Novel Synthesis of Barbiturates

Ashnagar, A.; Naseri, N. G.; Sheeri, Behrang

doi:10.1002/cjoc.200790073

Cited by 28 publications

(24 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[9][10][11][12] Benzylidenebarbiturates are employed in several well known reactions in the literature 10,[13][14][15][16][17] and have even been used as methionine aminopeptidase inhibitors. 18 The preparation of the 5-chloro-5-benzolbarbiturates was Vol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants

Vieira¹,

Gomes²,

Matheus³

et al. 2011

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Uma nova família de barbituratos, ácidos 5-cloro-5-benzilbarbitúricos, foi preparada usando um método simples e eficiente a partir de aldeídos aromáticos e ácido barbitúrico, seguido de redução e cloração usando ácido tricloroisocianúrico, com rendimento global de 53 a 70%. Por avaliação in vivo com camundongos, os produtos apresentaram atividade tranqüilizante.A new family of barbiturates, 5-chloro-5-benzylbarbituric acids, was prepared using a simple efficient synthetic method from aromatic aldehydes and barbituric acid, followed by reduction and chlorination with trichloro-isocyanuric acid, affording overall yields of 53 to 70%. The in vivo evaluation with mice showed that these compounds present tranquilizing activity.Keywords: 5-chloro-5-benzylbarbituric acids, tranquilizers, benzylidenebarbiturates, trichloroisocyanuric acid, rota-rod tests IntroductionBarbiturates are very well known drugs with activity at the central nervous system (CNS), with specific activity as anticonvulsants, anxiolytics, tranquilizers and sedatives-hypnotics. 1 The mechanism of action of barbiturates at the CNS is not well known, but it has been shown that they are able to interfere with acetylcholine, norepinephrine and glutamate activity and also that they can inhibit the calcium uptake of nerve terminals, thus allowing their use as analgesics. 2,3 In fact, today barbiturates are commonly used to induce anesthesia in surgery procedures. They are also known as GABA-mimetics, thus functioning as agonists of GABA receptors. 3,4 For many years the barbiturates were the main drugs used to cause effects on the CNS. However, after the discovery of the very effective benzodiazepines, their use became less common simply because benzodiazepines have less potential for lethal overdoses. 5,6 The main cause of death by overdoses of barbiturates is respiratory failure, because they are very potent respiratory depressants. Today, the main uses of barbiturates are the induction of anesthesia and for the treatment of refractory status epilepticus. 7 Regarding the significant historical and actual use of barbiturates as neurological drugs, and the importance of this type of disease in the actual condition of mankind, we developed a very simple new family of barbiturates with CNS activity. Interestingly, 5-chlorobarbituric acid and their derivatives have been rarely investigated. The only similar compounds that have been reported as anticonvulsants are the 5-chloro-5-phenyl barbiturates. 8 Surprisingly, 5-benzyl-5-chlorobarbituric acids have not been reported in the literature. We developed a very simple and efficient method for the preparation of this new family of barbiturates as potential tranquilizers. Results and DiscussionOur strategy for the preparation of 5-benzyl-5-chlorobabiturates was based on the use of benzylidenebarbiturates as intermediates, which are very easy to prepare. [9][10][11][12] Benzylidenebarbiturates are employed in several well known reactions in the literature 10,13-17 and have even been used as methionine aminopeptidas...

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants

Vieira¹,

Gomes²,

Matheus³

et al. 2011

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…Also, penicillins are classified as either bacteriocides or bacteriostatics. Because of the wide spread use and therapeutically significance of these drugs on the one hand and the fact that the efficacy of a drug depends largely upon the purity of the active ingredient and the excipiants, on the other hand, and also the fact that these medicines and their active ingredients used in this research are purchased and imported from various countries around the world; obviously their qualities may be different from one another to some extent and therefore must be checked regularly; we decided to carry out the following objectives, as with other similar works published by this research group [7][8][9][10][11] , in this research: (i)…”

Section: Resultsmentioning

confidence: 99%

Analysis of Three Penicillin Antibiotics (Ampicillin, Amoxicillin and Cloxacillin) of Several Iranian Pharmaceutical Companies by HPLC

Ashnagar

Naseri

2007

Journal of Chemistry

View full text Add to dashboard Cite

Penicillin has been the most widely used antibiotic for many grampositive bacterial infections. In this research the purity of the standard active ingredients of the various dosage forms of three penicillins (Amoxicillin, Cloxacillin and Ampicillin) imported and the purity percentage of the active ingredients in each of the various dosage forms of these drugs manufactured by several pharmaceutical companies of Iran (Kosar, Farabi and Jaber Ibn Hayan) were investigated and determined by HPLC technique. The analyses were made by using a Knauer (Germany) Spherimage-80, ODS, 2-5 µm C 18 column with 30 cm length, and i.d. 4.5 mm. A 20 µL solution from each individual sample and the standard solution were injected separately onto the column of an HPLC instrument which was equipped with ECW 2000 software of Knauer, Germany. The results obtained in this research have shown that the purity percentage of the active ingredients of the standard powder and the various dosage forms of all the drugs used, were 100%.

show abstract

“…There are several methods reported in the literature for the synthesis of arylidene-pyrimidine-2,4,6-triones and arylidene-2-thioxo-dihydro-pyrimidine-4,6-diones such as [30][31][32][33][34][35][36][37][38][39][40] base, acetic acid as catalyst in water under reflux conditions, montmorillonite KSF clay under microwave irradiation, ammonium acetate in acetic acid, montmorillonite K-10, silica gel, basic alumina, NaCl, montmorillonite KFS, KSF/NaCl, BiCl 3 . Each of these methods have their own advantages but also be affected from disadvantages such as long reaction times, low to moderate yields, tedious work-up procedures, requirement of special apparatus, use of organic solvents, requirement of excess of catalysts and difficulty in recovery and reusability of the catalysts.…”

Section: Research Articlementioning

confidence: 99%

Facile and Green Syntheses of 5-Arylidene-pyrimidine-2,4,6-triones and 5-Arylidene-2-thioxo-dihydro-pyrimidine-4,6-diones Using L-Tyrosine as an Efficient and Eco-Friendly Catalyst in Aqueous Medium

Thirupathi¹,

Venkatanarayana²,

Dubey³

et al. 2013

Chem Sci Trans

View full text Add to dashboard Cite

show abstract

Novel Synthesis of Barbiturates

Abstract: Knovenagel reaction of barbituric acid with different aldehydes were used to synthesize new barbiturates.This is a novel method which can be used to synthsis various types of new generation of barbiturates which are different from the previously reported.

Cited by 28 publications

References 3 publications

Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants

Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants

Analysis of Three Penicillin Antibiotics (Ampicillin, Amoxicillin and Cloxacillin) of Several Iranian Pharmaceutical Companies by HPLC

Facile and Green Syntheses of 5-Arylidene-pyrimidine-2,4,6-triones and 5-Arylidene-2-thioxo-dihydro-pyrimidine-4,6-diones Using L-Tyrosine as an Efficient and Eco-Friendly Catalyst in Aqueous Medium

Contact Info

Product

Resources

About