01772nas a2200205 4500008004100000022001400041245012400055210006900179260007100248300001400319490000700333520095600340100002501296700002501321700002301346700002401369700002601393700002301419856012401442 2009 eng d a0022-326300aSynthesis and conformational study of chiral oxepines: the baylis-hillman reaction and RCM approach with sugar aldehyde0 aSynthesis and conformational study of chiral oxepines the baylis a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcSEP a6486-64940 v743 a

The Baylis-Hillman reaction of 3-O-allyl-alpha-D-xylo-pentodialdo-1,4-furanose 3 afforded a diastereomeric mixture of D-gluco- and L-ido-configured alpha-methylene-beta-hydroxy esters 4a and 4b, respectively, in a ratio of 2:3. Reduction of the ester functionality in 4a/4b gave alcohols 5a/5b. The diene thus formed in 5a/5b was subjected to ring-closing metathesis (Grubbs' second-generation catalyst) to afford oxa-bicyclic ring system 6a/6b in high yield. Further manipulation of the aectonide functionality in 6a and 6b afforded new polyhydroxylated oxepines 1a/2a and 1b/2b, respectively. The (1)H NMR of oxepines 1a and 1b in D(2)O showed doubling of signals indicating their existence in two different rotamers/conformers. This fact was substantiated by calculating energetics of 1 and 2 conformers using the density functional theory and correlating the calculated (1)H NMR chemical shift pattern with that of the experimental spectra.

1 aJadhav, Vrushali, H.1 aBande, Omprakash, P.1 aPinjari, Rahul, V.1 aGejji, Shridhar, P.1 aPuranik, Vedavati, G.1 aDhavale, Dilip, D. uhttps://library.ncl.res.in/content/synthesis-and-conformational-study-chiral-oxepines-baylis-hillman-reaction-and-rcm-001922nas a2200265 4500008004100000022001400041245010100055210006900156260007300225300001200298490000800310520097200318653001301290653002301303653002301326653002101349653001801370100002101388700002301409700002401432700002301456700002401479700002201503856013101525 2010 eng d a0022-286000aCrystal structure, NMR and theoretical investigations on 2-(o-hydroxy-anilino)-1,4-napthoquinone0 aCrystal structure NMR and theoretical investigations on 2ohydrox aPO BOX 211, 1000 AE AMSTERDAM, NETHERLANDSbELSEVIER SCIENCE BVcMAR a144-1510 v9663 a

Crystal structure, (1)H NMR and cyclic voltammetric investigations of 2-(o-hydroxy-anilino)-1,4-napthoquinone (HAN), resulting from coupling of aminophenol with 2-hydroxy-1,4-napthoquinone, have been carried out. X-ray structure reveals that the HAN ligand crystallizes in orthorhombic space group Pca2(1) with Z = 4. forming a chain via inter-molecular O2 center dot center dot center dot H1A-O1 and C15-H15 center dot center dot center dot O3 interactions. Both (1)H NMR and cyclic voltammetry experiments suggest the titled ligand is associated and exists as dinner in d(6)-DMSO while the monomer has been predicted in CDCl(3) solution. Density functional calculations can be utilized to gauge the strength of hydrogen-bonded interactions from the (1)H chemical shifts in the NMR spectra. Self-consistent reaction field (SCRF) calculations further support the inferences drawn from cyclic voltammetry experiments. (C) 2009 Elsevier B.V. All rights reserved.

10a(1)H NMR10acyclic voltammetry10aDensity functional10ahydrogen bonding10aNapthoquinone1 aFeizi, Nourollah1 aPinjari, Rahul, V.1 aGejji, Shridhar, P.1 aSayyed, Fareed, B.1 aGonnade, Rajesh, G.1 aRane, Sandhya, Y. uhttps://library.ncl.res.in/content/crystal-structure-nmr-and-theoretical-investigations-2-o-hydroxy-anilino-14-napthoquinone-002789nas a2200217 4500008004100000022001400041245014400055210006900199260007100268300001200339490000700351520192500358100002102283700002302304700002302327700002102350700002602371700002402397700002602421856012402447 2011 eng d a0020-166900aSynthesis, electronic structure, DNA and protein binding, DNA cleavage, and anticancer activity of fluorophore-labeled copper(II) complexes0 aSynthesis electronic structure DNA and protein binding DNA cleav a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcJAN a545-5580 v503 a

