Synthesis of Various Derivatives of [1,3]Selenazolo[4,5‐d]pyrimidine and Exploitation of These Heterocyclic Systems as Antibacterial, Antifungal, and Anticancer Agents

Abstract

A number of diversely functionalized derivatives of a novel [1,3]selenazolo[4,5‐d]pyrimidine have been synthesized through heterocyclization of some 2,4,5‐trisubstituted‐1,3‐selenazoles with orthoesters in refluxing acetic acid. The synthetic compounds were evaluated for their antimicrobial activity against a panel of microorganisms including Gram‐negative bacteria, Gram‐positive bacteria, and pathogenic fungi. The antifungal results revealed that the new selenium‐containing heterocycles were as good as or sometimes better than terbinafine and fluconazole. The in vitro anticancer activities of aforementioned heterocyclic compounds were screened against human breast carcinoma MCF‐7 and HeLa cervical cancer cells as well as HDF (human dermal fibroblast) normal cells. Antiproliferative results indicated that compounds with piperidine moiety on MCF‐7 cells and with morpholine moiety on HeLa cells exhibited well broad‐spectrum of anticancer activities with 397, 298 and 235 μM and 533, 390 and 204 μM of IC50 values after 24, 48 and 72 h of treatments, respectively, while they had no significant toxic effects on normal cells.

Pyrido[1,2-e]purine: Design and Synthesis of Appropriate Inhibitory Candidates against the Main Protease of COVID-19

“…These methods have shown multistep reactions in the construction of pyrido­[1,2- e ]­purine structures. As a continuation of our previous studies, − herein, we report a two-step, one-pot synthesis of pyrido­[1,2- e ]­purine derivatives, and considering the physicochemical and pharmacokinetic predictions, their inhibitory activity against SARS-CoV-2 3CL pro is evaluated using molecular docking and molecular dynamics approaches.…”

Synthesis of new derivatives of Alkylselanyl[1,2,4]triazolo[4,3‐a]pyrimidine asselenium‐containingheterocyclic system

“…As derivatives of [1,2,4]triazolo[4,3‐ a ]pyrimidine incorporating selenium has not been synthesized and studied, it is anticipated that these compounds are good candidates for biological activities. Therefore, in continuation of our previous studies, selenopheno[2,3‐e][1,2,4]triazolo[1,5‐c]pyrimidine derivatives [40], [1,3]selenazolo[5,4‐e][1,2,4]triazolo[1,5‐c]pyrimidine [41, 42], and pyrido[1,2‐e]purine [43], herein, we report the synthesis of organoselenides with metal‐free procedure comprising of the alkylation of selenium anions.…”

Synthesis and characterization of the novel pyrimidine’s derivatives, as a promising tool for antimicrobial agent and in-vitro cytotoxicity

“…The toxicity due to treatment with synthesized compounds may be attributed to apoptotic effects, DNA fragmentation, reduced potential for mitochondrial membrane, reactive oxygen species (ROS) generation, nuclear fragmentation, and inactivation of some enzymes such as lactate dehydrogenase [69][70][71]. In the current study, the hydrophobic chain that exists in the pyrimidine ring has a critical role to explain their cytotoxicity [72]. Moreover, the cytotoxic efficacy of heterocyclic compounds on the Hela cell line differs according to the hydrophobic chain length attached to the heterocyclic core [73].…”