Aminoderivatives of cycloalkanespirohydantoins: synthesis and biological activity

Naydenova, Emilia; Pencheva, Nevena; Popova, Julita; Stoyanov, Neyko; Lazarova, Maria; Aleksiev, B.

doi:10.1016/s0014-827x(01)01198-3

Cited by 39 publications

(21 citation statements)

References 7 publications

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“…The fact that the molecules in the pair's of cycloalkanespiro-5-hydantoin and their 3-aminoderivatives with 6-, 7-and 8-membered rings are structurally very similar gave rise to the assumption that the differences in the biological activity, anticonvulsant vi. inducing seizures [5], could be explained only by the contribution of the amino substituent, although this is clearly an oversimplification. First, we know from previous studies [20][21] that pharmacophore centre (N3) in 5,5-disubstituted hydantoins is more acidic than the corresponding (N1) centre.…”

Section: Dft Calculationsmentioning

confidence: 99%

“…The structural characteristics of hydantoins and spirohydantoins are interesting in view of the development of novel drugs [4] and for better understanding the structure-activity relationship. As part of our research on the characterization and biological activity of amino-cycloalkanespiro-5-hydantoins and their metal complexes, a series of five such compounds were synthesized and their biological activity described [5,6]. Recently the crystal structures of two polymorph modifications of 3-amino-cyclohexanespiro-5-hydantoin have been published [7].…”

Section: Introductionmentioning

confidence: 99%

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Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Todorov

Petrova²,

Naydenova

et al. 2009

Open Chemistry

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The crystal structures of 3-amino-cycloheptanespiro-4′-imidazolidine-2′,5′-dione (I) {systematic name: 3-amino-1,3-diazaspiro[4.6] undecane-2,4-dione} and 3-amino-cyclooctanespiro-4′-imidazolidine-2′,5′-dione (II) {systematic name: 3-amino-1,3-diazaspiro[4.7] dodecane-2,4-dione}, have been determined. In both compounds the polar hydantoin groups cause molecules to aggregate via N-H...O and N-H...N interactions, forming a layer structure, in which the cycloalkane rings project outwards from the central, more polar, region. The observed molecular structure is compared with that calculated by density functional theory methods.

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Section: Dft Calculationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Todorov

Petrova²,

Naydenova

et al. 2009

Open Chemistry

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“…Our initial aim was to obtain 9-amino-9H-fluorene-9-carboxylic acid, 4 by alkaline hydrolysis of 2 following the previously described procedure [21]. In reality, after the alkaline hydrolysis of compound 2 instead of the expected synthetic amino acid 4, (9H-fluorene-9-yl)urea, 3 was obtained.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Structural Characterization of Spiro(fluorene-9,4′-imidazolidine)-2′,5′-dione and (9H-Fluorene-9-yl)urea

et al. 2012

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Alkaline hydrolysis of spiro(fluorene-9,4 0 -imidazolidine)-2 0 ,5 0 -dione, 2 resulted in ring opening leading to (9H-fluorene-9-yl) urea, 3. The crystal structures 2 and 3 have been determined. Compound 2 crystallizes in the orthorhombic space group P2 1 2 1 2 1 with a = 7.2596(9) Å , b = 9.4497(14) Å , c = 17.304(3) Å and Z = 4 while compound 3 crystallizes in the monoclinic space group P2 1 /c with a = 4.6171(3) Å , b = 14.4713(9) Å , c = 16.9762(14) Å , b = 95.385(7)°and Z = 4. Both molecules have very similar bond lengths and angles pattern, even after the hydantoin ring opening. The 9H-fluorene moiety is nearly planar with rms of 0.007 and 0.032 Å for 2 and 3. The angle between the mean planes of the 9H-fluorene and the hydantoin or carbamide moieties is 86.92(4)°and 71.07(4)°respectively. In both structures N-HÁÁÁO hydrogen bonds connect molecules into the chains along a. The X-ray molecular structure and IR spectra for 2 and 3 are compared with those calculated by the density functional theory method.

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“…7 Recently, Naydoneva and coworkers reported the synthesis of a series of cycloalkanespirohydantoins 3 with n = 0, 1, 2, 3, and 7 and yields of 89-95% using the BuchererLieb conditions. 8 However, there is an inconvenience for this synthetic method from an experimental point of view. The use of cyanide ion and the high temperature required to obtain higher yields in the cyclization process can promote hydrogen cyanide and must be controlled to prevent the risk of intoxication or contamination.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of cycloalkanespirohydantoins and piperidylspirohydantoins as precursors of restricted α-amino acids

Rivero¹,

Reynoso²,

Ochoa-Terán³

2011

Arkivoc

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Cycloalkanespirohydantoins 3 and piperidinespirohydantoins 4 were synthesized from cycloalkanones 9 and piperidones 10 under microwave-assisted conditions. Results are compared with those obtained under thermal conditions. Cycloalkanespirohydantoins 3 were N-protected with Boc group and hydrolyzed under basic conditions to obtain five, six and seven-membered ring restricted α-amino acids 12 in very good overall yields (76-94%).

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Aminoderivatives of cycloalkanespirohydantoins: synthesis and biological activity

Cited by 39 publications

References 7 publications

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Synthesis and Structural Characterization of Spiro(fluorene-9,4′-imidazolidine)-2′,5′-dione and (9H-Fluorene-9-yl)urea

Microwave-assisted synthesis of cycloalkanespirohydantoins and piperidylspirohydantoins as precursors of restricted α-amino acids

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