A new class of fluorogenic thiazolo[2,3-b]quinazolinone receptor: selective detection towards mercury and hydrogen bisulfate ions in aqueous medium.

A series of fluorophoric and structurally diverse thiazoloquinazoline derivatives were synthesized in a one-pot multicomponent cascade reaction using a microwave irradiation technique. The unique structural arrangement of the synthesized compounds encouraged us to design a new type of bioactive molecular receptor. This receptor interacts with HSO4 - in 1 : 1 and Hg2+ in 1 : 2 binding stoichiometric ratios resulting in a change in fluorescence as well as absorption spectra in aqueous medium. The ion bonded receptor complex possibly enhances the fluorescence signal of the receptor via H-bonded complex formation with HSO4 - ions and co-ordinate complex formation with Hg2+ ions.

The construction of fluorophoric thiazolo-[2,3-b]quinazolinone derivatives: a multicomponent domino synthetic approach.

Acid-mediated one-pot domino reactions of substituted 2-amino thiazoles, substituted benzaldehydes and cyclic diketones have been developed for the synthesis of novel and architecturally unique thiazolo[2,3-b]quinazolinone derivatives under microwave irradiation. In this protocol, a series of thiazolo[2,3-b]quinazolinone derivatives have been synthesized and the excellent fluorescence behaviors of some of the molecules have been reported based on the incorporation of different electron-donating and electron-withdrawing substituents on the aryl moieties of the target molecules.

Unusual detritylation of tritylated tetrazole in Sartan molecules.

Tritylated tetrazole of 2a underwent unusual detritylation under basic reaction condition during the synthesis of methyl ether of olmesartan medoxomil 1. The unusual detritylation was found to be a common feature in the case of all tetrazole containing Sartan molecules (3-7).

Alpha-substituted 1-aryl-3-dimethylaminopropanone hydrochlorides: potent cytotoxins towards human WiDr colon cancer cells.

A series of 1-aryl-2-dimethylaminomethyl-2-propenone hydrochlorides 1 were prepared which possessed IC(50) values of less than 10 microM when examined towards human WiDr colon cancer cells. The related 1-aryl-2-dimethylaminomethyl-3-hydroxypropanone hydrochlorides 2, formed by hydration of the analogs in series 1, also had IC(50) values in the low micromolar range. On the other hand, conversion of 2-dimethylaminomethyl-1-(4-nitrophenyl)-2-propenone hydrochloride 1c into the corresponding 2-mercaptoethanol of adduct 3c led to a 37-fold reduction in potency. Two thirds of the compounds prepared in this study were more potent than a reference drug cisplatin while one third of these molecules displayed greater cytotoxicity to the WiDr cells than human CRL-2522 fibroblasts. A stability study of the 4-nitrophenyl analog in each of the series 1-3 in deuterium oxide was undertaken. In the case of 1c, replacement of the dimethylamino hydrochloride group by a hydroxy function was noted while in series 2, the loss of both water and dimethylamine hydrochloride gave rise to a mixture of two enones. The mercaptoethanol adduct 3c underwent deamination. The data obtained provide guidelines for amplifying the project in the future.