6-Aryl-4-cycloamino-1,3,5-triazine-2-amines: synthesis, antileukemic activity, and 3D-QSAR modelling.

Despite significant progress in immunotherapy and chimeric antigen receptor T cell therapy of leukemia, chemotherapy is the major treatment option for the disease. Therefore, the development of potent and safe drugs for standard and targeted chemotherapy of leukemia remains an important task for medicinal chemists. A library of 94 diverse 6-aryl-4-cycloamino-1,3,5-triazine-2-amines was prepared using a one-pot microwave-assisted protocol, which involves a three-component reaction of cyanoguanidine, aromatic aldehydes and cyclic amines, and subsequent dehydrogenative aromatization of the dihydrotriazine intermediates in the presence of alkali.

Discovery of indoleninyl-pyrazolo[3,4-b]pyridines as potent chemotherapeutic agents against colorectal cancer cells.

A new series of indolenines decorated with pyrazolo[3,4-b]pyridines were designed and synthesized in up to 96% yield from the acid-catalyzed cyclocondensation of 1,3-dialdehydes with 3-aminopyrazoles. X-ray crystallography on a representative derivative, 5n, revealed two close to planar conformations whereby the N-atom of the pyridyl residue was syn or anti to the pyrrole-N atom in the two independent molecules of the asymmetric unit. The computational and DNA binding data suggest that 5n is a strong DNA intercalator with the results in agreement with its potent cytotoxicity against two colorectal cancer cell lines (HCT 116 and HT-29).

Synthesis and Staphylococcus aureus biofilm inhibitory activity of indolenine-substituted pyrazole and pyrimido[1,2-b]indazole derivatives.

Staphylococcus aureus is a highly adaptable opportunistic pathogen that can form biofilms and generate persister cells, leading to life-threatening infections that are difficult to treat with antibiotics alone. Therefore, there is a need for an effective S. aureus biofilm inhibitor to combat this public health threat.

Structural insights and cytotoxicity evaluation of benz[e]indole pyrazolyl-substituted amides.

Five new compounds of benz[e]indole pyrazolyl-substituted amides (2a-e) were synthesised in low to good yields via the direct amide-coupling reaction between a pyrazolyl derivative containing a carboxylic acid and several amine substrates. The molecular structures were determined by various spectroscopic methods, such as NMR (H, C and F), FT-IR and high-resolution mass spectrometry (HRMS). X-ray crystallographic analysis on the 4-fluorobenzyl derivative (2d) reveals the amide-O atom to reside to the opposite side of the molecule to the pyrazolyl-N and pyrrolyl-N atoms; in the molecular packing, helical chains feature amide-N‒H⋯N(pyrrolyl) hydrogen bonds.

Synthesis, spectral characterisation, biocidal investigation, and molecular docking studies of 4-[(2-chloro-4-methylphenyl)carbamoyl]butanoic acid derived triorganotin(IV) compounds.

Three triorganotin(IV) compounds, RSn(L), with R = CH (), -CH () and CH (), and LH = 4-[(2-chloro-4-methylphenyl)carbamoyl]butanoic acid, were prepared and confirmed by various techniques. A five-coordinate, distorted trigonal-bipyramidal geometry was elucidated for tin(IV) centres both in solution and solid states. An intercalation mode was confirmed for the compound SS-DNA interaction by UV-visible, viscometric techniques and molecular docking.

Synthetic strategies and diversification of dibenzo[1,5]diazocines.

Dibenzo[1,5]diazocine scaffolds are present in a wide range of organic building blocks, for example in pharmaceuticals, materials and structural chemistry. However, the development of these structural frameworks has not received significant attention owing to limited synthetic protocols and strategies. Herein, a summary of the attractive synthetic approaches for the construction of dibenzo[1,5]diazocines, epiminodibenzo[1,5]diazocines and epoxydibenzo[1,5]diazocines developed over the past two decades is presented.

Cadmium(II) compounds of the bis-cyanoethyl derivative (L) of Me[14]aneC (L): characterization and antibacterial studies.

The isomeric ligand L, a saturated analogue of 2,9-C-meso-Me[14]diene, on reflux with excess acrylonitrile afforded 1,8-N-pendant cyanoethyl derivative L. Interaction of L with cadmium(II) perchlorate, nitrate, acetate, and chloride salts produced six coordinated octahedral compounds, [Cd(L) (ClO)]∙2HO, [Cd(L) (NO)], [Cd(L) (CHCOO)], and [Cd(L)Cl], respectively. Further, axial substitution reactions between [Cd(L) (ClO)]∙2HO and KI, KBr, KCl, KSCN, and NaNO in a 1:2 ratio yielded six coordinated octahedral compounds, [Cd(L)I]∙HO, [Cd(L)Br]∙2HO, [Cd(L)Cl(ClO)]∙2HO, [Cd(L) (NCS)]∙HO, and [Cd(L) (NO) (ClO)]∙2HO, respectively.

