A perspective on environmentally benign protocols of thiazole synthesis

Chowdhury, Arnab; Patel, Sagarkumar; Sharma, Ayushi; Das, Anwesha; Meshram, Payal; Shard, Amit

doi:10.1007/s10593-020-02680-x

Cited by 18 publications

(13 citation statements)

References 30 publications

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“…Previous studies have discovered that a thiazoline ring of the original structure should be conserved for emitting bioluminescence, whereas an aromatic ring and its substituents could be modified [ 26 ]. A thiazole ring containing firefly luciferin is responsible for the characteristic yellow-light emission from fireflies [ 27 ]. Bioluminescent systems have important roles in medicinal biology and clinical applications for the design of protein-based biosensors for detection of the SARS-CoV-2 virus [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

Minickaitė

Grybaitė

Vaickelionienė

et al. 2022

IJMS

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It is well-known that thiazole derivatives are usually found in lead structures, which demonstrate a wide range of pharmacological effects. The aim of this research was to explore the antiviral, antioxidant, and antibacterial activities of novel, substituted thiazole compounds and to find potential agents that could have biological activities in one single biomolecule. A series of novel aminothiazoles were synthesized, and their biological activity was characterized. The obtained results were compared with those of the standard antiviral, antioxidant, antibacterial and anticancer agents. The compound bearing 4-cianophenyl substituent in the thiazole ring demonstrated the highest cytotoxic properties by decreasing the A549 viability to 87.2%. The compound bearing 4-trifluoromethylphenyl substituent in the thiazole ring showed significant antiviral activity against the PR8 influenza A strain, which was comparable to the oseltamivir and amantadine. Novel compounds with 4-chlorophenyl, 4-trifluoromethylphenyl, phenyl, 4-fluorophenyl, and 4-cianophenyl substituents in the thiazole ring demonstrated antioxidant activity by DPPH, reducing power, FRAP methods, and antibacterial activity against Escherichia coli and Bacillus subtilis bacteria. These data demonstrate that substituted aminothiazole derivatives are promising scaffolds for further optimization and development of new compounds with potential influenza A-targeted antiviral activity. Study results could demonstrate that structure optimization of novel aminothiazole compounds may be useful in the prevention of reactive oxygen species and developing new specifically targeted antioxidant and antibacterial agents.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

Minickaitė

Grybaitė

Vaickelionienė

et al. 2022

IJMS

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“…Typically, 2aminothiazoles are obtained by two-component reactions from α-halocarbonyl compounds I with thioureas. [1][2][3]11 In our previous work we described the synthesis of 2-aminothiazoles by reaction of thioureas with 3-aryl-2-chloropropanals, obtained by Meerwein arylation of acrolein. 4 2-Aminothiazoles substituted at the N atom or in the positions 3, 4, and 5 can be prepared from α-thiocyanato carbonyl compounds II, 12−16 which are available by nucleophilic substitution of α-haloketones, 12−14 direct thiocyanation of ketones, 15−17 or by water addition to thiocyanatoalkynes.…”

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confidence: 99%

“…Substituted 2-aminothiazoles − are of great importance in heterocyclic chemistry and the privileged scaffolds of a great variety of bioactive compounds, among which are anticancer, , antibacterial, antitubercular, and antileishmanial substances. Consequently, the 2-aminothiazole core is found in many clinical drugs such as Cefditoren, Pramipexole, Alpelisib, Dasatinib, and others (Figure ).…”

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confidence: 99%

“…Consequently, the 2-aminothiazole core is found in many clinical drugs such as Cefditoren, Pramipexole, Alpelisib, Dasatinib, and others (Figure ). Apart from that, aminothiazole derivatives are building blocks of numerous materials, tunable fluorescent dyes, and analytical reagents …”

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confidence: 99%

“…2-Aminothiazoles can be prepared by the formation of one or two bonds from suitable starting materials by cyclization of bifunctional acyclic precursors I – II − ,− or functionalization of an existing thiazole ring III (Figure ). Typically, 2-aminothiazoles are obtained by two-component reactions from α-halocarbonyl compounds I with thioureas. − , In our previous work we described the synthesis of 2-aminothiazoles by reaction of thioureas with 3-aryl-2-chloropropanals, obtained by Meerwein arylation of acrolein …”

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confidence: 99%

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Thiocyanatoarylation of Methyl Vinyl Ketone under Meerwein Conditions for the Synthesis of 2-Aminothiazole-Based Heterocyclic Systems

Ostapiuk

Goreshnik

et al. 2022

Org. Lett.

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4-Aryl-3-thiocyanatobutan-2-ones were prepared by Meerwein reactions from methyl vinyl ketone and aryldiazonium salts under copper(II) catalysis in 35−75% yields. α-Thiocyanato ketones regioselectively react with 1-methyl-3-aminopyrazole forming N-(3pyrazolyl)-substituted 2-aminothiazoles in 80−91% yields. An ester group in position 3 of the pyrazole induced a regioselective ring-closure reaction followed by an intramolecular cyclization, which gave first representatives of a new heterocyclic system, pyrazolo[4,3-e]thiazolo-[3,2-a]pyrimidine, in 74−93% yields. In addition, the preparations of 5benzyl-4-methylthiazol-2-ones in 84−93% yields are described.

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KI/K₂S₂O₈ Mediated Cascade C(sp³)−H/C(sp²)−H Thiolation for the Synthesis of Multi‐Substituted Thiazoles

Zhang

2022

Eur J Org Chem

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Thiazole and carbonyl often act as core functional or regulative moieties in biological molecules as well as optical materials. Designing and synthesis of carbonyl‐containing thiazoles are of great importance for related fields, hence, a simple and practical method was developed using commercially xanthates, benzylamine, and readily available alkynones as substrates. The reaction was achieved using one‐pot Michael addition and cascade iodine mediated C−H thiolation under mild conditions. This method features a broad substrate scope with high yield. Remarkably, the obtained carbonyl substituted thiazoles bearing electronic‐donating substituents exhibit promising performance for aggregation‐induced emission (AIE) and have been successfully used in biological imaging.

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A perspective on environmentally benign protocols of thiazole synthesis

Cited by 18 publications

References 30 publications

Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

Thiocyanatoarylation of Methyl Vinyl Ketone under Meerwein Conditions for the Synthesis of 2-Aminothiazole-Based Heterocyclic Systems

KI/K₂S₂O₈ Mediated Cascade C(sp³)−H/C(sp²)−H Thiolation for the Synthesis of Multi‐Substituted Thiazoles

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A perspective on environmentally benign protocols of thiazole synthesis

Cited by 18 publications

References 30 publications

Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

Thiocyanatoarylation of Methyl Vinyl Ketone under Meerwein Conditions for the Synthesis of 2-Aminothiazole-Based Heterocyclic Systems

KI/K2S2O8 Mediated Cascade C(sp3)−H/C(sp2)−H Thiolation for the Synthesis of Multi‐Substituted Thiazoles

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KI/K₂S₂O₈ Mediated Cascade C(sp³)−H/C(sp²)−H Thiolation for the Synthesis of Multi‐Substituted Thiazoles