1-(2-(trifluoromethyl)phenyl)-1H-pyrazole-4-carbaldehyde | 1329422-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-(trifluoromethyl)phenyl)-1H-pyrazole-4-carbaldehyde
• 英文别名: 1-[2-(Trifluoromethyl)phenyl]pyrazole-4-carbaldehyde；1-[2-(trifluoromethyl)phenyl]pyrazole-4-carbaldehyde
• CAS: 1329422-97-0
• 化学式: C₁₁H₇F₃N₂O
• 分子量: 240.185
• InChiKey: DDUZTGREOSAGEM-UHFFFAOYSA-N

物化性质

• 沸点：
  323.2±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-(trifluoromethyl)phenyl)-1H-pyrazole-4-carbaldehyde 在 sodium azide 、 羟胺 、 氯化铵 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 108.0h， 生成 5-(1-(2-(trifluoromethyl)phenyl)-1H-pyrazol-4-yl)-1H-tetrazole
  参考文献：
  名称：

  新吡唑化合物的设计，合成和药理评估。

  摘要：

  目的这项研究调查了新型吡唑化合物LQFM011（5），LQFM043（6）和LQFM044（7）的抗伤害感受和抗炎作用，以及其作用机制和急性体外毒性。 主要方法使用乙酸诱导的腹部扭体试验，福尔马林诱导的疼痛试验和Randall-Selitto试验评估抗伤害感受活性。使用角叉菜胶诱导的爪水肿和胸膜炎模型评估抗炎活性；评估细胞迁移，肿瘤坏死因子α（TNF-α）和髓过氧化物酶（MPO）酶的活性。此外，还具有体外抑制磷脂酶A2（PLA2）并与PLA2对接的能力。通过中性红吸收试验评估小鼠的急性口服全身毒性。 主要发现合成的化合物（5 - 7），在70，140或280通过管饲法（PO）递送微摩尔/千克，减少乙酸诱导的扭体的数量; 这三种化合物（280 µmol / kg po）在福尔马林测试的第一和第二阶段减少了舔爪时间，并在Randall-Selitto测试中降低了伤害感受性阈值变化。此外，该剂量

  DOI：

  10.1007/s10787-020-00727-1
• 作为产物：
  描述：

  2-(三氟甲基)苯基肼 在 盐酸 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 1-(2-(trifluoromethyl)phenyl)-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Discovery and optimisation studies of antimalarial phenotypic hits

  摘要：

  There is an urgent need for the development of new antimalarial compounds. As a result of a phenotypic screen, several compounds with potent activity against the parasite Plasmodium falciparum were identified. Characterization of these compounds is discussed, along with approaches to optimise the physicochemical properties. The in vitro antimalarial activity of these compounds against P. falciparum K1 had EC50 values in the range of 0.09-29 mu M, and generally good selectivity (typically >100-fold) compared to a mammalian cell line (L6). One example showed no significant activity against a rodent model of malaria, and more work is needed to optimise these compounds. (C) 2015 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2015.08.044

文献信息

• Complete assignment of NMR data of 22 phenyl-1<i>H</i> -pyrazoles' derivatives
  作者：Aline Lima de Oliveira、Carlos Henrique Alves de Oliveira、Laura Maia Mairink、Francine Pazini、Ricardo Menegatti、Luciano Morais Lião

  DOI：10.1002/mrc.2773

  日期：2011.8

  Complete assignment of 1H and 13C NMR chemical shifts and J(1H/1H and 1H/19F) coupling constants for 22 1‐phenyl‐1H‐pyrazoles' derivates were performed using the concerted application of 1H 1D and 1H, 13C 2D gs‐HSQC and gs‐HMBC experiments. All 1‐phenyl‐1H‐pyrazoles' derivatives were synthesized as described by Finar and co‐workers. The formylated 1‐phenyl‐1H‐pyrazoles' derivatives were performed under

  22 1-苯基-1H-吡唑衍生物的 1H 和 13C NMR 化学位移和 J（1H/1H 和 1H/19F）耦合常数的完整分配是使用 1H 1D 和 1H、13C 2D gs-HSQC 的协同应用完成的和 gs-HMBC 实验。所有 1-苯基-1H-吡唑衍生物均按照Finar 及其同事的描述合成。甲酰化 1-苯基-1H-吡唑衍生物在达夫条件下进行。版权所有 © 2011 John Wiley & Sons, Ltd.
• Discovery and Structure–Activity Relationships of Pyrrolone Antimalarials
  作者：Dinakaran Murugesan、Alka Mital、Marcel Kaiser、David M. Shackleford、Julia Morizzi、Kasiram Katneni、Michael Campbell、Alan Hudson、Susan A. Charman、Clive Yeates、Ian H. Gilbert

