Biologically active perspective synthesis of heteroannulated 8-nitroquinolines with green chemistry approach.

A new class of pyrazolo[4,3-c]quinoline (5a-i, 7a-b) and pyrano[3,2-c]quinoline (9a-i) derivatives were designed and synthesized in moderate to good yields by microwave conditions. To enhance the yield of pyrano[3,2-c]quinoline derivatives, multicomponent one-pot synthesis has been developed. The synthesized compounds were identified by spectral and elemental analyses. Compounds 9a and 9i showed good antibacterial activity against Gram-positive and Gram-negative bacterial strains. All of the new compounds exhibited weak to moderate antioxidant activity, compound 9d exerted significant antioxidant power. The cytotoxicity of these compounds were also evaluated against MCF-7 (breast) and A549 (Lung) cancer cell lines. Most of the compounds displayed moderate to good cytotoxic activity against these cell lines. Compound 9i was found to be significantly active in this assay and also induced cell death by apoptosis. Molecular docking studies were carried out using EGFR inhibitor in order to determine the molecular interactions.

Synthesis of first ever 4-quinolone-3-carboxylic acid-appended spirooxindole-pyrrolidine derivatives and their biological applications.

A series of 4-quinolone-3-carboxylic acid-containing spirooxindole-pyrrolidine derivatives was synthesized via multicomponent 1,3-dipolar cycloaddition reactions of azomethine ylides with new (E)-4-oxo-6-(3-phenyl-acryloyl)-1,4-dihydroquinoline-3-carboxylic acids in good yields with high regioselectivity. The cycloadducts were characterized by analytical and spectral data including [Formula: see text], [Formula: see text], 2D NMR and mass spectroscopy. The structure of one of the compounds (8a) was investigated theoretically by computational techniques. DFT studies support the proposed mechanism for this cycloaddition reaction. Furthermore, antibacterial activities of the new compounds were evaluated against Gram-positive and Gram-negative bacterial strains. Compounds 8f, 8m and 8p showed potent inhibition activities against selected bacteria. The in vitro cytotoxicity of spirooxindole derivatives (8a-r) was evaluated against MCF-7 breast cancer cell line. Among the various compounds tested, compound 8f [Formula: see text] showed significant cytotoxic activity compared to the standard drug doxorubicin [Formula: see text].

Hepatoprotective and Cytotoxic Activities of Abietic Acid from Isodon wightii (Bentham) H. Hara.

UNLABELLED: Isodon (Lamiaceae) is a known source of bioactive terpenoids. Diterpenoids isolated from Isodon wightii (Bentham) H. Hara showed antibacterial, antiacetylcholinesterase, antioxidant, anticancer, and anticarcinogenic activities, etc., Hepatoprotective activity of ABA against lipopolysaccharide (LPS) induced liver injury in BALB/c mice was studied. Cytotoxic activity of ABA was tested against cervical cancer cells (HeLa) using MTT assay followed by propidium iodide (PI) staining to identify apoptosis. Histopathological analysis revealed that 1.5 ॖg/mL LPS induced liver damage was attenuated by ABA in a dose dependent manner. ABA showed cytotoxicity with IC50 value of 176.28 ± 0.02 ॖg/mL and PI staining of treated cells showed apoptosis. This study proves that ABA would be a promising natural compound for herbal drug preparation. SUMMARY: In the present study, abietic acid isolated from I. wightii had potent hepatoprotective effect on LPS induced liver damage in BALB/c mice. Abietic acid also showed cytotoxic activity on HeLa cells followed by apoptosis induction confirmed by PI staining. Abbreviation Used: ABA: Abietic acid; LPS: Lipopolysacharride; PBS: Phosphate buffer saline; PI: Propidium iodide; NMR: Nuclear magnetic resonance; COSY: Correlation spectroscopy; HSQC: Heteronuclear single quantum correlation; HMBC: Heteronuclear multi - bond correlation; MTT: 3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide.

Crystal structure of 4'-(2-meth-oxy-quinolin-3-yl)-1'-methyl-dispiro-[indan-2,2'-pyrrolidine-3',3''-indoline]-1,3,2''-trione.

In the title compound, C30H23N3O4, the central 1-methyl-pyrrolidine ring adopts a twist conformation on the N-CH2 bond. The pyrrolidin-2-one ring of the indolin-2-one ring system also has a twist conformation on the C-C bond involving the spiro C atom and the carbonyl C atom. The five-membered ring of the indene-1,3-dione moiety has an envelope conformation with the spiro C atom as the flap. The quinoline ring system adopts an almost planar conformation (r.m.s. deviation = 0.04 Å). The mean planes of the indolin-2-one ring system, the indene-1,3-dione ring system and the the quinoline ring system are inclined to the mean plane of the central 1-methyl-pyrrolidine ring by 77.97 (7), 86.98 (7) and 46.58 (6)°, respectively. In the crystal, mol-ecules are linked via N-H⋯N hydrogen bonds, forming chains along the b axis. The chains are linked via a number of C-H⋯O hydrogen bonds, and C-H⋯π and π-π inter-actions [inter-centroid distance = 3.7404 (9) Å], forming a three-dimensional network.