Domino Palladium-Catalyzed Double Norbornene Insertion/Annulation Reaction: Expeditious Synthesis of Overcrowded Tetrasubstituted Olefins.

A Pd-catalyzed domino process involving a double norbornene insertion/annulation reaction was developed for the expeditious synthesis of overcrowded olefins. In this one-pot reaction, four new C-C bond formations were achieved by three consecutive Heck carbopalladations and C-H activation across the C≡C triple bond of 2-alkynyl bromobenzenes with two norbornene rings via a reactive vinylic-Pd(II) species. This protocol provides a step-economical synthetic system to access the structurally identical molecular machine motifs of overcrowded olefins with high yields.

Rhodium(iii)-catalysed decarbonylative annulation through C-H activation: expedient access to aminoisocoumarins by weak coordination.

Rhodium-catalysed decarbonylative annulation of isatoic anhydrides with alkynes through C-H activation for the synthesis of aminoisocoumarins was developed. This enables the gram-scale transformation to iodoisocoumarin which is a vital building block in transition-metal-catalysed cross couplings. These compounds exhibit blue-emitting luminescence properties.

Ru(II)-Catalyzed Regiospecific C-H/O-H Oxidative Annulation to Access Isochromeno[8,1-]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging.

A facile ruthenium(II)-catalyzed regiospecific C-H/O-H oxidative annulation methodology was developed to construct isochromeno[8,1-]phenazines. This methodology delivers various advantages, such as scope for diverse substrates, tolerance to a range of functional groups, stability under air, and yields regioselective products. This methodology was successfully applied to synthesize far red (FR) fluorescent probes for live cancer cell imaging.

Nanofibrous matrixes with biologically active hydroxybenzophenazine pyrazolone compound for cancer theranostics.

The nanomaterial with the novel biologically active compounds has been actively investigated for application in cancer research. Substantial use of nanofibrous scaffold for cancer research with potentially bioactive compounds through electrospinning has not been fully explored. Here, we describe the series of fabrication of nanofibrous scaffold loaded with novel potential biologically active hydroxybenzo[a]phenazine pyrazol-5(4H)-one derivatives were designed, synthesized by a simple one-pot, two step four component condensation based on Michael type addition reaction of lawsone, benzene-1,2-diamine, aromatic aldehydes and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one as the substrates.

Synthesis and Fabrication of Collagen-Coated Ostholamide Electrospun Nanofiber Scaffold for Wound Healing.

A novel scaffold for effective wound healing treatment was developed utilizing natural product bearing collagen-based biocompatible electrospun nanofibers. Initially, ostholamide (OSA) was synthesized from osthole (a natural coumarin), characterized by H, C, DEPT-135 NMR, ESI-MS, and FT-IR spectroscopy analysis. OSA was incorporated into polyhydroxybutyrate (PHB) and gelatin (GEL), which serve as templates for electrospun nanofibers.

Design and characterization of 3D hybrid collagen matrixes as a dermal substitute in skin tissue engineering.

The highly interconnected porous dressing material was fabricated with the utilization of novel collagen (COL-SPG) for the efficient healing of the wound. Herein, we report the fabrication of 3D collagen impregnated with bioactive extract (COL-SPG-CPE) to get rid of infection at the wound site. The resultant 3D collagen matrix was characterized physiochemically using Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM) and mechanical property.

Synthesis of Ni(II) complexes bearing indole-based thiosemicarbazone ligands for interaction with biomolecules and some biological applications.

A series of new Ni(II) complexes containing indole-based thiosemicarbazone ligands was synthesized and characterized by elemental analyses, and UV-visible, FT-IR, H & C NMR and mass spectroscopic techniques. The Ni(II) complexes (1-4) bear the general formula [Ni{CHNNHCSNH(R)}] where R = hydrogen (1), 4-methyl (2), 4-phenyl (3) and 4-cyclohexyl (4). Molecular structure of ligands (L3 and L4) and complexes (2, 3 and 4) was confirmed by single crystal X-ray crystallography.

Synthesis of cinnolines via Rh(iii)-catalysed dehydrogenative C-H/N-H functionalization: aggregation induced emission and cell imaging.

Rhodium catalysed dehydrogenative C-H/N-H functionalization was developed to construct phthalazino[2,3-a]-/indazolo[1,2-a]cinnolines by reacting N-phenyl phthalazine/indazole with alkynes. The synthesized compounds exhibit prominent fluorescence properties in solid and aggregation states. Their application in cell imaging was investigated using various cancer cell lines.

