2-chloro-3-[3-(2,5-dichlorothiophen-3-yl)-4,5-dihydro-1H-pyrazol-5-yl]-8-methylquinoline | 1313405-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-chloro-3-[3-(2,5-dichlorothiophen-3-yl)-4,5-dihydro-1H-pyrazol-5-yl]-8-methylquinoline
• CAS: 1313405-90-1
• 化学式: C₁₇H₁₂Cl₃N₃S
• 分子量: 396.727
• InChiKey: APIFRSHWKYCEEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯-8-甲基喹啉-3-甲醛 在 一水合肼 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 2-chloro-3-[3-(2,5-dichlorothiophen-3-yl)-4,5-dihydro-1H-pyrazol-5-yl]-8-methylquinoline
  参考文献：
  名称：

  Novel quinolyl-thienyl chalcones and their 2-pyrazoline derivatives with diverse substitution pattern as antileishmanial agents against Leishmania major

  摘要：

  A series of twenty-two new pyrazoline derivatives was prepared from quinoline-based chalcones which in turn were synthesized by condensing formylquinolines with diverse acetylthiophenes. The titled compounds were characterized by spectroscopic techniques (NMR, IR and MS) and elemental analysis. All the compounds were screened for antileishmanial activities. Compounds 1e, 1f, 2a, 2c, 2d, 2g, 2k, and 4a were found potentially active antileishmanial agents. Bioassay results show that the type and positions of the substituents seem to be critical for their antileishmanial activities.

  DOI：

  10.1007/s00044-011-9647-8

文献信息

• Monoamine Oxidase Inhibition and Molecular Modeling Studies of Piperidyl-thienyl and 2-Pyrazoline Derivatives of Chalcones
  作者：Sumera Zaib、Syed Farooq Rizvi、Sana Aslam、Matloob Ahmad、Mariya al-Rashida、Jamshed Iqbal

  DOI：10.2174/1573406410666141229101130

  日期：2015.6.30

  A series of piperidyl-thienyl & 2-pyrazoline derivatives of quinolyl-thienyl chalcones were tested to observe the structural characteristics for the monoamine oxidase inhibitory (MAO) activity. In both these series, a diverse range of substituted thiophenes are used which enable the structure activity relationship. The compounds showed enhanced inhibition against MAO-A & B as compared to reference compounds. Compound 1c exhibited most potent MAO-A inhibition having IC50 value of 0.062 M, while 1j showed excellent inhibitory potency against MAO-B having IC50 value of 0.088 M. The present investigation demonstrated that among piperidyl-thienyl chalcones, almost all the compounds exhibit significant MAO-A inhibition, thus may have antidepressant activity. Whereas among the 2-pyrazoline derivatives of chal-cones, many compounds revealed MAOB inhibition and hence may be applied in the control of senile dementia. Molecular docking studies were carried out against human MAO-A and MAO-B to rationalize important binding site interactions.

  为了观察单胺氧化酶抑制（MAO）活性的结构特征，我们测试了一系列哌啶基噻吩和 2-吡唑啉衍生物的喹啉基噻吩查耳酮。 在这两个系列中，使用了各种不同的取代噻吩，从而实现了结构活性关系。与参考化合物相比，这些化合物对 MAO-A 和 B 的抑制作用更强。化合物 1c 对 MAO-A 的抑制作用最强，其 IC50 值为 0.062 M，而 1j 对 MAO-B 的抑制作用极佳，其 IC50 值为 0.088 M。而在查耳酮的 2-吡唑啉衍生物中，许多化合物显示出 MAOB 抑制作用，因此可用于控制老年痴呆症。针对人类 MAO-A 和 MAO-B 进行了分子对接研究，以理顺重要结合位点的相互作用。
• Cholinesterases inhibition and molecular modeling studies of piperidyl-thienyl and 2-pyrazoline derivatives of chalcones
  作者：Muhammad Shakil Shah、Shafi Ullah Khan、Syeda Abida Ejaz、Saifullah Afridi、Syed Umar Farooq Rizvi、Muhammad Najam-ul-Haq、Jamshed Iqbal

  DOI：10.1016/j.bbrc.2016.11.082

  日期：2017.1

  Herein, we report a series of newly synthesized chalcone derivatives with anti-AD potential. For this purpose, a series of piperidyl-thienyl and 2-pyrazoline derivatives of chalcones were tested for their cholinesterases (AChE & BChE) inhibitory activity. All compounds were found as selective inhibitor of AChE. In piperidyl chalcones derivatives compound 1e having IC50 of 0.16 ± 0.008 μM and 2m in 2-pyrazoline

  胆碱酯酶（乙酰胆碱酯酶和丁酰胆碱酯酶）的超活化与各种神经系统疾病有关，最确切地说是阿尔茨海默氏病（AD），这会导致老年性痴呆。因此，胆碱酯酶（AChE＆BChE）抑制被认为是治疗阿尔茨海默氏病的有前途的策略。FDA批准用于治疗AD的药物，属于胆碱酯酶抑制剂的一组。但是，它们都不能抵抗或完全消除疾病的进展。本文中，我们报道了一系列具有抗AD潜力的新合成查尔酮衍生物。为此，测试了查耳酮的一系列哌啶基-噻吩基和2-吡唑啉衍生物的胆碱酯酶（AChE和BChE）抑制活性。发现所有化合物都是AChE的选择性抑制剂。在哌啶基查耳酮衍生物中，化合物1e的IC50为0.16±0.008μM，2吡唑啉查耳酮中的2m化合物的IC50为0.13±0.006μM，被发现是AChE最有效的抑制剂，其抑制潜能约为142倍和173倍与参考抑制剂新斯的明（IC50±SEM = 22.2±3.2μM）相比。进行了大多数有效抑
• Novel quinolyl-thienyl chalcones and their 2-pyrazoline derivatives with diverse substitution pattern as antileishmanial agents against Leishmania major
  作者：Syed Umar Farooq Rizvi、Hamid Latif Siddiqui、Muhammad Nisar Ahmad、Matloob Ahmad、Mujahid Hussain Bukhari

  DOI：10.1007/s00044-011-9647-8

  日期：2012.7

  A series of twenty-two new pyrazoline derivatives was prepared from quinoline-based chalcones which in turn were synthesized by condensing formylquinolines with diverse acetylthiophenes. The titled compounds were characterized by spectroscopic techniques (NMR, IR and MS) and elemental analysis. All the compounds were screened for antileishmanial activities. Compounds 1e, 1f, 2a, 2c, 2d, 2g, 2k, and 4a were found potentially active antileishmanial agents. Bioassay results show that the type and positions of the substituents seem to be critical for their antileishmanial activities.