Design, synthesis, and preliminary evaluation as antimicrobial activity of novel spiro-1, 3-thiazolidine C-acyclic nucleoside analogs

Abstract

Synthesis of a new class of 1, 3-thiazolidine nucleoside analogs is described. Reaction of 2-amino-2-deoxy-D-glucopyranose hydrochloride 2 with carbon disulfide yielded 5-hydroxy-4-(D-arabino-1, 2, 3, 4-tetrahydroxybutyl)-thiazolidin-2-thione 3, which on acetylation yielded 5-acetoxy-4-(D-arabino-1, 2, 3, 4-tetraacetoxy-butyl)-thiazolidin-2-thione 4. The acetylated sugar 4 reacted with hydrazonoyl chlorides 1a-f, affording the 5-acetoxy-4-(D-arabino-1, 2, 3, 4-tetraacetoxybutyl)-spiro-[1,3]thiazolidine-2,2 -[1,3,4]thiadiazole derivatives 8a-f. The antibacterial activity of the novel 1, 3-thiazolidine-2,2 -spiro-[1,3,4]thiadiazole nucleoside analogs is highlighted. All compounds with free NH group in the thiazolidine series 8a-f showed significant biological activity against all the standard strains.

Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents

“…Heterocycles are an important framework for the development of new drugs, especially S-containing heterocycles which have been found to have the ability to induce apoptosis of various cells [ 16 ]. Thiazolidine drugs containing N and S atoms can exert drug effects through various mechanisms of action, such as inhibiting neuraminidase of influenza A virus [ 17 ], inhibiting protein synthesis [ 18 ], accelerating cell apoptosis [ 16 , 19 ], enhancing antioxidant capacity [ 7 ], immune stimulation [ 20 ], etc. Some thiazolidine-4-carboxylic acid derivatives can also oxidatively cleave DNA and interact with metal ions [ 21 ].…”

Synthesis, Antibacterial Activity and DFT Calculations of Some Thiazolidine-4-Carboxylic acid Derivatives and Their Complexes with Cu(II), Fe(II) and VO(II)

“…In the pharmaceutical industry, thiazolidines and their derivatives find applications as potent enzyme [6], receptor antagonists and important building blocks for medicines [7,8]. Therefore, thiazolidine-4-carboxylic acid allows restoring "contact inhibition" pertaining to tumour cells and its interaction with metal ions is regarded to be of key significance [9,10]. The derivatives pertaining to 2-substituted thiazolidine -4-carboxylic acids find application as key intermediates in peptide synthesis [11], as well as preparation of antiviral [2], microencapsulated liposomal and immunostimulating biological drugs [7,12].…”