Two mononuclear fluorophore-labeled copper(II) complexes [Cu(nip)(acac)](+) (2) and [Cu(nip)(2)](2+) (3), where fluorophore is 2-(naphthalen-1-yl)-1H-imidazo[4,5-f][1,10]phenanthroline (nip) (1) and acac is acetylacetone, have been synthesized aid characterized by various techniques. The ligand 1 and complex 2 are structurally characterized by single-crystal X-ray diffraction. The coordination geometries around the copper are square planar in solid as well as solution state as evidenced by electron paramagnetic resonance (EPR) spectroscopy. The density functional calculations carried out on 1-3 have shown that electron-rich regions in the highest occupied orbital are localized on the naphthalene end partly on the phenanthroline moiety. Both complexes 2 and 3 in dimethyl sulfoxide (DMSO) exhibit near square planar structure around the metal ion in their ground state. Time-dependent density functional theory (TD-DFT) calculations reveal that Cu(II) ion in complex 2 shows tetrahedral coordination around the metal while 3 retains its square planar geometry in the lowest excited state. The interaction of complexes with calf-thymus DNA (CT DNA) has been explored by using absorption, emission, thermal denaturation, and viscosity studies, and the intercalating mode of DNA binding has been proposed. The complexes cleave DNA oxidatively without any exogenous additives. The protein binding ability has been monitored by quenching of tryptophan emission in the presence of complexes using bovine serum albumin (BSA) as model protein. The compounds showed dynamic quenching behavior. Further, the anticancer activity of the complexes on MCF-7 (human breast cancer), HeLa (human cervical cancer), HL-60 (human promyelocytic leukemia), and MCF-12A (normal epithelial) cell lines has been studied. It has been observed that 3 exhibits higher cytotoxicity than 2, and the cells undergo apoptotic cell death.

1 aBhat, Satish, S.1 aKumbhar, Anupa, A.1 aHeptullah, Hussain1 aKhan, Ayesha, A.1 aGobre, Vivekanand, V.1 aGejji, Shridhar, P.1 aPuranik, Vedavati, G. uhttps://library.ncl.res.in/content/synthesis-electronic-structure-dna-and-protein-binding-dna-cleavage-and-anticancer-001651nas a2200253 4500008004100000022001400041245011400055210006900169260011000238300001200348490000700360520067200367100002201039700002301061700002101084700002101105700002501126700002401151700002601175700002301201700002401224700002201248856012701270 2014 eng d a1144-054600aCu(II) conjugation along the transformation of a vitamin K-3 derivative to a dinaphthoquinone methide radical0 aCuII conjugation along the transformation of a vitamin K3 deriva aTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLANDbROYAL SOC CHEMISTRYcJAN a277-2840 v383 a

1,1'-Methide-bi-vitamin K-3 (B) has been isolated as a dinaphthoquinone methide radical (DNQM) by the transformation of 1-imino(acetylhydrazino)-vitamin K-3 (A). The transformation follows a biomimetic activation pathway mediated via Cu(II) ion catalyzed oxidative coupling. Single crystal X-ray and electron spin resonance (ESR) experiments combined with density functional calculations elucidate the ``resonance structure'' of the DNQM radical (B). Fluorescence investigations reveal that DNQM facilitates interaction with the cysteine residue. As compared to the parent substrate, B shows a depletion in the level of GSH, triggering apoptosis in HeLa cells.

1 aBadave, Kirti, D.1 aPatil, Shalaka, S.1 aKhan, Ayesha, A.1 aSrinivas, Darbha1 aButcher, Raymond, J.1 aGonnade, Rajesh, G.1 aPuranik, Vedavati, G.1 aPinjari, Rahul, V.1 aGejji, Shridhar, P.1 aRane, Sandhya, Y. uhttps://library.ncl.res.in/content/cuii-conjugation-along-transformation-vitamin-k-3-derivative-dinaphthoquinone-methide-002215nas a2200277 4500008004100000022001400041245010800055210006900163260007300232300001000305490000900315520124800324653001301572653000801585653002101593653002301614653001401637653001501651100002101666700002401687700002201711700002301733700002601756700002701782856012801809 2015 eng d a0022-286000aFirst naphthosemiquinone complex of K+ with vitamin K3 analog: experiment and density functional theory0 aFirst naphthosemiquinone complex of K with vitamin K3 analog exp aPO BOX 211, 1000 AE AMSTERDAM, NETHERLANDSbELSEVIER SCIENCE BVcMAY a56-630 v10883 a

Synthesis and characterization of potassium complex of 2-hydroxy-3-methyl-1,4-naphthoquinone (phthiocol), the vitamin K3 analog, has been carried out using FT-IR, UV-Vis, H-1 and C-13 NMR, EPR, cyclic voltammetry and single crystal X-ray diffraction experiments combined with the density functional theory. It has been observed that naphthosemiquinone binds to two K+ ions extending the polymeric chain through bridging oxygens O(2) and O(3). The crystal network possesses hydrogen bonding interactions from coordinated water molecules showing water channels along the c-axis. C-13 NMR spectra revealed that the complexation of phthiocol with potassium ion engenders deshielding of C(2) signals, which appear at delta = similar to 14.6 ppm whereas those of C(3) exhibit up-field signals near delta similar to 6.9 ppm. These inferences are supported by the M06-2x based density functional theory. Electrochemical experiments further suggest that reduction of naphthosemiquinone results in only a cathodic peak from catechol. A triplet state arising from interactions between neighboring phthiocol anion lead to a half field signal at g = 4.1 in the polycrystalline X-band EPR spectra at 133 K. (C) 2015 Elsevier B.V. All rights reserved.

