Synthesis and crystallographic evaluation of diazenyl- and hydrazothiazoles. [5.5] sigmatropic rearrangement and formation of thiazolium bromide dihydrate derivatives

Synthesis and biological evaluation of FJ-809, a compound originally described as MIM1 and an inhibitor of the anti-apoptotic protein Mcl-1

“…On the other hand, it has been described in the literature that when R 2 is H or an alkyl group then pathway 1 occurs, 10 and a similar result was obtained if R 2 is a COPh. 11 Based on this information, for the synthesis of compound FJ-809 with the originally assigned structure 1 , we designed a strategy using a Boc group in the R 2 position and this was performed according to Scheme 2.…”

Synthesis and structure confirmation of 2,4-disubstituted thiazole and 2,3,4-trisubstituted thiazole as thiazolium bromide salts

“…Also, in this paper we investigate the reactions between 1,4-disubstituted thiosemicarbazides 7a-7e and phenacyl bromide (2a) in ethyl acetate at room temperature resulting in the formation of 4-aryl-2-(amino)-3-(phenylamino) thiazol-3-ium bromide derivatives 8a-8e in high yields (88-97%) instead of (Z)-3-substituted 4-diphenyl-2-(2phenylhydrazono)-2,3-dihydrothiazoles 9a-9e [23] (Scheme 3). Here, we try to carry out the reaction in a variety of solvents and conditions; we found that the products were formed in high yields and purity when the reactions were carried out in ethyl acetate at room temperature (Table 1).…”

“…Reactions between mono-substituted thiosemicarbazides with phenacyl bromide derivatives in ethanol at refluxing temperature have been reported and gave 2-amino-5-(4aminophenyl)-4-(phenyl)-1,3-thiazol-3-ium bromide dihydrate derivatives. Also the same reactions have been carried out using Eschenmoser coupling reaction conditions, triethyl amine (base) and triphenylphosphine (thiophile) in acetonitrile resulting in the formation of diazinylthiazole derivatives [23].…”

New water-soluble isoxazole-linked 1,3,4-oxadiazole derivative with delocalized positive charge

“…Taking into account, our efforts have continued in the last years studies on isoxazole and oxadiazole derivatives in searching for new biological active derivatives. [5][6][7] Although, there are known molecules with positive charge localized at the nitrogen atom, [8][9][10][11] in the literature there is less mentioned about compounds possessing local positive charge at the carbon atom, and they are limited to small molecules. 12,13 Tailoring the chemical and physical properties of molecules by rational planning to improve overall stability, solubility or to reduce toxicity when designing new compounds with expecting application in medicine, continues to be an important research attempt.…”