Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone

We employed (Z)‐N'‐[phenyl(pyrimidin‐2‐yl)methylene]nicotinohydrazide (2) and (Z)‐4‐(dimethylamino)‐N'‐[phenyl(pyrimidin‐2‐yl)methylene]benzohydrazide (3) as cores of dynamic chemical systems whose different states are modulated, in a reversible fashion, through specific physical and chemical stimuli. The structure of the compounds was determined by Nuclear Magnetic Resonance (NMR) techniques (1D and 2D) and confirmed by single‐crystal X‐ray diffraction. By Variable temperature (VT) 1H NMR experiments and DFT calculations, the conformational isomerism of 2 was studied and added as an additional input for the dynamic system. Additionally, 2 exhibits configurational E/Z isomerization mediated by pH variations and UV light. On the other hand, configurational isomerism locks an unlocks a tridentate pocket for metal cation coordination in both 2 and 3. All the different dynamic states configurational/conformational isomerism and locked and unlocked coordination constitute a development in the field of systems of multiple dynamics suitable for molecular machines.

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Multiple Reversible Dynamics of Pyrimidine Based Acylhydrazones

Arango

Wist

Ellena

et al. 2020

Eur J Org Chem

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Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline

et al. 2019

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A new quinoline-based hydrazone, C16H12ClN3, was synthesized by a condensation reaction of 2-chloro-3-formylquinoline with phenylhydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring. The molecule adopts an E configuration with respect to the central C=N bond. In the crystal, molecules are linked by a C—H...π-phenyl interaction, forming zigzag chains propagating along the [10\overline{3}] direction. The N—H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent molecule, so linking the chains via weak N—H...π interactions to form of a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (35.5%), C...H/H...C (33.7%), Cl...H/H...Cl (12.3%), N...H/H...N (9.5%) contacts.

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Synthesis and In vitro Evaluation of Hydrazonomethyl-Quinolin–8–ol and Pyrazol–3–yl-Quinolin–8–ol Derivatives for Antimicrobial and Antimalarial Potential

Kumar

Shah

Tripathi

et al. 2022

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Background: Quinoline is a well-established nucleus displaying various biological activities. Quinoline-8-ol containing compounds are reported for antimicrobial as well as antimalarial activity. Hydrazone and pyrazole containing compounds are also reported for antimicrobial activity. In this work, we have synthesized hydrazonomethyl-quinolin–8–ol and pyrazol–3–yl-quinolin–8–ol derivatives retaining quinoline 8-ol along with hydrazone/pyrazole pharmacophores. Objective: Objective of this work is synthesis and in vitro evaluation of hydrazonomethyl-quinolin–8–ol and pyrazol–3–yl-quinolin–8–ol derivatives for antifungal, antibacterial and antimalarial activity. Method: Designed and synthesized hydrazonomethyl-quinolin–8–ol and pyrazol–3–yl-quinolin–8–ol derivatives were evaluated for antifungal (against Candida albicans, Aspergillus fumigatus and Cryptococcus neoformans), antibacterial (against methicillin resistant Staphylococcus aureus (MRSA), Escherichia Coli, Pseudomonas aeruginosa and Klebsillae pneumoniae) as well as antimalarial (against Plasmodium falciparum D6 and W2 strains) activity. Result: Hydrazonomethyl-quinolin–8–ol (15.1-15.28) and pyrazol–3–yl-quinolin–8–ol derivatives (16.1-16.21 and 20.1-20.18) were synthesized in good to moderate yield. One pot synthesis of pyrazol–3–yl-quinolin–8–ol derivatives (16.1-16.21 and 20.1-20.18) was achieved. Compounds 15.3, 15.6, 15.7, 15.9-15.14, 15.16-15.19, 15.22 and 15.24 were found more potent than reference standard fluconazole (IC50 = 3.20 µM) against C. albicans with IC50 value less than 3 µM. Compounds 15.1, 15.2, 15.21 and 15.23 showed almost similar activity with reference standard fluconazole against C. albicans. Compounds 15.1-15.3, 15.9-15.12, 15.14-15.17, and 15.21-15.23 also showed good activity against fluconazole resistant strain A. fumigatus with IC50 value less than 3 µM. Compounds 15.2-15.4, 15.7, 15.9, 15.17, 15.20 showed good antimalarial activity against P. falciparum D6 as well as P. falciparum W2 with IC50 values of 1.84, 1.83, 1.56, 1.49, 1.45, 1.97, 1.68 µM and 1.86, 1.40, 1.19, 1.71, 1.16, 1.34, 1.61 µM, respectively. 5-Pyrazol–3–yl-quinolin–8–ol derivatives such as 16.3, 16.5, 16.11, 16.13, 16.19, 16.20 also showed antimalarial activity against P. falciparum D6 and W2 strains with IC50 values 2.23, 2.16, 2.99, 2.99, 2.73, 2.12 µM and 2.91, 3.60, 4.61, 2.71, 2.31, 2.66 µM, respectively. Conclusion: Most of the 5-hydrazonomethyl-quinolin–8–ol derivatives showed good antifungal activity against C. albicans, A. fumigatus and C. neoformans. Most of the 5-hydrazonomethyl-quinolin–8–ol derivatives were found more potent than reference standard fluconazole. These derivatives may be considered as leads for further development of antifungal agents.

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Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone

Cited by 4 publications

References 26 publications

Multiple Reversible Dynamics of Pyrimidine Based Acylhydrazones

Multiple Reversible Dynamics of Pyrimidine Based Acylhydrazones

Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline

Synthesis and In vitro Evaluation of Hydrazonomethyl-Quinolin–8–ol and Pyrazol–3–yl-Quinolin–8–ol Derivatives for Antimicrobial and Antimalarial Potential

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