Utility of 2-(5-methyl-1-phenyl-1<i>H</i>-pyrazol-4-yl)-2-oxo-<i>N</i>′-phenylaceto-hydrazonoyl bromide as precursor for synthesis of new functionalized heterocycles

Abdelhamid, Abdou O.; Gomha, Sobhi M.; Abdel‐Riheem, Nadia A.

doi:10.1080/00397911.2017.1303071

Cited by 11 publications

(7 citation statements)

References 30 publications

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“…The hydrazonoyl bromide 205 was synthesized by treatment of sulfonium bromide 203 with an equivalent amount of N ‐nitrosoacetanilide in ethanol at room temperature. N ‐Arylmaleimide derivatives 206a,b were reacted with 205 in toluene in the presence of triethylamine to afford dihydropyrrolo[3,4‐ c ]pyrazole derivatives 207a and 207b , respectively (Scheme ) .…”

Section: Chemistry Of 4‐acetyl‐1h‐pyrazolesmentioning

confidence: 99%

“…The formation of 1,3‐thiazines could be suggested by addition of thiol group in thiosemicarbazone moiety to the activated double bond to give the non‐isolable intermediates 271a–d . Intramolecluar cyclization of intermediates 271a–d via addition of amino group to the nitrile group afforded 6 H ‐1,3‐thiazine derivatives 272a–d (Scheme ) .…”

Section: Chemistry Of 4‐acetyl‐1h‐pyrazolesmentioning

confidence: 99%

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The Chemistry of Acetylpyrazoles and Its Utility in Heterocyclic Synthesis

Abdelhamid

Gomha

2019

Journal of Heterocyclic Chem

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A literature survey revealed that a great deal of interest has been focused on the synthesis of functionalized pyrazole derivatives due to their synthetic and biological potentialities. The pharmacological activities that have been found for some pyrazole derivatives include selective enzyme inhibition, antiviral, estrogen receptor agonist, anti‐inflammatory, anticancer, antiobesity, and antitumor properties. Other activities such as potential inhibitors of HIV‐1, pesticides, fungicides, and antihypertensive agents were reported for other pyrazole derivatives. This review summarizes the synthetic methods and reactions of 3‐acetyl‐pyrazoles, 4‐acetyl‐pyrazoles, and 3,4‐di‐acetyl‐pyrazoles. Most reaction types have been successfully applied and used in the production of biologically active compounds. The aim of this review is to focus mainly on the utility of acetylpyrazole derivatives in the synthesis of heterocyclic compounds during the period 1990–2018.

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Section: Chemistry Of 4‐acetyl‐1h‐pyrazolesmentioning

confidence: 99%

Section: Chemistry Of 4‐acetyl‐1h‐pyrazolesmentioning

confidence: 99%

The Chemistry of Acetylpyrazoles and Its Utility in Heterocyclic Synthesis

Abdelhamid

Gomha

2019

Journal of Heterocyclic Chem

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“…Hydrazonoyl halides have attracted the attention of chemists in organic synthesis, since they exhibit valuable applicability as precursors for the synthesis of various heterocyclic compounds, such as pyrazoles [1], thiazoles [2,3], imidazoles [4], triazoles [5,6], thiadiazoles [7,8], and tetrazines [9].…”

Section: Introductionmentioning

confidence: 99%

Angular Regioselective Synthesis of Varied Functionalized Hexahydro-1,2,4-triazolo[4,3-a]quinazolin-9-ones and Their Antiproliferative Action

et al. 2023

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New 2-thioxopyrimidin-4-ones capable of participating in regioselective reactions with functionally diverse hydrazonoyl chlorides towards angular regioisomers, rather than linear ones, were designed and synthesized to form stereoisomeric cis- and trans-hexahydro [1,2,4]triazolo[4,3-a]quinazolin-9-ones to be tested as antitumor candidates. The angular regiochemistry of the products was verified through crystallographic experiments and NMR studies. In addition, the regioselectivity of the reaction was found to be independent of the stereochemistry of the used 2-thioxopyrimidin-4-one. Only compound 4c demonstrated satisfactory growth inhibition against all the cancer cells used among all the produced drugs.

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“…In continuation of our studies dealing with the utility of hydrazonoyl halides for synthesis of various bridgehead nitrogen polyheterocycles , the synthesis of coumarins and their derivatives have attracted considerable attention from organic and medicinal chemists for many years because of their wide range of medicinal applications such as antitumoral, anti‐inflammatory, antiviral, CNS active, anti‐HIV, and antioxidant activities . Pyrazole derivatives are characterized by their biological and pharmacological activities as potential inhibitors of HIV‐1, pesticides, antihypertensive, fungicides, analgesic, antipyretic, antidepressant, antirheumatic, antiviral, and anticancer agents .…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Pyrazolo[3,4‐c]pyrazoles Bearing Coumarine Ring as Anticancer Agents

Gomha

Abdel‐aziz

Elreedy

2018

Journal of Heterocyclic Chem

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In the present study, 2‐(2‐oxo‐2H‐chromene‐3‐carbonyl)‐5‐phenyl‐2,4‐dihydro‐3H‐pyrazol‐3‐one was prepared and reacted with various hydrazonoyl halides to give a series of 2‐(2‐oxo‐2H‐chromene‐3‐carbonyl)‐5‐phenyl‐4‐((2‐phenylhydrazono)methyl)‐2,4‐dihydro‐3H‐pyrazol‐3‐one in good yield. Cyclization of the latter hydrazone with POCl3 yielded the respective 3‐(3‐phenyl‐ 4,6‐disubstituted‐1,6‐dihydropyrazolo[3,4‐c]pyrazole‐1‐carbonyl)‐2H‐chromen‐2‐ones. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences and their alternative syntheses. The newly synthesized compounds were evaluated for their antitumor activities against hepatocellular carcinoma (HepG2) cell line and the results revealed promising activities of compounds 4e, 4c, and 4d with IC50 equal 0.92 ± 0.22, 1.43 ± 0.19, and 2.17 ± 0.21 μM, respectively.

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Utility of 2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-N′-phenylaceto-hydrazonoyl bromide as precursor for synthesis of new functionalized heterocycles

Cited by 11 publications

References 30 publications

The Chemistry of Acetylpyrazoles and Its Utility in Heterocyclic Synthesis

The Chemistry of Acetylpyrazoles and Its Utility in Heterocyclic Synthesis

Angular Regioselective Synthesis of Varied Functionalized Hexahydro-1,2,4-triazolo[4,3-a]quinazolin-9-ones and Their Antiproliferative Action

Facile Synthesis of Pyrazolo[3,4‐c]pyrazoles Bearing Coumarine Ring as Anticancer Agents

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