10.1007/s13738-015-0655-3
The research focuses on the development of a novel, cost-effective nanocatalyst, nano-sawdust-OSO3H, for the one-pot synthesis of biologically important pyrano[2,3-d]pyrimidines, which are known for their potential pharmaceutical applications such as antibacterial, antitumor, and analgesic activities. The experiments involved the use of reactants like barbituric acid or thiobarbituric acid, malononitrile, and a variety of aldehydes. The nanocatalyst was prepared by treating sawdust with chlorosulfonic acid, resulting in particles below 100 nm as observed through SEM imaging. The catalyst's morphology, chemical composition, thermal stability, and surface acidity were analyzed using techniques such as SEM, EDX, TGA/DTG, and FT-IR spectroscopy. The study demonstrated that nano-sawdust-OSO3H is an efficient catalyst, offering excellent yields in short reaction times and with mild reaction conditions, aligning with the principles of green chemistry.
10.1021/jm901183d
The research focuses on the discovery of a novel glitazone, (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, as an orally active and readily available treatment for Concanavalin A-induced acute liver injury in BALB/c mice. The study involves the synthesis and screening of 53 small molecules from a small-molecule library, using a quick screening method to evaluate their potency in inhibiting chemotaxis of RAW264.7 cells stimulated by monocyte chemoattractant protein 1 (MCP-1). The most effective compounds were identified through in vitro inhibitory effects and further assessed in vivo for their hepatoprotective effects. The experiments utilized various reactants, including aromatic aldehydes, β-alanine, barbituric acid, thiobarbituric acid, and other chemical reagents, and employed techniques such as Knoevenagel reaction, Wittig reaction, and HPLC for compound synthesis and purity analysis. The biological activity was assessed through chemotaxis assays, serum aminotransferase level measurements, and histopathological evaluations. The study demonstrated that compound 4f significantly reduced serum levels of alanine aminotransaminase (ALT) and asparate aminotransaminase (AST) and showed hepatoprotective effects in the liver injury model, with minimal toxicity observed in histopathological assessments of major organs.
10.1021/ja01334a060
The study explores the synthesis and properties of various naphthyl derivatives of barbituric acid. The research focuses on creating compounds where the naphthyl group is either directly attached to the 5-carbon atom or connected via methylene groups. The chemicals involved include a-naphthylmethyl bromide and a-naphthylethyl bromide, which were used for alkylation to introduce naphthylmethyl and naphthylethyl groups into barbituric acids. The study also utilized alkyl barbituric acids, sodium acetate, and urea in the synthesis processes. The goal was to investigate the potential therapeutic properties of these derivatives as sedatives and hypnotics, similar to known compounds like barbital and amytal. The study reports the successful synthesis of several derivatives, including 5,5-ethyl-a-naphthylmethylbarbituric acid, 5,5-n-butyl-a-naphthylmethylbarbituric acid, and 5,5-allyl-a-naphthylmethylbarbituric acid, among others. However, none of the synthesized compounds exhibited desirable physiological effects comparable to barbital or amytal. The study also details the preparation methods and the physical and analytical data of the synthesized compounds.
10.1002/jhet.1533
The study, titled "Synthesis of New Azocompounds and Fused Pyrazolo[5,1-c][1,2,4]triazines Using Heterocyclic Components," investigates the synthesis of new azocompounds and tricyclic pyrazolo[5,1-c][1,2,4]triazines using various heterocyclic components. The key chemical involved is 3-methyl-4-phenyl-1H-pyrazol-5-amine, which is diazotized to form pyrazole-3(5)-diazonium chloride. This diazonium salt undergoes azocoupling reactions with a variety of heterocyclic compounds, including barbituric acid, thiobarbituric acid, 2-hetarylpyrimidine-4,6-diones, 4-hydroxy-6-methylpyridin-2(1H)-one, 4-hydroxy-6-methyl-2H-pyran-2-one, 4-hydroxy-1-p-tolyl-1H-pyrazole-3-carboxylic acid ethyl ester, 1,3-thiazolidine-2,4-dione, and 2-thioxo-1,3-thiazolidin-4-one. These reactions yield new pyrazolylazo derivatives and fused pyrazolo[5,1-c][1,2,4]triazines through subsequent heterocyclization processes. The study explores the synthetic potential of these heterocyclic components in azocoupling reactions, highlighting their potential applications in industrial azo dyes, analytical indicators, and bioactive compounds related to purines.
10.1002/hlca.201000325
The research explores the novel synthesis of 5-aryl-1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-diones and their 2-thioxo analogs through convergent domino Knoevenagel hetero-Diels-Alder and domino oxidation hetero-Diels-Alder reactions. The purpose of this study is to develop a one-pot synthetic strategy for these compounds, which have significant biological activities, including antiviral, antibacterial, and antifungal properties. Barbituric acid is a key component in the Knoevenagel condensation step. It reacts with various benzaldehyde derivatives to form 5-arylidenebarbituric acid derivatives (II). These derivatives are essential intermediates that act as dienes in the subsequent hetero-Diels-Alder reaction. 2-Thiobarbituric acid is used similarly to barbituric acid but introduces a sulfur atom into the structure, leading to the formation of 2-thioxo analogs of the target compounds. Like barbituric acid, it undergoes Knoevenagel condensation with benzaldehydes to form the corresponding 5-arylidene derivatives. Both barbituric acid and 2-thiobarbituric acid are essential for generating the dienes required for the hetero-Diels-Alder reaction. Their ability to form reactive intermediates and participate in multiple reaction pathways is critical for the success of the convergent domino reactions described in the study.
10.1007/BF02236429
The study focuses on the chemical modification of plant alkaloids, specifically the aminomethylation of barbituric acid derivatives by cytisine. The researchers used cytisine, a plant alkaloid found in the seeds of certain plants, and barbituric acid derivatives to synthesize new compounds with potential biological activity. The purpose of these modifications is to create new cytisine derivatives that could have applications in medicine, particularly as respiratory analeptics and central nervous system regulators, given the physiological activities of cytisine and its synthetic derivatives. The study details the synthesis process, which involves the reaction of cytisine with 1-mono- and 1,3-disubstituted 5-arylmethylbarbituric acids in the presence of formaldehyde, leading to the formation of 5-cytisylmethylbarbituric acids. The structures of these products were confirmed using PMR spectroscopy and mass spectrometry, and the study also discusses the stereoselectivity of the reaction and the potential pharmaceutical applications of the synthesized compounds.
10.1021/ja01299a015
The study focuses on the preparation and pharmacological investigation of di- and trialkyl barbituric acids. The researchers synthesized various malonic esters by reacting alkyl halides with sodiomalonic ester or sodioalkylmalonic ester, and then used these esters to prepare barbituric acids by condensing them with urea, methyl urea, or ethyl urea in the presence of sodium ethoxide. The barbituric acids were purified by recrystallization or fractional distillation. The study also involved converting these acids into their sodium salts and testing their pharmacological effects on laboratory animals, primarily white rats. The results indicated that the introduction of a third alkyl group generally lessened the duration of action, and in some cases, alkylating the nitrogen group made the barbituric acids less effective. The study provides insights into the relationship between the chemical structure of barbituric acids and their pharmacological properties.
