- Hypolipidemic Activity of Phthalimide Derivatives. 2. N-Phenylphthalimide and Derivatives
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A series of substituted N-phenylphthalimide derivatives was synthesized and examined for their ability to lower serum cholesterol and triglyceride levels in mice at 20 (mg/kg)/day, ip.Of the newly synthesized compounds, the most potent compound, o-(N-phthalimido)acetophenone, lowered serum cholesterol 57percent after 16 days and lowered serum triglyceride levels 44percent after 14 days. o-(N-Phthalimido)acetophenone was observed to be active in both normogenic (normal blood lipids levels) and hyperlipidemic mice and normogenic rats.In the latter, the reduction of serum lipids was reversible.The mode of action of this compound appeared to be multiple, including blockage of the de novo synthesis of lipids and acceleration of the excretion of lipids.The lipoprotein fractions of rat blood were reduced significantly in cholesterol, triglyceride, and neutral lipid content after 14 days treatment with o-(N-phthalimido)acetophenone.
- Chapman, James M.,Voorstad, P. Josee,Cocolas, George H.,Hall, Iris H.
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- Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes
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In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.
- Kuribara, Takahito,Nakajima, Masaya,Nemoto, Tetsuhiro
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supporting information
p. 2235 - 2239
(2020/03/13)
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- Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
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The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.
- Jha, Amitabh,Chou, Ting-Yi,ALJaroudi, Zainab,Ellis, Bobby D.,Cameron, T. Stanley
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supporting information
p. 848 - 857
(2014/05/06)
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