In vitro evaluation of 5-arylidene-2-thioxo-4-thiazolidinones active as aldose reductase inhibitors

Maccari, Rosanna; Corso, Antonella Del; Giglio, M.; Moschini, Roberta; Mura, Umberto; Ottanà, Rosaria

doi:10.1016/j.bmcl.2010.11.041

Cited by 59 publications

(38 citation statements)

References 29 publications

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“…Aldose Reductase Inhibitors. Due to the numerous negative effects of increased AR activity during chronic hyperglycemia, the inhibition of this enzyme remains an attractive strategy for treating DPN (Oates, 2008 sorbitol and fructose by reducing the flux of glucose through the polyol pathway and are represented by three chemical classes; acetic acid compounds, spirohydantoins, and a succinimide (Schemmel et al, 2010), although new agents also continue to be evaluated (Maccari et al, 2011;Rapposelli et al, 2011).…”

Section: B Targeting Casual Mechanismsmentioning

confidence: 99%

Diabetic Peripheral Neuropathy: Should a Chaperone Accompany Our Therapeutic Approach?

Farmer

Dobrowsky

2012

Pharmacol Rev

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Section: B Targeting Casual Mechanismsmentioning

confidence: 99%

Diabetic Peripheral Neuropathy: Should a Chaperone Accompany Our Therapeutic Approach?

Farmer

Dobrowsky

2012

Pharmacol Rev

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“…In addition, thiazolidin‐4‐ones are interesting class of heterocyclic compounds that possess all types of biological activities . Therefore, thiazolidin‐4‐ones are known to have antimicrobial , antitubercular , anticancer , anti‐inflammatory , anticonvulsant , and antiviral/anti‐HIV activities. In continuation of our research work on the construction of biologically active 1,3‐thiazole and 1,3,4‐thiadiazole derivatives , this contribution is aimed at the synthesis of some new 1,3,4‐thiadiazole, 1,3‐thiazolidinones and 1,3‐thiazoles derivatives having (thiazolyl)imino moiety utilizing 1‐(5‐acetyl–4‐methylthiazol–2‐yl)‐3‐phenylthiourea 2 as key starting substrate.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactivity of Phenylthiourea Derivatives: An Efficient Synthesis of New Thiazole‐Based Heterocycles

Sayed

Raslan

Dawood

2015

Journal of Heterocyclic Chem

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Reaction of 1‐(5‐acetyl‐4‐methylthiazol–2‐yl)–3‐phenylthiourea 2 with hydrazonoyl chlorides (3a, 3b, 3c, 3d, 3e, 3f) and 9 yielded the corresponding (thiazolyl)imino–1,3,4‐thiadiazole derivatives (6a, 6b, 6c, 6d, 6e, 6f) and 12, respectively. Reaction of 2 with ethyl chloroacetate 13 gave (thiazolyl)imino‐1,3‐thiazolidin‐4‐one derivative 15, which upon condensation with aromatic aldehyde derivatives yielded the 5‐benzylidene derivatives (16a, 16b). In addition, treatment of 2 with 3‐chloropenta‐2,4‐dione 17 afforded the corresponding (thiazolyl)imino‐1,3‐thiazole derivative 19. The newly synthesized compounds were confirmed from their elemental analyses and spectral data.

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“…We have found that the quinazolines and condensed quinazolines are versatile classes of fused heterocycles that are of considerable interest because of the diverse range of their biological properties and the potent pharmacological activities such as anticancer [6,7], antitumor [8,9], anti-oxidant [10], analgesic [11], anti-inflammatory [7,12], anti-convulsant [13], anti HIV, antibacterial, antifungal [14-17], antihypertensive [18], antileishmanial [19] and CNS depressant activity [20]. On the other hand, the considerable biological and medicinal activities of the thiazoles and their derivatives have also attracted continuing interest over the years because of their varied biological activities exemplified as antibacterial, antifungal [21-24], antitubercular [25], anticancer [26-28], antidiabetic [29], anti HIV [30] in addition to large applications in the drug development for the treatment of many disease. So, on the basis of the above findings the quinazoline and thiazole are privileged structures, which attracted considerable attention in the designing of biologically active molecules and combining them in one molecule exemplified by the thiazoloquinazoline system it is expected to furnish biologically active molecule with characteristic features.…”

Section: Introductionmentioning

confidence: 99%

Organocatalysis in heterocyclic synthesis: DABCO as a mild and efficient catalytic system for the synthesis of a novel class of quinazoline, thiazolo [3,2-a]quinazoline and thiazolo[2,3-b] quinazoline derivatives

Behbehani

Ibrahim

2013

Chemistry Central Journal

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BackgroundThere are only limited publications devoted to the synthesis of especially thiazolo[3,2-a]quinazoline which involved reaction of 2-mercaptopropargyl quinazolin-4-one with various aryl iodides catalyzed by Pd-Cu or by condensation of 2-mercapto-4-oxoquinazoline with chloroacetic acid, inspite of this procedure was also reported in the literature to afford the thiazolo [2,3-b] quinazoline. So the multistep synthesis of the thiazolo[3,2-a]- quinazoline suffered from some flaws and in this study we have synthesized a novel class of thiazoloquinazolines by a simple and convenient method involving catalysis by 1,4-diazabicyclo[2.2.2]octane (DABCO).ResultsA new and convenient one-pot synthesis of a novel class of 2-arylidene-2H-thiazolo[3,2-a]quinazoline-1,5-diones 9a-i was established through the reaction between methyl-2-(2-thio-cyanatoacetamido)benzoate (4) and a variety of arylidene malononitriles 8a-i in the presence of DABCO as a mild and efficient catalytic system via a Michael type addition reaction and a mechanism for formation of the products observed is proposed. Moreover 4 was converted to ethyl-2-[(4-oxo-3,4-dihydroquinazolin-2-yl)thio]acetate (10) upon reflux in ethanol containing DABCO as catalyst. The latter was reacted with aromatic aldehydes and dimethylformamide dimethylacetal (DMF-DMA) to afford a mixture of two regioselectively products with identical percentage yield, these two products were identified as thiazolo[3,2-a]quinazoline 9,13 and thiazolo[2,3-b]quinazoline 11,12 derivatives respectively. The structure of the compounds prepared in this study was elucidated by different spectroscopic tools of analyses also the X-ray single crystal technique was employed in this study for structure elucidation, Z/E potential isomerism configuration determination and to determine the regioselectivity of the reactions.ConclusionA simple and efficient one-pot synthesis of a novel class of 2-arylidene-2H-thiazolo[3,2-a]quinazoline-1,5-diones 9a-i was established through DABCO catalyzed Michael type addition reaction. In addition many fused quinazoline and quinazoline derivatives were synthesized which appeared as valuable precursors in synthetic and medicinal chemistry.

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In vitro evaluation of 5-arylidene-2-thioxo-4-thiazolidinones active as aldose reductase inhibitors

Cited by 59 publications

References 29 publications

Diabetic Peripheral Neuropathy: Should a Chaperone Accompany Our Therapeutic Approach?

Diabetic Peripheral Neuropathy: Should a Chaperone Accompany Our Therapeutic Approach?

Synthesis and Reactivity of Phenylthiourea Derivatives: An Efficient Synthesis of New Thiazole‐Based Heterocycles

Organocatalysis in heterocyclic synthesis: DABCO as a mild and efficient catalytic system for the synthesis of a novel class of quinazoline, thiazolo [3,2-a]quinazoline and thiazolo[2,3-b] quinazoline derivatives

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