Synthesis of new series of Pyrazoline, and study their Kinetics and Reaction Mechanism

Kaka, Kosrat N.; Taher, Salam G.; Hamad, Wali M.; Ibrahim, Aram H.

doi:10.14500/aro.10508

Cited by 6 publications

(6 citation statements)

References 11 publications

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“…It is worth to realize that the activation enthalpies reached the lower value for trans transition state TS2b and highest value cis TS2a, whereas opposite trends were found for TS1a and TS1b this is due to the stereoselectivity in transition states and products. The Gibbs free energies for all products are found to be negative and very close to each other, which indicate that pathways have the same route and no side reactions were found (Kaka, et al, 2019). The enthalpies for products were also found to be negative that indicate that the reactions are possible to occur.…”

Section: Resultsmentioning

confidence: 68%

Theoretical Study of Diels-Alder Reaction of But-3-en-2-one with Hexa-1,2,4-triene: A Density Functional Theory Study

Hassan

Abdallah

2020

ARO

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The Diels-Alder reaction between but-3-en-2-one with hexa-1,2,4-triene was studied using density functional theory method at B3LYP-D3/6-311++G(d,p) level of theory. The geometries of the transition states were determined. Moreover, calculations of the vibrational frequencies permitted computation of the activation enthalpies and entropies. The computational results show that the cycloadducts from trans conformer have the lower relative energies (−46.48 and −47.50 kcal/mol) as compared to the cis conformer of cycloadducts (−44.45 and −45.87 kcal/mol). The global reactivity indices were analyzed at the ground state of reactants to predict the reactivity of the studied organic molecules in the cycloaddition reactions. The electronic chemical potential of hexa-1,2,4-trien found to be than but-3-en-2-one, which indicates that the net charge transfer will be from hexa-1,2,4-trien toward the electron-deficient but-3-en-2-one reactant.

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Section: Resultsmentioning

confidence: 68%

Theoretical Study of Diels-Alder Reaction of But-3-en-2-one with Hexa-1,2,4-triene: A Density Functional Theory Study

Hassan

Abdallah

2020

ARO

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“…Formation of pyrazolines 4a , b and 5a , b can be rationalized on the basis of the reaction pathway. Firstly, formation of hydrazone intermediate followed by subsequent addition of N‐H proton to benzylidene bond moiety followed by ring closure [38, 40, 41], to give the dihydropyrazolines 5a and 5b as final products. While in the case of pyrazolines 4a and 4b the reaction took place through the forming of the dihydropyrazolines intermediate which underwent autoxidation by the loss of hydrogen molecule with the formation of 4a and 4b (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

“…The results showed the apoptotic effect of compounds 5b and 15 by increasing the percentage of positive apoptotic cells in (upper right + lower right) quadrants from 1.63% to 48. 41 respectively with regard to the control, with more significance of the late apoptosis. In the same context, compounds 5b and 15 caused a 9.04-and 7.22-fold increase in their necrotic ability compared to the control, Figure 7.…”

