Synthesis, Antimicrobial and Antifungal Activity of a New Class of Spiro pyrrolidines

Raj, A. Amal; Raghunathan, R.; SrideviKumari, M.R; Raman, Namrata

doi:10.1016/s0968-0896(02)00439-x

Cited by 348 publications

(132 citation statements)

References 15 publications

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“…Since various kinases are involved in the growth of microorganisms and because many oxindoles are kinases' inhibitors [3], [4], [5], [6], [7] and [8], these compounds could exert antibacterial activities as it was shown previously for several oxindole derivatives ( Fig. 1) [9], [10] and [11]. We have reported, in a previous paper, the synthesis and antiproliferative activities, toward various human tumor cell lines, of indolin-2-one derivatives substituted in the 3-position by an aminomethylene group bearing different amino acid moieties (Scheme 1) [2].…”

Section: Introductionmentioning

confidence: 72%

Synthesis and biological evaluation of diversely substituted indolin-2-ones

Bouchikhi

Rossignol

Sancelme

et al. 2008

European Journal of Medicinal Chemistry

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The synthesis of indolin-2-one derivatives substituted in the 3-position by an aminomethylene group bearing either an ornithine or a lysine residue is described. The inhibitory activities of these compounds toward a panel of eight kinases were examined. Furthermore, the antibacterial activities of the prepared compounds were tested against two Gram-positive bacteria Bacillus cereus and Streptomyces chartreusis, a Gram-negative bacterium Escherichia coli and a yeast Candida albicans.

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Section: Introductionmentioning

confidence: 72%

Synthesis and biological evaluation of diversely substituted indolin-2-ones

Bouchikhi

Rossignol

Sancelme

et al. 2008

European Journal of Medicinal Chemistry

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“…[21][22][23][24] According to a recent report, treatment of N-acyl isothiocyanate substituted isatin 7 with hydrazine hydrate in boiling dry benzene afforded compound 8. 25 The latter compound, on refluxing in freshly distilled acetic anhydride, yielded 1-[(5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl) methyl]-1H-indole-2,3-dione 9 (Scheme 5).…”

Section: Methodsmentioning

confidence: 99%

Reactivity and diverse synthetic applications of acyl isothiocyanates

Bedane¹,

Singh²

2015

Arkivoc

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Isothiocyanates constitute a group of heterocumulenes containing N=C=S functionality that is of immense importance in organic synthesis. The presence of carbonyl group in acyl isothiocyanates imparts unique reactivity to acyl isothiocyanates. The chemistry of acyl isothiocyanates, in particular, is very rich and diverse, and has been employed in synthesis of a number of biologically important heterocycles. This review article discusses the acyl isothiocyanate chemistry leading to the synthesis of biologically important heterocyclic skeletons. These include highly functionalized thiazoles, thiadiazoles, triazoles, benzimidazoles, dithiolane, spiro-fused oxazolines, triazines, and oxazines, etc. The role of acyl isothiocyanates as acylating agent and thiocyanate transfer reagent is also discussed.

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“…Indole derivatives exhibit antibacterial, antifungal (Singh et al 2000), antitumor (Andreani et al, 2001), antihepatitis B virus (Chai et al, 2006) and anti-inflammatory (Rodriguez et al, 1985) activities. They are also used as bioactive drugs (Stevenson et al, 2000) and exhibit high aldose reductase inhibitory (Rajeswaran et al, 1999) and antimicrobial activities (Amal Raj et al, 2003). Against this background, we synthesized the title compound and report herein on its crystal structure.…”

Section: Structure Descriptionmentioning

confidence: 99%

5-Benzoyl-2-(5-bromo-1H-indol-3-yl)-4-(4-methoxyphenyl)-1H-pyrrole-3-carbonitrile

et al. 2016

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In the title compound, C27H18BrN3O, the indole and central pyrrole ring systems are inclined to one another by 13.15 (15)°. The carbonitrile group is almost coplanar with its attached pyrrole ring, the C[triple-bond]N bond making a dihedral angle of 1.9 (2)° with the ring plane. The 4-methoxybenzene ring and the benzoyl ring are inclined to the central pyrrole ring by 55.1 (2) and 51.5 (2)°, respectively. The dihedral angle between these two benzene rings is 37.68 (17)°. In the crystal, molecules are linked by pairs of N—H...N hydrogen bonds, forming inversion dimers with anR22(16) ring motif. The dimers are linked by offset π–π interactions [intercentroid distance = 3.614 (2) Å], which leads to the formation of chains propagating in the [010] direction.

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Synthesis, Antimicrobial and Antifungal Activity of a New Class of Spiro pyrrolidines

Cited by 348 publications

References 15 publications

Synthesis and biological evaluation of diversely substituted indolin-2-ones

Synthesis and biological evaluation of diversely substituted indolin-2-ones

Reactivity and diverse synthetic applications of acyl isothiocyanates

5-Benzoyl-2-(5-bromo-1H-indol-3-yl)-4-(4-methoxyphenyl)-1H-pyrrole-3-carbonitrile

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