Synthesis and in vitro antiproliferative activity of 5-alkyl-12(H)-quino[3,4-b] [1,4]benzothiazinium salts

Functionalized 1,4‐Benzothiazine: A Versatile Scaffold with Diverse Biological Properties

“…The activity of the obtained 5‐alkyl‐12( H )‐quino[3,4‐ b ][1,4]benzothiazinium salts 74 was investigated in vitro using cultured HCT116 and LLC cell lines 32. Substitution of butyl and decyl moieties at the quinoline nitrogen atom of compounds 74 and 75 increased their lipophilicity parameters, lowering at the same time the antiproliferative activity when compared to compound 76 which features a methyl substituent and has highest activity on the LLC cell line (IC 50 = 2.3 ± 0.6 µg/mL).…”

“…Moreover, much researches have been carried out toward improving benzothiazine‐based drugs and to avoid the adverse effects 12, 13. Generally, benzothiazine and derivatives have found widespread application as analgesic 14, 15, antibacterial 16–18, anticancer 19, 20, anticonvulsant 21, antidiabetic 22, antifungal 23, 24, anthelmintic 25, 26, anti‐HCV 27, antihypertensive 28, antimalarial 29, antimicrobial 30, 31, antiproliferative 32, antipsychotropic 33, 34, antithyroid 35, antitubercular 36, antiviral agents 37, and calcium antagonist 38 among others. Furthermore, 1,4‐benzothiazine is the core structure in many drugs such as antibiotic 1 and blood cholesterol lowering drug 2 39.…”

Studies on antimicrobial effects of four ligands and their transition metal complexes with 8-mercaptoquinoline and pyridine terminal groups

“…In a long period of time, the quinoline terminal group is found in a large variety of natural compounds and also chemically mediates diverse bioactivities. [2][3][4][5][6][7][8] Yet, no one can ignore the important role of pyridine as an imperative heterocyclic for its countless derivatives and antimicrobial activity. 9 Moreover, multicomponent reactions were employed as a powerful tool to synthesize diverse and complex heterocyclic compounds due to their advantages of the intrinsic atom economy, simpler procedures, structural diversity, and reduced waste.…”

Synthesis and in vitro antiproliferative activity of novel 12(H)-quino[3,4-b][1,4]benzothiazine derivatives

“…In our previous papers, we reported a novel method of synthesizing quinoline fragment-containing phenothiazine derivatives that possess the structure of 5-alkyl-12( H )-quino[3,4- b ][1,4] benzothiazinium salts 2 . These compounds contain a totally planar tetracyclic fragment and have interesting antimicrobial and antiproliferative properties (Zięba et al ,2010, 2012). In this study, we present details of synthesis of novel quinobenzothiazine derivatives as free quinoline bases, and their derivatives containing aminoalkyl substituents at the thiazine nitrogen atom.…”