New Indazol-Pyrimidine-Based Derivatives as Selective Anticancer Agents: Design, Synthesis, and In Silico Studies.

In this research study, the authors successfully synthesized potent new anticancer agents derived from indazol-pyrimidine. All the prepared compounds were tested for cell line inhibitory activity against three different cancerous cell lines. Results demonstrated that five of the novel compounds-, , , , and -possessed significant cytotoxic inhibitory activity against the MCF-7 cell line, with IC values of 1.

Synthesis and Biological Evaluation of Imadazo[1,2-]pyrazines as Anticancer and Antiviral Agents through Inhibition of CDK9 and Human Coronavirus.

In this work, novel imadazo[1,2-]pyrazine derivatives were synthesized and evaluated as CDK9 inhibitors. The results of CDK9 assay showed that the derivatives with pyridin-4-yl in position 2 and benzyl in position 3 of imadazo[1,2-]pyrazine displayed the most potent CDK9 inhibitory activity with IC of 0.16 µM.

X-ray and theoretical investigation of ()-3-(adamantan-1-yl)-1-(phenyl or 3-chlorophenyl)--(4-bromobenzyl)isothioureas: an exploration involving weak non-covalent interactions, chemotherapeutic activities and QM/MM binding energy.

A detailed exploration of crystal packing of two adamantane-isothiourea hybrid derivatives along with a known closely related structure has been performed to delineate the effect of halogen substituents and the role of weak intermolecular interactions in their supramolecular architectures. The adamantane-isothiourea hybrid derivatives used in the present study are ()-3-(Adamantan-1-yl)--(4-bromobenzyl)-1-phenylisothiourea (), CHBrNS and ()-3-(Adamantan-1-yl)--(4-bromobenzyl)-1-(3-chlorophenyl)isothiourea (), CHBrClNS, characterized by X-ray crystallography. The X-ray structures revealed that the molecular conformation of and are different and stabilized by intramolecular C-H···N interactions.

Synthesis and Evaluation of New Coumarin Derivatives as Antioxidant, Antimicrobial, and Anti-Inflammatory Agents.

New pyranocoumarin and coumarin-sulfonamide derivatives were prepared and evaluated for their antioxidant, antimicrobial, and/or anti-inflammatory activities. Coumarin-sulfonamide compounds demonstrated significant antioxidant activity, while ,, ,, and , exhibited antimicrobial activity equal to or higher than the standard antimicrobials against at least one tested microorganism. Regarding the anti-inflammatory testing, pyranocoumarins , , and and coumarin-sulfonamide compound showed more potent antiproteinase activity than aspirin in vitro; however, five compounds were as potent as aspirin.

Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives.

The reaction of 1-adamantyl isothiocyanate 4 with the various cyclic secondary amines yielded the corresponding N-(1-adamantyl)carbothioamides 5a-e, 6, 7, 8a-c and 9. Similarly, the reaction of 4 with piperazine and trans-2,5-dimethylpiperazine in 2:1 molar ratio yielded the corresponding N,N'-bis(1-adamantyl)piperazine-1,4-dicarbothioamides 10a and 10b, respectively. The reaction of N-(1-adamantyl)-4-ethoxycarbonylpiperidine-1-carbothioamide 8c with excess hydrazine hydrate yielded the target carbohydrazide 11, in addition to 4-(1-adamantyl)thiosemicarbazide 12 as a minor product.

FT-IR and FT-Raman spectroscopic signatures, vibrational assignments, NBO, NLO analysis and molecular docking study of 2-{[5-(adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N,N-dimethylethanamine.

FT-Raman and FT-IR spectra of the title compound 2-{[5-(adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N,N-dimethylethanamine were recorded and investigated. The DFT/B3LYP/6-311++G(d,p) method was used to compute the vibrational wavenumbers. A good coherence between experimental and theoretical wavenumbers shows the preciseness of the assignments.

Antimicrobial and hypoglycemic activities of novel N-Mannich bases derived from 5-(1-adamantyl)-4-substituted-1,2,4-triazoline-3-thiones.

