Cellulose Sulfuric Acid as an Eco-Friendly Catalyst for Novel Synthesis of Pyrido[2,3-<i>d</i>][1,2,4]triazolo[4,3-<i>a</i>]pyrimidin-5-ones

Gomha, Sobhi M.; Riyadh, Sayed M.

doi:10.5935/0103-5053.20150052

Cited by 3 publications

(2 citation statements)

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“…In continuation of our studies dealing with the utility of hydrazonoyl halides for synthesis of various bioactive bridgehead nitrogen polyheterocycles [ 21 – 30 ], we wish to report herein a new facile synthesis of new heterocycles containing thiazole and 1,3,4-thiadiazole or two thiazole rings in one molecular frame. We anticipated that the synthesized compounds would have potent pharmacological activities.…”

Section: Introductionmentioning

confidence: 99%

A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents

Gomha

Abdelaziz

Kheder

et al. 2017

Chemistry Central Journal

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BackgroundMany heterocyclic compounds containing thiazole or 1,3,4-thiadiazole ring in their skeletons have been reported to possess various pharmacological activities especially anticancer activities.Results4-Methyl-2-phenylthiazole-5-carbohydrazide (2) was used as a synthon to prepare 2-(4-methyl-2-phenylthiazole-5-carbonyl)-N-phenylhydrazinecarbothioamide (3) and 2-(2-(4-methyl-2-phenylthiazole-5-carbonyl)hydrazono)-N′-phenylpropane hydrazonoyl chlorides 5a–c. In addition, thioamide 3 was used as starting material for preparation of a new series of thiadiazole derivatives via its reaction with hydrazonoyl chlorides 5a–c in dioxane using triethylamines as catalyst. In addition, a series of thiazole derivatives was synthesized by reaction of thioamide 3 with a number of α-halo compounds, namely, 3-chloropentane-2,4-dione (8) or 2-chloro-3-oxo-N-phenyl butanamide (10) phenacyl bromide 12 ethyl chloroacetate (14) in EtOH in the presence of triethylamine. The structures assigned for all the new products were elucidated based on both elemental analyses and spectral data and the mechanisms of their formation was also discussed. Moreover, the new products was evaluated in vitro by MTT assays for their anticancer activity against cell lines of Hepatocellular carcinoma cell line (HepG-2). The best result observed for compounds 7b (IC50 = 1.61 ± 1.92 (μg/mL)) and 11 (IC50 = 1.98 ± 1.22 (μg/mL)). The structure–activity relationships have been suggested based on their anticancer results.ConclusionsA novel series of new pharmacophores containing thiazole moiety have been synthesized using a facile and convenient methods and evaluated as potent anticancer agents.

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Section: Introductionmentioning

confidence: 99%

A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents

Gomha

Abdelaziz

Kheder

et al. 2017

Chemistry Central Journal

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“…Pyridopyrimidines and their intertwined heterocyclic ring frameworks are of current interest [ 1 – 4 ]. Pyrido[2,3- d ]pyrimidines are annulated uracil which, have gotten significant consideration over the last years because of their extensive variety of biological and pharmacological activities, such as anticancer [ 5 – 9 ], antimicrobial [ 10 , 11 ], antiviral [ 12 , 13 ], anti-inflammatory agents [ 14 ] antifolate [ 15 , 16 ], PDE IV inhibitors [ 17 ], and Inhibitors for hepatitis B virus [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents

Zaki

Gomha

Mohamed

2017

Chemistry Central Journal

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BackgroundPyridopyrimidines are of current interest because of their extensive variety of biological and pharmacological activities.ResultsA series of pyrido[2′,3′:4,5]pyrimido[2,1-b][1,3,5]thiadiazinones was obtained by aminomethylation of pyridopyrimidinethione with formaldehyde solution (37%) and different primary aromatic amines. Another series of pyrido[2′,3:4,5]pyrimido[2,1-b][1,3]thiazinones was prepared by Michael addition reaction of pyridopyrimidinethione to the activated double bond of a number of arylidene malononitrile and 2-(benzo[d][1,3]dioxol-5-ylmethylene)malononitrile. The mechanisms of formation of the synthesized compounds were discussed and the assigned structure was established via microanalysis and spectral data (IR, 1H NMR, and Ms.). A comparative study of the biological activity of the synthesized compounds with chloramphenicol and trimethoprim/sulphamethoxazole is shown in Table 1. Generally, all synthesized compounds showed adequate inhibitory effects on the growth of Gram-positive and Gram-negative bacteria. ConclusionsIn this study, we use a simple (synthetic) strategy for the synthesis of pyrimidothiadiazines, based on their aminomethylation through the Mannich reaction; they have also been synthesized by the application of the Michael addition to activated nitriles. Mechanisms and structures of the newly synthesized compounds were examined: the antimicrobial activity of some selected compounds was evaluated, which demonstrated adequate inhibitory effects. Graphical abstractThe strategic structures of the products (7a–g).

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Recent Advances on Cellulose Sulfuric Acid as Sustainable and Environmentally Benign Organocatalyst for Organic Transformations

Agarwal

Lathwal

Nath

2021

COCAT

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Cellulose sulfuric acid has proved its competence as a potential bio-compatible, non-toxic and inexpensive heterogeneous solid acid catalyst in synthetic organic chemistry. Owing to its remarkable properties such as non-hygroscopic nature, recyclability, superior catalytic activity and high stability it has been actively explored as an efficient and biodegradable organocatalyst in diverse chemical transformations of synthetic relevance. This review attempts to summarize a significant advancement and catalytic applications of cellulose sulfuric acid for the synthesis of plethora of biologically relevant organic molecules

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Cellulose Sulfuric Acid as an Eco-Friendly Catalyst for Novel Synthesis of Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5-ones

Cited by 3 publications

References 2 publications

A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents

A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents

Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents

Recent Advances on Cellulose Sulfuric Acid as Sustainable and Environmentally Benign Organocatalyst for Organic Transformations

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