Utility of Octadecyl Amine in the Synthesis of Various Nitrogen Heterocycles: A Preliminary Investigation on Their Surface and Biological Activities

Abstract

in Wiley Online Library (wileyonlinelibrary.com).The present work describes the synthesis of some heterocyclic compounds based pyrazole, triazole, pyrimidine, and pyridine derivatives. The synthesis of these heterocycles have been carried out by the reaction of ethyl-3-(octadecylamino)-3-oxopropanoate (2) with various reagents under suitable reaction conditions. Propoxylation of these heterocycles by using a number of propylene oxide moles afforded nonionic surface active agents, incorporating long alkyl chain having suitable molecular weight to obtain amphiphilic materials with hydrophilic-lipophilic equilibrium, which enhances solubility and biodegradability, hence lowers the toxicity to human beings, and becomes environmentally friendly. A series of useful properties such as surface and interfacial tensions, cloud point, wetting time, foam height, emulsion stability, critical micelle concentration (CMC), surface tension at the CMC (γ CMC ), efficiency (PC 20 ), effectiveness (π CMC ), surface excess (Γ max ), and surface area (A min ) have been estimated. In addition, the antimicrobial activities of these compounds were screened.

Synthesis of Potential Pharmaceutical Heterocycles as Surface Active Agents

“…82-84°C, IR (m/cm -1 ); 3319 (NH), 2848-2915 (CH-aliph), 1677, 1658 (CO), 1275 (epoxy linkage). 1 Synthesis of N-(4-(4-Hydroxy-5-phenyl-4,5dihydroisoxazol-3-yl)phenyl)stearamide (19) A solution of compound 18 (1 g, 2 mmol) and hydroxylamine hydrochloride (0.14 g, 2 mmol) in EtOH (20 mL) with pyridine (0.5 mL) was heated for 8 h, and poured onto ice water/dil HCl, filtered and crystallized from EtOH. A deep yellow solid was formed.…”

“…These surface active agents are inexpensive to produce and have various applications in industry, because of applications as emulsifiers, foam stabilization, wetting agents, facilitate solubilization and several biotechnological processes [40][41][42][43][44][45][46]. Addition of number of moles of propylene oxide (10 moles) to the synthesized compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) which have active hydrogen atoms in the presence of KOH as a catalyst produced nonionic surface active agents (21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37), respectively, which may have broader formulation flexibility. The structure of propoxylated products (21)(22)(23)(24)(25)…”

“…Chalcone derivatives are acknowledged to be a tool in the synthesis of pharmacologically interesting heterocyclic systems such as pyrazoles, which are attracting interest due to their bioactivity [13]. Oleochemicals are necessary to a variety of applications such as plastics, surface treatments, paints, lubricants, pharmaceuticals, pesticides, detergents, soaps, textiles, and cosmetic [14][15][16][17][18][19][20]. Extending our past research in this area [21][22][23][24][25][26], we sought to prepare some new isoxazole, pyrazole, puran, pyridine and pyrimidine derivatives and evaluating their surface and biological activities to determine suitability for the applications above.…”

Fluorene Derivatives with Multi‐addressable Properties: Synthesis, Characterization, and Reactivity

“…We have been involved in the development of simple procedures for the synthesis of effective, cheap, functionally substituted heterocycles with biological activities [13][14][15][16][17][18][19]. The derivatives of fatty compounds based on these heterocyclic compounds can be used as valuable oleochemicals [20][21][22].…”