N-Cyclo­hexyl­cyclo­hexa­naminium chloride

In the title salt, C12H24N+·Cl−, both cyclo­hexyl rings adopt chair conformations and the NH2 unit is situated in the equatorial position with respect to the rings in the cation. The large C—N—C bond angle [117.99 (14)°] in the cation is a result of linking two bulky cyclo­hexyl rings to the N atom. The aminium H atoms are involved in inter­molecular N—H⋯Cl hydrogen bonds, forming an infinite zigzag chain parallel to the c axis. The crystal studied was a racemic twin with a twin fraction of 0.28 (18)

Phenyl bis­(morpholin-4-yl­amido)­phosphinate

In the title compound, C14H23N4O4P, the P atom is in a distorted tetra­hedral environment with bond angles in the range 96.87 (6)–119.86 (6)°. The two morpholinyl groups adopt a chair conformation. The phenyl ring is disordered over two sets of sites with equal occupancies [0.500 (2)]. In the crystal, adjacent mol­ecules are linked via N—H⋯O hydrogen bonds into an extended chain running parallel to the a axis. Only one of the amidate N—H groups is involved in hydrogen bonding

Phenyl bis­(m-tolyl­amido)­phosphinate

The P atom of the title compound, C20H21N2O2P, has a distorted tetra­hedral configuration; the bond angles at P are in the range 96.11 (6)–117.32 (8)°. The N atom exhibits sp 2 character. In the crystal, mol­ecules are connected via N—H⋯O hydrogen bonds into bands along the a axis, consisting of R 2 2(8) rings

N,N′-Dibenzyl-N′′-(2-chloro­acet­yl)-N,N′-dimethyl­phospho­ric triamide

In the title mol­ecule, C18H23ClN3O2P, the P atom is bonded in a distorted tetra­hedral environment. The P=O and N—H groups are syn with respect to each other. The angles at the tertiary N atoms confirm their sp 2 character. In the crystal, pairs of inter­molecular P=O⋯H—N hydrogen bonds form centrosymmetric dimers

N,N′-Bis(4-methyl­phen­yl)-N′′-(2,2,2-trichloro­acet­yl)phospho­ric triamide

The P atom in the title compound, C16H17Cl3N3O2P, is bonded in a distorted tetra­hedral geometry with the phosphoryl and carbonyl groups anti with respect to one another. In the crystal, mol­ecules are linked through (N—H)2⋯O(=P) and N—H⋯O(=C) hydrogen bonds into chains along [001]. The phosphoryl O atom acts as a double hydrogen-bond acceptor

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

rac-Phenyl (benzylamido)(p-tolyl­amido)­phosphinate

The title compound, C20H21N2O2P, was synthesized from (RS)-(C6H5O)P(O)Cl(NHC6H4-p-CH3) and benzyl­amine. The product crystallizes as a racemate in a polar space group. The phospho­rus atom has a distorted tetra­hedral configuration: the bond angles at the P atom are in the range 103.2 (1)–118.4 (1)°. The P—N(benzyl­amido) bond [1.615 (2) Å] is slightly shorter than the P—N(p-tolyl­amido) bond [1.630 (2) Å]. Both N—H groups adopt an anti orientation relative to the phosphoryl group. In the crystal, the adjacent mol­ecules are linked via N—H⋯O hydrogen bonds, forming R 2 2(8) rings, into a one-dimensional arrangement parallel to the x axis

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

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

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