4-(1-Adamantylmeth­yl)-N-(2-chloro-9-isopropyl-9H-purin-6-yl)aniline

The asymmetric unit of the title compound, C25H30ClN5, consists of two mol­ecules with slightly different geometrical parameters. The dihedral angles between the purine and benzene rings are 39.54 (5) and 23.69 (5)° in the two mol­ecules. The adamantane cages consist of three fused cyclo­hexane rings in classical chair conformations, with C—C—C angles in the range 108 (2)–111 (2)°. In the crystal, mol­ecules are linked into dimers via two N—H⋯N hydrogen bonds

Completely dissimilar: The reactivity of 1-unsubstituted 3-chloroquinoline-2,4-diones with ethylene diamine and ethanolamine to form new molecular rearrangements

3-Chloroquinoline-2,4-diones react with ethanolamine to give 3-hydroxyethylaminoquinoline-2,4-diones. By reacting with isothiocyanic acid, these compounds cyclize to form thioxoimidazo derivatives. If a benzyl group is attached to carbon atom C-3, it is cleaved off. Simultaneously, molecular rearrangement proceeds through the formation of compounds with quinazoline skeletons. However, when using ethylene diamine, the compounds are subject to new types of molecular rearrangement leading to the formation of new quinazoline derivatives. © AUTHOR(S)TBU in Zlin [IGA/FT/2019/010

4-(1-adamantylmethyl)-N-(2-chlor-9-isopropyl-9H-purin-6-yl)anilin

Asymetrická jednotka titulní látky obsahuje dvě molekuly s mírně odlišnými strukturními parametry. Dihedrální úhly mezi purinovým a benzenovým cyklem jsou 39.54 (5)° případně 23.69 (5)°. Adamantanový skelet se sestává ze tří kondenzovaných cyklohexanových kruhů v téměř ideální židličkové konformaci s valenčními úhly v rozmezí 108 (2)?111 (2)°. Molekuly v krystalu jsou spojeny do párů prostřednictvím N?H???N vodíkových vazeb.The asymmetric unit of the title compound, C25H30ClN5, consists of two molecules with slightly different geometrical parameters. The dihedral angles between the purine and benzene rings are 39.54 (5) and 23.69 (5)° in the two molecules. The adamantane cages consist of three fused cyclohexane rings in classical chair conformations, with C?C?C angles in the range 108 (2)?111 (2)°. In the crystal, molecules are linked into dimers via two N?H???N hydrogen bonds

1-Adamantylmethyl 2-amino­benzoate

The asymmetric unit of the title compound, C18H23NO2, consists of two crystallographically independent mol­ecules bearing an adamantane cage consisting of three fused cyclo­hexane rings in almost ideal chair conformations, with C—C—C angles in the range 108.47 (16)–110.59 (15)°. Both aryl rings are essentially planar, the maximum deviation from the best plane being 0.0125 (19) Å. One conformer forms chains parallel to the b axis via N—H⋯O hydrogen bonds, whereas the second exhibits only an intra­molecular N—H⋯O hydrogen bond. The crystal structure is stabilized by further weak N—H⋯O and N—H⋯N inter­actions

Reaction of 1-substituted 3-(2-hydroxyethylamino)quinoline-2,4(1H,3H)-diones with isothiocyanic acid

3-Chloroquinoline-2,4-diones react with ethanolamine to form 3-(3-hydroxyethylamino)quinoline-2,4-diones. These compounds afford, depending on substituents in positions 1 and 3, four different products from their reaction with isothiocyanic acid: 3-(2-hydroxyethyl)-2-thioxo-3,3a-dihydro-1H-imidazo[4,5-c]quinolin-4(5H)-ones, 9b-hydroxy-3-(2-hydroxyethyl)-2-thioxo-3,3a,5,9b-tetrahydro-1Himidazo[4,5-c]quinolin-4(2H)-ones, 3-(2-hydroxyethyl)-2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-4(5H)-ones, or 1 '-methyl-7a-phenyl-5-thioxo-3,5,6,7a-tetrahydro-2H-spiro[imidazo[5,1-b]oxazole-7,3 '-indolin]-2 '-one.TBU in Zlin [IGA/FT/2019/010

