Synthesis of New Furo-Imidazo[3.3.3]propellanes

Hassan, Alaa A.; Mohamed, Nasr K.; El-Haleem, Lamiaa E. Abd; Bräse, Stefan; Nieger, Martin

doi:10.2174/1570179412666150513003813

Cited by 6 publications

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“…15 In addition, the coupling reaction between heteroylthiosemicarbazides and 2 afforded naphthothiazoles and naphthothiadiazines. 14 The single crystal X-ray structure analysis of (Z)-N- [ In the crystal structure, the chloride ion is linked with cation NH-attached to sulfonyl group and NHEt via hydrogen bonding interactions (Figure 2).…”

Section: Syn Thesismentioning

confidence: 99%

“…12 Naphtho[2,3-d]thiazole-4,9-diones are one of the most important compounds, and these are prepared during the condensation between bromolawsone and thiosemicarbazones. 13 Recently the condensation of 2,3-dichloro-1,4-naphthoquinone (2) with N-hetero- 14 and N-substituted (E)-hexenylidenehydrazinecarbothioamides afforded naphtho [2,3d]thiazole derivatives. 14,15 The Eschenmoser coupling reaction is one of the most important key steps in carbon-carbon bond formation.…”

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confidence: 99%

“…13 Recently the condensation of 2,3-dichloro-1,4-naphthoquinone (2) with N-hetero- 14 and N-substituted (E)-hexenylidenehydrazinecarbothioamides afforded naphtho [2,3d]thiazole derivatives. 14,15 The Eschenmoser coupling reaction is one of the most important key steps in carbon-carbon bond formation. 16 This method was reviewed by Hussaini et al 17 for the preparation of several heterocyclic rings, natural products, and dicarbonyl compounds, and the formation of conjugated alkenes.…”

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confidence: 99%

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Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbothioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives

et al. 2017

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N-Unsubstituted and N-substituted 2-phenylhydrazinecarbothioamides react with 2,3-dichloro-1,4-naphthoquinone to give a series of unprecedented 3-amino- and 3-(alkylamino)-1-phenyl-1H-benzo[f]indazole-4,9-diones in good yields. On the other hand, the reaction of N-substituted 2-tosylhydrazinecarbothioamides with 2,3-dichloro-1,4-naphthoquinone afforded (Z)-N-[3-(tosylamino)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]thiazol-2(3H)-ylidene]-substituted aminium chlorides and (Z)-N-[(2-substituted imino)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]thiazol-3(2H)-yl]-4-toluenesulfonamide hydrates.

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Section: Syn Thesismentioning

confidence: 99%

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Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbothioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives

et al. 2017

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“…Propellanes-type-indane bearing a rigid three dimensioned structure is very appealing as some functional groups can be introduced to the indandione moiety to show in the desired direction. Because of these findings, our group has reported a direct and concise synthetic method for the preparation of imidazopropellanes by reaction of indandione (CNIND), N-substituted-2-heteroylthiosemicarbazides [32], with thiocarbohydrazides [33] and with N-substituted 2-(2,4-dinitrophenyl) hydrazinecarbothioamides [34].…”

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confidence: 99%

Stereoselective synthesis of homochiral paracyclophanylindenofuranylimidazo[3.3.3]propellanes

et al. 2021

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The reaction between N-paracyclophanyl-substituted hydrazinecarbothioamides and dicyanomethylene-1,3-indanedione (CNIND), furnished planar and central chiral substituted (epiminomethanoimino)indenofuranyl)-1,4-(1,4-dibenzenocyclohexaphane)-1,2-carboxamides as a type of paracyclophanylfuroimidazo[3.3.3]propellanes in (35-81% yields) as a major product as single diastereomers, and substituted spiro[indene-2,4'-indeno-pyran]-3'-carbonitrile (9-12% yields) as a minor product. To prepare the homochiral paracyclophanylpropellane, oxidation of scalemic  Alaa A. Hassan

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“…Due to our continuous interest in the design and synthesis of new heterocycles with antitumor activity [30,31], in this study we synthesized a new group of hetero [3.3.3]propellanes by reacting heteroyl-hydrazinecarbothioamides with 1 to give furoimidazo [3.3.3]propellanes [32]. Also, nucleophilic addition of thiocarbohydrazide derivatives with 1 gave furo-imidazo [3.3.3]propellanes [33].…”

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confidence: 99%

Design, synthesis, and DNA interaction studies of furo-imidazo[3.3.3]propellane derivatives: Potential anticancer agents

Hassan

Aly

Mohamed

et al. 2019

Bioorganic Chemistry

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A large number of natural products containing the propellane scaffold have been reported to exhibit cytotoxicity against several cancers; however, their mechanism of action is still unknown. Anticancer drugs targeting DNA are mainly composed of small planar molecule/s that can interact with the DNA helix, causing DNA malfunction and cell death. The aim of this study was to design and synthesize propellane derivatives that can act as DNA intercalators and/or groove binders. The unique structure of the propellane derivatives and their ability to display planar ligands with numerous possible geometries, renders them potential starting points to design new drugs targeting DNA in cancer cells. New substituted furo-imidazo[3.3.3]propellanes were synthesized via the reaction of substituted alkenylidene-hydrazinecarbothioamides with 2-(1,3-dioxo-2,3dihydro-1H-2-ylidene) propanedinitrile in tetrahydrofuran at room temperature. The structures of the products were confirmed by a combination of elemental analysis, NMR, ESI-MS, IR and single crystal X-ray analysis. Interestingly, 5c, 5d and 5f showed an ability to interact with Calf Thymus DNA (CT-DNA). Their DNA-binding mode was investigated using a combination of absorption spectroscopy, DNA melting, viscosity, CD spectroscopy measurements, as well as competitive binding studies with several dyes. Their cytotoxicity was evaluated against the NCI-60 panel of cancer cell lines. 5c, 5d and 5f exhibited similar anti-proliferative activity against the A549 non-small cell lung cancer (NSCLC) cell line. Further mechanistic studies revealed their ability to induce DNA damage in the A549 cell line, as well as apoptosis, evidenced by elevated *

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Synthesis of New Furo-Imidazo[3.3.3]propellanes

Cited by 6 publications

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Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbothioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives

Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbothioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives

Stereoselective synthesis of homochiral paracyclophanylindenofuranylimidazo[3.3.3]propellanes

Design, synthesis, and DNA interaction studies of furo-imidazo[3.3.3]propellane derivatives: Potential anticancer agents

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Synthesis of New Furo-Imidazo[3.3.3]propellanes

Cited by 6 publications

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Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbo­thioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives

Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbo­thioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives

Stereoselective synthesis of homochiral paracyclophanylindenofuranylimidazo[3.3.3]propellanes

Design, synthesis, and DNA interaction studies of furo-imidazo[3.3.3]propellane derivatives: Potential anticancer agents

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Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbothioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives

Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbothioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives