Crystal structure of 4-cyclo-hexyl-1-(propan-2-yl-idene)thio-semicarbazide.

In the title compound, C10H19N3S, the cyclo-hexyl group adopts a chair conformation and adopts a position approximately syn to the thione S atom. The CN2S thio-urea moiety makes dihedral angle of 13.13 (10)° with the propan-2-yl-idene-amino group. An intra-molecular N-H⋯N hydrogen bond is noted. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R (2) 2(8) loops.

Crystal structure and Hirshfeld surface analysis of rac-2-[2-(4-chloro-phen-yl)-3,4-di-hydro-2H-1-benzo-pyran-4-yl-idene]hydrazine-1-carbo-thio-amide.

In the title compound, C16H14N3OSCl, a Schiff base derivative of a thio-semicarbazide with a flavanone, the 4-chlorophenyl ring is inclined to the benzene ring of the chromane ring system by 30.72 (12)°. The pyran ring has an envelope conformation with the methine C atom as the flap. The mean plane of the thio-urea unit is twisted with respect to the benzene ring of the chromanone ring system, subtending a dihedral angle of 19.78 (19)°. In the crystal, mol-ecules are linked by two pairs of N-H⋯S hydrogen bonds, forming inversion dimers enclosing R 2 2(8) ring motifs, which are linked to form ribbons propagating along the b-axis direction. The inter-molecular contacts in the crystal have been analysed using Hirshfeld surface analysis.

Synthesis, in vitro biological evaluation and in silico studies of certain arylnicotinic acids conjugated with aryl (thio)semicarbazides as a novel class of anti-leishmanial agents.

Herein we introduce new compounds as conjugates of arylnicotinic acids with aryl (thio)semicarbazide derivatives. Based on a structure-guided approach, they were designed to possess anti-leishmanial activity through anti-folate mechanism, via targeting Leishmania major pteridine reductase 1 (Lm-PTR1). The in vitro anti-promastigote and anti-amastigote activity were promising for many thiosemicarbazide derivatives and superior to the reference miltefosine. The most active compounds 8i and 8j exhibited their anti-amastigote activity with IC50 values of 4.2 and 3.3 µM, respectively, compared to reference miltefosine (IC50 value of 7.3). Their anti-folate mechanism was confirmed via the ability of folic and folinic acids to reverse the anti-leishmanial activity of these compounds, comparably to Lm-PTR1 inhibitor trimethoprim. Interestingly, the in vitro cytotoxicity test of the most active compounds displayed higher selectivity indices than that of miltefosine emphasizing their safety on mammalian cells. Furthermore, the docking experiments on Lm-PTR1 as a putative target rationalized the in vitro anti-leishmanial activity. The in silico predictions exhibited promising pharmacokinetics and drug-likeness profiles of the most active compounds. Generally, this work introduces a fruitful matrix for new anti-leishmanial chemotype which would extend the chemical space for the anti-leishmanial activity.

Synthesis and crystal structure of N-(4-chloro-phen-yl)-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-amine.

The title compound, C13H12ClN5, was synthesized by the cyclization of 1-(4,6-di-methyl-pyrimidin-2-yl)-4-phenyl-thio-semicarbazide in the presence of Ni(NO3)2. The mol-ecular structure of the compound is essentially planar. In the crystal, mol-ecules form dimers via pairs of N-H⋯N hydrogen bonds between the H atom of the exocyclic amino group and the N atom at the 4-position of the triazole ring. The resulting dimers are packed into layers which are connected by π-stacking inter-actions between the aromatic systems of the pyrimidine and benzene nuclei, and between the triazole cores.

Tri-color emission and colorimetric recognition of acetate using semicarbazide and thio-semicarbazide derivatives: Experimental and computational studies.

Two new fluorescence probes having semicarbazide (DSC) and thio-semicarbazide (DTSC) units have been derived upon reaction with 2-hydroxy-5-methylbenzene-1,3-dialdehyde. Both the probes show excellent selectivity for acetate ion in DMSO medium whereby DTSC generates tricolor emission. The association constants of DSC and DTSC for acetate are 6.6×10(4)M(-1) and 2×10(3)M(-1) respectively with corresponding detection limits, 1.06×10(-7)M and 2.5×10(-6)M. Density functional theoretical (DFT) studies nicely demonstrate the interaction between the DTSC and acetate ion.

Crystal structure of 2'-hy-droxy-aceto-phenone 4-methyl-thio-semicarbazide.

In the organic mol-ecule of the title hydrate, C11H15N3OS·H2O, {systematic name: 3-ethyl-1-{(E)-[1-(2-hy-droxy-phen-yl)ethyl-idene]amino}-thio-urea monohydrate}, a dihedral angle of 5.39 (2)° is formed between the hy-droxy-benzene ring and the non-H atoms comprising the side chain (r.m.s. deviation = 0.0625 Å), with the major deviation from planarity noted for the terminal ethyl group [the C-N-C-C torsion angle = -172.17 (13)°]. The N-H H atoms are syn and an intra-molecular hy-droxy-imine O-H⋯N hydrogen bond is noted. In the crystal, the N-bonded H atoms form hydrogen bonds to symmetry-related water mol-ecules, and the latter form donor inter-actions with the hy-droxy O atom and with a hy-droxy-benzene ring, forming a O-H⋯π inter-action. The hydrogen bonding leads to supra-molecular tubes aligned along the b axis. The tubes are connected into layers via C-H⋯O inter-actions, and these stack along the c axis with no directional inter-actions between them.