Methods for the synthesis of 2-aminothiophenes and their reactions (review)

Gewald, K.

doi:10.1007/bf00945583

Cited by 54 publications

(56 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Also, some thieno [2,3-d]pyrimidines show CNS depressing activity [14] and are useful as muscle relaxants [15], sedatives [15], diuretics [16], pesticides and herbicides [17]. Various methods have already been proposed for the synthesis of these compounds and the most general ones involves cyclocondensation of suitably functionalized thiophenes with different electrophiles such as chloroformamidine [18], a-substituted acetonitriles [19], formic acid [19], phosgen [20], ethyl chloroformate [21] and guanidine [22].…”

Section:    Accessmentioning

confidence: 99%

Anti-hyperlipidemic Activity of Thieno - [2, 3-d] - Pyrimidin-4-(3H)-ones

Rangappa¹,

Venkataranganna²,

Saravanan³

2011

Macedonian Journal of Medical Sciences

View full text Add to dashboard Cite

Aim: The present study was aimed to evaluate some newly synthesized thieno -[2, 3-d] -pyrimidin-4-(3H)-ones namely SR-C1 to SR-C12 for their anti-hyperlipidemic activity. Materials and Methods:Anti-hyperlipidemic activity was evaluated using Triton 1339-induced hyperlipedemia in rats as an experimental model. Plasma triglycerides, total cholesterol, HDL-C, LDL-C, atherogenic index (AI) and LDL-C/HDL-C ratio were determined to assess the anti-hyperlipidemic activity.Results: SR-C1,SR-C4, SR-C5, SR-C6, SR-C7, SR-C11 and SR-C12 have shown significant antihyperlipidemic activity by decreasing the total cholesterol and triglyceride, LDL-cholesterol, atherogenic index and LDL/HDL ratio (p < 0.001) and by increasing the HDL-Cholesterol (p < 0.001). Conclusion:The findings of the present study clearly demonstrates that methyl, methoxy, chloro, dimethylamino, dimethoxy and trimethoxy functional groups possess cholesterol-suppressive capacities and has an ability to attenuate the accelerated development of atherosclerosis in hypercholesterolemic models. However, hydroxyl and nitro derivatives did not show any hypolipidemic activity.

show abstract

Section:    Accessmentioning

confidence: 99%

Anti-hyperlipidemic Activity of Thieno - [2, 3-d] - Pyrimidin-4-(3H)-ones

Rangappa¹,

Venkataranganna²,

Saravanan³

2011

Macedonian Journal of Medical Sciences

View full text Add to dashboard Cite

show abstract

“…The Gewald reaction [29,30] of pyrazolopyrimidinone derivative 3 with elemental sulfur and cyclohexanone in ethanol containing morpholine as a basic catalyst led to functionalized thiophene derivative 12, as confirmed by elemental analysis and spectral data (Scheme 3). As an extension of our study, the behavior of compound 3 towards salicylaldehyde as a convenient synthetic route to a chromene ring connected to the pyrazolo [3,4-d]pyrimidin-4-one moiety was also investigated.…”

Section: Methodsmentioning

confidence: 85%

Synthesis and Antioxidant Activity of Some New Heterocycles Incorporating the Pyrazolo-[3,4-D]Pyrimidin-4-One Moiety

El‐Mekabaty

2015

Chem Heterocycl Comp

View full text Add to dashboard Cite

moiety. Representative compounds of the synthesized series were tested and evaluated as antioxidants. Two of the tested compounds (pyrazole and thiophene derivatives) showed antioxidant activity nearly equal to that of ascorbic acid.Pyrazole derivatives are both important synthetic intermediates and compounds with interesting biological and pharmacological activities [1,2]. They are useful as starting materials for the synthesis of several polysubstituted fused pyrazoles [2,3]. For instance, 5-aminopyrazoles have been extensively used as precursors in the preparation of other fused heterocyclic systems like pyrazolotriazinones, pyrazolotriazepinones, and pyrazolopyrimidinones [2, 3]. We have recently reviewed the methods for preparation and the chemical reactivity of 5-amino-1-phenyl-1H-pyrazole-4-carboxamide as a building block for the synthesis of polyfunctionalized heterocyclic compounds with pharmacological interest [4].Pyrazolopyrimidinones, being purine analogs, are of considerable chemical and pharmacological importance. Literature survey reveals that they have antibacterial [5,6], antiproliferative [7, 8], CNS modulating [9], antiviral [10], antifungal [11], anticancer [12] and anti-inflammatory [13] activities. These molecules have shown affinity towards adenosine receptors [14] and 5HT-6 and CRF-1 [15] receptors.Further, it has been found that substitution of the pyrazole 1-NH proton of the pyrazolo[3,4-d]pyrimidine ring system with other bioactive moieties leads to interesting pharmacological properties probably by increasing the π-stacking [16][17][18][19][20][21]. In view of the above-mentioned facts and in continuation of an ongoing program aimed at finding new structural leads with potential chemotherapeutic activities [22][23][24], we report herein the synthesis and antioxidant activity of some novel structure hybrids incorporating the pyrazolo[3,4-d]-pyrimidin-4-one moiety joined with the thiazole, tetrazole, thiophene, chromene, pyridine or pyrazole ring systems through different linkages. This combination was suggested as a means of discovering a new lead structure that would have a significant antioxidant activity.

show abstract

“…The Finally, in view of the growing biological importance of thiazolidinone, pyrrolidinone, and chromene derivatives [31][32][33][34], it was of interest to turn our attention to study the applicability and synthetic potency of 2-aminothiophene-3-carboxylate (1) to develop a facile and convenient route to these classes of compounds. Thus, the solvent-free reaction of (1) with benzaldehyde in the presence of sodium acetate at 155-160°C afforded the corresponding Schiff's base (18). Cyclization of the latter with thioglycolic acid in dry pyridine under reflux led to the formation of the corresponding thiazolidin-4-one derivative (19), on the basis of its spectral data.…”

Section: Resultsmentioning

confidence: 98%

Efficient Syntheses of Some New Thiophene‐Based Heterocycles

El‐Mekabaty

Habib

Moawad

et al. 2016

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

In this effort, 2‐aminothiophene‐3‐carboxylate (1) was prepared using Gewald's methodology. This 2‐aminothiophene derivative was diazotized and coupled with malononitrile to obtain the nitrile derivative (2), which was utilized as key synthon for the synthesis of polyfunctionally substituted heterocycles via its reactions with some nitrogen and carbon nucleophiles. On the other hand, a facile and convenient syntheses of thiazolidinone, pyrrolidinone, and chromene derivatives incorporating thiophene moiety via the versatile, readily accessible 2‐aminothiophene‐3‐carboxylate (1) were also described.

show abstract

Methods for the synthesis of 2-aminothiophenes and their reactions (review)

Cited by 54 publications

References 58 publications

Anti-hyperlipidemic Activity of Thieno - [2, 3-d] - Pyrimidin-4-(3H)-ones

Anti-hyperlipidemic Activity of Thieno - [2, 3-d] - Pyrimidin-4-(3H)-ones

Synthesis and Antioxidant Activity of Some New Heterocycles Incorporating the Pyrazolo-[3,4-D]Pyrimidin-4-One Moiety

Efficient Syntheses of Some New Thiophene‐Based Heterocycles

Contact Info

Product

Resources

About