Synthesis and self-assembly of novel fluorous cationic amphiphiles with a 3,4-dihydro-2(1H)-pyridone spacer

Gene delivery agents possessing antiradical activity: self-assembling cationic amphiphilic 1,4-dihydropyridine derivatives

“…Similar findings have been reported by other groups related to cationic amphiphiles with a 3,4-dihydro-2(1H)-pyridone spacer. 39 For self-assembling compounds, the concentration above which micelles and other nanoparticles are formed, called the critical micelle concentration (CMC), is an important characterisation. In this study CMC was determined for tested amphiphiles 1, 5, 11 and 15 in aqueous media by the DLS technique according to the procedure described by Topel et al 40 To determine CMC, an aqueous solution of amphiphiles was prepared within the concentration range of 0.5 mg mL À1 to 0.1 Â 10 À2 mg mL À1 starting from concentrated stock solution, which was subjected to a serial two-fold dilution each time with water.…”

Pleiotropic Properties of Amphiphilic Dihydropyridines, Dihydropyridones, and Aminovinylcarbonyl Compounds

“…Polyfunctional self-assembling synthetic lipid-like compounds, such as pharmacological and chemotherapeutical agents, namely, 3,5-dialkoxycarbonyl-1,4-dihydropyridines (1,4-DHPs) comprising pyridinium or ammonium substituents at the 2 and 6 positions; structurally related compounds, derivatives of 3,4-dihydro-2-oxopyridines as isomeric 3,4-dihydropyridine structures with an additional intracyclic carbonyl group; and the N- β -carbonylvinylamido system, namely, 2-amino-3-alkoxycarbonylalkylammonium halides as open chain analogues of the first type of the abovementioned compounds, were studied. The main properties and major functions of these compounds are their amphiphilic character, liposome-forming ability, RNA transfection (by self-assembling compounds), antiradical and antioxidant properties, growth regulation—both in malignant and nonmalignant cell types—anticancer properties due to cytotoxicity, and MDR inhibition [ 13 , 16 , 27 , 28 , 31 , 33 ].…”

3,4-Dihydro-2(1H)-Pyridones as Building Blocks of Synthetic Relevance

“…3,4-DHPo moiety plays a key role as a scaffold for attaching cationic head groups. [9] Instead, Dostanic et al published about the synthesis of (substituted phenylazo)-pyridones in the presence of KOH and acetone to obtain 11-61% yield. [41] These were used dyeing polyester fabrics as yellow dyes.…”

“…The synthesis of 3,4-dihydropyridine-2(1H)-ones catalyzed by ZnBr2, FeCl3, AlCl3, BF3, Cu(OTf)2, In(OTf)2, and BF3 OEt2 was reported by Meng et al [49] This method was developed via Blaise reaction forming a cyclic intermediate (9) from benzonitrile (10) and Reformatsky reagents, which was generated in situ from ethyl bromoacetate (11) and zinc power in ethyl acrylate (12) and tetrahydrofuran with 0-81% yield (Scheme 7). Paravidino et al [50] developed a novel four-multicomponent reaction (4CR) of phosphonate (13), aldehydes derivatives (14), nitriles (15), and α-acidic isonitriles (16) to obtain 3,4-DHPo derivatives in 53-88% of yield and with complete diastereoselectivity in favor of the cis-diastereomer (Scheme 8).…”

“…In this context, DHPo's as the Milrinone and the Amrinone are drugs with cardiotonic activity successfully used to treat heart failure (Figure 1). [2] In addition, they and their derivatives have also been reported to possess antitumor [3], antibacterial [4] anti-HIV [5], and other biological activities [6][7][8][9]. These results encourage many research groups to search potentially active DHPo's analogs.…”