- Synthesis, Spectral Characterization, and In Vitro Biological Evaluation of Some Novel Isoquinolinone-based Heterocycles as Potential Antitumor Agents
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A series of new N-substituted isoquinolin-1,3-dione derivatives were prepared, starting from reaction of (Z)-4-((E)-3-phenylallylidene)isochromane-1,3-dione 4 with different nitrogen nucleophiles. The assigned structures of the prepared compounds were elucidated by spectral methods (IR, 1H NMR, 13C NMR, and mass spectroscopy). Some of the newly prepared compounds were tested in vitro against a panel of three human tumor cell lines, namely, hepatocellular carcinoma (liver) HepG2, colon cancer HCT-116, and mammary gland breast MCF-7. Also, they were tested as antioxidants. Some of the tested compounds showed very strong cytotoxic activity with respect to the standard.
- Hekal, Mohamed H.,Abu El-Azm, Fatma S. M.,Sallam, Hanan A.
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p. 795 - 803
(2019/02/03)
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- Synthesis of 4-arylideneisochroman-1,3-dione under microwave irradiation
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Homophthalic acid (1) and arylcarboxyaldehydes were condensed to form 4-arylideneisochroman-1,3-dione (3) in acetic anhydride in the presence of ammonium acetate under focused microwave irradiation. The stereochemistry of the products was determined by NMR and by X-ray diffraction of one isomer.
- Villemin, Didier,Bar, Nathalie,Khalid, Mohamed,Jaffres, Paul-Alain,Sopkova-De Oliveira Santos, Jana
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p. 433 - 435
(2007/10/03)
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- Effect of the Structure of 1-Aza-1,3-dienes on 1,2- Versus 3,4-Selectivity in Cycloaddition Reactions with Homophthalic Anhydride
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The reaction of homophthalic anhydride 1 with N-(cinnamylidene)tritylamine 2a proceeds as a 3,4-cycloaddition to give 4-oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylic acids 3, with N-(cinnamylidene)benzylamine 2b as a 1,2-cycloaddition with the predominant formation of a 1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid, and with either 2a or cinnamaldehyde in the presence of Et3N with the formation of a 2-oxonaphtho[1,2-b]pyran-6-carboxylic acid.
- Georgieva, Angelina,Spassov, Stefan,Stanoeva, Elena,Topalova, Ivanka,Tchanev, Christo
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p. 148 - 149
(2007/10/03)
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- Cyclocondensations of homophthalic anhydrides with 1-aza-1,3-dienes
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α,β-Unsaturated aldimines (1-aza-1,3-butadienes) 2, 4 and 7a-d react with homophthalic anhydrides 1a,b to give 3,4-dihydro-1(2H)-naphthalenone-4-carboxylic acids 3, 5 8a-d (R2 = H) as main products. Homophthalic anhydride 1a and cinnamaldimine 7d gave rise to the diastereoisomeric naphthalenones 8d (R2 = H), along with the 3,4-dihydro-1(2H)-isoquinolinone-4-carboxylic acids 10 (R2 = H), and 3,4-dihydro-1(2H)-pyridinone 11 (R2 = H) as products 3,4-, 1,2- and 1,4-addition to the 1-aza-1,3-butadiene, respectively. The effect of the reaction conditions on the ratio of adducts, produced by 1a and 7d, was studied. The structure and relative configurations of 3, 5, 8a-d, 10 and 11 were determined by NMR spectroscopy. In the case of cis-naphthalenone 8c and dihydropyridinone 11, the structure was confirmed by X-ray crystal structure analysis.
- Georgieva, Angelina,Stanoeva, Elena,Spassov, Stefan,Haimova, Marietta,De Kimpe, Norbert,Boelens, Mark,Keppens, Marian,Kemme, Andrejs,Mishnev, Anatoly
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p. 6099 - 6114
(2007/10/02)
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