1-(4-methylphenyl)-3-(4-nitrophenyl)-1H-pyrazole-4-carboxaldehyde | 618098-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-methylphenyl)-3-(4-nitrophenyl)-1H-pyrazole-4-carboxaldehyde
• 英文别名: 3-(4-Nitrophenyl)-1-P-tolyl-1H-pyrazole-4-carbaldehyde；1-(4-methylphenyl)-3-(4-nitrophenyl)pyrazole-4-carbaldehyde
• CAS: 618098-92-3
• 化学式: C₁₇H₁₃N₃O₃
• 分子量: 307.309
• InChiKey: DCEVNQYGNZHCCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-methylphenyl)-3-(4-nitrophenyl)-1H-pyrazole-4-carboxaldehyde 以 乙醇 为溶剂， 生成 N-{4-acetyl-5-[1-(4-methylphenyl)-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-4,5-dihydro-1,3,4-thiadiazol-2-yl}-N-phenylacetamide
  参考文献：
  名称：

  New heterocyclic hybrids of pyrazole and its bioisosteres: Design, synthesis and biological evaluation as dual acting antimalarial-antileishmanial agents

  摘要：

  A new series of pyrazole derivatives were synthesized by hybridization with five-membered heterocyclic moieties such as thiazoles, thiazolidinones, 1,3,4-thiadiazoles and pyrazolines. The compounds were evaluated for their in vivo antimalarial activity against Plasmodium berghei infected mice and the most active derivatives were further examined for their in vitro antimalarial activity against chloroquine resistant (RKL9) strain of Plasmodium falciparum. Compounds 2c, 2d, 4b, 4c, 4d, 5a, 6c, 8c and 9b had more than 90% parasite suppression activity of that found with the antimalarial reference standard drug, chloroquine phosphate and had lower IC50 values than chloroquine. Compounds 4b and 9b were the most active derivatives, and their activities were 5-fold higher than chloroquine. All the newly synthesized compounds were evaluated for their in vitro antileishmanial activity against Leishmania aethiopica promastigotes and amastigote. The results showed that compounds 2c, 2d, 3d, 4b, 4c, 4d and 5a had lower or similar IC50 values than the reference standard drugs, amphotericin B and miltefosine. Compound 3d had the highest antileishmanial activity. Collectively, compounds 2c, 2d, 4b, 4c, 4d and 5a exhibited dual activity against malaria and leishmaniasis and were safe and well tolerated by the experimental animals orally up to 300 mg/kg and parenterally up to 100 mg/kg. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

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

  4-甲基苯肼盐酸盐 在 sodium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 1.25h， 生成 1-(4-methylphenyl)-3-(4-nitrophenyl)-1H-pyrazole-4-carboxaldehyde
  参考文献：
  名称：

  New heterocyclic hybrids of pyrazole and its bioisosteres: Design, synthesis and biological evaluation as dual acting antimalarial-antileishmanial agents

  摘要：

  A new series of pyrazole derivatives were synthesized by hybridization with five-membered heterocyclic moieties such as thiazoles, thiazolidinones, 1,3,4-thiadiazoles and pyrazolines. The compounds were evaluated for their in vivo antimalarial activity against Plasmodium berghei infected mice and the most active derivatives were further examined for their in vitro antimalarial activity against chloroquine resistant (RKL9) strain of Plasmodium falciparum. Compounds 2c, 2d, 4b, 4c, 4d, 5a, 6c, 8c and 9b had more than 90% parasite suppression activity of that found with the antimalarial reference standard drug, chloroquine phosphate and had lower IC50 values than chloroquine. Compounds 4b and 9b were the most active derivatives, and their activities were 5-fold higher than chloroquine. All the newly synthesized compounds were evaluated for their in vitro antileishmanial activity against Leishmania aethiopica promastigotes and amastigote. The results showed that compounds 2c, 2d, 3d, 4b, 4c, 4d and 5a had lower or similar IC50 values than the reference standard drugs, amphotericin B and miltefosine. Compound 3d had the highest antileishmanial activity. Collectively, compounds 2c, 2d, 4b, 4c, 4d and 5a exhibited dual activity against malaria and leishmaniasis and were safe and well tolerated by the experimental animals orally up to 300 mg/kg and parenterally up to 100 mg/kg. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.038

