Synthesis and biological activity of 4-thiazolidinone derivatives of phenothiazine

Abstract

A new series of N-[3-(10H-phenothiazinyl)-propyl]-2-(substituted phenyl)-4-oxo-5-( substituted benzylidene)-1,3-thiazolidine-carboxamide, 5(as) have been synthesized. The cycloaddition reaction of thioglycolic acid with N-[3-(10H-phenothiazinyl)-propyl]-N’-[(substituted phenyl)-methylidene]- urea, 3(a-s) in the presence of anhydrous ZnCl2 afforded new heterocyclic compounds N-[3-(10H-phenothiazinyl)-propyl]-2-(substituted phenyl)-4-oxo- 1,3-thiazolidine-carboxamide, 4(a-s). The later product on treatment with several selected substituted aromatic aldehydes in the presence of C2H5ONa undergoes Knoevenagel reaction to yield 5(a-s). The structure of compounds 1, 2, 3(a-s), 4(a-s) and 5(a-s) were confirmed by IR, 1H NMR, 13C NMR, Fmass and chemical analysis. All above compounds were screened for their antimicrobial activity against some selected bacteria and fungi and for antituberculosis activity compounds have been screened against the bacterium M. tuberculosis

Structure, MESP and HOMO-LUMO study of 10-Acetyl- 10H-phenothiazine 5-oxide using vibrational spectroscopy and quantum chemical methods

“…Alconea Palafox et al [14] had given a complete vibrational analysis of the Fourier transform (FT) infrared (IR) and FT-Raman spectra of both phenothiazine (PTZ) and N-methylphenothiazine molecules using ab initio method as well as quantum chemical calculations. Sharma et al [15] found the better biological activity of 4-thiazolidinone derivatives of phenothiazine. Dixit et al [2] had synthesized some 10H-phenothiazine sulphone derivatives and characterized them with selected bands of IR and 1H NMR spectroscopic methods.…”

Synthesis and Antimicrobial Activity of 4-Oxo-Thiazolidines and 5-Arylidene Derivatives of 2-Amino-5-Ethyl-1,3,4-Thiadiazole

“…The broad and potent activity of thiadiazole and their derivatives has established them as pharmacologically significant scaffolds. Thiazolidinones scaffolds are reviewed extensively in literature for its vibrant activities such as antibacterial (Kandapalli V. G. et al 2010), antifungal (Sharma R. et al 2012), antioxidant (Parmeshwaran M. et al 2009), cytotoxic (Jubie S. et al 2009), antiinflammatory (Goel B. et al 1999), anticonvulsant (Chaudhary M. et al 1976), anti-HIV (Rawal R. et al 2005), anti-tubercular (Aamer S. et al 2007), antiviral activities (Murugesan S. et al 2012) and DNA Binding Agent (War J. et al 2017). The incorporation of 4-oxothiazolidine and 5-arylidene moieties in 2amino-5-ethyl-1,3,4-thiadiazole frame work has been found to enhance the activity.…”

NBO, nonlinear optical and thermodynamic properties of 10-Acetyl-10H-phenothiazine 5-oxide

“…Antihistamines, diuretics, analgesics, neurolepitcs, antileukemic, antimutagenic, antileishmanial etc. are some of their main potential applications [2][3][4][5][6][7] of the drugs that containing phenothiozenes. Pallafox et.…”

“…al. [7] reported various remarkable biological activities of thiazolidines. Previously, we have revealed vibrational analysis of 10-Acetyl-10H-phenothiazine5-oxide [APTZ] using quantum chemical calculations [8].…”