  DOI：10.1021/jm400009c

  日期：2013.4.11

  In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 similar to 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.
• Chemoselective and Regiospecific Formylation of 1-Phenyl-1<i>H</i>-pyrazoles Through the Duff Reaction
  作者：C. H. A. de Oliveira、L. M. Mairink、F. Pazini、L. M. Lião、A. L. de Oliveira、C. Viegas、V. de Oliveira、L. C. Cunha、F. G. F. Oliveira、J. L. Paz、M. N. Eberlin、Ricardo Menegatti

  DOI：10.1080/00397911.2012.657764

  日期：2013.6.18

  The synthesis of formylated 1-phenyl-1H-pyrazole derivatives under the Duff reaction conditions is reported. Our results indicate that 1-phenyl-1H-pyrazole systems containing electron-withdrawing and electron-donating substituents at the phenyl moiety react under the Duff reaction conditions to furnish formylated derivatives in good yields.
• Discovery and optimisation studies of antimalarial phenotypic hits
  作者：Alka Mital、Dinakaran Murugesan、Marcel Kaiser、Clive Yeates、Ian H. Gilbert

  DOI：10.1016/j.ejmech.2015.08.044

  日期：2015.10

  There is an urgent need for the development of new antimalarial compounds. As a result of a phenotypic screen, several compounds with potent activity against the parasite Plasmodium falciparum were identified. Characterization of these compounds is discussed, along with approaches to optimise the physicochemical properties. The in vitro antimalarial activity of these compounds against P. falciparum K1 had EC50 values in the range of 0.09-29 mu M, and generally good selectivity (typically >100-fold) compared to a mammalian cell line (L6). One example showed no significant activity against a rodent model of malaria, and more work is needed to optimise these compounds. (C) 2015 The Authors. Published by Elsevier Masson SAS.
• Design, synthesis and pharmacological assessment of new pyrazole compounds
  作者：Jordana C. Oliveria、Daiany P. B. Silva、Iziara F. Florentino、Lidya C. da Silva、Germán Sanz、Boniek G. Vaz、Francine Pazini、Flávio S. de Carvalho、Luciano M. Lião、Thaís Rosa Marques dos Santos、Marize C. Valadares、Elson A. Costa、Fernanda Cristina Alcantara dos Santos、Bianca Villavicencio、Hugo Verli、Ricardo Menegatti

  DOI：10.1007/s10787-020-00727-1

  日期：2020.8

  AimsThis study investigated the antinociceptive and anti-inflammatory effects of new pyrazole compounds LQFM011(5), LQFM043(6) and LQFM044(7) as well as the mechanisms of action and acute in vitro toxicity. Main methodsThe antinociceptive activity was evaluated using the acetic acid-induced abdominal writhing test, formalin-induced pain test and the Randall–Selitto test. The anti-inflammatory activity

  目的这项研究调查了新型吡唑化合物LQFM011（5），LQFM043（6）和LQFM044（7）的抗伤害感受和抗炎作用，以及其作用机制和急性体外毒性。 主要方法使用乙酸诱导的腹部扭体试验，福尔马林诱导的疼痛试验和Randall-Selitto试验评估抗伤害感受活性。使用角叉菜胶诱导的爪水肿和胸膜炎模型评估抗炎活性；评估细胞迁移，肿瘤坏死因子α（TNF-α）和髓过氧化物酶（MPO）酶的活性。此外，还具有体外抑制磷脂酶A2（PLA2）并与PLA2对接的能力。通过中性红吸收试验评估小鼠的急性口服全身毒性。 主要发现合成的化合物（5 - 7），在70，140或280通过管饲法（PO）递送微摩尔/千克，减少乙酸诱导的扭体的数量; 这三种化合物（280 µmol / kg po）在福尔马林测试的第一和第二阶段减少了舔爪时间，并在Randall-Selitto测试中降低了伤害感受性阈值变化。此外，该剂量