Synthesis of 1,4-phenylene bridged bis-heterocyclic compounds

Shaker, Raafat M.

doi:10.3998/ark.5550190.0013.101

Cited by 5 publications

(3 citation statements)

References 25 publications

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“…TLC using Merck 60 F-254 silica gel plates was used to follow the progress of every reaction. 1, 1, 1, 17.43. Found: C,48.46;H,4.16;N,17.48%.…”

Section: Methodsmentioning

confidence: 99%

“…Thiazolopyrimidines as purine antagonists are known to have potential biological importance. 1,2 In general, they are widely used in the fields of medicine and pesticides. [3][4][5] The [4,5-d] isomer of thiazolopyrimidine can be considered as the 7-thia analogues of guanine and adenine due to the replacement of a nitrogen by a sulfur atom at position 7 of the purine ring.…”

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confidence: 99%

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One-Pot Three-Component Synthesis of bis[2-(methylthio)-7-oxothiazolo[4,5-d]pyrimidin-6(7H)-yl]benzenes

Fang

Zheng

2013

Journal of Chemical Research

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Three-component reactions of ethyl 2-methylthio-4-[(triphenylphosphanylidene)amino] thiazole-5-carboxylate with aromatic diisocyanates and secondary amines produced novel bis [2-methylthio-7-oxothiazolo[4,5-d]pyrimidin-6(7H)yl]benzenes in the presence of EtONa in 67-93% yields. This method provides an effective synthesis of nitrogencontaining heterocycles with the advantages of mild reaction conditions, simple operation and good yields. The structures of the products were confirmed by 1 H NMR, IR, MS and elemental analysis.

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“…TLC using Merck 60 F-254 silica gel plates was used to follow the progress of every reaction. 1, 1, 1, 17.43. Found: C,48.46;H,4.16;N,17.48%.…”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

One-Pot Three-Component Synthesis of bis[2-(methylthio)-7-oxothiazolo[4,5-d]pyrimidin-6(7H)-yl]benzenes

Fang

Zheng

2013

Journal of Chemical Research

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“…In recent decades, there have been a considerable interest in the synthesis and biological activities of phenylene-bridged bis-heterocyclic compounds [11][12][13][14][15][16]. In the drug design, pharmacophore hybrid approach is an effective protocol in the search for novel drug candidates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative and Antilipolytic Activities of a Series of 1,3- and 1,4-Bis[5-(R-sulfanyl)-1,2,4-triazol-3-yl)benzenes

et al. 2021

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A series of 1,3 and 1,4-bis[5-(R-sulfanyl)-1,2,4-triazol-3-yl)benzene derivatives were synthesized by the reac tion of isophthalic and terephthalic acid hydrazides with methyl and aryl isothiocyanates, followed by base-catalyzed cyclization and alkylation of the resulting bis-triazolethiols with alkyl bromides. The suggested obesity-colorectal cancer association initiated evaluation of the antiproliferative activity of the newly syn thesized compounds against a panel of obesity-related colorectal cells and inhibition of pancreatic lipase (PL). In vitro enzymatic, colorimetric, and cell culture bioassays were carried out with respective reference agents. Among the tested compounds, 1,3-bis{5-[(4-bromobenzyl)sulfanyl]-4-methyl-4H-1,2,4-triazol-3-yl}ben zene showed clearly promising, though unselective, cytotoxicity in HT29, HCT116, SW620, CACO2, and SW480 cancer cells with a PL-IC 50 value of 9.57±1.21 μM (<10 μM). Hence, the pharmacophores of most promising compounds can be druggable leads with a novel duality of antidiabesity-antineoplastic capacities and optimized potency and safety. Mechanistic examinations for hindrance of lipolysis catalysis and apoptogenic growth inhibition propensity may be attempted.

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One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

Bhat

2020

ChemistrySelect

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Bis‐heterocycles (BHCs) are hybrid molecules comprising two linked, bound, spacer, or fused heterocyclic skeletons. In recent years, these compounds have attracted increased attention of scientific communities because of their improved potential applications than their discrete units. The emergence of numerous synthetic protocols utilizing Isocyanide as one of the components in multicomponent reactions has unleashed innumerable openings to design and synthesize diverse heterocyclic scaffolds and thus Isocyanide based multicomponent reactions (IMCRs) are leading today's MCR chemistry. To date, there has not been any exclusive review on the construction of BHCs via direct IMCRs or its combination with other reaction sequences in one‐pot. This article presents the first overview of IMCRs such as Ugi, Groebke‐Blackburn‐Bienaymé (GBBR), their sequential combination with other reactions, and new IMCRs established for the one‐pot synthesis of BHCs in the last two decades.

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Synthesis of 1,4-phenylene bridged bis-heterocyclic compounds

Abstract: The synthesis of 1,4-phenylene bis-heterocyclic compounds is comprehensively reviewed.

Cited by 5 publications

References 25 publications

One-Pot Three-Component Synthesis of bis[2-(methylthio)-7-oxothiazolo[4,5-d]pyrimidin-6(7H)-yl]benzenes

One-Pot Three-Component Synthesis of bis[2-(methylthio)-7-oxothiazolo[4,5-d]pyrimidin-6(7H)-yl]benzenes

Synthesis and Antiproliferative and Antilipolytic Activities of a Series of 1,3- and 1,4-Bis[5-(R-sulfanyl)-1,2,4-triazol-3-yl)benzenes

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

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