Thiazolidin-4-one and thiazinan-4-one derivatives analogous to rosiglitazone as potential antihyperglycemic and antidyslipidemic agents

Raza, Saman; Srivastava, Swayam Prakash; Srivastava, Daya Shankar Lal; Srivastava, Arvind K.; Haq, W.; Katti, S. B.

doi:10.1016/j.ejmech.2013.01.054

Cited by 69 publications

(41 citation statements)

References 33 publications

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“…Rosiglitazone (RSG), a wonderful insulin sensitizer by binding to the peroxisome proliferators-activated receptor-g, promoting synthesis of glucose transporters and activating adipocyte differentiation [22]. Based on the structureeactivity relationship (SAR) data reported in the literature it appears that the acidic head group may be one of the factors responsible for side effects of RSG [23]. Researches also confirmed that replacement the acidic thiazolidinedione head group of RSG with other heterocycles could obtain significant bioactivities like anti-hyperglycemic and antidyslipidemic [23,24].…”

Section: Introductionmentioning

confidence: 98%

Synthesis and lipid-lowering evaluation of 3-methyl-1H-purine-2,6-dione derivatives as potent and orally available anti-obesity agents

Pei

et al. 2014

European Journal of Medicinal Chemistry

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Section: Introductionmentioning

confidence: 98%

Synthesis and lipid-lowering evaluation of 3-methyl-1H-purine-2,6-dione derivatives as potent and orally available anti-obesity agents

Pei

et al. 2014

European Journal of Medicinal Chemistry

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“…There is still scope to improve the productive cost efficiency by optimizing the reaction conditions of this practical linear synthesis route based on the following five sequential reaction steps: Intermediate 6 is first obtained via alkylation on secondary amine 3 with pyridine chloride 2. Further etherification of alcohol 6 with 4-fluorobenzaldehyde (4a) affords 7 [18]. Knoevenagel condensation between aldehyde 7 and 5 provides the intermediate 8.…”

Section: Introductionmentioning

confidence: 99%

Synthetic optimization of rosiglitazone and related intermediates for industrial purposes

et al. 2015

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As an important newly Food and Drug Administration (FDA)-approved drug for treating diabetes, rosiglitazone (1) has received much attention from researchers in many areas. To search for an economical and convenient synthesis method for 1, we explored the reaction conditions and workup of a scalable five-step synthetic route by an orthogonal method to determine the best condition for each reaction step. The starting materials are commercially available, including 2-chloropyridine (2), N-methylethanolamine (3), 4-fluorobenzaldehyde (4a) or 4-hydroxybenzaldehyde (4b), and 1,3-thiazolidine-2,4-dione (5). The five sequential reaction steps are cyclization, alkylation, etherification, condensation, and reduction, having optimal yield of 90, 99, 59, 75, and 91 %, respectively. The best overall yield to synthesize rosiglitazone based on compound 2 was 40 %, being suitable for industrial purposes, using water as a green solvent and avoiding column chromatography during the last three reaction steps.

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“…Six-membered thiazinanones show important biological properties as antioxidant, anti-inflammatory, anti-diabetic and antimicrobial. [15][16][17][18] The strategies to the synthesis of thiazinanones are quite similar to the strategies to the synthesis of analogue five-membered thiazolidinones. Thus, thiazinanones could be obtained by a multicomponent reaction between a primary amine, an aldehyde (or ketone) and the mercaptopropionic acid 15,17,19 or by a reaction between thioureas and β-propylhaloacetic acid.…”

Section: Introductionmentioning

confidence: 99%

“…[15][16][17][18] The strategies to the synthesis of thiazinanones are quite similar to the strategies to the synthesis of analogue five-membered thiazolidinones. Thus, thiazinanones could be obtained by a multicomponent reaction between a primary amine, an aldehyde (or ketone) and the mercaptopropionic acid 15,17,19 or by a reaction between thioureas and β-propylhaloacetic acid. 18 Moreover, these methods can be applied in two steps, multicomponent (all reactants together in the beginning of reaction) or onepot reactions, under catalysis or not.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel 2-Aryl-3-(2-morpholinoethyl)-1,3-thiazinan-4-ones Via Ultrasound Irradiation

Gouvêa¹,

Berwaldt²,

Neuenfeldt³

et al. 2016

Journal of the Brazilian Chemical Society

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This study describes the synthesis of fourteen thiazinanones from a multicomponent reaction of 2-morpholinoehtylamine (as primary amine), arenealdehydes (as carbonyl compound) and the mercaptopropionic acid using both conventional (thermal heating) and ultrasound methodologies. Through thermal heating methodology, the thiazinanones were obtained in 49 to 97% yields for 16 hours and through sonochemistry methodology, the reaction time was reduced for 25 minutes with yields 41 to 88%. The full identification and characterization of unpublished heterocycles were achieved by proton ( 1 H) and carbon 13 ( 13 C) nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry and infrared. Some of them were also characterized by elemental analysis.

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Thiazolidin-4-one and thiazinan-4-one derivatives analogous to rosiglitazone as potential antihyperglycemic and antidyslipidemic agents

Cited by 69 publications

References 33 publications

Synthesis and lipid-lowering evaluation of 3-methyl-1H-purine-2,6-dione derivatives as potent and orally available anti-obesity agents

Synthesis and lipid-lowering evaluation of 3-methyl-1H-purine-2,6-dione derivatives as potent and orally available anti-obesity agents

Synthetic optimization of rosiglitazone and related intermediates for industrial purposes

Synthesis of Novel 2-Aryl-3-(2-morpholinoethyl)-1,3-thiazinan-4-ones Via Ultrasound Irradiation

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