3-(Adamantan-1-yl)-4-methyl-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione dichloro­methane hemisolvate

The asymmetric unit of the title dichloro­methane hemisolvate, C24H33N5S·0.5CH2Cl2, comprises an adamantan­yl/triazole derivative and half a CH2Cl2 mol­ecule of crystallization; the latter is disordered about a twofold axis of symmetry. The piperazine ring has a chair conformation and the two N-bound substituents occupy equatorial positions. The piperazine residue is almost normal to the triazole ring [N—N—C—N torsion angle = −79.9 (3)°] so that to a first approximation, the mol­ecule has an L-shape. Linear supra­molecular chains parallel to [001] are formed via C—H⋯S inter­actions. Two such chains are linked into a double chain via C—H⋯Cl inter­actions involving the disordered CH2Cl2 mol­ecules of solvation

3-(Adamantan-1-yl)-1-[(4-benzyl­piperazin-1-yl)meth­yl]-4-[(E)-(2-hy­droxy­benzyl­idene)amino]-1H-1,2,4-triazole-5(4H)-thione

In the title compound, C31H38N6OS, the conformation about the N=C [1.285 (2) Å] imine bond is E. The piperazine ring has a chair conformation and occupies a position almost perpendicular to the plane through the triazole ring; the benzene ring forms a dihedral angle of 31.95 (10)° with the triazole ring. Overall, the mol­ecule has the shape of a flattened bowl. The hy­droxy group is disordered over two positions. The major component has a site-occupancy factor of 0.762 (3) and forms an intra­molecular O—H⋯N(imine) bond to close an S(6) loop. The minor component of the disordered hy­droxy group forms an O—H⋯N(piperazine) hydrogen bond. These, along with C—H⋯S and C—H⋯N inter­actions, link mol­ecules into a three-dimensional architecture

3-(Adamantan-1-yl)-1-[(4-ethyl­piperazin-1-yl)meth­yl]-4-[(E)-(4-hy­droxy­benzyl­idene)amino]-1H-1,2,4-triazole-5(4H)-thione

In the title thione, C26H36N6OS, the 1,2,4-triazole ring is planar (r.m.s. deviation = 0.020 Å) and the benzene ring is twisted out of this plane [dihedral angle = 62.35 (12)°]. Supra­molecular zigzag chains feature in the crystal packing. These are sustained by O—H⋯N(piperazine) hydrogen bonds, and are connected into the three-dimensional crystal structure by C—H⋯S and C—H⋯O inter­actions. The crystal studied was a racemic twin

N′-[(2-n-Butyl-4-chloro-1H-imidazol-5-yl)­methyl­idene]adamantane-1-carbo­hydrazide sesquihydrate ethanol hemi­solvate

In the asymmetric unit of the title compound, C19H27ClN4O·0.5C2H6O·1.5H2O, there are two mol­ecules of the Schiff base, which has a rigid adamantyl cage at one end of the C(= O)NH–N=CH– chain and an almost planar [torsion angles = 1.3 (1) and 7.9 (2)° imidazolyl ring at the other end, three mol­ecules of water and one mol­ecule of ethanol. In both independent mol­ecules of the Schiff base, this chain displays an extended zigzag configuration. All their amino groups function as hydrogen-bond donors to water mol­ecules; these are linked to other acceptor atoms, generating a layer structure. O—H⋯O and O—H⋯N inter­actions involving the water mol­ecules also occur

Synthesis 4-[2-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-ethyl]-benzenesulfonamides with subnanomolar carbonic anhydrase II and XII inhibitory properties

Condensation of substituted anthranilic acids with 4-isothiocyanatoethyl-benzenesulfonamide led to series of heterocyclic benzenesulfonamides incorporating 2-mercapto-quinazolin-4-one tails. These sulfonamides were investigated as inhibitors of the human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms hCA I and II (cytosolic isozymes), as well as hCA XII (a transmembrane, tumor-associated enzyme also involved in glaucoma-genesis). The new sulfonamides acted as medium potency inhibitors of hCA I (KIs of 28.5– 2954 nM), being highly effective as hCA II (KIs in the range of 0.62–12.4 nM) and XII (KIs of 0.54– 7.11 nM) inhibitors. All substitution patterns present in these compounds (e.g., halogens, methyl and methoxy moieties, in positions 6, 7 and/or 8 of the 2-mercapto-quinazolin-4-one ring) led to highly effective hCA II/XII inhibitors. These compounds should thus be of interest as preclinical candidates in pathologies in which the activity of these enzymes should be inhibited, such as glaucoma (CA II and XII as targets) or some tumors in which the activity of isoforms CA II and XII is dysregulated

Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines

The reaction of adamantane-1-carbohydrazide (1) with heterocyclic aldehydes, namely 5-(4-chlorophenyl)isoxazole-3-carboxaldehyde (2a), 5-(4-methylphenyl)isoxazole-3-carboxaldehyde (2b), 5-(4-methoxyphenyl)isoxazole-3-carboxaldehyde (2c), 1H-imidazole-2-carboxaldehyde and 2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde, in ethanol, yielded the corresponding N′-heteroarylidene-1-adamantylcarbohydrazides 3a, 3b, 3c, 4 and 5, respectively, in good yields. The 4-acetyl-1,3,4-oxadiazoline analogues 6a‑c were prepared in 48–55% yields by heating their corresponding N′-heteroarylidene-1-adamantylcarbohydrazides 3a–c with acetic anhydride for two hours. Compounds 3a–c, 4, 5 and 6a–c were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 4 and 5 displayed potent broad-spectrum antimicrobial activity, while compounds 3a–c showed good activity against the Gram-positive bacteria

Crystal structure of 5-(adamantan-1-yl)-3-[(4-chloroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C19H22ClN3OS

C19H22ClN3OS, orthorhombic, P212121 (no. 19), a = 7.0418(2) Å, b = 10.8802(3) Å, c = 23.5506(6) Å, V = 1804.36(8) Å3, Z = 4, Rgt(F) = 0.0413, wRref(F2) = 0.1110, T = 100 K.The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for funding this work through the Research Group Project No. PRG-1436–23. We also acknowledge the financial support from Spanish Ministerio de Economía y Competitividad (MINECO-13-MAT2013–40950-R, FPI grant BES-2011–046948 to MSM-A).Peer Reviewe