Oxadiazole-substituted naphtho[2,3- b ]thiophene-4,9-diones as potent inhibitors of keratinocyte hyperproliferation. Structure−activity relationships of the tricyclic quinone skeleton and the oxadiazole substituent

Basoglu, Atila; Dirkmann, Simone; Golpayegani, Nader Zahedi; Vortherms, Silke; Tentrop, Jan; Nowottnik, Dominica; Prinz, Helge; Fröhlich, Roland; Müller, Klaus

doi:10.1016/j.ejmech.2017.03.084

Cited by 12 publications

(6 citation statements)

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“…Final oxidation and ether cleavage using diammonium cerium(IV) nitrate provided the target structure 5c ( Scheme 5 ). Finally, following previously reported procedures, the compound N , N -diethyl-4,9-dioxo-4,9-dihydronaphtho[2,3- b ]furan-2-carboxamide ( 6 ) [ 19 ], as well as the naphthothiophene derivatives 8-hydroxy-2-(thiophen-2-ylcarbonyl)naphtho[2,3- b ]thiophene-4,9-dione ( 7 ) [ 20 ], 8-chloro- N , N -diethyl-4,9-dioxo-4,9-dihydronaphtho[2,3- b ]thiophene-2-carboxamide ( 8 ) [ 21 ], and 2-(3-ethyl-1,2,4-oxadiazol-5-yl)naphtho[2,3- b ]thiophene-4,9-dione ( 9 ) [ 22 ] were synthesized.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Anti-Proliferative Activity Evaluation and 3D-QSAR Study of Naphthoquinone Derivatives as Potential Anti-Colorectal Cancer Agents

et al. 2018

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Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 < IC50 < 18.11 μM). The naphtho[2,3-b]thiophene-4,9-dione analogs showed potent cytotoxicity, 8-hydroxy-2-(thiophen-2-ylcarbonyl)naphtho[2,3-b]thiophene-4,9-dione being the compound with the highest potency and selectivity. Our results suggest that the toxicity is improved in molecules with tricyclic naphtho[2,3-b]furan-4,9-dione and naphtho[2,3-b]thiophene-4,9-dione systems 2-substituted with an electron-withdrawing group. A 3D-QSAR study of comparative molecular field analysis (CoMFA) was carried out, resulting in the generation of a reliable model (r2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Anti-Proliferative Activity Evaluation and 3D-QSAR Study of Naphthoquinone Derivatives as Potential Anti-Colorectal Cancer Agents

et al. 2018

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“…Melting points are uncorrected and were determined in an apparatus according to Dr. Tottoli (Büchi). 1 H and 13 C NMR spectra were recorded on a Bruker Avance 400 MHz spectrometer (at 400 MHz for 1 H NMR, 101 MHz for 13 C NMR). Multiplicities are described by using the following abbreviations: s = singlet, d = doublet, t = triplet, q = quartet, and m = multiplet.…”

Section: Methodsmentioning

confidence: 99%

“…Compounds containing of thiophene and tetrazole cycles are reported as antibacterial nonpeptide antagonists platelet aggregators, antithrombotic agents [0, 2] and nonlinear optical materials [3]. Similarly, these derivatives are well known to exhibit various activities such as anti-inflammatory [4,5], antibacterial [4][5][6], anticancer [7][8][9][10][11], antiviral [11], antifungal [12], inhibition of keratinocyte hyperproliferation [13] activities. In particular, thiophene-containing compounds are of considerable interest as anticancer drugs [7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of substituted 5-(thiophen-2-yl)-1H-tetrazoles

Shehedyn¹,

Barabash²,

Ostapiuk³

et al. 2022

Visnyk Lviv Univ. Ser. Chem.

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“…Naphtho[2,3- b ]thiophene-4,9-dione (NT) derivatives are investigated in medicinal chemistry as bioactive synthetic products possessing anticancer, − antiprotozoal, − and antipsoriatic properties. − In materials chemistry, NTs are promising precursors for the synthesis of electron-deficient compounds − and the preparation of building blocks for air-stable organic semiconductors. − …”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of 2-R-Naphtho[2,3-b]thiophene-4,9-diones via Cyclization of 2-(R-Ethynyl)-1,4-naphthoquinones with Na₂S₂O₃

et al. 2021

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The concise and efficient one-pot synthesis of 2-Rnaphtho [2,3-b]thiophene-4,9-diones from 2-bromo-1,4-naphthoquinone and alkynes has been developed. The reaction proceeds through the formation of 2-(R-ethynyl)-1,4-naphthoquinones, which undergo transformation with Na 2 S 2 O 3 to 2-R-naphtho[2,3b]thiophene-4,9-diones via C−H sulfuration, accompanied by the formation of the aromatic Bunte salt, followed by its air oxidation and 5-endo-dig cyclization. The protocol is characterized by simplicity, good tolerance for functional groups, relatively mild conditions, and commercially available starting compounds.

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Oxadiazole-substituted naphtho[2,3- b ]thiophene-4,9-diones as potent inhibitors of keratinocyte hyperproliferation. Structure−activity relationships of the tricyclic quinone skeleton and the oxadiazole substituent

Cited by 12 publications

References 63 publications

Synthesis, Anti-Proliferative Activity Evaluation and 3D-QSAR Study of Naphthoquinone Derivatives as Potential Anti-Colorectal Cancer Agents

Synthesis, Anti-Proliferative Activity Evaluation and 3D-QSAR Study of Naphthoquinone Derivatives as Potential Anti-Colorectal Cancer Agents

Synthesis of substituted 5-(thiophen-2-yl)-1H-tetrazoles

One-Pot Synthesis of 2-R-Naphtho[2,3-b]thiophene-4,9-diones via Cyclization of 2-(R-Ethynyl)-1,4-naphthoquinones with Na₂S₂O₃

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Oxadiazole-substituted naphtho[2,3- b ]thiophene-4,9-diones as potent inhibitors of keratinocyte hyperproliferation. Structure−activity relationships of the tricyclic quinone skeleton and the oxadiazole substituent

Cited by 12 publications

References 63 publications

Synthesis, Anti-Proliferative Activity Evaluation and 3D-QSAR Study of Naphthoquinone Derivatives as Potential Anti-Colorectal Cancer Agents

Synthesis, Anti-Proliferative Activity Evaluation and 3D-QSAR Study of Naphthoquinone Derivatives as Potential Anti-Colorectal Cancer Agents

Synthesis of substituted 5-(thiophen-2-yl)-1H-tetrazoles

One-Pot Synthesis of 2-R-Naphtho[2,3-b]thiophene-4,9-diones via Cyclization of 2-(R-Ethynyl)-1,4-naphthoquinones with Na2S2O3

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One-Pot Synthesis of 2-R-Naphtho[2,3-b]thiophene-4,9-diones via Cyclization of 2-(R-Ethynyl)-1,4-naphthoquinones with Na₂S₂O₃