Cyclization of Active Methylene Isocyanides with α-Oxodithioesters Induced by Base: An Expedient Synthesis of 4-Methylthio/Ethoxycarbonyl-5-acylthiazoles

Kiran, Kuppalli R.; Swaroop, Toreshettahally R.; Rajeev, Narasimhamurthy; Anil, Seegehalli M; Rangappa, Kanchugarakoppal S.; Sadashiva, M. P.

doi:10.1055/s-0039-1690821

Cited by 28 publications

(9 citation statements)

References 26 publications

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“…As a reference compound, doxorubicin was used. The evaluation revealed that disubstituted compounds 2,4-dichloro (74d) and 3,4-dichloro (74h) displayed the best activity against four tumor cell lines (NCI-H292, HEp-2, HT- 29 Thus, the presence of di-Cl substitution was beneficial for cytotoxic activity. Compound 74b with an electron withdrawal group (4-NO 2 ) was found to be more active against NCI-H292 with an IC 50 of 7.41 ± 1.37 µM than 74c with a 3-NO 2 group (IC 50 of 22.77 ± 2.77 µM), indicating the importance of not only the nature but also of the position of the substituent at the thiazole ring as far as the activity is concerned.…”

Section: Thiazole Derivatives As Anticancer Agentsmentioning

confidence: 99%

Thiazole Ring—A Biologically Active Scaffold

2021

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Background: Thiazole is a good pharmacophore nucleus due to its various pharmaceutical applications. Its derivatives have a wide range of biological activities such as antioxidant, analgesic, and antimicrobial including antibacterial, antifungal, antimalarial, anticancer, antiallergic, antihypertensive, anti-inflammatory, and antipsychotic. Indeed, the thiazole scaffold is contained in more than 18 FDA-approved drugs as well as in numerous experimental drugs. Objective: To summarize recent literature on the biological activities of thiazole ring-containing compounds Methods: A literature survey regarding the topics from the year 2015 up to now was carried out. Older publications were not included, since they were previously analyzed in available peer reviews. Results: Nearly 124 research articles were found, critically analyzed, and arranged regarding the synthesis and biological activities of thiazoles derivatives in the last 5 years.

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Section: Thiazole Derivatives As Anticancer Agentsmentioning

confidence: 99%

Thiazole Ring—A Biologically Active Scaffold

2021

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“…In 2020, Sadashiva and co‐workers put forth the synthesis of 4‐methylthio‐5‐acylthiazoles 98 and 4‐ethoxycarbonyl‐5‐acylthiazole 99 by cyclization of tosylmethyl isocyanide 55 and ethyl isocyanoacetate respectively [83] . The reaction conditions showcase considerable substrate scope, irrespective of the electronic nature of the functional groups present on the α ‐oxodithioester (Scheme 55).…”

Section: Synthesis Of Thiazolesmentioning

confidence: 99%

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Kant,

Patel,

Banerjee

et al. 2023

ChemistrySelect

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Nitrogen‐containing heterocycles such as imidazoles, thiazoles, and oxazoles play a significant role in the fields of biological and pharmaceutical chemistry. These compounds were widely used for agrochemical, pesticide, medicinal, and industrial applications. Due to the wide spectrum of structural diversity as well as the biological and pharmaceutical activity of N‐heterocycles, a plethora of reports on their synthesis have appeared in the last few decades. However, developments in various bond‐forming strategies such as C−C, C−N, C−O, C−S, and N−N, as well as C−H activation, have been used as a powerful synthetic tool to derive copious N‐heterocycles. The most prominent and fascinating reports on the synthesis of imidazole, thiazole, oxazoles, and benzimidazole moieties by C−C and C−N coupling reactions, multi‐component and cycloaddition reactions, C−H activation, etc. are discussed in this study. These studies demonstrated the enormous potential of such methods for accelerating modern chemical synthesis and establishing molecular beauty through bonding. The various aspects of the methodologies, like optimized conditions, substrate scope, and mechanistic investigations, are discussed in detail.

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“…More recently, an efficient cyclization reaction produced 4‐methylthio‐5‐acylthiazoles from a reaction of isocyanoacetate and α‐oxodithioester in the presence of DBU/ethanol (Figure 1C). [25] …”

Section: Introductionmentioning

confidence: 99%

“…More recently, an efficient cyclization reaction produced 4-methylthio-5-acylthiazoles from a reaction of isocyanoacetate and α-oxodithioester in the presence of DBU/ethanol (Figure 1C). [25] Another attractive pharmacophore for drug discovery is chalcone. 1,3-Diphenyl-2-propen-1-ones are α, β-unsaturated carbonyl compounds with two aromatic rings attached, known as chalcones or chalconoids.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Anticancer Screening and Molecular Modelling Studies of Novel Thiazoles

Abu Nuwar,

Jaradat,

Chandrasekaran

et al. 2023

ChemistrySelect

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A library of novel benzamide‐thiazolyl‐chalcone compounds was synthesized via Claisen‐Schmidt reaction and spectroscopically characterized using FT‐IR, 1H‐NMR, 13C‐NMR, LC–MS, and HR‐MS. The synthesized compounds were biologically evaluated using in vitro MTT assay against different cancer cell lines (MCF‐7, MDA‐AMB‐231, Caco‐2, A549, and H1299). Amongst all compounds screened, (E)‐N‐(5‐(3‐(4‐hydroxyphenyl)‐3‐oxoprop‐1‐en‐1‐yl)thiazol‐2‐yl)benzamide and (E)‐N‐(5‐(3‐(4‐methoxyphenyl)‐3‐oxoprop‐1‐en‐1‐yl)thiazol‐2‐yl)benzamide showed potent anti‐proliferation against breast (MCF‐7) and colon cancer cell lines reaching 88.56 % and 84.36 % with IC50 values of 44.00 μM and 58.88 μM, respectively. All synthesized compounds exhibited no significant cytotoxicity to normal cells. Structure‐activity relationship studies demonstrated the effect of electron‐donating and electron‐withdrawing groups on the anticancer activity of the molecules under investigation. This was also corroborated by theoretical DFT studies. Thus, these molecules may serve as potential lead candidates for further development of novel anticancer agents against breast and colon cancers.

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Cyclization of Active Methylene Isocyanides with α-Oxodithioesters Induced by Base: An Expedient Synthesis of 4-Methylthio/Ethoxycarbonyl-5-acylthiazoles

Cited by 28 publications

References 26 publications

Thiazole Ring—A Biologically Active Scaffold

Thiazole Ring—A Biologically Active Scaffold

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Design, Synthesis, Anticancer Screening and Molecular Modelling Studies of Novel Thiazoles

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