Synthesis and Antioxidant Activity of New Pyrazolo[1,5‐a]Pyrimidine Derivatives Incorporating a Thiazol‐2‐yldiazenyl Moiety

Abstract

4‐(Thiazol‐2‐yldiazenyl)‐1H‐pyrazole‐3,5‐diamine (2) was prepared by the reaction of 2‐thiazolylazomalononitrile (1) with hydrazine hydrate in boiling ethanol and used as key intermediate for the synthesis of polyfunctionally substituted pyrazolo[1,5‐a]pyrimidines via its reactions with reagents having 1,3‐dielectrophilic centers. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. Representative compounds of the synthesized products were tested and evaluated as antioxidant agents. The results revealed that compounds (3), (4), (5), and (9) displayed promising antioxidant activity compared to the activity of ascorbic acid.

Cerebroprotective Activity of New Derivatives of Pirimidine4 1h One Pir9 and Pir10 in Irreversible Occlusion of the Common Carotid Artery

“…В настоящее время на основе производных пиримидина создаются новые высокоэффективные биологически активные вещества [8][9][10]. Исходя из литературных и экспериментальных данных, производные пиримидина проявляют нейропротекторную [11][12][13][14][15], антигипоксическую [16], эндотелиопротекторную [17][18][19], антиагрегационную [20], антиоксидантную [21][22][23][24] виды активностей. Также установлено поло-жительное влияние некоторых производных пиримидин-4-(1H)-она на тяжесть неврологического дефицита и поведенческую активность крыс при ишемии головного мозга [25], вследствие этого можно предположить наличие церебропротекторной активности у соединений данного класса (PIR-9 и PIR-10), синтезированных на кафедре органической химии Пятигорского медико-фармацевтического института -филиала ФГБОУ ВО ВолгГМУ МЗ РФ [8,25,26].…”

“…Nowadays on the basis of derivatives of pyrimidine new highly effective biologically active substances are being created [8][9][10]. According to the literary and experimental data, the derivatives of pyrimidine exhibit neuroprotective [11][12][13][14][15], antihypoxic [16], endotheliopathy [17][18][19], anti-aggregating [20], antioxidant [21][22][23][24] types of activities. The positive effect of some derivatives of pyrimidine-4-(1H)-ONE on the severity of neurological de cit and behavioral activity of rats with cerebral ischemia has also been established [25].…”

Green Synthesis of Pyrazolo [3,4]-Pyrimidine-Thiones Using Ionic Liquid 2-Methyl-Imidazolium-Oxalate as Potent Ehrlich Ascites Carcinoma Receptor Antagonists

“…Pyrazolo [3,4-d]-pyrimidines are analogs of most purine-based drugs, having huge scope in the past decade for a consequence of their wide usage in medicinal field [1]. On literature studies, pyrazolopyrimidine derivatives have considerable potential in the field of chemotherapy, as they were found to exhibit their antitumor activity by inhibiting different types of enzymes such as cyclin-dependent kinase [2][3][4], Src and Abl tyrosine kinase [5], glycogen synthase kinase-3 [6][7][8], adenosine deaminase [9], and epidermal growth factor receptor protein tyrosine kinase. We synthesized pyrazolo [3,4-d]-pyrimidinethiones through ethyl acetoacetate, hydrazine hydrate, thiourea, and different benzaldehydes by the ultrasonication under solvent-free condition.…”

Rro/antioxidant activity of a new pir-10 substance (pyrimidine derivative) under experimentally simulated focal cerebral iscemia in rats

“…Previously conducted experiments allowed to determine potential cerebral-protective effects produced by a new pyrimidine derivative with a laboratory cipher PIR-10 when global cerebral ischemia was simulated [8]. Experts have also examined influences exerted by some substances belonging to pyrimidine group on the AOP system [9,10]. Hence we can assume that this derivative of pyrimidine-4(1H)-on has some antioxidation properties as a possible action mechanism that can help to considerably improve the epidemiologic situation as regards pathologies related to cerebral circulation disorders as well as substantially facilitate management of ischemic stroke risks.…”