N-benzyl-9-isopropyl-9H-purin-6-amine

The asymmetric unit of the title compound, C15H17N5, consists of two molecules in which the dihedral angles between the best planes of the purine ring system (r.m.s. deviations = 0.0060 and 0.0190 Å) and the benzene ring are 89.21 (3) and 82.14 (4)°. The molecules within the asymmetric unit are linked into dimers by pairs of N - H⋯N hydrogen bonds. Weak C - H⋯π contacts and π-π interactions [centroid-centroid = 3.3071 (1) Å] further connect the molecules into a three-dimensional network. © Gergela et al. 2013.Internal Founding Agency of Tomas Bata University in Zlin [IGA/FT/2013/008

Adamantane-substituted purine nucleosides: Synthesis, host–guest complexes with β-cyclodextrin and biological activity

Purine nucleosides represent an interesting group of nitrogen heterocycles, showing a wide range of biological effects. In this study, we designed and synthesized a series of 6,9-disubstituted and 2,6,9-trisubstituted purine ribonucleosides via consecutive nucleophilic aromatic substitution, glycosylation, and deprotection of the ribofuranose unit. We prepared eight new purine nucleosides bearing unique adamantylated aromatic amines at position 6. Additionally, the ability of the synthesized purine nucleosides to form stable host-guest complexes with beta-cyclodextrin (beta-CD) was confirmed using nuclear magnetic resonance (NMR) and mass spectrometry (ESI-MS) experiments. The in vitro antiproliferative activity of purine nucleosides and their equimolar mixtures with beta-CD was tested against two types of human tumor cell line. Six adamantane-based purine nucleosides showed an antiproliferative activity in the micromolar range. Moreover, their effect was only slightly suppressed by the presence of beta-CD, which was probably due to the competitive binding of the corresponding purine nucleoside inside the beta-CD cavity./0.0/0.0/18_046/0015974, CZ.02.1.01; IGA/FT/2019/007, IGA/FT2018/001; Ministerstvo Školství, Mládeže a Tělovýchovy, MŠMT: LM2018127; Grantová Agentura České Republiky, GA ČR: 21-06553SInternal Founding Agency of Tomas Bata University in Zlin [IGA/FT2018/001, IGA/FT/2019/007]; Czech Science Foundation [21-06553S]; MEYS CR [LM2018127]; European Regional Development Fund-Project "UP CIISB" [CZ.02.1.01./0.0/0.0/18_046/0015974

A new hyaluronan modified with β-cyclodextrin on hydroxymethyl groups forms a dynamic supramolecular network

A new hyaluronan derivative modified with β-cyclodextrin units (CD-HA) was prepared via the click reaction between propargylated hyaluronan and monoazido-cyclodextrin (CD) to achieve a degree of substitution of 4%. The modified hyaluronan was characterized by 1H-nuclear magnetic resonance spectroscopy (NMR) and size exclusion chromatography. Subsequent 1H-NMR and isothermal calorimetric titration experiments revealed that the CD units on CD-HA can form virtual 1:1, 1:2, and 1:3 complexes with one-, two-, and three-site adamantane-based guests, respectively. These results imply that the CD-HA chains used the multitopic guests to form a supramolecular cross-linked network. The free CD-HA polymer was readily restored by the addition of a competing macrocycle, which entrapped the cross-linking guests. Thus, we demonstrated that the new CD-HA polymer is a promising component for the construction of chemical stimuli-responsive supramolecular architectures. © 2019 by the authors.Internal Funding Agency of the Tomas Bata University in Zlin [IGA/FT/2019/007

Reaction of tertiary 2-chloroketones with cyanide ions: Application to 3-chloroquinolinediones

3-Chloroquinoline-2,4-diones react with cyanide ions in dimethyl formamide to give 3-cyanoquinoline-2,4-diones in small yields due to the strong hindrance of the substituent at the C-3 atom. Good yields can be achieved if the substituent at this position is the methyl group. In the methanol solution, the reaction proceeds by an addition mechanism to form 2-oxo-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-7b-carbonitriles, from which 4-hydroxy-3-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-4-carbonitriles are subsequently formed by opening of the epoxide ring with methanol. Some minor products of these reactions have also been isolated. The 1 H, 13 C and 15 N NMR spectra of the prepared compounds were measured, and all resonances were assigned using appropriate two-dimensional spectra. © 2021 The Authors. Published by Wiley-VCH GmbH.Tomas Bata University in Zlin [IGA/FT/2020/007] Funding Source: MedlineUniverzita Tomáše Bati ve Zlíně: IGA/FT/2020/00

3-(Adamantan-1-yl)-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

In the title compound, C14H21N3S, the 1,2,4-triazole ring is nearly planar, with a maximum deviation of 0.003 (4) Å. In the crystal, mol­ecules are linked into inversion dimers by pairs of N—H⋯S hydrogen bonds