Indoleninyl-substituted pyrimido[1,2-]indazoles a facile condensation reaction.

A new series of pyrimido[1,2-]indazoles bearing indolenine moieties was synthesized through a simple condensation reaction with up to 94% yield. The present method features the versatile formation of a pyrimidine ring with a broad range of substrates, great functional group compatibility and facile synthetic operation. The work offers opportunities in drug development as well as in materials science.

Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-]pyrimidin-4-ones.

A practical three-component method for the synthesis of pyrazolo[3,4-]pyrimidin-4-ones was developed. The reaction was performed in a one-pot manner under controlled microwave irradiation using easily accessible methyl 5-aminopyrazole-4-carboxylates, trimethyl orthoformate, and primary amines. Under the optimized conditions, challenging substrates, such as N-1 unsubstituted 5-aminopyrazole-4-carboxylates with another substituted amino group in position 3, reacted selectively affording 5-substituted 3-arylamino-1,5-dihydro-4-pyrazolo[3,4-]pyrimidin-4-ones.

[-1,8-Bis(2-carbamoyleth-yl)-5,5,7,12,12,14-hexa-methyl-1,4,8,11-tetra-aza-cyclo-tetra-deca-ne]copper(II) di-acetate tetra-hydrate: crystal structure and Hirshfeld surface analysis.

The title Cu macrocyclic complex salt tetra-hydrate, [Cu(CHNO)](CHO)·4HO, sees the metal atom located on a centre of inversion and coordinated within a 4 + 2 (NO) tetra-gonally distorted coordination geometry; the N atoms are derived from the macrocycle and the O atoms from weakly associated [3.2048 (15) Å] acetate anions. Further stability to the three-ion aggregate is provided by intra-molecular amine-N-H⋯O(carboxyl-ate) hydrogen bonds.

Water-Soluble Dioxidovanadium(V) Complexes of Aroylhydrazones: DNA/BSA Interactions, Hydrophobicity, and Cell-Selective Anticancer Potential.

Five new anionic aqueous dioxidovanadium(V) complexes, [{VOL}A(HO)] (-), with the aroylhydrazone ligands pyridine-4-carboxylic acid (3-ethoxy-2-hydroxybenzylidene)hydrazide (HL) and furan-2-carboxylic acid (3-ethoxy-2-hydroxybenzylidene)hydrazide (HL) incorporating different alkali metals (A = Na, K, Cs) as countercation were synthesized and characterized by various physicochemical techniques. The solution-phase stabilities of - were determined by time-dependent NMR and UV-vis, and also the octanol/water partition coefficients were obtained by spectroscopic techniques. X-ray crystallography of - confirmed the presence of vanadium(V) centers coordinated by two -oxido-O atoms and the O, N, and O atoms of a dianionic tridentate ligand.

Bis{'-[3-(4-nitro-phen-yl)-1-phenyl-prop-2-en-1-yl-idene]--phenyl-carbamimido-thio-ato}zinc(II): crystal structure, Hirshfeld surface analysis and computational study.

The title zinc bis-(thio-semicarbazone) complex, [Zn(CHNOS)], comprises two ,-donor anions, leading to a distorted tetra-hedral NS donor set. The resultant five-membered chelate rings are nearly planar and form a dihedral angle of 73.28 (3)°.

1-{()-[4-(4-Hy-droxy-phen-yl)butan-2-yl-idene]amino}-3-phenyl-thio-urea: crystal structure, Hirshfeld surface analysis and computational study.

The title thio-urea derivative, CHNOS, adopts a U-shaped conformation with the dihedral angle between the terminal aromatic rings being 73.64 (5)°. The major twist in the mol-ecule occurs about the ethane bond with the C-C-C-C torsion angle being -78.

Di--but-yl['-(3-meth-oxy-2-oxidobenzyl-idene)--phenyl-carbamohydrazono-thio-ato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study.

The title diorganotin Schiff base derivative, [Sn(CH)(CHNOS)], features a penta-coordinated tin centre defined by the N,,-donor atoms of the di-anionic Schiff base ligand and two methyl-ene-C atoms of the -butyl substituents. The resultant CNOS donor set defines a geometry inter-mediate between trigonal-bipyramidal and square-pyramidal. In the crystal, amine-N-H⋯O(meth-oxy) hydrogen bonding is found in a helical, supra-molecular chain propagating along the -axis direction.

Ethyl 3,4-bis-(acet-yloxy)-2-(4-meth-oxy-phen-yl)pyrrol-idine-1-carboxyl-ate.

The title pyrrolidine compound, CHNO, is a tetra-substituted species in which the five-membered ring has a twisted conformation with the twist occurring in the C-C bond bearing the adjacent acet-yloxy substituents; the C-C-C-C torsion angle is -40.76 (18)° [m = methyl-ene, a = acet-yloxy and p = phen-yl]. The N atom, which is -hybridized [sum of bond angles = 359.

