Novel thiophene derivatives with sulfonamide, isoxazole, benzothiazole, quinoline and anthracene moieties as potential anticancer agents

A novel series of thiophenes having biologically active sulfonamide (2-11), 3-methylisoxazole (12), 4-methoxybenzo[d]thiazole (13), quinoline (14, 15), benzoylphenylamino (16) and anthracene-9,10-dione (17) moieties were prepared. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. All newly synthesized compounds were evaluated for their in vitro anticancer activity against human breast cancer cell line (MCF7). Most of the screened compounds showed cytotoxic activities compared to doxorubicin as a positive control. Compounds 6, 7, 9 and 13 (IC50 values 10.25, 9.70, 9.55 and 9.39 µmol L–1 revealed higher cytotoxic activities than that of doxorubicin (IC50 = 32.00 µmol L). Also, compounds 5, 8 and 10 were found nearly as active as doxorubicin (IC50 values 28.85, 23.48 and 27.51 µmol L–1)

Design, synthesis and potential anti-proliferative activity of some novel 4-aminoquinoline derivatives

Novel nineteen compounds based on a 4-aminoquinoline scaffold were designed and synthesized as potential anti-proliferative agents. The new compounds were N-substituted at the 4-position by aryl or heteroaryl 1-9, quinolin-3-yl 10, 2-methylquinolin-3-yl 11, thiazol-2-yl 12, and dapsone moieties 13, 14 and 18. Bis-compounds 15, 16 and 19 were also synthesized to assess their biological activity. All the newly synthesized comounds were tested for in vitro antiproliferative activity against the MCF-7 breast cancer cell line. Seventeen of the novel compounds showed higher activity than the reference drug doxorubicin. The corresponding 7-(trifluoromethyl)-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine 1, N-(7-(trifluoromethyl)quinolin-4-yl)quinolin-3-amine (10), 2-methyl-N-(7-trifluorome-thyl)quinolin-4-yl)quinolin-3-amine (11) and N-(4-(4-aminophenylsulf-onyl)phenyl)-7-chloroquinolin-4-amine (13) were almost twice to thrice as potent as doxorubicin

(3Z,3′Z)-3,3′-(3,5-Dimethyl­furan-2,4-diyl)bis­(4-hy­droxy­pent-3-en-2-one)

In the title mol­ecule, C16H20O5, the two 4-hy­droxy­pent-3-en-2-one units are essentially planar, with r.m.s. deviations of 0.0183 (2) and 0.0134 (2) Å for the non-H atoms, and make dihedral angles of 81.20 (10) and 84.44 (10)° with the central furan ring. The dihedral angle between these two side units is 22.06 (9)°. Two intra­molecular O—H⋯O hydrogen bonds generate two S(6) ring motifs. A weak inter­molecular C—H⋯O inter­action is also observed

1-(3-Ethyl­phen­yl)-4,6-dimethyl-2-oxo-1,2-dihydro­pyridine-3-carbonitrile

In the title compound, C16H16N2O, the essentially planar 1,2-dihydro­pyridine ring [maximum deviation = 0.021 (1) Å] makes a dihedral angle of 85.33 (8)° with the benzene ring. In the crystal, mol­ecules are linked into a chain along the b axis via C—H⋯O inter­actions

(E)-3-Dimethyl­amino-1-(2,5-dimethyl­thio­phen-3-yl)prop-2-en-1-one

In the title compound, C11H15NOS, the 3-(dimethyl­amino)­prop-2-en-1-one unit is approximately planar [maximum deviation = 0.0975 (14) Å] and its mean plane of seven non-H atoms makes a dihedral angle of 6.96 (10)° with the thio­phene ring. In the crystal, mol­ecules are linked by pairs of C—H⋯O hydrogen bonds into inversion dimers with R 2 2(14) ring motifs. The dimers are stacked along the c axis through C—H⋯π inter­actions. The two methyl groups, attached to the thio­phene ring and the amino N atom, are each disordered over two orientations, with site-occupancy ratios of 0.59 (4):0.41 (4) and 0.74 (4):0.26 (4), respectively

