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首页> 美国卫生研究院文献>EXCLI Journal >Physicochemical analyses of a bioactive 4-aminoantipyrine analogue - synthesis crystal structure solid state interactions antibacterial conformational and docking studies
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Physicochemical analyses of a bioactive 4-aminoantipyrine analogue - synthesis crystal structure solid state interactions antibacterial conformational and docking studies

机译：生物活性4-氨基安替比林类似物的理化分析-合成晶体结构固态相互作用抗菌构象和对接研究

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摘要

A novel Schiff base derivative of 4-aminoantipyrine, that is, (E)-4-(2-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (MBA-dMPP), was synthesized and characterized by FT-IR, 1H-NMR, and EI-MS. Single-crystal X-ray diffraction data revealed MBA-dMPP adopts a trans configuration around its central C=N double bond, and forms orthorhombic crystals. XRD revealed that MBA-dMPP possess two different planes, in which the pyrazolone and benzylidene groups attached to C9 of the pyrazolone ring are almost coplanar and the phenyl ring connected to the N1 atom of the pyrazolone moiety lies in another plane. The intermolecular, host-guest C-H…O, C-H…N, and C-H…C van der Waals interactions were found to form a 3D network and confer stability to the MBA-dMPP crystal structure. The quantitative and qualitative solid state behaviors of MBA-dMPP were subjected to 3D Hirshfeld surface analysis and 2D fingerprint plotting. Reciprocal H…H contacts contributed most (52.9 %) to the Hirshfeld surface, followed by C…H/H…C contacts (30.2 %), whereas, O…H/H…O and N…H/H…N interactions contributed 15.5 % to the Hirshfeld surface. Electrostatic potentials were mapped over the Hirshfeld surface to analyze electrostatic complementarities within the MBA-dMPP crystal. In addition, geometrical descriptors were also analyzed to the extent of surface interactions. MBA-dMPP was also investigated for in vitro antibacterial activity against Gram-positive and Gram-negative bacterial strains, and showed highest activity against Bacillus cereus (MIC = 12.5 μg mL-1) and Salmonella tythimurium (MIC = 50 μg mL-1). In silico screening was conducted by docking MBA-dMPP on the active site of S12 bacterial protein (an important therapeutic target of antibacterial agents) and its binding properties were compared with those of ciprofloxacin. Moreover, a field points map of MBA-dMPP ligand was studied to determine electrostatic and van der Waals forces, hydrophobic potentials, and positions involved in ligand-receptor interactions. Finally, the torsion energies of crystal structure and optimized and bioactive conformers of MBA-dMPP were compared to predict its bioactive conformation.
机译：4-氨基安替比林的新型席夫碱衍生物，即（E）-4-（2-甲氧基苄叉亚氨基）-1,5-二甲基-2-苯基-1H-吡唑-3（2H）-one（MBA-dMPP）通过FT-IR， 1 H-NMR和EI-MS进行合成和表征。单晶X射线衍射数据显示MBA-dMPP在其中心C = N双键周围采用反式构型，并形成正交晶体。 XRD显示MBA-dMPP具有两个不同的平面，其中连接到吡唑啉酮环的C9的吡唑啉酮和亚苄基几乎共面，并且连接到吡唑啉酮部分的N1原子的苯环位于另一个平面。发现分子间，客体C-H…O，C-H…N和C-H…C Van der Waals相互作用形成了3D网络，并赋予了MBA-dMPP晶体结构稳定性。对MBA-dMPP的定量和定性固态行为进行了3D Hirshfeld表面分析和2D指纹图绘制。相互的H…H接触对Hirshfeld表面的贡献最大（52.9％），其次是C…H / H…C接触（30.2％），而O…H / H…O和N…H / H…N的相互作用最多到Hirshfeld表面的15.5％。将静电势绘制在Hirshfeld表面上，以分析MBA-dMPP晶体内的静电互补性。此外，还对几何描述符进行了表面相互作用的分析。还研究了MBA-dMPP对革兰氏阳性和革兰氏阴性细菌菌株的体外抗菌活性，并显示了对蜡状芽孢杆菌（MIC = 12.5μgmL -1 ）和鼠伤寒沙门氏菌（MIC）的最高活性。 = 50μgmL -1 ）。通过将MBA-dMPP停靠在S12细菌蛋白（抗菌剂的重要治疗靶标）的活性位点上进行计算机筛选，并将其结合特性与环丙沙星进行比较。此外，研究了MBA-dMPP配体的场点图，以确定静电力和范德华力，疏水势以及与配体-受体相互作用有关的位置。最后，比较了晶体结构的扭转能和MBA-dMPP的优化生物活性构象，以预测其生物活性构象。

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