53385-83-4Relevant academic research and scientific papers
Design, synthesis, DNA assessment and molecular docking study of novel 2-(pyridin-2-ylimino)thiazolidin-4-one derivatives as potent antifungal agents
Metwally, Nadia Hanafy,Radwan, Ibrahim Taha,El-Serwy, Walaa Salah,Mohamed, Mohamed Ahmed
, p. 456 - 467 (2019)
A series of novel 2-imino-4-thiazolidinone derivatives 4a,b was synthesized through reaction of unsymmetrical thioureas 3a,b with chloroacetic acid. Condensation of 4a,b with aromatic aldehydes 5a-eyielded the corresponding 5-arylidene derivatives 6a-j. In addition, the reaction of 4a,b with 4-arylazo-3-hydroxybenzaldehydes 8a-c furnished the respective mono-arylazo-4-thiazolidinones10a-f. All the newly synthesized compounds were confirmed by their elemental analysis and spectral data. The antifungal activity of the newly synthesized compounds was assessed and the compounds 6d, 6e, 6i, 6j, 9a,b and 10a-frevealedhigher antifungal activity towards Alternaria solani than to the standard Ridomil gold plus. Moreover, the DNA toxicity of 4-thiazolidinone derivatives 6d, 9a, 10b, 10c and 10f on the nucleic acid of Alternaria solani (KT354939) was performed and the results showed qualitatively more than 70% cleavage. Also, compounds 6i, 6j, 9b, 10c and 10f were docked inside the active site of 1ZOYenzyme and suitable binding with the active site of amino acids, were displayed according to their bond lengths, angles and conformational energy.
Diversity-Oriented Synthesis of Thiazolidine-2-imines via Microwave-Assisted One-Pot, Telescopic Approach and Its Interaction with Biomacromolecules
Saikia, Ananya Anubhav,Rao, Ramdas Nishanth,Maiti, Barnali,Balamurali, Musuvathi Motilal,Chanda, Kaushik
, p. 630 - 640 (2020/12/15)
In this work, a one-pot, telescopic approach is described for the combinatorial library of thiazolidine-2-imines. The synthetic manipulation proceeds smoothly via the reaction of 2-aminopyridine/pyrazine/pyrimidine with substituted isothiocyanates followed by base catalyzed ring closure with 1,2-dibromoethane to obtain thiazolidine-2-imines with broad substrate scope and high functional group tolerance. The synthetic strategy merges well with the thiourea formation followed by base catalyzed ring closure reaction for the thiazolidine-2-imine synthesis in a more modular and straightforward approach. The synthetic procedure reported herein represents a cleaner route toward thiazolidine-2-imines as compared to traditional methodologies. Moreover, the biological significance of combinatorially synthesized thiazolidin-2-imines has been investigated for their use as possible inhibitors for acetyl cholinesterase through molecular docking studies.
2-aminothiazoles as therapeutic leads for prion diseases
Gallardo-Godoy, Alejandra,Gever, Joel,Fife, Kimberly L.,Silber, B. Michael,Prusiner, Stanley B.,Renslo, Adam R.
experimental part, p. 1010 - 1021 (2011/04/25)
2-Aminothiazoles are a new class of small molecules with antiprion activity in prion-infected neuroblastoma cell lines (J. Virol. 2010, 84, 3408). We report here structure-activity studies undertaken to improve the potency and physiochemical properties of 2-aminothiazoles, with a particular emphasis on achieving and sustaining high drug concentrations in the brain. The results of this effort include the generation of informative structure-activity relationships (SAR) and the identification of lead compounds that are orally absorbed and achieve high brain concentrations in animals. The new aminothiazole analogue (5-methylpyridin-2-yl)-[4-(3-phenylisoxazol-5-yl)-thiazol-2-yl]-amine (27), for example, exhibited an EC50 of 0.94 μM in prion-infected neuroblastoma cells (ScN2a-cl3) and reached a concentration of ～25 μM in the brains of mice following three days of oral administration in a rodent liquid diet. The studies described herein suggest 2-aminothiazoles as promising new leads in the search for effective therapeutics for prion diseases.
Structural, spectral and thermal studies of substituted N-(2-pyridyl)-N′-phenylthioureas
Valdés-Martínez, Jesús,Hernández-Ortega, Simón,Espinosa-Pérez, Georgina,Presto, Carmina A,Hermetet, Anne K,Haslow, Kristin D,Ackerman, Lily J,Szczepura, Lisa F,Goldberg, Karen I,Kaminsky, Werner,West, Douglas X
, p. 77 - 87 (2007/10/03)
N-2-(3-picolyl)-N′-phenylthiourea, 3PicTuPh, monoclinic, P21/n, a = 7.617(2) b = 7.197(5), c = 22.889(5) ?, β = 94.63(4)°, V = 1250.7(1) ?3 and Z = 4; N-2-(4-picolyl)-N′-phenylthiourea, 4PicTuPh, triclinic, P-1, a = 7.3960(5), b = 7.
Synthesis and antimicrobial activity of pyridines bearing thiazoline and thiazolidinone moieties
Hassan, Hoda Y.,El-Koussi, Nawal A.,Farghaly, Zeinab S.
, p. 863 - 866 (2007/10/03)
Two series of new pyridines bearing thiazoline (3a - n) and thiazolidinone (5a - e) moieties were prepared via the cyclization of the corresponding substituted pyridyl thiourea (2a - g) with an appropriately substituted phenacyl bromide or chloroacetic ac
Molecular Conformation of N,N'-Diarylthioureas: an Assessment by 1H NMR and Infrared Spectroscopy
Sudha, L. V.,Manogaran, S.,Sathyanarayana, D. N.
, p. 591 - 596 (2007/10/02)
Several N,N'-dipyridyl- and N-phenyl-N'-pyridyl-thioureas were examined in different solvents at various temperatures by 1H NMR in order to study their conformational properties.The influence of concentration and the methyl substituent in the pyridine ring on the chemical shifts of the NH and pyridine groups was investigated.The observed chemical shifts are analysed in terms of the conformational properties of the molecules.Free energy barriers to the internal rotation about the C-N bonds have been determined.Infrared spectra have been measured to supplement the NMR studies.Intramolecular hydrogen bonding played a major role in the preferred conformation of pyridylthioureas.The data further revealed an interesting dynamic exchange phenomenon occuring in symmetric N,N'-dipyridylthioureas between two intramolecularly hydrogen bonded conformers.
