5-(2-Methoxy­benz­yl)-4-(2-methoxy­phen­yl)-4H-1,2,4-triazol-3-ol

In the mol­ecule of the title compound, C17H17N3O3, the triazole ring is oriented at dihedral angles of 88.09 (3) and 83.72 (3)° with respect to the 2-methoxy­benzyl and 2-methoxy­phenyl rings, respectively. The dihedral angle between the 2-methoxy­benzyl and 2-methoxy­phenyl rings is 52.95 (3)°. In the crystal structure, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into centrosymmetric dimers. There is a π–π contact between the 2-methoxy­phenyl rings [centroid–centroid distance = 3.811 (3) Å]

4-(4-Methoxy­phen­yl)-3-[2-(2-methoxy­phen­yl)eth­yl]-1H-1,2,4-triazol-5(4H)-one

The title compound, C18H19N3O3, is a biologically active triazole derivative. The five-membered ring is oriented with respect to the six-membered rings at dihedral angles of 51.59 (4) and 61.37 (4)°. The crystal structure is stabilized by inter­molecular N—H⋯O hydrogen-bond inter­actions between centrosymmetrically related mol­ecules [the dihedral angle between the benzene rings is 47.44 (5)°]

4-(2-Methoxy­phenyl)-3-(3,4,5-tri­methoxy­phen­ethyl)-2H-1,2,4-triazole-5(4H)-thione

The title compound, C20H23N3O4S, is an important biologically active heterocyclic compound. The five-membered ring is oriented with respect to the six-membered rings at dihedral angles of 78.60 (3) (trimethoxyphenyl ring) and 71.57 (3)° (methoxyphenyl ring). In the crystal structure, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into infinite chains along the c axis

2,2′-[Naphthalene-1,5-diylbis(nitrilo­methanylyl­idene)]diphenol

The title compound, C24H18N2O2, lies about an inversion centre and the asymmetric unit contains one half-mol­ecule. An intra­molecular O—H⋯N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The crystal packing exhibits inter­molecular π–π stacking inter­actions between the aromatic rings with a centroid–centroid distance of 3.851 (2) Å

5-(3-Methoxy­pheneth­yl)-4-(2-methoxy­phen­yl)-4H-1,2,4-triazol-3-ol

In the mol­ecule of the title compound, C18H19N3O3, the triazole ring is oriented with respect to the 3-methoxy­phenyl and 2-methoxy­phenyl rings at dihedral angles of 11.79 (3) and 89.22 (3)°, respectively. The dihedral angle between the two benzene rings is 85.95 (3)°. In the crystal structure, inter­molecular O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules. There is a π–π contact between the triazole and 3-methoxy­phenyl rings [centroid–centroid distance = 3.916 (3) Å]. There is a π–π contact between the triazole and one of the 3-methoxy­phenyl rings [centroid–centroid distance = 3.916 (3) Å ]. C—H⋯π contacts are also found between the benzene ring and the methyl groups of their 3-methoxy-substituents

3-(3-Methoxy­benz­yl)-4-(2-methoxy­phen­yl)-1H-1,2,4-triazole-5(4H)-thione

In the title compound, C17H17N3O2S, the five-membered ring forms dihedral angles of 53.02 (3) and 78.57 (3)° with the 3-meth­oxy-substituted and 2-meth­oxy-substituted benzene rings, respectively. In the crystal structure, mol­ecules are linked into centrosymmetric dimers via inter­molecular N—H⋯S hydrogen bonds

N-[(4-Amino-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-3-yl)meth­yl]-4-methyl­benzamide

In the title compound, C11H13N5OS, the dihedral angle between the triazole ring and the benzene ring is 84.21 (7)°. The amino group adopts a pyramidal configuration. An intra­molecular N—H⋯O hydrogen bond stabilizes the mol­ecular structure and generates an S(8) ring. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O, N—H⋯S, N—H⋯N and C—H⋯S hydrogen bonds into layers lying parallel to the bc plane. The crystal structure is further stabilized by aromatic π–π stacking inter­actions [centroid–centroid distance = 3.3330 (7) Å]

4-[(1-Hy­droxy-2-naphth­yl)methyl­ene­amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

The title anti­pyrine derivative, C22H19N3O2, was synthesized by the reaction of 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro­pyrazol-3-one and 1-hy­droxy­naphthalene-2-carbaldehyde in methanol solution. As expected, the compound adopts a trans configuration about the central C=N bond. The N atom is involved in an intra­molecular O—H⋯N bond which stabilizes the mol­ecular configuration. In the crystal structure, adjacent mol­ecules stack with no short contacts

Synthesis and Antimicrobial Activity of 2-[2-(2,6-dichloro phenyl)amino]benzyl-3-(5-substituted phenyl-4,5-dihydro-1H-pyrazol-3-yl-amino)-6,8-dibromoquinazolin-4(3H)ones

A series of 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-(5-substituted phenyl-4,5-dihydro-1H-pyrazol-3-yl-amino)-6,8-dibromoquinazolin-4(3H) ones 6a-m have been synthesized by the reaction of 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-substituted phenylacrylamido-6,8-dibromoquinazolin-4(3H) ones 5a-m with hydrazine hydrate in the presence of glacial acetic acid. The chalcones 5a-m were prepared by the condensation of 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-acetamido-6,8-dibromoquinazolin-4(3H)one 4 with different substituted aromatic aldehyde. The benzoxazinone 2 was synthesized from 2-[2-(2,6-dichlorophenyl)amino]phenyl acetyl chloride 1 on treatment with 3,5-dibromoanthranilic acid in pyridine, which on reaction with hydrazine hydrate and then on acetylation reaction yielded 4. The structures of these compounds have been elucidated by elemental analyses, IR, and NMR spectral data. The title compounds pyrazolyl-quinazolin-4(3H)ones 6a-m were evaluated for their antibacterial and antifungal activities in vitro

Design, synthesis and SAR exploration of tri-substituted 1,2,4-triazoles as inhibitors of the annexin A2–S100A10 protein interaction

Recent target validation studies have shown that inhibition of the protein interaction between annexin A2 and the S100A10 protein may have potential therapeutic benefits in cancer. Virtual screening identified certain 3,4,5-trisubstituted 4H-1,2,4-triazoles as moderately potent inhibitors of this interaction. A series of analogues were synthesized based on the 1,2,4-triazole scaffold and were evaluated for inhibition of the annexin A2–S100A10 protein interaction in competitive binding assays. 2-[(5-{[(4,6-Dimethylpyrimidin-2-yl)sulfanyl]methyl}-4-(furan-2-ylmethyl)-4H-1,2,4-triazol-3-yl)sulfanyl]-N-[4-(propan-2-yl)phenyl]acetamide (36) showed improved potency and was shown to disrupt the native complex between annexin A2 and S100A10