Synthesis of pyrrolo-/indolo[1,2-a]quinolines and naphtho[2,1-b]thiophenes from gem-dibromovinyls and sulphonamides.

A highly efficient and simple route for the synthesis of pyrrolo-/indolo[1,2-a]quinolines and naphtho[2,1-b]thiophenes from gem-dibromovinyls and sulphonamides is reported. The noteworthy feature of this report is that the methodology involves a two-step protocol to synthesize tri- and tetracyclic heterocycles in a one-pot fashion through the Cu(I)-catalyzed formation of ynamide followed by a Ag(I)-assisted intramolecular hydroarylation. The photophysical properties of representative examples of pyrrolo- and indolo[1,2-a]quinolines in solid and solution states have also been studied.

Synthesis and SAR study of novel anticancer and antimicrobial naphthoquinone amide derivatives.

A series of novel naphthoquinone amide derivatives of the bioactive quinones, plumbagin, juglone, menadione and lawsone, with various amino acids were synthesized. The compounds were characterized by (1)H NMR, (13)C NMR, Mass, IR and elemental analysis. All the compounds were evaluated for their anticancer activity against HeLa and SAS cancer cell lines and 3D-QSAR indicated the presence of electron donating group near sulphur enhanced the activity against HeLa cells.

Synthesis of tetracyclic chromenones via platinum(II) chloride catalysed cascade cyclization of enediyne-enones.

PtCl2 catalysed cascade cyclization of an enediyne-enone system to afford a tetracyclic chromenone is reported, which proceeds through two consecutive highly regioselective 6-endo-dig cyclizations in a single step with the formation of two new C-C bonds and two new rings in excellent yield. A mechanism for this transformation is proposed based on the isolated intermediates.

CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: an efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a]quinazolines.

A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.

Pd(0)-catalyzed regio- and stereoselective cyclization of alkynes: selective synthesis of (E)-4-(isobenzofuran-1(3H)-ylidene)-1,2,3,4-tetrahydroisoquinolines and aze/oxepinoindoles.

Palladium-catalyzed highly regio- and stereoselective 6-exo-dig and 7-endo-dig cyclization of functionalized propargylic compounds has been developed for the synthesis of (E)-4-(isobenzofuran-1(3H)-ylidene)-1,2,3,4-tetrahydroisoquinolines and aze/oxepinoindoles.

Synthesis of 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives and their screening for antimicrobial and antioxidant properties.

Novel 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives have been synthesized using boron trifluoride diethyl etherate catalyzed Diels-Alder reaction.

Tetrasubstituted olefinic xanthene dyes: synthesis via Pd-catalyzed 6-exo-dig cyclization/C-H activation of 2-bromobenzyl-N-propargylamines and solid state fluorescence properties.

Tetrasubstituted olefin based new xanthene derivatives have been synthesized via palladium-catalyzed carbopalladation/C-H activation of 2-bromobenzyl-N-propargylamine derivatives. The synthesized compounds display a pronounced solid state fluorescence due to their restricted internal rotation of a C-Ar bond in the solid or aggregation state.

Synthesis of quinoline derivatives for fluorescent imaging certain bacteria.

Highly fluorescent quinoline derivatives were synthesized using Sc(OTf)(3) catalyzed imino Diels-Alder reaction. Both the aromatic and their analogous tetradehydroquinoline derivatives were explored for the detection of bacteria using fluorescent imaging studies. Surprisingly the aromatic quinoline derivatives show a remarkable fluorescent response that can be useful in the detection of both gram positive and gram negative bacteria even at a concentration in the range of 0.

Synthesis of novel spirooxindole derivatives by one pot multicomponent reaction and their antimicrobial activity.

A series of novel spirooxindoles have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine or l-proline with the dipolarophile 1,4-naphthoquinone followed by spontaneous dehydrogenation. Synthesised compounds were evaluated for their antimicrobial activities against eight bacteria and three fungi. All the spirooxindole derivatives exhibited significant antibacterial activity against Staphylococcus aureus, S.

New types of reactivity of α,β-unsaturated N,N-dimethylhydrazones: chemodivergent diastereoselective synthesis of functionalized tetrahydroquinolines and hexahydropyrrolo[3,2-b]indoles.

