Synthesis and anti-rotavirus activity of some nitrogen heterocycles integrated with pyrazole scaffold

El‐Helw, Eman A. E.; Gado, Marwa M.; El‐Ziaty, Ahmed K.

doi:10.1007/s13738-020-01873-7

Cited by 21 publications

(7 citation statements)

References 31 publications

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“…Herein, 2‐cyano‐3‐(1,3‐diphenyl‐1 H ‐pyrazol‐4‐yl)propenoyl chloride (1) [ 4 ] was successfully used as a key starting material for constructing a new series of pharmaceutically active compounds through its treatment with some nucleophilic reagents containing O, S or N‐atoms. Initially, when the acid chloride, 1, reacted with 4‐(benzo[ d ]thiazol‐2‐yl)phenol (2) , 2‐mercaptobenzoic acid, benzylamine, or dodecylamine, the ester, 3 , thioester, 4, and acrylamides, 5, 6, were obtained in good yields, respectively (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…The key starting material, 2-cyanopropenoyl chloride derivative (1), was previously prepared by us. [4] Reaction of propenoyl chloride derivative 1 with 4-(benzo General procedure for the reaction of 1 with benzylamine and dodecylamine. Benzylamine (0.32 g, 3 mmol) or dodecylamine (0.55 g, 3 mmol) was added to a stirred solution of propenoyl chloride derivative, 1 (1 g, 3 mmol), in dry dioxane (10 mL), including triethylamine (2-drops), at room temperature.…”

Section: Discussionmentioning

confidence: 99%

“…The key starting material, 2‐cyanopropenoyl chloride derivative (1), was previously prepared by us. [ 4 ]…”

Section: Methodsmentioning

confidence: 99%

“…Considering its large pharmacological scope, substituted pyrazole skeleton is one of the worthy structure fragments in the synthetic and medicizznal chemistry, such as anti‐influenza, [ 1,2 ] antiviral, [ 3–6 ] anticancer, [ 7–12 ] anti‐inflammatory, [ 13,14 ] antitubercular, antiangiogenic, [ 15,16 ] antimicrobial, antioxidant, antidepressant, and insecticidal activities. [ 17–21 ] Moreover, the pyrazole ring is considered as an auspicious skeleton providing fair anti‐CDK2 (cyclin‐dependent kinases) behavior with selective and low toxic effects, for example, PNU‐292137 and ethyl 4‐amino‐1 H ‐pyrazole‐3‐carboxylate [ 22 ] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, antiproliferative activity, and molecular docking of some N‐heterocycles bearing a pyrazole scaffold against liver and breast tumors

Ramadan

El‐Ziaty

Ali

2020

Journal of Heterocyclic Chem

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A new series of some 1,3‐diphenylpyrazole‐based heterocycles were constructed from 2‐cyano‐3‐(1,3‐diphenyl‐1H‐pyrazol‐4‐yl)propenoyl chloride (1). The titled acid chloride was submitted to react with mono‐nucleophilic reagents, including oxygen, sulfur, or nitrogen, to afford new acrylate, thioacrylate, and acrylamide derivatives, respectively. Meanwhile, condensation of 1 with some 1,2‐ and 1,3‐binucleophiles led to the construction of oxadiazepine, pyridopyrimidine, and thiadiazolopyrimidine derivatives (16, 18, 20, 23). In turn, two benzoxazinone derivatives (27, 28) were synthesized upon treating 1 with substituted anthranilic acids followed by heating with acetic anhydride. The antiproliferative activity of the compounds developed against two tumors (HePG2 and MCF7) was evaluated. Compounds 4, 6, 11, 25, and 26 exhibited strong activity and compounds 3, 5, 16, 18, 27, and 28 exhibited moderate activity. A molecular modeling study was conducted by utilizing molecular modeling environment to test the binding free energies of the studied compounds toward human cyclin‐dependent kinase 2. The compounds, 4, 25, and 26, displayed the best docking score. The orientation and hydrogen bond pattern of these compounds in the active site correspond to that of PNU‐292137, which had been approved as a selective CDK2 inhibitor.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

