Cycloalkanoindoles. 1. Syntheses and antiinflammatory actions of some acidic tetrahydrocarbazoles, cyclopentindoles, and cycloheptindoles

Asselin, A. A.; Humber, Leslie G.; Dobson, T. A.; Komlossy, J.; Martel, R. R.

doi:10.1021/jm00228a010

Cited by 34 publications

(9 citation statements)

References 13 publications

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“…After optimization of reaction conditions, we applied this protocol to a range of hydrazine substrates, including aryl and heteroaryl hydrazines (Schemes 2, 3 and 4). This sequential process, however, was reported to be sensitive and chemoselectively controlled by the percentage of the acidic catalyst that is added to this reaction [38,39]. High conversions of substrates were successfully realized when the condensations were carried out in refluxed EtOH under the catalysis of Bronsted acids.…”

Section: Chemistrymentioning

confidence: 99%

Design and synthesis of novel tetrahydro-2H-Pyrano[3,2-c]Pyridazin-3(6H)-one derivatives as potential anticancer agents

Al‐Tel

2010

European Journal of Medicinal Chemistry

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Section: Chemistrymentioning

confidence: 99%

Design and synthesis of novel tetrahydro-2H-Pyrano[3,2-c]Pyridazin-3(6H)-one derivatives as potential anticancer agents

Al‐Tel

2010

European Journal of Medicinal Chemistry

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“…Then Dy(OTf) 3 (0.4 mmol) was added, and the mixture was reacted at 20Ϫ50°C for 5Ϫ10 h. The reaction was quenched with 10% aqueous NaHCO 3 , and extracted with CH 2 Cl 2 . The organic phase was dried with anhydrous Na 2 SO 4 , and the solvents were evaporated.…”

Section: Procedures B1mentioning

confidence: 99%

“…A series of aminotetrahydrocarbazole derivatives was found to act on the central nervous system. [1] Cycloalkanoindoles have been studied for their anti-inflammatory, [2] antidepressant [3] and analgesic properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Cycloalkanoindoles by an Unusual DAST‐Triggered Rearrangement Reaction

et al. 2004

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A series of 1,1‐bis(indol‐3‐yl) and 1‐(indol‐2‐yl)‐1‐(indol‐3‐yl)‐ψ‐hydroxyalkanes, prepared from the corresponding indole derivatives and suitable hydroxyaldehydes via routine coupling reactions, were treated with DAST (diethylaminosulfur trifluoride) under mild conditions, to generate a small library of cycloalkanoindoles. Irrespective of the substitution pattern, i.e. whether they are symmetrical or unsymmetrical derivatives, the same mixture of products is produced, in which the tetrahydro‐1H‐carbazole and hexahydrocyclohepta[b]indole scaffolds are substituted by a indol‐3‐yl nucleus on one of the two α‐carbon atoms of the cycloalkane moieties. Thus, speculations on the reaction mechanism with the prediction of a common reaction intermediate are presented. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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“…A series of similar compounds 5a-e were realized with 4a-e.The reaction of 2-(4'-methoxy)-benzylidineindolo[2,[3][4][5][6]cyclopentan-l-ones 5a-e with hydroxylamine hydrochloride in pyridine yielded 3-(4"-methoxy)-phenylisoxazolo[3',4':5,4]cyclopenta[0]indoles 6a-e in moderate yields. The compound 5a was characterized on the basis of spectral and analytical data.…”

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confidence: 99%

TETRACYCLIC COMPOUNDS FROM CYCLOPENT[b]lNDOLES. SYNTHESIS OF ISOXAZOLO[3',4':5,4]CYCLOPENT[b]INDOLES.

Sangeetha¹,

Prasad²

2002

Heterocyclic Communications

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Cyclopentan-1 ',2'-dione-1 '-arylhydrazones 3 obtained from the Japp-Klingemann reaction of diazotised aniline derivatives i and 2-hydroxymethylenecyclopentanone 2 on acid catalysed cyclization afforded cyclopent [6]indoles 4. These on mixed aldol condensation with 4-methoxybenzaldehyde followed by reaction with hydroxylamine hydrochloride gave isoxazolo [3',4':5,4]cyclopent[6]indoles 6. IntroductionThe chemistry of Indole alkaloids and related compounds have been studied more extensively during the past few decades owing to their potential applications in diverse pharmacological field'"® In particular they were reported to have antitumour, antibacterial and antifungal activities'^. Based on these facts we proposed to undertake a novel attempt towards the synthesis of cyclopentanone ring fused with indoles, cyclopent[6] indoles 4 from the diazotised anilines I and 2-hydroxymethylenecyclopentanone 2 followed by acid catalysed cyclisation which were used as synthons to derive the titled isoxazolo[3',4':5,4]cyclopent[Z>]indoles 6 through the intermediates, 2benzylidenecyclopent[i]indoles 5 (schemel). Experimental General informationPurification of the crude products was carried out using chromatographic columns. Melting points were determined on a Mettler fp-5 instrument. Infrared spectra of the compounds were recorded in KBr pellets using PERKIN-ELMER model-1600 spectrometer. The 'H-NMR spectra were recorded on AMX-400 spectrometer using tetramethylsilane (TMS) as an internal referance and chemical shifts are reported in parts per million (δ) downfield from the internal standard. The signal multiplicities are represented by s (singlet), d (doublet), b s (broad singlet) and m (multiplet). The microanalytical data are obtained on carlo Erba 1106 Perkin Elmer model 240 CHN analyzer. General procedures. Preparation of 2-hdroxymethyIenecyclopentanone 2Cyclopentanone (1.6 ml, 0.02 mol) was added to a well cooled, vigorously stirred mixture of sodium methoxide (from 5.17 g of sodium in 5 ml of abolute methanol), dryether (4 ml) and ethyl formate (1.8ml, 0.02 mol) in a small portions over a period of 10 minutes. The resulting mixture was stirred continuously for one hour in an ice bath and kept at room temperature . After a period of 24 hours, the yellow solid mass obtained was dissolved by adding ice water and neutralized with concentrated HCl. The oily mass that separated out upon acidification was extracted with ether, washed with brine and cold water and dried over anhydrous sodium sulphate. The residual oil after the removal of solvent by distillation to give 2-hydroxymethylenecyclopentanone 2 as viscous liquid in good quantity (65% yield). Preparation of cyclopentan-r,2'-dione-l'-aryl hydra zones 3_.A mixture consisting of 2-hydroxymethylenecyclopentanone 2 (0.004 mol) and sodium acetate trihydrate (lg) in methanol (6ml) was kept in ice bath. A solution of the respective aniline derivative (0.004 mol) in aqueous hydrochloric Brought to you by | Biblioteca de la Universidad de Sevilla

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Cycloalkanoindoles. 1. Syntheses and antiinflammatory actions of some acidic tetrahydrocarbazoles, cyclopentindoles, and cycloheptindoles

Cited by 34 publications

References 13 publications

Design and synthesis of novel tetrahydro-2H-Pyrano[3,2-c]Pyridazin-3(6H)-one derivatives as potential anticancer agents

Design and synthesis of novel tetrahydro-2H-Pyrano[3,2-c]Pyridazin-3(6H)-one derivatives as potential anticancer agents

Synthesis of Cycloalkanoindoles by an Unusual DAST‐Triggered Rearrangement Reaction

TETRACYCLIC COMPOUNDS FROM CYCLOPENT[b]lNDOLES. SYNTHESIS OF ISOXAZOLO[3',4':5,4]CYCLOPENT[b]INDOLES.

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