5-chloro-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbaldehyde | 957354-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 5-chloro-1-(4-methoxyphenyl)-3-methylpyrazole-4-carbaldehyde
• CAS: 957354-73-3
• 化学式: C₁₂H₁₁ClN₂O₂
• 分子量: 250.685
• InChiKey: MQDHNQRECPEHAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbaldehyde 在 盐酸 、 potassium permanganate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  吡唑哌嗪酰胺杨梅素衍生物的合成及生物活性。

  摘要：

  本文通过酰胺键将药效基团吡唑环和哌嗪环引入天然产物杨梅素结构中，合成了一系列衍生物。使用碳谱和氢谱高分辨率质谱测定结构。测试了这些化合物针对细菌的生物活性，包括 Xac（Xanthomonas axonopodis pv. Citri）、Psa（Pseudomonas syringae pv. Actinidiae）和 Xoo（Xanthomonas oryzae pv. Oryzae）。值得注意的是，D6 对 Xoo 表现出显着的生物活性，EC50 值为 18.8 μg/mL，高于对照药物噻二唑铜 (EC50 = 52.9 μg/mL) 和双噻唑 (EC50 = 69.1 μg/mL)。此外，还评估了目标化合物对十种植物病原真菌的抗真菌活性。他们之中，D1 对拟茎点霉表现出优异的抑制活性。EC50 值为 16.9 μg/mL，优于对照剂嘧菌酯 (EC50 = 50.7 μg/mL) 和氟吡菌酰胺

  DOI：

  10.3390/ijms241310442
• 作为产物：
  描述：

  (4-甲氧基苯基)肼 在 三氯氧磷 作用下， 反应 4.08h， 生成 5-chloro-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Noveltris-(吡唑基)甲烷的微波加速和无催化剂合成

  摘要：

  吡唑衍生物构成了一个重要的化合物家族，因为它们可用作药物、农用化学品和染料。1-3 例如，2,4-二氢-3H-吡唑-3-酮衍生物......

  DOI：

  10.1080/00304948.2016.1206426

文献信息

• Microwave-Assisted Synthesis of Ethyl 1,3-Disubstituted-1,6-dihydropyrrolo[2,3-c]pyrazole-5-carboxylates
  作者：Lijun Gu、Xiangguang Li

  DOI：10.1002/jhet.1115

  日期：2013.3

  A novel series of ethyl 1,3‐disubstituted‐1,6‐dihydropyrrolo[2,3‐c]pyrazole‐5‐carboxylates can be rapidly and efficiently synthesized in excellent yields by condensing a variety of 1,3‐substituted‐4‐formyl‐5‐chloropyrazole with ethyl isocyanoacetate in the presence of 1‐methyl‐3‐butylimidazolium hydroxide under microwave irradiation. The simple experimental procedure, DMSO‐free condition, short period

  通过缩合各种1,3-取代的-4--羟基化合物，可以快速有效地合成一系列新颖的1,3-二取代的-1,6-二氢吡咯并[2,3-c]吡唑-5-羧酸乙酯。在微波辐射下，在1-甲基-3-丁基咪唑鎓氢氧化物存在下，将甲酰基-5-氯吡唑与异氰基乙酸乙酯混合。简单的实验程序，无DMSO的条件，短的转化时间和优异的收率是本方法的优势。新型化合物的结构已通过IR，1 H NMR，13 C NMR，MALDI-TOF MS和元素分析得到证实。
• Synthesis, Biological Evaluation, DFT Studies and Molecular Docking of Novel 4-(5-(1H-Imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-amino-3-methyl- 1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile and its Derivatives
  作者：Rajat Patel、Puja Sharma、Rohit R. Koshti、Akshay Vyas、Chetan B. Sangani

  DOI：10.14233/ajchem.2023.27921

  日期：——

  A novel series consisting of eight imidazol-pyrazole hybrids ( 9a-h) are synthesized using a base catalyzed one pot multi-component reaction (MCR) and screened for in vitro biological activities. All compounds were found to display high biological activities but compound 9g was found to be the most active against EGFR (IC50 of 0.11 ± 0.02 μm), A549 and HepG2, while compound 9h was found to be most active against FabH (IC50 of 2.6 μm) E. coli. The DFT studies and molecular docking was done for compounds 9a-h to calculate the distance and angle between the active parts of the molecules and charge density over the molecules affecting the binding of molecules in the active pockets with greater binding affinity.

