Diverse Derivatives of Selenoureas: A Synthetic and Single Crystal Structural Study

Abstract

Reacting aroyl chlorides with an equivalent of potassium selenocyanate, followed by treating with an equivalent of 1,2,4-tri-tert-butylaniline at room temperature, resulted in the expected selenoureas and unusual diselenazoles. The selenation of selenourea by Woollins Reagent gave a new selenoformamide. Nucleophilic addition of selenoureas with acyl bromides led to the formation of new carbamimidoselenoates rather than the expected 1,3-selenazoles. The novel compounds prepared were characterised spectroscopically and crystallographically.

Novel N,N′-Disubstituted Acylselenoureas as Potential Antioxidant and Cytotoxic Agents

“…The general structure of the designed compounds is depicted in Figure 2, with carbo-and hetero-cyclic moieties (in blue) and variability on aniline substitution (in green). The proposed synthesis of these compounds was similar to the protocols reported previously for analogous compounds [43,[53][54][55]. Keeping all this previous experience in mind, in this work, we planned the design of a new library of forty seven acylselenoureas with both a potential anticancer and antioxidant activity following a fragment-based approach for drug design [48], varying the two sides of the molecule, searching for a synergistic effect between the fragments and the acylselenourea itself.…”

“…The general structure of the designed compounds is depicted in Figure 2, with carbo-and hetero-cyclic moieties (in blue) and variability on aniline substitution (in green). The proposed synthesis of these compounds was similar to the protocols reported previously for analogous compounds [43,[53][54][55]. The dose-and time-dependent radical scavenging activity of all of the synthesized compounds were assessed in vitro using the colorimetric assays of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS).…”

Biotin–Avidin System-Based Delivery Enhances the Therapeutic Performance of MSC-Derived Exosomes

“…As a consequence of the strong electron-withdrawal effect of the nitrogen-containing group, the change in the N−H group interfered with intramolecular and intermolecular hydrogen bonding, which resulted in a significant shift of the absorption peak between 3100 and 3700 cm −1 (Figure 1f and Figures S1−S3). 42,43 The FT-IR fitting results also showed significant variances in the subpeaks between 3100 and 3700 cm −1 , demonstrating that the hydrogen bond system was changed by the N−H group (Figure S4). All these results indicated that NHS-PEG 12 -biotin reacted effectively with GelMA to form a stable amide bond.…”

Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates

“…Selenoureas served as starting materials to the synthesis of further organoselenium derivatives [59]. Selenocarbamates showed antiproliferative [60], cytotoxic [61], antioxidant [22], pesticidal [24,26], and effective superoxide anion scavenger [62] activities.…”