71306-89-3Relevant academic research and scientific papers
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.
High-pressure-promoted condensation of isothiocyanates with aminopyridines: Efficient synthesis of pyridine-thiourea conjugates as building blocks for hydrogen-bonding receptors
Kumamoto, Koji,Misawa, Yoshihiro,Tokita, Sumio,Kubo, Yuji,Kotsuki, Hiyoshizo
, p. 1035 - 1038 (2007/10/03)
New N-pyridinothiourea derivatives have been prepared by the high-pressure-promoted condensation of isothiocyanates with aminopyridines under uncatalyzed conditions. Complexation of the prototype 3c with diphenyl hydrogen phosphate was investigated by 1H NMR, and the results suggest that it may be useful as a building block for hydrogen-bonding receptors.
