Insight into the corrosion inhibiting potential and anticancer activity of 1-(4-methoxyphenyl)-5-methyl-N’-(2-oxoindolin-3-ylidene)-1H-1,2,3-triazole-4-carbohydrazide via computational approaches
Oluwatoba Emmanuel OyeneyinAbdulwasiu IbrahimNureni IpinlojuAdeniyi John AdemoyegunNathanael Damilare Ojo
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AbstractCancer is a major health concern globally. Orthodox and traditional medicine have actively been explored to manage this disease. Also, corrosion is a natural catastrophe that weakens and deteriorates metallic structures and their alloys causing major structural failures and severe economic implications. Designing and exploring multi-functional materials are beneficial since they are adaptive to different fields including engineering and pharmaceutics. In this study, we examined the anti-corrosion and anti-cancer potentials of 1-(4-methoxyphenyl)-5-methyl-N'-(2-oxoindolin-3-ylidene)-1H-1,2,3-triazole-4-carbohydrazide (MAC) using computational approaches. The molecular reactivity descriptors and charge distribution parameters of MAC were studied in gas and water at density functional theory (DFT) at B3LYP/6-311++G(d,p) theory level. The binding and mechanism of interaction between MAC and iron surface was studied using Monte Carlo (MC) and molecular dynamics (MD) simulation in hydrochloric acid medium. From the DFT, MC, and MD simulations, it was observed that MAC interacted spontaneously with iron surface essentially via van der Waal and electrostatic interactions. The near-parallel alignment of the corrosion inhibitor on iron plane facilitates its adsorption and isolation of the metal surface from the acidic solution. Further, the compound was docked in the binding pocket of anaplastic lymphoma kinase (ALK: 4FNZ) protein to assess its anti-cancer potential. The binding score, pharmacokinetics, and drug-likeness of MAC were compared with the reference drug (Crizotinib). The MAC displayed binding scores of −5.729 kcal/mol while Crizotinib has −3.904 kcal/mol. MD simulation of the complexes revealed that MAC is more stable and exhibits more favourable hydrogen bonding with the ALK receptor's active site than Crizotinib.Communicated by Ramaswamy H. SarmaKeywords: Anaplastic lymphoma kinasemolecular dynamicsmolecular dockingpair distribution functionDFTcorrosion AcknowledgmentsThe authors would like to appreciate the Theoretical and Computational Chemistry Unit, Adekunle Ajasin University, for resources made available to conduct this research (Monte Carlo, MD simulation with Fe 110). Oyeneyin Oluwatoba Emmanuel acknowledges computational cluster resources at the Center for High Performance Computing (CHPC), Cape Town, South Africa for DFT and MD (ligand-receptor complexes).Disclosure statementNo potential conflict of interest was reported by the authors.Additional informationFundingThe author(s) reported there is no funding associated with the work featured in this article.Keywords:
Carbohydrazide
Triazole
1,2,4-Triazole
In the title compound, C12H10ClN7S, the dihedral angles made by the plane of the thione-substituted triazole ring with the planes of the other triazole ring and the benzene ring are 73.57 (3) and 46.65 (2)°, respectively. Inter- and intramolcular hydrogen bonds and π-π stacking interactions stabilize the structure.
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1,2,4-Triazole
Triazole
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In the title compound, C 12 H 10 N 8 O 2 S, the triazole and benzene rings make dihedral angles of 72.16 (2) and 7.39 (3)°, respectively, with the thione-substituted triazole ring. In the crystal structure, intermolecular N—H...N hydrogen bonds link the molecules into chains running in the [101] direction.
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A reaction of equimolar equivalents of 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (1) and indoline-2,3-dione (2) in boiling ethanol for 4 h under acidic conditions gave 1-(4-methoxyphenyl)-5-methyl-N’-(2-oxoindolin-3-ylidene)-1H-1,2,3-triazole-4-carbohydrazide (3) in 88% yield. The structure of 3 was ascertained by NMR spectroscopy and single-crystal X-ray diffraction.
Carbohydrazide
1,2,4-Triazole
Triazole
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In the title compound, C12H10N8O2S, the thione-substituted triazole ring forms dihedral angles of 79.86 (2) and 9.86 (3)°, respectively, with the other triazole ring and the benzene ring. Intermolecular N—H⋯N hydrogen bonds link the molecules into chains extended along the [101] direction. The crystal packing is further stabilized by van der Waals forces.
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1,2,4-Triazole
Triazole
Derivative (finance)
1,2,3-Triazole
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In the title compound, C12H11N7OS, the dihedral angles made by the thione-substituted triazole ring with the other triazole ring and the benzene ring are 71.56 (2) and 47.89 (3)°, respectively. Inter- and intramolcular hydrogen-bond interactions stabilize the structure.
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In the title compound, C12H10FN7S, the dihedral angles made by the plane of the thione-substituted triazole ring with the planes of the other triazole ring and the benzene ring are 74.55 (2) and 11.50 (3)°, respectively. The structure shows a number of N—H⋯N intermolecular hydrogen-bonding interactions, and weak C—H⋯S intra- and intermolecular interactions.
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1,2,4-Triazole
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Nitrogen-rich cation 5-amino-1H-1,2,4-triazole-3-carbohydrazide and its derivatives were synthesized by a new molecular design strategy based on the energetic moiety combination. All derivatives were fully characterized by vibrational spectroscopy (IR), multinuclear (1H, 13C) NMR spectroscopy, elemental analysis, differential scanning calorimetry (DSC), and impact and friction-sensitivity tests. The structures of compounds 1-4, 7 and 8 were further confirmed by single-crystal X-ray diffraction and six different types of crystal packing were surprisingly discovered. The results show that the extensive hydrogen bonding interactions between the cations and anions lead to a complex 3D network, which contribute greatly to the high density, insensitivity and thermal stability of the 5-amino-1H-1,2,4-triazole-3-carbohydrazide salts. It is also found that the cationic form of 5-amino-1H-1,2,4-triazole-3-carbohydrazide can decrease the sensitivity and elevate the nitrogen content of the target salts effectively. Some of these salts exhibit reasonable physical properties, such as good thermal stability (up to 407 °C) and reasonable impact sensitivities (IS = 5-80 J). In addition, theoretical detonation properties of the energetic salts obtained with EXPLO 5 (version 6.02) confirm them as competitively energetic compounds comparable to those of RDX or HMX.
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