Efficient One-pot Synthesis of Pyrrolo[2,1-a]isoquinoline and Pyrrolo[1,2-a]quinoline Derivatives
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Isoquinoline
Quinoline
Acetylenedicarboxylate
Dimethyl acetylenedicarboxylate
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Several 4H-pyrano[3,2-h]quinoline 3,4,7-9, 7H-pyrimido[4',5':6,5]pyrano[3,2-h]quinoline 10a,b and 14Hpyrimido[ 4',5':6,5]pyrano[3,2-h][1,2,4]triazolo[1,5-c]quinoline 11a-c derivatives were obtained by treatment of (E) 2-(4- chlorostyryl)-8-hydroxyquinoline 1, (E) 2-amino-4-(4-chlorophenyl)-9-(4-chlorostyryl)-4H-pyrano[3,2-h]quinoline-3- carbonitr-ile 3 or (E) 9-amino-7-(4-chlorophenyl)-2-(4-chlorostyryl)-8-imino-8,9-dihydro-7H-pyrimido-[4',5':6,5]pyrano [3,2-h]quinoline 10b with different electrophiles followed by nucleophilic reagents. Structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR, 13C NMR-DEPT, 13C NMR-APT and MS data. The antitumor activity of the synthesized compounds was investigated and compared with that of the standard drug vinblastine, a well-known anticancer drug, using MTT colorimetric assay. Among them, compounds 10b and 3 showed the most potent activity against the human breast tumor cells (MCF-7) and the human lung carcinoma cells (HCT), while compound 10b exhibited the most potent activity against the human hepatocellular carcinoma cells (HepG-2). The structure-activity relationships are discussed Keywords: HIV integrase, anti-proliferative effects, styrylquinoline derivatives, quinoline nucleus, benzaldehyde, HCT, IR spectrum, S.pyogens
Quinoline
DEPT
Benzaldehyde
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Key words spiro compounds - polycyclic heterocycles - isatins - uracils - three-component reaction
Isatin
Derivative (finance)
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1, 2, 3, 6, 7, 12b-Hexahydro-4H-1, 3-dioxolo [j] pyridazo [3, 2-a] isoquinoline (II) was synthesized by cyclizing 2-(3, 4-methylenedioxyphenethyl) hexahydro-3-pyridazinone followed by reduction with sodium borohyride. This is the first exmple of azabenzoquinoline type of compound recorded in literature. Phrmacological property of the compound (II) is now being examined.
Isoquinoline
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Isoquinoline
Quinoline
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The tricyclic isatin, 5,6‐dihydro‐4 H ‐pyrrolo[3,2,1‐ ij ]quinoline‐1,2‐dione ( 1 ), reacts with a combination of an aryl cyanomethyl ketone 8 and a 5‐amino‐1‐arylpyrazole 7 to generate spirocyclic products 9 .
Quinoline
Isatin
Tricyclic
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Quinoline
Oxalyl chloride
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Isoquinoline
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Abstract (XIVd) hergestellt.
Indolizine
Quinoline
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