The reaction of 5-(1-adamantyl)-4-ethyl or allyl-1,2,4-triazoline-3-thione with formaldehyde solution and various 1-substituted piperazines yielded the corresponding N-Mannich bases. The newly synthesized N-Mannich bases were tested for in vitro inhibitory activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Six compounds showed potent antibacterial activity against one or more of the tested microorganisms, while two compounds exhibited moderate activity against the tested Gram-positive bacteria.

Spectroscopic (FT-IR, FT-Raman, and UV-visible) and quantum chemical studies on molecular geometry, Frontier molecular orbitals, NBO, NLO and thermodynamic properties of 1-acetylindole.

Quantum chemical calculations of ground state energy, geometrical structure and vibrational wavenumbers of 1-acetylindole were carried out using density functional (DFT/B3LYP) method with 6-311++G(d,p) basis set. The FT-IR and FT-Raman spectra were recorded in the condensed state. The fundamental vibrational wavenumbers were calculated and a good correlation between experimental and scaled calculated wavenumbers has been accomplished.

Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO analyses and NBO study of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6-(4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione.

The FT-IR and FT-Raman spectra of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6-(4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione were recorded. In this work, experimental and theoretical study on the molecular structure and vibrational wavenumbers of the title compound are presented. The vibrational wavenumbers were obtained theoretically at the DFT level and were compared with the experimental results.

Vibrational spectroscopic studies (FT-IR, FT-Raman) and quantum chemical calculations on 5-(Adamantan-1-yl)-3-[(4-fluoroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, a potential chemotherapeutic agent.

The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 5-(Adamantan-1-yl)-3-[(4-fluoroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione are investigated experimentally and theoretically using Gaussian09 software package. Potential energy distribution of normal modes vibrations was done using GAR2PED program. The HOMO and LUMO analysis are used to determine the charge transfer within the molecule.

Synthesis, antimicrobial, and anti-inflammatory activity, of novel S-substituted and N-substituted 5-(1-adamantyl)-1,2,4-triazole-3-thiols.

The reaction of 5-(1-adamantyl)-4-phenyl-1,2,4-triazoline-3-thione (compound 5) with formaldehyde and 1-substituted piperazines yielded the corresponding N-Mannich bases 6a-f. The reaction of 5-(1-adamantyl)-4-methyl-1,2,4-triazoline-3-thione 8 with various 2-aminoethyl chloride yielded separable mixtures of the S-(2-aminoethyl) 9a-d and the N-(2-aminoethyl) 10a-d derivatives. The reaction of compound 5 with 1-bromo-2-methoxyethane, various aryl methyl halides, and ethyl bromoacetate solely yielded the S-substituted products 11, 12a-d, and 13.

Vibrational spectroscopy of N'-(Adamantan-2-ylidene)thiophene-2-carbohydrazide, a potential antibacterial agent.

Vibrational states of the newly synthesized molecule N'-(Adamantan-2-ylidene)thiophene-2-carbohydrazide, a potential antibacterial agent, are examined experimentally for the crystalline phase and analyzed based on quantum chemical modelling of the solitary molecule and of the dimer, and assignment of the observed vibrational frequencies is proposed. Modelling of the title molecule dimer is found to describe better the experimentally observed vibration frequencies for the crystalline phase than calculations performed for a solitary molecule. Contributions from adamantane and thiophene parts within the molecule are identified.

Use of vibrational spectroscopy to study 4-benzyl-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thione: A combined theoretical and experimental approach.

In this study, the experimental and theoretical vibrational frequencies of a newly synthesized potential anti-inflammatory agent namely, 4-benzyl-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thione have been investigated. The experimental FT-IR (4000-400cm(-1)) and Laser-Raman spectra (4000-100cm(-1)) of the molecule in solid phase have been recorded. The theoretical vibrational frequencies and the optimized geometric parameters (bond lengths, bond angles and dihedral angles) have been calculated using density functional theory methods (DFT/B3LYP: Becke, 3-parameter, Lee-Yang-Parr and DFT/M06-2X: the highly parameterized, empirical exchange correlation function) with 6-311++G(d,p) basis set by Gaussian 09W software, for the first time.

3-(Adamantan-1-yl)-4-ethyl-1-{[4-(2-meth-oxy-phen-yl)piperazin-1-yl]meth-yl}-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C26H37N5OS, the piperazine ring adopts a chair conformation. The triazole ring forms dihedral angles of 67.85 (9) and 59.