“…The key starting material, 2‐cyanopropenoyl chloride derivative (1), was previously prepared by us. [ 4 ]…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, antiproliferative activity, and molecular docking of some N‐heterocycles bearing a pyrazole scaffold against liver and breast tumors

Ramadan

El‐Ziaty

Ali

2020

Journal of Heterocyclic Chem

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“…Pyrazole analogs are useful building blocks in designing pharmaceuticals. In comparison with the other tested compounds, Compound 7 manifested the highest anti-HAV (hepatitis-A virus) activity at a concentration of 20 μg/105 cells [ 32 ].…”

Section: Biological Activitymentioning

confidence: 99%

Selected β2-, β3- and β2,3-Amino Acid Heterocyclic Derivatives and Their Biological Perspective

Bąchor¹,

Mączyński²

2021

Molecules

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Heterocyclic moieties, especially five and six-membered rings containing nitrogen, oxygen or sulfur atoms, are broadly distributed in nature. Among them, synthetic and natural alike are pharmacologically active compounds and have always been at the forefront of attention due to their pharmacological properties. Heterocycles can be divided into different groups based on the presence of characteristic structural motifs. The presence of β-amino acid and heterocyclic core in one compound is very interesting; additionally, it very often plays a vital role in their biological activity. Usually, such compounds are not considered to be chemicals containing a β-amino acid motif; however, considering them as this class of compounds may open new routes of their preparation and application as new drug precursors or even drugs. The possibility of their application as nonproteinogenic amino acid residues in peptide or peptide derivatives synthesis to prepare a new class of compounds is also promising. This review highlights the actual state of knowledge about β-amino acid moiety-containing heterocycles presenting antiviral, anti-inflammatory, antibacterial compounds, anaplastic lymphoma kinase (ALK) inhibitors, as well as agonist and antagonists of the receptors.

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Evaluation of some new heterocycles bearing 2‐oxoquinolyl moiety as immunomodulator against highly pathogenic avian influenza virus (H₅N₈)

El‐Helw

Morsy

Hashem

2021

Journal of Heterocyclic Chem

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The hydrazide obtained from furan‐2(3H)‐one integrated with a quinolin‐2(1H)‐one core reported previously by our research group was utilized as a building block synthon to obtain some pyrrolone, pyridazinone, oxadiazole, and triazole derivatives through treating with some carbon electrophilic reagents, for example, chloroacetyl chloride, benzoyl chloride, acetic anhydride, carbon disulfide, 3,4‐dimethoxybenzaldehyde, and 2‐oxoquinolin‐3‐carbaldehyde to achieve the target heterocycles. The newly synthesized compounds were evaluated as immunomodulator against highly pathogenic avian influenza virus (H5N8). The compounds 1, 11, and 17 displayed the highest potency (100% protection).

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Synthesis and anti-rotavirus activity of some nitrogen heterocycles integrated with pyrazole scaffold

Cited by 21 publications

References 31 publications

Synthesis, antiproliferative activity, and molecular docking of some N‐heterocycles bearing a pyrazole scaffold against liver and breast tumors

Synthesis, antiproliferative activity, and molecular docking of some N‐heterocycles bearing a pyrazole scaffold against liver and breast tumors

Selected β2-, β3- and β2,3-Amino Acid Heterocyclic Derivatives and Their Biological Perspective

Evaluation of some new heterocycles bearing 2‐oxoquinolyl moiety as immunomodulator against highly pathogenic avian influenza virus (H₅N₈)

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Synthesis and anti-rotavirus activity of some nitrogen heterocycles integrated with pyrazole scaffold

Cited by 21 publications

References 31 publications

Synthesis, antiproliferative activity, and molecular docking of some N‐heterocycles bearing a pyrazole scaffold against liver and breast tumors

Synthesis, antiproliferative activity, and molecular docking of some N‐heterocycles bearing a pyrazole scaffold against liver and breast tumors

Selected β2-, β3- and β2,3-Amino Acid Heterocyclic Derivatives and Their Biological Perspective

Evaluation of some new heterocycles bearing 2‐oxoquinolyl moiety as immunomodulator against highly pathogenic avian influenza virus (H5N8)

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Evaluation of some new heterocycles bearing 2‐oxoquinolyl moiety as immunomodulator against highly pathogenic avian influenza virus (H₅N₈)