1-(4-bromophenyl)-3-(4-methylphenyl)-1H-pyrazole-4-carboxaldehyde | 618098-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-bromophenyl)-3-(4-methylphenyl)-1H-pyrazole-4-carboxaldehyde
• 英文别名: 1-(4-Bromophenyl)-3-p-tolyl-1h-pyrazole-4-carbaldehyde；1-(4-bromophenyl)-3-(4-methylphenyl)pyrazole-4-carbaldehyde
• CAS: 618098-52-5
• 化学式: C₁₇H₁₃BrN₂O
• 分子量: 341.207
• InChiKey: ARNCWEIEKFVTDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 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：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-3-(4-methylphenyl)-1H-pyrazole-4-carboxaldehyde 以 乙醇 为溶剂， 生成 N-{4-acetyl-5-[1-(4-bromophenyl)-3-(4-methylphenyl)-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-溴苯肼盐酸盐 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-bromophenyl)-3-(4-methylphenyl)-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

• Structural optimization, synthesis and in vitro synergistic anticancer activities of combinations of new N3-substituted dihydropyrimidine calcium channel blockers with cisplatin and etoposide
  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

  T型钙通道被认为是对抗癌症的潜在药物靶点。将T型钙通道阻滞剂与常规化疗药物相结合代表了成功治疗癌症的有希望的策略。从这个角度来看，我们在本研究中报告了一系列新型N 3 取代的二氢嘧啶 (DHPM) 作为顺铂 (Cis) 和依托泊苷 (Eto) 的抗癌佐剂的设计和合成。使用 FT-IR、1 H NMR、13 C NMR 和 HRMS对新化合物进行了全光谱表征。2D NMR 1 H-H COSY、HSQC 和 NOESY 实验证实了结构解析。测试了新衍生物的 Ca 2+通过采用全细胞膜片钳技术进行通道阻断活动。结果表明，大多数化合物是潜在的T型钙通道阻滞剂，其中基于三唑的C12和C13是对 Ca V 3.2 通道最具选择性的药物。进一步的电生理研究表明，C12和C13 分别抑制了 Ca V 3.2 电流，亲和力分别为 2.26 和 1.27 µM，并在半失活电位中引起了 5 mV 的超极化位移
• New heterocyclic hybrids of pyrazole and its bioisosteres: Design, synthesis and biological evaluation as dual acting antimalarial-antileishmanial agents
  作者：Adnan A. Bekhit、Ahmed M.M. Hassan、Heba A. Abd El Razik、Mostafa M.M. El-Miligy、Eman J. El-Agroudy、Alaa El-Din A. Bekhit

  DOI：10.1016/j.ejmech.2015.02.038

  日期：2015.4

  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.