N-(Adamantan-1-yl)-1,2,3,4-tetra-hydro-iso-quinoline-2-carbo-thio-amide.

In the title compound, C20H26N2S, the N-containing six-membered ring adopts a boat conformation and the dihedral angle between the thio-carbamide group and the benzene ring is 49.67 (9)°. An intra-molecular C-H⋯S hydrogen bond generates an S(6) ring motif.

3-(Adamantan-1-yl)-1-[(4-benzyl-piperazin-1-yl)meth-yl]-4-ethyl-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C26H37N5S, the piperazine ring adopts a chair conformation with the exocyclic N-C bonds in pseudo-equatorial orientations. The piperazine ring (all atoms) subtends dihedral angles of 79.47 (9) and 73.

3-(Adamantan-1-yl)-4-[(E)-(2,6-di-fluoro-benzyl-idene)amino]-1-[(4-ethyl-piperazin-1-yl)meth-yl]-4,5-di-hydro-1H-1,2,4-triazole-5-thione.

In the title compound, C26H34F2N6S, the triazole ring is linked to a benzene ring via an imine bond [N=C = 1.255 (2) Å; conformation: E], with a dihedral angle of 25.21 (11)° between the rings.

5-(Adamantan-1-yl)-3-(benzyl-sulfan-yl)-4-methyl-4H-1,2,4-triazole.

In the asymmetric unit of the title adamantyl derivative, C(20)H(25)N(3)S, there are two crystallographic independent mol-ecules with slightly different conformations. In one mol-ecule, the whole benzyl group is disordered over two orientations with the refined site-occupancy ratio of 0.63 (2):0.

3-(Adamantan-1-yl)-4-ethyl-1-[(4-phenyl-piperazin-1-yl)meth-yl]-1H-1,2,4-triazole-5(4H)-thione.

The title compound, C(25)H(35)N(5)S, has an approximately C-shaped conformation. The dihedral angle between the triazole and phenyl planes is 79.5 (2)°.

5-(Adamantan-1-yl)-3-[(2-meth-oxy-eth-yl)sulfan-yl]-4-phenyl-4H-1,2,4-triazole.

In the title adamantyl derivative, C(21)H(27)N(3)OS, the terminal meth-oxy-ethyl unit is disordered over two orientations with a refined site-occupancy ratio of 0.846 (6):0.154 (6).

3-(Adamantan-1-yl)-4-[(E)-(2,6-difluoro-benzyl-idene)amino]-1-[(4-phenyl-piperazin-1-yl)meth-yl]-1H-1,2,4-triazole-5(4H)-thione.

The imine residue [C=N = 1.268 (3) Å; conformation = E] is twisted [N-N-C-N = 87.8 (2)°] out of the plane (r.

Synthesis, molecular docking and preliminary in-vitro cytotoxic evaluation of some substituted tetrahydro-naphthalene (2',3',4',6'-tetra-O-acetyl-β-D-gluco/-galactopyranosyl) derivatives.

A facile, convenient and high yielding synthesis of novel S-glycosides and N-glycosides incorporating 1,2,3,4-tetrahydronaphthalene and or 1,2-dihydropyridines moieties has been described. The aglycons 2, 4, and 7 were coupled with different activated halosugars in the presence of basic and acidic medium. The preliminary in-vitro cytotoxic evaluation revealed that compounds 3c, 3f, 5c and 7b show promising activity.

Ethyl 4-{[3-(adamantan-1-yl)-4-phenyl-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-1-yl]meth-yl}piperazine-1-carboxyl-ate.

The title mol-ecule, C(26)H(35)N(5)O(2)S, displays a chair-shaped piperazine ring, as well as a planar triazole ring whose phenyl substituent is perpendicular to the mean plane of the five-membered ring [dihedral angle = 90.00 (13)°]. The methyl-ene substituent on the piperazine ring occupies an equatorial site.

3-(Adamantan-1-yl)-4-phenyl-1-[(4-phenyl-piperazin-1-yl)meth-yl]-1H-1,2,4-triazole-5(4H)-thione.

The title mol-ecule, C(29)H(35)N(5)S, displays a chair-shaped piperazine ring, as well as an approximately planar triazole ring (r.m.s.