Evaluation of bioactivities of chlorokojic acid derivatives against dermatophytes couplet with cytotoxicity

Mannich bases in medicinal chemistry and drug design

“…Mannich bases 125 of chlorokojic acid (Fig. 23) had good anti-Candida activity (MIC values between 4 and 16 mg/mL) [152e154], but the antifungal activity against dermatophytes was slightly poorer [304]. In contrast, Mannich bases 174 (Fig.…”

Eco-friendly one-pot, three-component synthesis of novel derivatives of kojic acid by the Mannich-type reaction under solvent-free ball-milling conditions

“…This observation shows the importance of the highly efficient mixing of reagents under a ball-milling process in comparison with convenient solvent-free conditions. Furthermore, the model reaction was examined in the presence of different quantities of Ce 2 (SO 4 ) 3 Á5H 2 O in ball-milling under solvent-free conditions ( Table 1, entries [19][20][21][22]. The best result (87 % yield) was obtained when the After optimization of the reaction conditions, in order to explore the scope and generality of this procedure, condensation reactions of kojic acid derivatives with a variety of aromatic aldehydes and heteroaromatic amines (Fig.…”

“…Because of biological activates of Mannich bases, this reaction has attracted increased interest (Compounds II, Fig. 1) [19][20][21][22][23][24]. However, a literature survey shows that most reported articles of Mannich reactions concern the study of kojic acid, To the best of our knowledge, there are no reports on three-component coupling of kojic acid, aromatic aldehydes and heteroaromatic amines to produce a new class of kojic acid derivatives as novel Mannich bases. In recent years, the use of ball-milling (intense mechanical grinding) as an efficient and green tool in organic synthesis has garnered great interest [25][26][27][28][29][30][31][32].…”

A kojic acid derivative promotes intrinsic apoptotic pathway of hepatocellular carcinoma cells without incurring drug resistance

“…In synthesis process, chlorokojic acid (2‐chloromethyl‐5‐hydroxy‐4 H ‐pyran‐4‐one, CKA) was obtained from commercially available kojic acid in a one‐step reaction. 2‐Substituted‐6‐(hydroxymethyl/chloromethyl)‐3‐hydroxy‐4 H ‐pyran‐4‐one (compounds 1 , 2 , 5 and 8 ) derivatives were synthesized with the reaction of appropriate substituted benzylpiperazine derivatives with KA or CKA and formaline at room temperature (Aytemir et al, ; Aytemir, Ozcelik, & Karakaya, ; Karakaya, Aytemir, Ozcelik, & Calis, ; Karakaya et al, ). Finally, Mannich bases of CKA reacted with piperidine or pyrrolidine moieties in the dimethylformamide (DMF) in presence of K 2 CO 3 to synthesize compounds with the structure of 2‐substituted‐3‐hydroxy‐6‐(piperidinylmethyl/pyrrolidinylmethyl)‐4 H ‐pyran‐4‐one (compounds 3 , 4 , 6 , 7 , 9 , and 10) (Karakaya et al, , ).…”