Synthesis, photochemical synthesis, DNA binding and antitumor evaluation of novel cyano- and amidino-substituted derivatives of naphtho-furans, naphtho-thiophenes, thieno-benzofurans, benzo-dithiophenes and their acyclic precursors

Starčević, Kristina; Kralj, Marijeta; Piantanida, Ivo; Šuman, Lidija; Pavelić, Krešimir; Karminski‐Zamola, Grace

doi:10.1016/j.ejmech.2006.03.012

Cited by 49 publications

(33 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The structures of the latter products were established on the basis of analytical and spectral data . 1 H NMR spectrum of 3b ,as an example showed 1.79-2.02 (m, 8H, 4CH 2 ), 4.44(s, 2H, NH 2 7.27-7.36 ( m, 4H, benzene-CH), 8.64 ) ( s, 1H, NH, D 2 O-exchangeable) . The 2-amino present in compounds 3a,b showed interesting activity towards anilide formation.…”

Section: Resultsmentioning

confidence: 99%

New Approaches for the Synthesis of Thiophene Derivatives with Antitumor Activities

2012

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

New Approaches for the Synthesis of Thiophene Derivatives with Antitumor Activities

2012

View full text Add to dashboard Cite

show abstract

“…In parallel, we also synthesized and characterized the antitumor activities of novel cyano-and amidino-substituted derivatives of naphtho-furans, naphtho-thiophenes, thieno-benzofurans, benzo-dithiophenes, and their acyclic precursors [7]. The prime objective of these studies was to create compounds with strong antiproliferative activity, primarily through the introduction of various cyano-and amidino-substituted derivatives that would increase the DNA-binding affinity of the lead compounds.…”

Section: Introductionmentioning

confidence: 99%

Putative mechanisms of antitumor activity of cyano-substituted heteroaryles in HeLa cells

et al. 2010

Self Cite

View full text Add to dashboard Cite

Six recently synthesized cyano-substituted heteroaryles, which do not bind to DNA but are highly cytotoxic against the human tumor cell line HeLa, were analyzed for their antitumor mechanisms of action (MOA). They did not interfere with the expression of human papillomavirus oncogenes integrated in the HeLa cell genome, but they did induce strong G1 arrest and result in the activation of caspase-3 and apoptosis. A computational analysis was performed that compared the antiproliferative activities of our compounds in 13 different tumor cell lines with those of compounds listed in the National Cancer Institute database. The results indicate that interference with cytoskeletal function and inhibition of mitosis are the likely antitumor MOA. Furthermore, a second in silico investigation revealed that the tumor cells that are sensitive to the cyano-substituted compounds show differences in their expression of locomotion genes compared with that of insensitive cell lines, thus corroborating the involvement of the cytoskeleton. This MOA was also confirmed experimentally: the cyano-substituted heteroaryles disrupted the actin and the tubulin networks in HeLa cells and inhibited cellular migration. However, further analysis indicated that multiple MOA may exist that depend on the position of the cyano-group; while cyano-substituted naphthiophene reduced the expression of cytoskeletal proteins, cyano-substituted thieno-thiophene-carboxanilide inhibited the formation of cellular reactive oxygen species.

show abstract

“…For instance, many synthetic naphthofurans have been demonstrated to possess antiviral, [1] antifungal, [2] antibacterial, [3] and antitumor activities. [4] Naphthofurans isolated from natural sources also have a broad spectrum of biological activities, for example, antiviral activity against HIV [5] as well as anticancer [6] and analgesic activities. [7] Up to now, the most useful methodology described for the preparation of these heterocycles is intermolecular annulation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Naphthofurans by tBuOK‐Catalyzed Intramolecular Anionic Cycloaddition of Unsymmetrical Bis‐propargyl Ethers

2015

View full text Add to dashboard Cite

The tBuOK-catalyzed intramolecular anionic cycloaddition of unsymmetrical bis-propargyl ethers has been applied to the synthesis of naphthofurans. A systematic study of the cyclization system revealed that the amount of base and solvent played an essential role in this reaction. The results showed that the cyclization preceded cleanly and smoothly under mild reaction conditions, employing a catalytic amount of tBuOK as base, THF as solvent, at room temperature in a short reaction time (15 min). The reaction was regioselective,

show abstract

Synthesis, photochemical synthesis, DNA binding and antitumor evaluation of novel cyano- and amidino-substituted derivatives of naphtho-furans, naphtho-thiophenes, thieno-benzofurans, benzo-dithiophenes and their acyclic precursors

Cited by 49 publications

References 23 publications

New Approaches for the Synthesis of Thiophene Derivatives with Antitumor Activities

New Approaches for the Synthesis of Thiophene Derivatives with Antitumor Activities

Putative mechanisms of antitumor activity of cyano-substituted heteroaryles in HeLa cells

Synthesis of Naphthofurans by tBuOK‐Catalyzed Intramolecular Anionic Cycloaddition of Unsymmetrical Bis‐propargyl Ethers

Contact Info

Product

Resources

About