文献信息

• Design and synthesis of novel quinazolinone-pyrazole derivatives as potential α-glucosidase inhibitors: Structure-activity relationship, molecular modeling and kinetic study
  作者：Fateme Azimi、Homa Azizian、Mohammad Najafi、Farshid Hassanzadeh、Hojjat Sadeghi-aliabadi、Jahan B. Ghasemi、Mohammad Ali Faramarzi、Somayeh Mojtabavi、Bagher Larijani、Lotfollah Saghaei、Mohammad Mahdavi

  DOI：10.1016/j.bioorg.2021.105127

  日期：2021.9

  structure–activity relationship suggested that the variation in the inhibitory activities of the compounds affected by different substitutions on phenyl rings of diphenyl pyrazole moiety. The enzyme kinetic studies of the most potent compound 9i revealed that it inhibited α-glucosidase in a competitive mode with a Ki of 56 μM. Molecular docking study was performed to predict the putative binding interaction. As expected

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  作者：Marwa H. El-Wakil、Mohamed Teleb、Marwa.M. Abu-Serie、Sun Huang、Gerald W. Zamponi、Hesham Fahmy

  DOI：10.1016/j.bioorg.2021.105262

  日期：2021.10

  HSQC and NOESY experiments. Novel derivatives were tested for their Ca2+ channel blocking activity by employing the whole cell patch-clamp technique. Results demonstrated that most compounds were potential T-type calcium channel blockers with the triazole-based C12 and C13 being the most selective agents against CaV3.2 channel. Further electrophysiological studies demonstrated that C12 and C13 inhibited

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• Kinetic studies, molecular docking, and antioxidant activity of novel 1,3-diphenyl pyrazole-thiosemicarbazone with anti-tyrosinase and anti-melanogenesis properties
  作者：Fateme Azimi、Mohammad Mahdavi、Mehdi Khoshneviszadeh、Fatemeh Shafiee、Mahin Azimi、Farshid Hassanzadeh、Farhad Haji Ashrafee

  DOI：10.1016/j.bioorg.2024.107722

  日期：2024.11

  the 3-position of the pyrazole ring demonstrated IC values of 2.09 and 3.18 µM, respectively. The potency of these compounds was approximately 5–8 times higher than that of KA. The melanin content of 6g or 6n-treated melanoma cells resulted in significant efficacy in melanin reduction. The DPPH assay result revealed that the tyrosinase inhibition mechanism for these derivatives was independent of a

  本研究报告了一系列新型 1,3-二苯基吡唑-缩氨基硫脲作为新型酪氨酸酶抑制剂 (TYRI) 的设计假设。制备了设计的化合物并研究了它们的TYRI活性和机制。结果表明，所选化合物表现出比曲酸（KA）更强的酪氨酸酶抑制活性。先导候选物（表示为 6g 和 6n）在吡唑环的 3 位上连接有对羟基苯基，其 IC 值分别为 2.09 和 3.18 µM。这些化合物的效力大约比 KA 高 5-8 倍。 6g或6n处理的黑色素瘤细胞的黑色素含量在减少黑色素方面具有显着功效。 DPPH测定结果表明，这些衍生物的酪氨酸酶抑制机制不依赖于氧化还原效应，并且对应于与酪氨酸酶的相互作用。根据 Lineweaver-Burk 图，最有效的化合物 6g 和 6n 表现出混合类型的抑制，主要是非竞争性抑制。采用分子对接研究来确定结合模式并详细探索设计假设。结果表明，这些化合物可以被认为是进一步开发治疗酪氨酸酶相关疾病的新型抑制剂的有希望的先导化合物。
• Design and synthesis of novel pyrazole-phenyl semicarbazone derivatives as potential α-glucosidase inhibitor: Kinetics and molecular dynamics simulation study
  作者：Fateme Azimi、Jahan B. Ghasemi、Homa Azizian、Mohammad Najafi、Mohammad Ali Faramarzi、Lotfollah Saghaei、Hojjat Sadeghi-aliabadi、Bagher Larijani、Farshid Hassanzadeh、Mohammad Mahdavi

  DOI：10.1016/j.ijbiomac.2020.10.263

  日期：2021.1