Utility of bis(methylthio)methylene malononitrile as a synthon in the synthesis of new poly-functionalized cyanoiminopyrimidines

Moustafa, Amr H.; Amer, Amer Anwar

doi:10.1007/s00706-017-2037-2

Cited by 5 publications

(1 citation statement)

References 19 publications

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“…Recently, quinazoline compounds and the other heterocyclic compounds attracted many scientists due to their various uses and bioactivities such as antiviral activities, anticancer, antitumor, antidiabetic, antiplasmodium, antiparasite, antioxidant, antimicrobial, anti-inflammatory, and antitubercular. − Notable examples of quinazoline-based drugs include gefitinib and erlotinib, which are tyrosine kinase inhibitors used in the treatment of nonsmall cell lung cancer. These drugs have demonstrated significant efficacy and have revolutionized targeted cancer therapy.…”

Section: Introductionmentioning

confidence: 99%

Preparation, Agricultural Bioactivity Evaluation, Structure–Activity Relationships Estimation, and Molecular Docking of Some Quinazoline Compounds

Hussein,

Moustafa,

Abdou

et al. 2024

J. Agric. Food Chem.

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Quinazoline compounds have gained significant attention in the fields of agriculture and chemistry due to their diverse activities. In this study, we focused on a series of quinazoline derivatives (4a−l). The objectives involved multiple aspects, including preparation, evaluation of their agricultural bioactivity against the maize aphid (Rhopalosiphum maidis), estimation of the structure−activity relationships (SAR), and conducting molecular docking analysis. The results of the agricultural bioactivities revealed that compound (4b) possesses the highest insecticidal activity, and the other compounds have good potential as insecticidal agents. We conducted the SARs and also molecular docking investigation to elucidate the binding modes and interactions of these compounds with target proteins relevant to the agricultural bioactivity. The docking results provided valuable information on the binding affinities and molecular interactions, aiding in the rationalization of the observed bioactivity trends. The enzyme, acetylcholinesterase (AChE), was docked with the 12 synthetic compounds (4a−l). Among these compounds, (4b), (4i), and (4e)exhibited the highest binding affinity, with docking scores (S) of −7.96, −7.83, and −7.73 kcal/mol, respectively. They were followed by compounds (4d) (S = −7.57 kcal/mol), (4c) (S = −7.53 kcal/mol), (4g) (S = −7.34 kcal/mol), (4f) (S = −7.23 kcal/ mol), (4h) (S = −7.14 kcal/mol), (4k) (S = −6.61 kcal/mol), (4j) (S = −6.57 kcal/mol), (4a) (S = −6.28 kcal/mol), and finally (4l) (S = −6.01 kcal/mol). These compounds were shown to have a variety of binding interactions within the 2ACE active site, as evidenced by protein−ligand docking configurations. This study gives evidence that those compounds have AChE-inhibitory capabilities and, hence, may be used for AChE-targeting development. Also, the findings in this study highlight the potential of these compounds as agricultural agents and provide valuable insights for the design and development of some quinazoline derivatives with enhanced bioactivity for crop protection.

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Section: Introductionmentioning

confidence: 99%

Preparation, Agricultural Bioactivity Evaluation, Structure–Activity Relationships Estimation, and Molecular Docking of Some Quinazoline Compounds

Hussein,

Moustafa,

Abdou

et al. 2024

J. Agric. Food Chem.

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Reaction of arylglyoxal hydrate derivatives with cyanoguanidine under benzilic rearrangement effect

Moustafa

Hussein

2021

Monatsh Chem

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Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin

Mabied,

Moustafa,

Abdelhamid

et al. 2023

Sci Rep

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The optimized synthesis of [5-oxo-4,4-diphenylimidazolidin-2-ylidene]cyanamide, which is known as 2-cyanoguanidinophenytoin (CNG-DPH) (3), and (imidazo[4,5-d]imidazole-2,5-diylidine)dicyanamide (4) has been reported in the present work. Furthermore, new Mannich bases derived from CNG-DPH were synthesized via its reaction with formaldehyde and using the corresponding amines, piperidine (base 5), and morpholine (base 6). Also, the antimicrobial activity and X-ray crystal structures for CNG-DPH and their Mannich bases were studied. The bases 3 and 6 crystallized in a monoclinic system; the crystal structure of 3 containing four molecules in the unit cell with a P21/c space group. The unit cell of 6 has eight molecules with a C2/c space group. The inter and intra hydrogen bond contacts packed and stabilized both of the structures. The morpholine ring of base 6 demonstrated a distinctive chair configuration. Mannich bases 5 and 6 showed promising antimicrobial effects. base 4 has a greater percentage for in vitro cytotoxicity (IC50) against normal cells, whereas 3 has the lowest ratio.

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Utility of bis(methylthio)methylene malononitrile as a synthon in the synthesis of new poly-functionalized cyanoiminopyrimidines

Cited by 5 publications

References 19 publications

Preparation, Agricultural Bioactivity Evaluation, Structure–Activity Relationships Estimation, and Molecular Docking of Some Quinazoline Compounds

Preparation, Agricultural Bioactivity Evaluation, Structure–Activity Relationships Estimation, and Molecular Docking of Some Quinazoline Compounds

Reaction of arylglyoxal hydrate derivatives with cyanoguanidine under benzilic rearrangement effect

Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin

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