69957-79-5Relevant academic research and scientific papers
Synthesis and spectral studies on Ni(II) complexes involving N-furfuryl-N-substituted benzyldithiocarbamates and PPh3: Anagostic and C–H…π(chelate) interactions in (N-furfuryl-N-(4-fluorobenzyl)dithiocarbamato-S,S′)(thiocyanato-N)(tr
Sathiyaraj,Thirumaran,Ciattini, Samuele
, p. 1042 - 1050 (2016)
Twelve new nickel(II) complexes of functionalized dithiocarabamates [Ni(S2CNRR?)2](1-6) and [Ni(S2CNRR?)(NCS)(PPh3)](7-12) [where R=furfuryl; R?=2-hydroxy benzyl (1,7), 3-hydroxy benzyl (2,8), 4-hydroxy benzyl (3,9), 4-methoxy benzyl
Synthesis and Cytotoxicity of Octahydroepoxyisoindole-7-carboxylic Acids and Norcantharidin–Amide Hybrids as Norcantharidin Analogues
Hizartzidis, Lacey,Gilbert, Jayne,Gordon, Christopher P.,Sakoff, Jennette A.,McCluskey, Adam
, p. 1152 - 1161 (2019/05/24)
Octahydroepoxyisoindole analogues of norcantharidin were accessed through a Diels–Alder reaction of an amine-substituted furan with maleic anhydride and subsequent reduction of the bicyclo[2.2.1]heptene olefin. Despite retention of the carboxylate and the ether bridgehead known to impart cytotoxic activity to norcantharidin, none of these analogues displayed notable cytotoxicity against the 11 cell lines examined: HT29 (colon), MCF-7 (breast), A2780 (ovarian), H460 (lung), A431 (skin), Du145 (prostate), BE2-C (neuroblastoma), SJ-G2 and U87 (glioblastoma), MIA (pancreatic), and SMA (spontaneous murine astrocytoma). The incorporation of an amino-substituted system post-synthesis of norcantharidin afforded facile access to 14 acid/amide-substituted norcantharidin analogues. Of these, only four displayed sufficient activity at the initial 25 μm compound screening dose to warrant full evaluation of growth inhibition. Common to these analogues was the presence of a 4-biphenyl moiety, and in particular 3-(2-(furan-2-ylmethyl)-3-(4-biphenylamino)-3-oxopropylcarbamoyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid (13 c) and 3-(2-(pyrrole-2-ylmethyl)-3-(4-biphenylamino)-3-oxopropylcarbamoyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid (24) displayed high levels of cytotoxicity, returning GI50 values of 15 nm (HT29) to 2.9 μm (U87) and 17 nm (SMA) to 2.8 μm (U87), respectively. These are the most cytotoxic norcantharidin analogues reported to date.
SYNTHETIC BIOREGULATORS OF POLY-CIS CAROTENOID BIOSYNTHESIS
Poling, Stephen M.,Hsu, Wan-Jean,Yokoyama, Henry
, p. 601 - 604 (2007/10/02)
Seventeen new bioregulators were synthesized and tested for their ability to induce the biosynthesis of poly-cis carotenes in the flavedo of Marsh white seedless grapefruit.The effects of these new bioregulators are the same as that of the previously reported dibenzylamines, but several of the new compounds are more effective and cause the accumulation of up to 162 μg/g dry wt of poly-cis carotenes in the flavedo as compared to the maximum of 74 μg/g dry wt observed previously.The compounds tested were substituted N-benzyl furfurylamines, N-benzyl, N-methyl furfurylamines and N-alkyl , N-methyl benzylamines.They demonstrate the ability of tertiary as well as secondary amines to stimulate the formation of poly-cis carotenes.The interaction of N-(4-bromobenzyl) furfurylamine, one of the more effctive of the new compounds, with lycopene and β-carotene inducers is also reported.Key Word Index - Citrus paradisi; Rutaceae; Marsh white seedles grapefruit; carotenoid biosynthesis; bioregulators; secondary amines; poly-cis carotenoids; prolycopene.
