Synthesis of spiro-pyrazole-3,3′-thiopyrano[2,3-b]pyridines and azolo[a]pyrido[2′,3′:5,6]thiopyrano[3,4-d]pyrimidines as new ring systems with antifungal and antibacterial activities

Dawood, Kamal M.

doi:10.1002/jhet.5570420207

Cited by 41 publications

(5 citation statements)

References 19 publications

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“…For example, the 1 H NMR spectrum of 7a showed two singlet signals at δ 2.96 and 3.72 ppm characteristic for -N(Me) 2 group, two doublet signals at δ about 5.75 and 7.64 ppm with coupling constant J = 13 Hz assignable to the two olefinic protons. The value of coupling constant is compatible with the E-configuration [24] depicted in Figure 2. Also its 13 C NMR spectrum showed two signals at δ 37.31 and 45.48 ppm assignable to -N(Me) 2 group [25], in addition to the signals of other carbon atoms.…”

Section: Resultssupporting

confidence: 72%

Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives

Hassaneen¹,

Mohammed²

2011

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The reaction of 1-methylisoquinoline 1 with hydrazonoyl halides 2 in ethanol in the presence of chitosan under microwave irradiation affords triazoloisoquinoline 4. Product 4 reacts with dimethylformamide-dimethylacetal to give enaminones 7 which react with hydrazonoyl halides to give pyrazolyl triazoloisoquinoline 13. Also, 1-methylisoquinoline 1 reacts with arylisothiocyanate to give thioanilide 15 which reacts with hydrazonoyl halides to give the corresponding thiadiazolyl isoquinoline derivatives 20, 24.

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Section: Resultssupporting

confidence: 72%

Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives

Hassaneen¹,

Mohammed²

2011

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“…Enaminones formerly have been employed as prospective precursors for fused heterocyclic sets, when responding with heterocyclic amines [54,55,56,57]. Consequently, the action of enaminone ( 4 ) with several heterocyclic amines, such as 3-amino-1 H -1,2,4-triazole, 5-phenyl-2 H -pyrazol-3-ylamine, and 5-amino-3-methylthiopyrazole-4-carbonitrile in acetic acid resulted in new ring systems of triazolo[4,3- a ]pyrimidine ( 16 ), pyrazolo[1,5- a ]pyrimidine ( 22 ), and pyrazolo[1,5- a ]pyrimidine-3-carbonitrile ( 28 ), respectively, Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

Rational Design and Synthesis of Diverse Pyrimidine Molecules Bearing Sulfonamide Moiety as Novel ERK Inhibitors

Halawa

Eskandrani

Elgammal

et al. 2019

IJMS

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Protein kinases orchestrate diverse cellular functions; however, their dysregulation is linked to metabolic dysfunctions, associated with many diseases, including cancer. Mitogen-Activated Protein (MAP) kinase is a notoriously oncogenic signaling pathway in human malignancies, where the extracellular signal-regulated kinases (ERK1/2) are focal serine/threonine kinases in the MAP kinase module with numerous cytosolic and nuclear mitogenic effector proteins. Subsequently, hampering the ERK kinase activity by small molecule inhibitors is a robust strategy to control the malignancies with aberrant MAP kinase signaling cascades. Consequently, new heterocyclic compounds, containing a sulfonamide moiety, were rationally designed, aided by the molecular docking of the starting reactant 1-(4-((4-methylpiperidin-1-yl)sulfonyl)phenyl)ethan-1-one (3) at the ATP binding pocket of the ERK kinase domain, which was relying on the molecular extension tactic. The identities of the synthesized compounds (4–33) were proven by their spectral data and elemental analysis. The target compounds exhibited pronounced anti-proliferative activities against the MCF-7, HepG-2, and HCT-116 cancerous cell lines with potencies reaching a 2.96 μM for the most active compound (22). Moreover, compounds 5, 9, 10b, 22, and 28 displayed a significant G2/M phase arrest and induction of the apoptosis, which was confirmed by the cell cycle analysis and the flow cytometry. Thus, the molecular extension of a small fragment bounded at the ERK kinase domain is a valid tactic for the rational synthesis of the ERK inhibitors to control various human malignancies.

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“…In the past few years, further discoveries have expanded the therapeutic potential of b-aminovinyl ketones beyond appreciation of their established anticonvulsant activity. Accordingly, they have been recognised recently by several research groups as compounds with a diverse range of interesting pharmacological properties in their own right, including antibacterial, [41] antifungal, [42] histaminergic, [3,43] and antimalarial [44] activities. Biologically active aminovinyl ketones also include the 2-alkylideneindole 15, which has anti-inflammatory potential, [45][46][47] the fused cyclopropane 16, and a synthetic analogue of the duocarmycin class of antitumour agents.…”

Section: Metabolic Studiesmentioning

confidence: 99%

Unlocking the Chemotherapeutic Potential of β‐Aminovinyl Ketones and Related Compounds

Gaber

Bagley

2009

ChemMedChem

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The role of beta-aminovinyl ketones as synthetic intermediates has been well categorised, but recent developments have shown an interesting array of applications and new chemotherapeutic potential, both in the preparation of biologically active heterocycles and as pharmacophores in their own right.Medicinal chemists are accustomed to using the products of Knoevenagel-type condensations as auxiliaries for the synthesis of N-containing heteroaromatic compounds. One such example of these chemical building blocks are beta-aminovinyl ketones-valuable synthetic intermediates that have been used in the preparation of pyridines, pyrimidines, pyrazoles, and many other heterocyclic motifs. This review highlights their recent use in the synthesis of biologically active targets as part of drug discovery programmes and in natural product synthesis. However, it is becoming increasingly evident that the enaminone motif may serve as a therapeutic pharmacophore in its own right. This review highlights the range of biological responses that beta-aminovinyl ketones elicit, including as antitumour, antibacterial, and anticonvulsant agents. Thus, with a broad spectrum of biological properties and as versatile chemical intermediates, it is clear that beta-aminovinyl ketones offer great potential in the search for new chemotherapeutic agents.

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Synthesis of spiro-pyrazole-3,3′-thiopyrano[2,3-b]pyridines and azolo[a]pyrido[2′,3′:5,6]thiopyrano[3,4-d]pyrimidines as new ring systems with antifungal and antibacterial activities

Cited by 41 publications

References 19 publications

Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives

Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives

Rational Design and Synthesis of Diverse Pyrimidine Molecules Bearing Sulfonamide Moiety as Novel ERK Inhibitors

Unlocking the Chemotherapeutic Potential of β‐Aminovinyl Ketones and Related Compounds

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