2619-87-6Relevant articles and documents
Synthesis of 5-heptadecyl- and 5-heptadec-8-enyl substituted 4-amino-1,2,4-triazole-3-thiol and 1,3,4-oxadiazole-2-thione from (Z)-octadec-9-enoic acid: preparation of Palladium(II) complexes and evaluation of their antimicrobial activity
Chehrouri, Manel,Gholinejad, Mohammad,Moreno-Cabrerizo, Cristina,Othman, Adil A.,Sansano, José M.
, (2020)
Abstract: Two 4-amino-1,2,4-triazoles and two 1,3,4-oxadiazoles are obtained in a common synthetic route including hydrogenation-hydrazidation of (Z)-methyl octadec-9-enoate to octadecanoic hydrazide under atmospheric air. Preservation of olefinic bond in heptadec-8-enyl group is achieved by carrying out hydrazidation reaction under the presence of an argon atmosphere. The disappearance of the olefinic bond is detected by physical data, IR, 1H, and13C NMR spectroscopy. New palladium complexes derived from 4-amino-5-heptadecyl-1,2,4-triazole-3-thiol and 5-heptadecyl-1,3,4-oxadiazole-2(3H)-thione are obtained and characterized by elemental analysis (solid state), IR, 1H, 13C NMR spectroscopy, XRD, and XPS. These resulting metallic entities are also identified in solution based in mass spectrometry (MS-ESI) experiments. Most compounds and their palladium(II) complexes are tested in vitro against Gram-positive, Gram-negative bacteria, and fungi, some of them showed variable activity. Graphic abstract: [Figure not available: see fulltext.].
Cyclocondensation between fatty acid hydrazides and 1,1,1-trifluoro-4-alkoxy-3-alken-2-ones: Introducing a trifluoromethylated head onto fatty acid moieties
Teixeira, Wystan K. O.,Gon?alves, Helena A.,de Mello, Débora L.,Moura, Sidnei,Flores, Darlene C.,Flores, Alex F. C.
, p. 2078 - 2086 (2017)
This paper reports the regioselective synthesis of new trifluoromethylated lipid derivatives, namely, 1-(5-hydroxy-5-trifluoromethyl-3-alkyl-4,5-dihydro-1H-pyrazol-1-yl)alkan-1-ones, through cyclocondensation reactions between a series of fatty hydrazides (palmitoyl, stearoyl, and oleoyl hydrazides) obtained from fatty acids from renewable resources (1,1,1-trifluoro-4-alkoxy-3-alken-2-ones [F3CC(O)CH?C(R1)OR, where R1 = H and R?Et; R1 = –(CH2)6CH3, –(CH2)6CH3, –(CH2)8CH3, –(CH2)9CH3, –(CH2)10CH3, –(CH2)12CH3, –(CH2)2Ph], and R?Me). Experimental observations showed that the lipophilic characteristic of 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazoles (5–7) prevent the acid catalyzed dehydration to aromatization of 1H-pyrazole ring, although in some cyclocondensations a proportion of the aromatic derivative 1-(5-trifluoromethyl-3-alkyl-1H-pyrazol-1-yl)alkan-1-one was obtained. All products were characterized using multinuclear (1H, 13C, 19F) NMR spectroscopy.
Synthesis and antimicrobial studies of 5-n-alkyl-1,3,4-oxadiazole-2-thiol derivatives from fatty acids
Naga Sudha,Yella Subbaiah,Srikanth,Venkata Ramana Reddy,Sneha Latha,Vijaya Lakshmi
, p. 2369 - 2371 (2017/10/31)
The novel 5-N-alkyl-1,3,4-oxadiazole-2-thiol derivatives have been synthesized by esterification of fatty acid followed by reaction the ester with hydrazine hydrate. The acid hydrazide was converted to 1,3,4-oxadiazole by ring closure mechanism. The synthesized compounds have been characterized by physical (melting point and TLC) and spectral (IR, 1H NMR and mass) data. All the compounds were screened for their antimicrobial activity. The compounds 3F1 & 3F4 showed good inhibition activity against all four types of bacteria; while compound 3F2 & 3F3 shown moderate activity.