Zero-, one-, two- and three-dimensional supramolecular architectures sustained by SeO chalcogen bonding: A crystallographic survey.

The Cambridge Structural Database was evaluated for crystals containing SeO chalcogen bonding interactions. These secondary bonding interactions are found to operate independently of complementary intermolecular interactions in about 13% of the structures they can potentially form. This number rises significantly when more specific interactions are considered, e.

[()--(3-Fluoro-phen-yl)--methyl-thio-carbamato-κ](tri-phenyl-phosphane-κ)gold(I): crystal structure, Hirshfeld surface analysis and computational study.

The title phosphanegold(I) thiol-ate, CHAuFNOPS or [Au(CHFNOS)(CHP)], has the Au centre coordinated by phosphane-P [2.2494 (8) Å] and thiol-ate-S [2.3007 (8) Å] atoms to define a close to linear geometry [P-Au-S = 176.

2-[(1)-[()-2-({[(1)-[()-2-[(2-Hy-droxy-phen-yl)methyl-idene]hydrazin-1-yl-idene]({[(4-methyl-phen-yl)meth-yl]sulfan-yl})meth-yl]disulfan-yl}({[(4-methyl-phen-yl)meth-yl]sulfan-yl})methyl-idene)hydrazin-1-yl-idene]meth-yl]phenol: crystal structure, Hirshfeld surface analysis and computational study.

The complete mol-ecule of the title hydrazine carbodi-thio-ate derivative, CHNOS, is generated by a crystallographic twofold axis that bis-ects the di-sulfide bond. The mol-ecule is twisted about this bond with the C-S-S-C torsion angle of 90.70 (8)° indicating an orthogonal relationship between the symmetry-related halves of the mol-ecule.

2,2'-(Disulfanedi-yl)di-benzoic acid ,-di-methyl-formamide monosolvate: crystal structure, Hirshfeld surface analysis and computational study.

The title 1:1 solvate, CHOS·CHNO, features a twisted mol-ecule of 2,2'-di-thiodi-benzoic acid (DTBA), with the central C-S-S-C torsion angle being -88.57 (6)°, and a mol-ecule of di-methyl-formamide (DMF). The carb-oxy-lic acid groups are, respectively, close to co-planar and twisted with respect to the benzene rings to which they are connected as seen in the CO/C torsion angles of 1.

4-Nitro-benzyl 3,4-bis-(acet-yloxy)-2-(4-meth-oxy-phen-yl)pyrrolidine-1-carboxyl-ate: crystal structure, Hirshfeld surface analysis and computational chemistry.

The title compound, CHNO, is a tetra-substituted pyrrolidine derivative with a twisted conformation, with the twist evident in the C-C bond bearing the adjacent acet-yloxy substituents. These are flanked on one side by a C-bound 4-meth-oxy-phen-yl group and on the other by a methyl-ene group. The almost -N atom [sum of angles = 357°] bears a 4-nitro-benzyl-oxycarbonyl substituent.

Methyl 3-[(1-benzyl-4-phenyl-1-1,2,3-triazol-5-yl)formamido]-propano-ate: crystal structure, Hirshfeld surface analysis and computational chemistry.

The title compound, CHNO, is constructed about a tri-substituted 1,2,3-triazole ring, with the substituent at one C atom flanked by the C and N atoms being a substituted amide group, and with the adjacent C and N atoms bearing phenyl and benzyl groups, respectively; the dihedral angle between the pendant phenyl rings is 81.17 (12)°, indicative of an almost orthogonal disposition. In the crystal, pairwise amide-N-H⋯O(carbon-yl) hydrogen bonds lead to a centrosymmetric dimer incorporating methyl-ene-C-H⋯π(benzene) inter-actions.

4-[(1)-({[(Benzyl-sulfan-yl)methane-thio-yl]amino}-imino)-meth-yl]benzene-1,3-diol chloro-form hemisolvate: crystal structure, Hirshfeld surface analysis and computational study.

The title hydrazine carbodi-thio-ate chloro-form hemisolvate, 2CHNOS·CHCl, comprises two independent hydrazine carbodi-thio-ate mol-ecules, and , and a chloro-form mol-ecule; the latter is statistically disordered about its mol-ecular threefold axis. The common features of the organic mol-ecules include an almost planar, central CNS chromophore [r.m.

Design, synthesis, and biological evaluation of new 6, -diaryl-1,3,5-triazine-2,4-diamines as anticancer agents selectively targeting triple negative breast cancer cells.

New 6, -diaryl-1,3,5-triazine-2,4-diamines were designed using the 3D-QSAR model developed earlier. These compounds were prepared and their antiproliferative activity was evaluated against three breast cancer cell lines (MDA-MB231, SKBR-3 and MCF-7) and non-cancerous MCF-10A epithelial breast cells. The synthesized compounds demonstrated selective antiproliferative activity against triple negative MDA-MB231 breast cancer cells.