Cytotoxicity of new pyrazino[1,2-b]isoquinoline and 6,15-iminoisoquino[3,2-b]3-benzazocine compounds
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Isoquinoline
Structure–activity relationship
Carcinoma Cell
An efficient synthetic organic transformation was developed to access isoquinoline-substituted isobenzofurans by reaction of substituted 1,5-diynes with isoquinoline N-oxides. Moderate to excellent yields of isoquinoline-derived isobenzofurans were achieved by formation of a new C–C and two C–O bonds in the presence of copper catalyst in one pot. whereas quinoline-substituted isobenzofurans were obtained when the reaction was conducted using quinoline N-oxides and 1,5-diynes in the presence copper catalyst.
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Abstract Die Isochinolin‐N‐oxide (I) und (IV) reagieren mit Propiolsäureester (II) zu Pyrrolo‐isochinolin‐Derivaten (III) und (V).
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A series of 9-O-acylisoaaptamine (3−14) and 4-N-acyl-dihydroaaptamine (16−19) derivatives have been prepared and evaluated for antitumor activity against murine P-388 and human tumor cells including KB16, A549, and HT-29 cell lines. All of compounds showed significant cytotoxicity against P-388 cells. Among them, compounds 9−11 showed potent activity as isoaaptamine (1). There was an apparent lack of linear relationship between cytotoxicity and carbon number of the side chain. The structure and activity relationship for these particular compounds are discussed.
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Abstract The cytotoxicity of 22 natural and semi-synthetic simple coumarins was evaluated in GLC 4 , a human small cell lung carcinoma cell line, and in COLO 320, a human colorectal cancer cell line, using the microculture tetrazolium (MTT) assay. With IC 50 values > 100 μᴍ , following a continuous (96h) incubation, most coumarins exhibited only low cytotoxicity. Several compounds, however, displayed significant potencies. As far as the structure -cytotoxicity relationship is concerned, it is conspicuous that all the potentially active natural compounds possess at least two phenolic groups in either the 6,7-or 6,8-positions. In addition, the 5-formyl-6-hydroxy substituted semi-synthetic analogue was found to be potent, reflecting the importance of at least two polar functions for high cytotoxicity.
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Abstract Routes towards the synthesis of the title compounds are described from isoquinoline derivatives.
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Carcinoma Cell
Structure–activity relationship
Growth inhibition
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In this paper,5-bromo-isoquinoline was synthesized with one step by use isoquinoline as start material.Then a series of isoquinoline derivatives such as 5-bromo-8-nitro-isoquinoline,8-amino-isoquinoline and 8-bromo-isoquinoline were synthesized from 5-bromo-isoquinoline.All products have been confirmed by IR,NMR and so on.
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Isoquinoline alkaloids are attractive natural products due to their diverse chemical structures as well as remarkable bioactivities. Herein, we report the concise total syntheses of two isoquinoline alkaloids, menisporphine and daurioxoisoporphine C, through a mild and efficient photoredox-catalyzed direct C–H arylation of isoquinoline core with aryldiazonium salt. This new strategy is complementary to the conventional isoquinoline synthesis and would provide us a useful means to achieve a more convergent and flexible approach to access diverse isoquinoline structures.
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