Synthesis and characterization of microwave‐assisted biologically active triazole silanes

Abstract

The alliance of new drug, green technology and public health initiatives is essential for the ecosystem. The microwave technique is used to synthesize new drugs cognate to metronidazole. A new family of triethoxysilanes (3a–3e) was synthesized after reconnaissance with terminal alkynes (2a–2e) as an array using the Huisgen 1,3‐dipolar cycloaddition. All products were obtained in excellent yield with recovery of the catalyst as well as the solvent, and in a short time span. The design feature of these compounds is the tailoring of two unsymmetrical triazole nuclei into a single scaffold. The pharmacokinetic profiles of the triazole scaffold were analyzed using MOLINSPIRATION and ADMET toolkits, which gave promising results that prompted the investigation of these compounds for anti‐parasitic activity against parasites (Giardia lamblia and Trichomonas vaginalis) in contrast to standard drug (metronidazole). Compound 3d manifested good efficacy against both strains amongst all the synthesized triazole analogs. Highlights By using microwave methodology, a series of triazole functionalized alkynes and triazole organo silanes were synthesized. This involves tailoring of the 1,2,4‐triazole nucleus to 1,2,3‐triazole moiety. The protocol afforded excellent yield in a short time span under eco‐friendly conditions. The hybrid molecules were screened for their physicochemical properties using MOLINSPIRATION software and ADMET web server. All the synthesized compounds were investigated for their antioxidant activity, anti‐giardial and anti‐trichomonal activities. Tris triazole silane (3d) was found to be the most significant against Giardia lamblia and Trichomonas vaginalis, respectively, and this low‐price, versatile drug will hopefully lead to the eventual elimination of parasitic disease from the human population. Thermal gravimetric analysis has been performed for compounds (2a–2e) and (3a–3e).

Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

“…In addition, 3‐aminopropylsilatranes and their derivatives show antimicrobial, [ 12,13 ] antiparasitic, [ 14 ] antihepatitis B, [ 15 ] antitumor, [ 16 ] immunomodulatory [ 17 ] and growth stimulating [ 18 ] activity.…”

“…[ 27,28 ] The MG approach is based on the principle “two heads are better than one”, which has been successfully employed to create novel hybrid compounds with anticancer, anti‐inflammatory, antimicrobial, and other activities. [ 12–14,29–33 ]…”

Design and Synthesis of Heterocyclic Encapsulated Organosilatranes for In Silico, In Vitro Antioxidant and Cytotoxicity Evaluation

“…The diverse biological significance attached with these N‐heterocyclic fragments is the motivation behind pursuing our research in this area. Because of the presence of the azomethine linkage, Schiff bases particularly those of nitrogen and oxygen containing heterocycles, play a pivotal role in drug chemistry because they display a wide range of activities such as anti‐cancer, antitumor, antibacterial, antioxidant, antifungal, anti‐viral, antiparasitic, anti‐inflammatory, anti‐HIV and herbicidal [9–18] …”

“…Because of the presence of the azomethine linkage, Schiff bases particularly those of nitrogen and oxygen containing heterocycles, play a pivotal role in drug chemistry because they display a wide range of activities such as anti-cancer, antitumor, antibacterial, antioxidant, antifungal, anti-viral, antiparasitic, anti-inflammatory, anti-HIV and herbicidal. [9][10][11][12][13][14][15][16][17][18] Another important genre of pharmacophore that have recently attracted the interest of medicinal chemists is Silatranes, caged compounds constituting a transannular dative bond between silicon and nitrogen. [19] Current revelation by our group has shown that nitrogen heterocycles like morpholine, piperidine and pyrrolidine linked with silatranyl fragments are promising drug candidates.…”

“…In silico physicochemical properties of N-heterocyclic tethered silatranes(7)(8)(9)(10)(11)(12).MW: molecular weight, mi Log P: logarithm of partition coefficient of compound between n-octanol and water, TPSA: topological polar surface area, n-ON acceptors: number of hydrogen bond acceptors, n-OHNH donors: number of hydrogen bonds donors, n-ROTB: number of rotatable bonds Pharmacokinetic descriptors of N-heterocyclic tethered organosilatranes(7)(8)(9)(10)(11)(12). HIA values > 70 % are regarded as well absorbed compounds and fromTable 3it can be seen that the compounds have HIA values lying between 97.37-97.76 thus demonstrating their excellent absorption behaviour.…”