  利用碱催化的一锅多组分反应（MCR）合成了由八个咪唑-吡唑杂环（9a-h）组成的新系列，并对其进行了体外生物活性筛选。 一锅多组分反应 (MCR) 合成了一个由八个咪唑-吡唑杂环（9a-h）组成的新系列，并对其进行了体外生物活性筛选。所有化合物 均显示出较高的生物活性，但发现化合物 9g 对表皮生长因子受体（EGFR）的活性最高（IC50 为 0.5%）。 对表皮生长因子受体（IC50 为 0.11 ± 0.02 μm）、A549 和 HepG2 的活性最强，而化合物 9h 对 FabH 的活性最强（IC50 为 0.11 ± 0.02 μm）。 而化合物 9h 对大肠杆菌 FabH 的活性最高（IC50 为 2.6 μm）。对 9a-h 化合物进行了 DFT 研究和分子对接。 9a-h 化合物进行了 DFT 研究和分子对接，以计算分子活性部分之间的距离和角度，以及分子上影响结合的电荷密度。 分子上的电荷密度会影响分子在活性口袋中的结合力。 结合亲和力。
• Straightforward copper-catalyzed synthesis of pyrrolopyrazoles from halogenated pyrazolecarbaldehydes
  作者：Maloy Nayak、Harikrishna Batchu、Sanjay Batra

  DOI：10.1016/j.tetlet.2012.05.148

  日期：2012.8

  Straightforward synthesis of a variety of pyrrolo-fused pyrazoles via a cascade reaction between halopyrazolecarbaldehydes and ethylisocyanoacetate in the presence of copper and a base is described. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis, Characterization, DFT Studies, Biological Investigation and Molecular Modelling of Novel 1-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)- 3-amino-2-cyano-N-phenyl-1H-benzo[f]chromene-5-carboxamide Derivatives
  作者：Rajat Patel、Puja Sharma、Rohit R. Koshti、Akshay Vyas、Chetan B. Sangani

  DOI：10.14233/ajchem.2024.30936

  日期：——

  In this work, a new series of imidazole-pyrazole-benzo[f]chromene hybrids were designed and synthesized by a base-catalyzed cyclo-condensation through a one-pot multicomponent reaction. All compounds were tested for in vitro antimicrobial and anticancer activities. Enzyme inhibitory activities of all compounds were carried out against FabH and EGFR. The majority of synthesized  compounds displayed promising antimicrobial as well as anticancer activity against used strains and cancer cell lines respectively. The  compounds were also tested for in vitro anticancer activities against two cancer cell lines A549 and Hep G2. Compound 7f (IC50 = 0.62  µM) against EGFR and (IC50 = 1.31 µM) against A549 kinase displayed the most potent inhibitory activity as compared to another  member of the series. In the molecular modelling study, compound 7e was bound into the active pocket of EGFR with one pi-pi  interaction and one hydrogen bond having minimum binding energy ∆Gb = −7.6894 kcal/mol. Moreover, FabH molecule 7d was found  to be binding in the active pocket with a minimum binding energy of −8.9117 kcal/mol. 
• Microwave-accelerated and Catalyst-free Synthesis of Novel<i>tris</i>-(Pyrazolyl)methanes
  作者：Maryam Beyrati、Alireza Hasaninejad

  DOI：10.1080/00304948.2016.1206426

  日期：2016.9.2

  Pyrazole derivatives constitute an important family of compounds due to their applications as pharmaceuticals, agrochemicals and dyestuffs.1–3 For example, 2,4-dihydro-3H-pyrazol-3-one derivatives ...

  吡唑衍生物构成了一个重要的化合物家族，因为它们可用作药物、农用化学品和染料。1-3 例如，2,4-二氢-3H-吡唑-3-酮衍生物......