Incorporation of an indole-containing diarylbutylamine pharmacophore into furo[2,3-a]carbazole ring systems

Maertens, Faye; Toppet, Suzanne; Hoornaert, Georges J.; Compernolle, Frans

doi:10.1016/j.tet.2004.12.049

Cited by 20 publications

(14 citation statements)

References 19 publications

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“…The residue was purified by column chromatography using silica gel and ethyl acetate/hexane (1:1). After the evaporation of solvent, the residue was recrystallized from methanol yielded β-ketoesters (2a, 2b, 2c, 7a [20], 7b [21], and 7c). General procedure reaction between β-ketoesters and acrylamide/acrylonitrile.…”

Section: Methodsmentioning

confidence: 99%

“…The solvent was evaporated under reduced pressure, and the resulting residue was chromatographed using silica gel and ethyl acetate-hexane (1:1). The solvent was removed, and then the product (3a, 3b, 3c, 4a, 4b, 4c, 9a [21], 9b [21], 9c, 8a, and 8b) was recrystallized from appropriate solvents. Methyl 2-(2-cyanoethyl)-4-methyl-1-oxo-1,2,3,4-tetrahydrocyclopenta [b]indole-2-carboxylate (4a).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Cycloalk[b]indole Bearing Spiropiperidine Derivatives

Hızlıateş

Gülle

Ergün

2015

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).The novel heterocyclic compounds that have cycloalk [b]indole moiety bearing spiropiperidinone and spiropiperidinedione (3a, 3b, 3c, 5a, 5b, 8a, 8b, and 10a) were synthesized for the first time. The synthesis of spiropiperidinone and spiropiperidinedione structures was performed by a new method. These compounds are similar to sedative and hypnotic drugs such as methyprylon, glutethimide, and thalidomide.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis of Cycloalk[b]indole Bearing Spiropiperidine Derivatives

Hızlıateş

Gülle

Ergün

2015

Journal of Heterocyclic Chem

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“…Vol 44 compound 5 [18]. Cyanomethylation of compound 5 utilizing cesium carbonate and iodoacetonitrile in tertbutyl alcohol gave the compound 6 [17,19].…”

Section: R Akdag and Y Ergunmentioning

confidence: 99%

“…Indol nitrogen atom of 3 was protected by methylation with potassium hydroxide and methyl iodide in acetone which yielded 4 [17]. Later we activated -position of carbonyl group of 4 using potassium hydride and diethyl carbonate which resulted in compound 5 [18]. Cyanomethylation of compound 5 utilizing cesium carbonate and iodoacetonitrile in tertbutyl alcohol gave the compound 6 [17,19].…”

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confidence: 99%

A new synthetic route to the synthesis of nordasycarpidone derivatives

Akdag

Ergün

2007

Journal of Heterocyclic Chem

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A new synthetic route for the synthesis of the nordasycarpidone derivative 11 which has hexahydro-1,5-methanoazocino[4,3-b]indol skeleton, is described. Construction of the tetracyclic structure was achieved by catalytic reduction and cyclization reaction of the nitrile derivative. Also many new tetrahydrocarbazole derivatives (4, 5, 6, 7, 8, 9) and a dasycarpidol derivative (10) were synthesized. Several routes to tetracyclic dasycarpidone derivatives (1a, 1b, 1c, 1d) of the strychnos-type alkaloids have been reported in the literature. Most of routs start with the aromatic A-ring and the heterocyclic D-ring and build the tetracyclic skeleton by closing the B and C in subsequent steps [1][2][3][4][5][6][7][8]. There are also a few attempts for the construction of D-ring from tetrahydrocarbazole derivatives via acid catalyst ring closure or intramolecular Aldol reaction [9][10][11][12]. In this paper we describe a synthetic route utilizing tetrahydrocarbazole which bears a nitrile side chain at the position 2 (carbazole numbering) as a key intermediate. This carbazole derivative allows the closure of the D-ring in the last synthetic step via catalytic hydrogenation, yielding a tetracyclic dasycarpidone alkaloid. The scope of this route is also valuable for the construction of the pentacyclic strychnos alkaloid condyfoline (2) [13][14][15].

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“…They were reported to possess many biological activities, such as antitumor activity [21], HIV integrase inhibition [22], prolonged analgesic activity [23], heat shock protein 90 (Hsp90) inhibition [24], mitogen-activated protein kinaseactivated protein kinase-2 (MAPKAP-k2) inhibition [25], antibacterial and antifungal activities [26]. Moreover, they had been increasingly important intermediates in the syntheses of various biological active heterocyclic compounds because of their unique structure, such as indolo [2,3-a]carbazoles [22], furo [2,3-a]carbazoles [27], pyrimidino [4,5-a]carbazoles [28], pyrazolino[3,2,1-j,k]carbazoles [29], thieno [2,3-a]carbazoles [30], and so on. This provided a great impetus to search for potential pharmacologically active drugs carrying a 1,2,3,4-tetrahydrocarbazole-1-one scaffold.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In‐Vitro Antitumor Activities of Some Mannich Bases of 9‐Alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones

Chen

Lou

Liu

et al. 2009

Archiv der Pharmazie

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A novel series of 2-substituted aminomethyl-9-alkyl-1,2,3,4-tetrahydrocarbazole-1-ones 5a-q was synthesized via aminomethylation of 9-alkyl-1,2,3,4-tetrahydrocarbazole-1-ones 4a-e with hydrochlorides of the respective amines 6a-m. The structures of these newly synthesized compounds were characterized by (1)H-NMR, MS, and elemental analysis. All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines including human non-small lung cancer cells (A549), human gastric adenocarcinoma (SGC), human colon cancer cell (HCT116), human myeoloid leukemia cells (K562), and one multi-drug resistant subline (KB-VCR). Most compounds showed moderate to potent cytotoxic activity against the tested cell lines. Preliminary mechanism research indicated that the most promising compound, 2-diethylaminomethyl-9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 5c, exhibited a potential inhibitory effect against microtubule.

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Incorporation of an indole-containing diarylbutylamine pharmacophore into furo[2,3-a]carbazole ring systems

Cited by 20 publications

References 19 publications

Synthesis of Cycloalk[b]indole Bearing Spiropiperidine Derivatives

Synthesis of Cycloalk[b]indole Bearing Spiropiperidine Derivatives

A new synthetic route to the synthesis of nordasycarpidone derivatives

Synthesis and In‐Vitro Antitumor Activities of Some Mannich Bases of 9‐Alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones

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