Refernces
10.1016/j.bmc.2016.12.010
The study focuses on the synthesis and biological evaluation of cis-restricted triazole/tetrazole mimics of combretastatin-benzothiazole hybrids, which are designed to inhibit tubulin polymerization and induce apoptosis in cancer cells. These compounds were synthesized by modifying the combretastatin pharmacophore, replacing ring B with benzothiazole scaffolds and incorporating triazole and tetrazole rings to restrict the cis configuration of the olefinic bond. The synthesized compounds were evaluated for their antiproliferative activity on selected cancer cell lines, and the structure-activity relationship was developed. The most potent compounds demonstrated effects comparable to combretastatin A-4 (CA-4), a known tubulin-binding ligand. The study aimed to develop new molecules with improved properties, such as better aqueous solubility and reduced toxicity, to target microtubules and disrupt cancer cell division. The chemicals used in the study include various substituted anilines, p-nitrobenzoylchlorides, Lawesson's reagent, and other reagents for the synthesis of the target compounds, as well as CA-4 as a reference compound for biological evaluation. The purpose of these chemicals was to create a series of novel tubulin inhibitors that could potentially be developed into anticancer drugs.
10.1021/acs.orglett.7b01333
The study presents a magnesium-catalyzed asymmetric ring-opening reaction of aziridines with substituted tetrazoles, resulting in the formation of desymmetrization products with high yields and good enantioselectivities. A new chiral ligand, synthesized from azetidine and (R)-BINOL, was used in the in situ generated magnesium catalyst to achieve these results. The reaction is significant for the synthesis of enantioenriched heterocyclic compounds, which are important in medicinal chemistry due to their presence in many drugs. The study also explores the scope of the reaction with various substituted tetrazoles and provides a proposed mechanism for the Mg(II)-mediated desymmetrization process. The chemicals used in the study include meso-aziridines, substituted tetrazoles, and a series of chiral ligands derived from BINOL, which serve to catalyze the reaction and direct the stereochemistry of the products.
10.1021/ol0521432
The research focuses on the selective diphosphorylation, dithiodiphosphorylation, triphosphorylation, and trithiotriphosphorylation of unprotected carbohydrates and nucleosides using solid-phase synthesis. The purpose of this study was to develop a method for the selective synthesis of these compounds, which are challenging to produce due to the lack of regioselectivity in traditional solution-phase methods. The researchers used aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol, which were subjected to reactions with diphosphitylating and triphosphitylating reagents to yield polymer-bound reagents. These were then reacted with unprotected carbohydrates and nucleosides to produce monosubstituted nucleoside and carbohydrate diphosphates, dithiodiphosphates, triphosphates, and trithiotriphosphates with high regioselectivity. The conclusions of the research highlight the advantages of the solid-phase approach, including the production of monosubstituted derivatives, high selectivity, facile isolation and purification of products, and the trapping of byproducts on resins. The chemicals used in the process included phosphorus trichloride, 3-hydroxypropionitrile, diisopropylamine, water, and 1H-tetrazole, among others, to synthesize the diphosphitylating and triphosphitylating reagents, as well as various unprotected nucleosides and carbohydrates for the reactions.
10.1016/S0960-894X(97)00247-3
The research aimed to develop substrate analog inhibitors for the 14 kDa phospholipase A2 (PLA2) enzyme, which is associated with inflammatory episodes, with the goal of creating novel anti-inflammatory agents. The study focused on replacing the sn-3 phosphate moiety in these inhibitors to improve cell permeability and metabolic stability. The researchers synthesized a series of compounds, with tetrazole being identified as an effective replacement for the sn-3 phosphate, as it maintained in vitro potency and demonstrated superior cell permeability. Key chemicals used in the synthesis process included various epoxides, phthalimides, and acetamides, as well as reagents like sodium azide, allyllithium, acetonitrile anion, and imidazole, among others. The conclusions of the study were that the tetrazole moiety is an effective replacement for the sn-3 phosphate in substrate analog inhibitors of PLA2, enhancing cell permeability while maintaining in vitro potency and improving chemical stability.
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