Highlights on the Synthesis and Biological Activity of 1,3-Selenazoles

Facchinetti, Victor; Nery, Ana C. S.; Avellar, Marcela M.; Gomes, Cláudia R. B.; Souza, Marcus V. N. de; Vasconcelos, Thatyana R. A.

doi:10.2174/1570179411666141201201009

Cited by 14 publications

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“…The 2-aminothiazole and 2-amino-1,3-selenazole ring systems have received much attention from medicinal chemists worldwide because of their wide range of biological activity, such as antimicrobial, anti-HIV, antioxidant, anticancer, among others. 1,2 In view of the importance of these heterocyclic cores, many synthetic methodologies have been reported in the literature. 2,3 Despite this, the Hantzsch condensation (1887) 4 of α-halocarbonyl compounds with thioureas or selenoureas remains a prominent method for the synthesis of these compounds.…”

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“…1,2 In view of the importance of these heterocyclic cores, many synthetic methodologies have been reported in the literature. 2,3 Despite this, the Hantzsch condensation (1887) 4 of α-halocarbonyl compounds with thioureas or selenoureas remains a prominent method for the synthesis of these compounds. 1 In the last few years, many novel protocols that improve Hantzsch's original procedure have been reported.…”

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An Eco-friendly, Hantzsch-Based, Solvent-Free Approach to 2-Aminothiazoles and 2-Aminoselenazoles

et al. 2015

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We report a simple, fast, and eco-friendly solvent-free protocol for the synthesis of 2-aminothiazoles and 2-amino-1,3-selenazoles (16 examples) through Hantzsch condensation without the use of a catalyst. It is noteworthy that this type of procedure is unprecedented for the synthesis of 1,3-selenazoles. Reactions proceed to completion in a few seconds and products are obtained in moderate to excellent yields after easy workup. Moreover, the synthesis of 4-(2-amino-1,3selenazol-4-yl)benzonitrile hydrobromide is reported for the first time.

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An Eco-friendly, Hantzsch-Based, Solvent-Free Approach to 2-Aminothiazoles and 2-Aminoselenazoles

et al. 2015

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“…[57][58][59][60][61][62] Amongst heterocyclic organoselenium cores, the 1,3-selenazole skeleton has received much attention in many pharmacologically active substances like selenazofurin (I) and amselamine (II). (Figure 1) Biological properties such as antioxidant, [13] anticancer, [8,63,64] human carbonic anhydrase IX inhibitory, [12] antimicrobial and anticonvulsant [39] activities are the other worldwide high profile of 1,3-selenazoles.…”

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Synthesis of Various Derivatives of [1,3]Selenazolo[4,5‐d]pyrimidine and Exploitation of These Heterocyclic Systems as Antibacterial, Antifungal, and Anticancer Agents

et al. 2020

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A number of diversely functionalized derivatives of a novel [1,3]selenazolo[4,5‐d]pyrimidine have been synthesized through heterocyclization of some 2,4,5‐trisubstituted‐1,3‐selenazoles with orthoesters in refluxing acetic acid. The synthetic compounds were evaluated for their antimicrobial activity against a panel of microorganisms including Gram‐negative bacteria, Gram‐positive bacteria, and pathogenic fungi. The antifungal results revealed that the new selenium‐containing heterocycles were as good as or sometimes better than terbinafine and fluconazole. The in vitro anticancer activities of aforementioned heterocyclic compounds were screened against human breast carcinoma MCF‐7 and HeLa cervical cancer cells as well as HDF (human dermal fibroblast) normal cells. Antiproliferative results indicated that compounds with piperidine moiety on MCF‐7 cells and with morpholine moiety on HeLa cells exhibited well broad‐spectrum of anticancer activities with 397, 298 and 235 μM and 533, 390 and 204 μM of IC50 values after 24, 48 and 72 h of treatments, respectively, while they had no significant toxic effects on normal cells.

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“…Despite the significance and unique behaviors of these compounds, limited synthetic approaches have been introduced for the preparation of these scaffolds in the literature . Fundamentally, the Hantzsch reaction, which consists of the condensation of α-halocarbonyl with thioamides or selenoamides, is the main path for the synthesis of these heterocycles.…”

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“…Fundamentally, the Hantzsch reaction, which consists of the condensation of α-halocarbonyl with thioamides or selenoamides, is the main path for the synthesis of these heterocycles. Despite widespread use of this approach, it suffers from utilizing hazardous solvents, harsh reaction conditions, low diversity, and expensive starting materials. , Therefore, devising a new and practical alternative protocol for the synthesis of diverse thiazoles and their derivatives to overcome these problems is highly desirable.…”

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Aryliodoazide Synthons: A Different Approach for Diversified Synthesis of 2-Aminothiazole, 1,3-Thiazole, and 1,3-Selenazole Scaffolds

et al. 2019

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Several straightforward and practical processes have been established for the construction of 2-aminothiazoles, 1,3-thiazoles and 1,3-selenazoles from aryliodoazides. These strategies successfully proceed with a wide spectrum of substituted thioamides and its derivatives producing the resulting five-membered heterocycles obtained in satisfactory yields. The unique features of these protocols are operational simplicity and highly functional group tolerance, which make them convenient and practical routes for the preparation of various libraries of 2-aminothiazoles, 1,3-thiazoles, and 1,3-selenazoles.

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Highlights on the Synthesis and Biological Activity of 1,3-Selenazoles

Cited by 14 publications

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An Eco-friendly, Hantzsch-Based, Solvent-Free Approach to 2-Aminothiazoles and 2-Aminoselenazoles

An Eco-friendly, Hantzsch-Based, Solvent-Free Approach to 2-Aminothiazoles and 2-Aminoselenazoles

Synthesis of Various Derivatives of [1,3]Selenazolo[4,5‐d]pyrimidine and Exploitation of These Heterocyclic Systems as Antibacterial, Antifungal, and Anticancer Agents

Aryliodoazide Synthons: A Different Approach for Diversified Synthesis of 2-Aminothiazole, 1,3-Thiazole, and 1,3-Selenazole Scaffolds

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