The indium trichloride-catalyzed reaction between aromatic imines and α,β-unsaturated N,N-dimethylhydrazones in acetonitrile afforded 1,2,3,4-tetrahydroquinolines bearing a hydrazone function at C4 through a one-pot diastereoselective domino process that involves the formation of two C-C bonds and the controlled generation of two stereocenters, one of which is quaternary. This reaction constitutes the first example of an α,β-unsaturated dimethylhydrazone that behaves as a dienophile in a hetero Diels-Alder reaction. The related reaction between anilines, aromatic aldehydes, and methacrolein dimethylhydrazone in CHCl(3) with BF(3)⋅Et(2)O as catalyst afforded polysubstituted 1,2,3,3a,4,8b-hexahydropyrrolo[3,2-b]indoles as major products through a fully diastereoselective ABB'C four-component domino process that generates two cycles, three stereocenters, two C-C bonds, and two C-N bonds in a single operation.

Regioselective synthesis and structural elucidation of 1,4-disubstituted 1,2,3-triazole derivatives using 1D and 2D NMR spectral techniques.

Regioselective synthesis of 2-[1-(2-oxo-2-phenylethyl)-1H-[1,2,3]triazol-4-ylmethoxy]-benzaldehyde derivatives was achieved by [3 + 2] cycloaddition reaction of 2-(prop)-2-ynyloxy-benzaldehyde derivatives with phenacyl azide. The regiochemistry and the spectral assignments of the synthesized triazole derivatives were studied using both 1D and 2D NMR spectral techniques in solution.

Gold(III) chloride catalyzed regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones and evaluation of anticancer potential towards human cervix adenocarcinoma.

A highly regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones via gold(III) chloride catalyzed cycloisomerization of 3-ethynyl-indole-2-carboxylic acid was achieved in good to excellent yields. These compounds were screened for their in vitro cytotoxicity against human cervical (HeLa) cell lines. Out of ten compounds, three compounds (7d, 7e and 7j) showed comparable proliferation inhibitory activity against the standard drug cisplatin.

Practical synthesis, anticonvulsant, and antimicrobial activity of N-allyl and N-propargyl di(indolyl)indolin-2-ones.

An operation friendly protocol for the synthesis of novel di(indolyl)indolin-2-ones via Cu(OTf)(2) catalyzed bis-addition of N-allyl and N-propargyl indole with isatin was developed. This methodology allowed us to achieve the products in excellent yields without requiring purification technique like column chromatography. All the synthesized compounds were evaluated for their in vivo anticonvulsant activity against maximal electroshock test.

InCl3 mediated one-pot multicomponent synthesis, anti-microbial, antioxidant and anticancer evaluation of 3-pyranyl indole derivatives.

A simple and convenient method for the one-pot three-component synthesis of 3-pyranyl indoles has been accomplished by tandem Knoevenagel-Michael reaction of 3-cyanoacetyl indole, various aromatic aldehydes and malononitrile catalyzed by InCl(3) in ethanol under reflux conditions. The newly synthesized 3-pyranyl indoles were evaluated for anti-microbial, antioxidant, and anticancer activities. Some of the compounds showed good anticancer activity against MCF-7 breast cancer cell lines on comparison with of standard drug.

One-pot multicomponent synthesis and anti-microbial evaluation of 2'-(indol-3-yl)-2-oxospiro(indoline-3,4'-pyran) derivatives.

A simple and efficient method for the one-pot three-component synthesis of new spirooxindoles in room temperature is described. The newly synthesized spirooxindoles were screened for anti-microbial activity and the results are good on comparison with of standard antibacterial compounds.

Effect of Single-Walled Carbon Nanotube Association upon H NMR Spectra of Representative Organonitrogen Compounds.

This report is important to achieving SWCNT solvation, understanding adsorption of molecules on SWCNT surfaces, and SWCNT characterization by NMR. Complexation of 1-methyl-2-pyrrolidone (NMP) and other selected organonitrogens with single-walled carbon nanotubes (SWCNTs) was studied by proton nuclear magnetic resonance (NMR). The magnitude of (1)H NMR chemical shift change upon SWCNT:organonitrogen complex formation represents the strength of the association.

Synthesis and NMR spectral assignments of indol-3-yl pyridines through one-pot multi-component reaction.

Asimple protocol for the efficient preparation of 6-(ferrocene-1-yl)-2-(indol-3-yl)pyridine and 2-(1H-indol-3-yl)-6-(2-thienyl)pyridine derivatives has been achieved through multi-component reaction, and these compounds were thoroughly characterised by 2D NMR spectral techniques.