Synthesis of n-glycosylthioureas, N-glycosylrhodanines, and N-glycosyl-2-aminothiazoles and their Antimicrobial Activity

Foye, William O.; An, Seung Ho

doi:10.1002/jps.2600700924

Cited by 5 publications

(1 citation statement)

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“…The exploration of effective approaches to access privileged structural motifs is one of the most important and urgent requirements in modern organic and pharmaceutical chemistry [1][2][3][4]. As a prime example, N-substituted rhodanines serve as versatile and useful subunits for numerous biological compounds, which are used in several pharmaceutical agents [5][6][7][8][9]. N-substituted rhodanines and their related heterocycles have been identified as synthetic building blocks and structural scaffolds which possess a unique biomolecular interaction profile [10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

A Concise Approach to N-Substituted Rhodanines through a Base-Assisted One-Pot Coupling and Cyclization Process

et al. 2020

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Section: Introductionmentioning

confidence: 99%

A Concise Approach to N-Substituted Rhodanines through a Base-Assisted One-Pot Coupling and Cyclization Process

et al. 2020

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ChemInform Abstract: SYNTHESIS OF N‐GLYCOSYLTHIOUREAS, N‐GLYCOSYLRHODANINES, AND N‐GLYCOSYL‐2‐AMINOTHIAZOLES AND THEIR ANTIMICROBIAL ACTIVITY

Foye¹,

An²

1982

Chemischer Informationsdienst

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Synthesis of certain exocyclic thiazole nucleosides related to tiazofurin. Formation of a unique acycloaminonucleoside

Sanghvi¹,

Larson²,

Robins³

et al. 1988

Journal of Heterocyclic Chem

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Several thiazole nucleosides structurally related to tiazofurin (1) and ARPP (2) were prepared, in order to determine whether these nucleosides had enhanced antitumor/antiviral activities. Ring closure of 1‐(2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranosyl)thiourea (4) with ethyl bromopyruvate (5a) gave ethyl 2‐(2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranosylamino)thiazole‐4‐carboxylate (6a). Treatment of 6a with sodium methoxide furnished methyl 2‐(β‐D‐ribopyranosylamino)thiazole‐4‐carboxylate (9). Ammonolysis of the corresponding methyl ester of 6a gave a unique acycloaminonucleoside 2‐[(1R, 2R, 3R, 4R)(1‐benzamido‐2,3,4,5‐tetrahydroxypentane)amino]‐thiazole‐4‐carboxamide (7a). Direct glycosylation of the sodium salt of ethyl 2‐mercaptothiazole‐4‐carboxylate (12) with 2,3,5‐tri‐O‐benzoyl‐D‐ribofuranosyl bromide (11) gave the protected nucleoside 10, which on ammonolysis provided 2‐(β‐D‐ribofuranosylthio)thiazole‐4‐carboxamide (3b). Similar glycosylation of 12 with 2‐deoxy‐3,5‐di‐O‐p‐toluoyl‐α‐D‐erythro‐pentofuranosyl chloride (13), followed by ammonolysis gave 2‐(2‐deoxy‐β‐D‐ribofuranosylthio)thiazole‐4‐carboxamide (3c). The structural assignments of 3b, 7a, and 9 were made by single‐crystal X‐ray analysis and their hydrogen bonding characteristics have been studied. These compounds are devoid of any significant antiviral/antitumor activity in vitro.

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Synthesis of n-glycosylthioureas, N-glycosylrhodanines, and N-glycosyl-2-aminothiazoles and their Antimicrobial Activity

Cited by 5 publications

References 12 publications

A Concise Approach to N-Substituted Rhodanines through a Base-Assisted One-Pot Coupling and Cyclization Process

A Concise Approach to N-Substituted Rhodanines through a Base-Assisted One-Pot Coupling and Cyclization Process

ChemInform Abstract: SYNTHESIS OF N‐GLYCOSYLTHIOUREAS, N‐GLYCOSYLRHODANINES, AND N‐GLYCOSYL‐2‐AMINOTHIAZOLES AND THEIR ANTIMICROBIAL ACTIVITY

Synthesis of certain exocyclic thiazole nucleosides related to tiazofurin. Formation of a unique acycloaminonucleoside

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