(E)-4-Amino-N-(1,2-dihydro­pyridin-2-yl­idene)benzene­sulfonamide nitro­methane monosolvate

In the title solvate, C11H11N3O2S·CH3NO2, the dihedral angle between the benzene ring and the N-containing ring is 85.94 (11)°, and an approximate V shape arises for the sulfonamide mol­ecule. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds and weak C—H⋯O inter­actions link the sulfonamide mol­ecules into a three-dimensional network. The nitro­methane solvent mol­ecules are located in the inter­stitial sites in the sulfonamide network

Absolute configuration of (1S,2S)-3-methyl-2-phenyl-2,3-dihydro­thia­zolo[2,3-b]quinazolin-5-one

The absolute structure of the molecule in the crystal of the title compound, C17H14N2OS, was determined by the refinement of the Flack parameter to 0.0 (2) based on 1011 Friedel pairs. The quinazoline ring is essentially planar, with a maximum deviation of 0.037 (2) Å. The thia­zole ring is distorted from planarity [maximum deviation = 0.168 (2) Å] and adopts a slightly twisted envelope conformation, with the C atom as the flap atom. The central thia­zole ring makes dihedral angles of 7.01 (8) and 76.80 (10)° with the quinazoline and phenyl rings, respectively. The corresponding angle between the quinazoline and phenyl rings is 3.74 (9)°. In the crystal, there are no classical hydrogen bonds but stabilization is provided by weak C—H⋯π inter­actions, involving the centroids of the phenyl rings

Proanthocyanidin-rich date seed extract protects against chemically induced hepatorenal toxicity

A hydroacetone extract was prepared from seeds of Phoenix dactylifera L. var. Khalas, which is an industrial by-product of date processing. The proanthocyanidin nature of the extract (coded as DTX) was characterized by phytochemical and nuclear magnetic resonance (NMR) analyses. The total phenol/proanthocyanidin content and antioxidant activity of DTX were estimated by Folin-Ciocalteu, vanillin-sulfuric acid, and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays, respectively. The hepatorenal protective activity of DTX was evaluated using CCl4-induced toxicity model in rats, in comparison with silymarin (SYL). Results of the histopathological examination and measurements of various hepatorenal serum indices and tissue biochemical markers demonstrated that DTX displayed marked protective potential against CCl4-induced liver and kidney injury at 100 mg/kg/rat. Relative to the control CCl4-intoxicated group, pretreatment with DTX significantly (P<.001) suppressed the elevated serum levels of alanine aminotransferase and aspartate aminotransferase (ALT and AST), alkaline phosphatase (ALP), γ-glutamyl transferase (GGT), total cholesterol (TC), low-density lipoprotein cholesterol (LDL-C), bilirubin, creatinine, and calcium, whereas it significantly (P<.001) increased the diminished serum levels of high-density lipoprotein cholesterol (HDL-C) and total protein (TP). Moreover, DTX significantly decreased malondialdehyde (MDA) formation and increased TP synthesis in hepatorenal tissues compared with the intoxicated control. The improvement in biochemical parameters by DTX was observed in a dose-dependent manner and confirmed by restoration of normal histological features. The acute toxicity test of DTX in rats revealed safety of the extract. This study reveals that DTX enhances the recovery from xenobiotics-induced toxicity initiated by free radicals

3-[(1-Hy­droxy-1-phenyl­propan-2-yl)amino]-5,5-dimethyl­cyclo­hex-2-enone

The asymmetric unit of the title compound, C17H23NO2, consists of two crystallographically independent mol­ecules (A and B). The cyclo­hexene rings in both mol­ecules adopt an envelope conformation. In the crystal, independent mol­ecules, A and B, are each linked by inter­molecular bifurcated (N,O)—H⋯O hydrogen bonds, generating R 2 1(7) ring motifs and forming infinite chains along the b axis