: 213.193
• InChiKey: YQLUTWUOVOGRDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-ethyl-4-nitro-1H-pyrazole-5-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 反应 22.0h， 以90.7%的产率得到ethyl 4-amino-1-ethyl-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of 1-ethylpyrazole-3-carboxamide compounds as novel hypoxia-inducible factor (HIF)-1 inhibitors

  摘要：

  Hypoxia-inducible factor (HIF)-1 is well known as a promising target for cancer chemotherapy. By screening an in-house chemical library using a hypoxia-responsive luciferase reporter gene assay, we identified CLB-016 (1) containing 1-ethylpyrazole-3-carboxamide as a HIF-1 inhibitor (IC50 = 19.1 mu M). In a subsequent extensive structure-activity relationship (SAR) study, we developed compound 11Ae with an IC50 value of 8.1 mu M against HIF-1-driven luciferase activity. Compounds 1 and 11Ae were shown to significantly suppress the HIF-1-mediated hypoxia response, including carbonic anhydrase IX (CAIX) gene expression and migration of human sarcoma HT1080 cells. These results revealed 1-ethylpyrazole-3-carboxamide as a novel scaffold to develop promising anti-cancer drugs targeting the HIF-1 signaling pathway. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.038
• 作为产物：
  描述：

  碘乙烷 、 4-硝基吡唑-3-甲酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 1-ethyl-4-nitro-1H-pyrazole-5-carboxylate 、 ethyl 1-ethyl-4-nitro-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Collaborative Virtual Screening Identifies a 2-Aryl-4-aminoquinazoline Series with Efficacy in an In Vivo Model of Trypanosoma cruzi Infection

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c00775

文献信息

• NITROGEN CONTAINING HETEROARYL COMPOUNDS
  申请人：Bleicher Konrad

  公开号：US20110306589A1

  公开（公告）日：2011-12-15

  The invention is concerned with novel nitrogen-containing heteroaryl compounds of formula (I) wherein A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit PDE10A and can be used as therapeutics.

  这项发明涉及一种新颖的含氮杂环芳基化合物，其化学式为（I），其中A1、A2、R1、R2、R3、R4、R5和R6如描述和索赔中所定义，并且其生理上可接受的盐和酯。这些化合物抑制PDE10A并可用作治疗药物。
• [EN] NITROGEN CONTAINING HETEROARYL COMPOUNDS<br/>[FR] COMPOSÉS HÉTÉROARYLES CONTENANT DE L'AZOTE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011154327A1

  公开（公告）日：2011-12-15

  The invention is concerned with novel nitrogen-containing heteroaryl compounds of formula (I) wherein A1, A2, (a), R1, R2, R3, R4, R5 and R6 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit PDE10A and can be used as medicaments.

  这项发明涉及一种新颖的含氮杂环化合物，其化学式为（I），其中A1、A2、（a）、R1、R2、R3、R4、R5和R6的定义如描述和索赔中所述，以及其生理上可接受的盐和酯。这些化合物抑制PDE10A，可用作药物。
• Regioselective synthesis of N1-substituted-4-nitropyrazole-5-carboxylates <i>via</i> the cyclocondensation of ethyl 4-(dimethylamino)-3-nitro-2-oxobut-3-enoate with substituted hydrazines
  作者：Rulin Zhao、Zhenqiu Hong、Bei Wang、James Kempson、Lyndon Cornelius、Jianqing Li、Yi-Xin Li、Arvind Mathur

  DOI：10.1039/d2ob02006h

  日期：——

  A simple and expeditious method for the regioselective synthesis of N1-substituted-4-nitropyrazole-5-carboxylates was developed. The method involves cyclocondensation of ethyl 4-(dimethylamino)-3-nitro-2-oxobut-3-enoate with a series of monosubstituted hydrazines to give N1-substituted-4-nitropyrazole-5-carboxylates with excellent regioselectivity and good yields. Solvent effects on regioselectivity

  开发了一种用于区域选择性合成 N1-substituted-4-nitropyrazole-5-carboxylates 的简单快捷的方法。该方法涉及 4-(二甲基氨基)-3-硝基-2-氧代丁-3-烯酸乙酯与一系列单取代肼的环化反应，得到 N1-取代的-4-硝基吡唑-5-羧酸酯，具有出色的区域选择性和良好的产率。检测了溶剂对环缩合区域选择性的影响。
• US8623866B2
  申请人：——

  公开号：US8623866B2

  公开（公告）日：2014-01-07
• US8703768B2
  申请人：——

  公开号：US8703768B2

  公开（公告）日：2014-04-22