Section: Cell Cycle Analysis and Apoptotic Study In Mda-mb-436 Cellsmentioning

confidence: 94%

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

Maigali

El-Shanawany

El‐Sayed

et al. 2022

Journal of Heterocyclic Chem

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A new series of spiro aryl dioxolane derivatives were synthesized and evaluated to find a new scaffold as potential poly(ADP-ribose)polymerases-1 (PARP-1) inhibitors. This key starting compound, 2,6-bis(methoxybenzylidene)cyclohexanone, was functionalized with different nucleophilic reagents via cyclocondensation reactions to obtain new benzylidene scaffolds containing diverse aryl groups such as spiroindazoleorquinazoline [1,3]dioxolane compounds. Furthermore, the Michael addition reaction of bis-benzylidene with some active methylene compounds afforded spirochromene-or naphthalene-[1,3]dioxolane compounds. All the synthesized compounds revealed promising inhibition with IC 50 values in the nanomolar range (0.997-2.698 nM), not significantly different from that of Olaparib (IC 50 = 0.861 nM). Compounds 5b and 15 (IC 50 = 1.009 and 0.997 nM) showed the highest potency among all the prepared compounds and accordingly their ability to inhibit the growth of BRCA1 mutated breast cancer cell line MDA-MB-436 was tested, where compound 5b (IC 50 = 0.67 μM) showed a potency ten folds higher than that of Olaparib but compound 15 (IC 50 = 7.47 μM) exerted lower activity but still comparable to that of Olaparib (IC 50 = 6.84 μM). Both resulted in the arrest of cell cycle at S phase and caused cell apoptosis. In silico studies including absorption, distribution, metabolism, excretion (ADME) properties, drug-likeness, and molecular docking were carried out to support the above-mentioned findings. This work presents compounds 5b and 15 as promising scaffolds as PARP-1 inhibitors. | INTRODUCTIONPoly(ADP-ribose) polymerases (PARPs) comprise a family of adenosine diphosphate ribosyltransferases (ADPribosyltransferases) found in all six major eukaryotic supergroups, as well as several species of prokaryotes and dsDNA virus. This family comprises 18 members that are implicated in different processes on the cellular level such as controlling genome integrity and checkpoints for the cell cycle and also have a role in the signaling pathways of DNA repair, transcription, and apoptosis. PARP proteins transfer ADP-ribose moieties to arginine, glutamate, aspartate, cysteine, lysine, and serine acceptor sites [1][2][3][4].The most abundant and well-known member is PARP-1, due to its important role in DNA damage

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“…Insulation on the pipe connections ensured that temperature fluctuations in the reaction cell were minimal. The study examined the kinetics of a reaction between Chalcone and Schiff base in DMSO and a basic medium of 10% sodium ethoxide in ethanol as a solvent (Kaka et al, 2019). The concentration of the Schiff base was 100 times greater than the concentration of Chalcone.…”

Section: General Procedures 211 Preparation Of N-(4methoxybenzylidene...mentioning

confidence: 99%

Synthesis, Kinetics, Reaction Mechanism and Biological Activity Studies of Novel 1, 3-Oxazine Compound

2023

ZJPAS

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A novel 1, 3-Oxazine compound ((E)-8-benzylidene-2-(4-methoxyphenyl)- 3,4,5,6,7,3]oxazine) was synthesized by reaction of N-(4-methoxybenzylidene)aniline(Schiff base) with 2,6-di((E)benzylidene)cyclohexan-1-one(chalcone). The structure of 1, 3-Oxazine compound was characterized through spectral data (FT-IR, 1H-NMR and Ultraviolet-Visible spectrophotometer). The kinetics study of the novel synthesized 1, 3-Oxazine compound was studied to determine the order of the reaction and the mechanism pathway. It was found that the reaction is first order undergoes via (imino-Diels-Alder). The reaction rate, Arrhenius factor (A), thermodynamic functions (E a (free energy of activation), S # (entropy of activation), and G # (Gibbs energy of activation)) were also calculated and confirmed the formation of 1, 3-Oxazine cycle. Finally, the antibacterial activities against gram negative (Escherichia coli) with gram positive (Staphylococcus aureus) were evaluated optical density for finding minimum inhibition concentration (MIC).

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Synthesis of new series of Pyrazoline, and study their Kinetics and Reaction Mechanism

Cited by 6 publications

References 11 publications

Theoretical Study of Diels-Alder Reaction of But-3-en-2-one with Hexa-1,2,4-triene: A Density Functional Theory Study

Theoretical Study of Diels-Alder Reaction of But-3-en-2-one with Hexa-1,2,4-triene: A Density Functional Theory Study

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

Synthesis, Kinetics, Reaction Mechanism and Biological Activity Studies of Novel 1, 3-Oxazine Compound

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