10aC-13 NMR10aDFT10ahydrogen bonding10aNaphthosemiquinone10aPhthiocol10aVitamin K31 aKathawate, Laxmi1 aGejji, Shridhar, P.1 aYeole, Sachin, D.1 aVerma, Prakash, L.1 aPuranik, Vedavati, G.1 aSalunke-Gawali, Sunita uhttps://library.ncl.res.in/content/first-naphthosemiquinone-complex-k-vitamin-k3-analog-experiment-and-density-functional-002237nas a2200229 4500008004100000022001400041245010600055210006900161260011000230300001600340490000600356520134200362100001701704700002801721700002101749700002001770700002401790700002601814700002601840700002701866856011401893 2015 eng d a2046-206900aTargeting a chemorefractory COLO205 (BRAF V600E) cell line using substituted benzo[alpha]phenoxazines0 aTargeting a chemorefractory COLO205 BRAF V600E cell line using s aTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLANDbROYAL SOC CHEMISTRYcSEP a82549-825630 v53 a

Mutational activations of the oncogene BRAF (especially BRAF V600E) result in a poor prognosis for colon cancer patients and are associated with chemoresistance rendering them refractory to treatment. The development of novel bioactive compounds with specific targeting abilities under such conditions is an urgent need in drug discovery. In this report we synthesize and characterize three fluorescent benzo[alpha]phenoxazine compounds (10R-benzo[alpha]phenoxazine-5-one, 1B; R = Cl, 2B; R = CH3, 3B; R = H) and their anticancer activities are evaluated in a COLO205 cell line. All three compounds with a log P value around 2 were cell permeable. However, 2B and 3B showed specific cytotoxicity in a malignant COLO205 cell line with a BRAF mutation (V600E) in comparison to a non-malignant wild-type BRAF HEK293T cell line. From further cell-based assays (cell cycle analysis, DNA fragmentation and caspase activation), we conclude that 2B and 3B treatment-induced selective cell death by inducing cell cycle arrest at the G0/G1 phase and caspase-mediated apoptosis (activation of the intrinsic and extrinsic pathways) are present only in BRAF V600E COLO205 cells. Further studies in the drug discovery pipeline might help develop these benzo[alpha]phenoxazines as promising chemotherapeutics for such refractory mutated cancers.

1 aPal, Sanjima1 aKonkimalla, Badireenath1 aKathawate, Laxmi1 aRao, Soniya, S.1 aGejji, Shridhar, P.1 aPuranik, Vedavati, G.1 aWeyhermueller, Thomas1 aSalunke-Gawali, Sunita uhttps://library.ncl.res.in/content/targeting-chemorefractory-colo205-braf-v600e-cell-line-using-substituted-001147nas a2200301 4500008004100000022001400041245010100055210006900156260000900225300001100234490000800245520016600253653000600419653001900425653001600444653002300460653002200483653002400505100001700529700002200546700002100568700002400589700002600613700002700639700002600666700002700692856012600719 2019 eng d a0277-538700aAmphiphilic polypyridyl ruthenium complexes: synthesis, characterization and aggregation studies0 aAmphiphilic polypyridyl ruthenium complexes synthesis characteri cMAY  a96-1070 v1643 a

{Synthesis and characterization of five amphiphilic ruthenium(11) complexes of the type [Ru(Cn)(3)]center dot(PF6)(2) (Cn = 4,4'-dialkyl-2,2'-bipyridine

10a210a2 `-bipyridine10aAggregation10aAmphiphilic ligand10aMetallosurfactant10aRuthenium complexes1 aBhand, Sujit1 aLande, Dipali, N.1 aPereira, Eulalia1 aGejji, Shridhar, P.1 aWeyhermueller, Thomas1 aChakravarty, Debamitra1 aPuranik, Vedavati, G.1 aSalunke-Gawali, Sunita uhttps://library.ncl.res.in/content/amphiphilic-polypyridyl-ruthenium-complexes-synthesis-characterization-and-aggregation02005nas a2200253 4500008004100000022001400041245007700055210006900132260000900201300001400210490000700224520117700231100002201408700002701430700002701457700002201484700002201506700002401528700002401552700002101576700002601597700002001623856010801643 2020 eng d a1144-054600aSynthesis and biological activity of imidazole based 1,4-naphthoquinones0 aSynthesis and biological activity of imidazole based 14naphthoqu cMAY  a6889-69010 v443 a

Design and development of drugs in multi-drug resistant (MDR) infections have been of growing interest. We report the syntheses, and antibacterial and antifungal activities of imidazole-based 1,4-naphthoquinones (I-1 to I-4; 1-alkyl-2-methyl-1H-naphtho[2,3-d]imidazole-4,9-dione (alkyl = methyl to butyl)) and their precursors (B-3; N-(3-chloro-1,-dioxo-1,4-dihydronaphthalen-2-yl)acetamide) and A-1 to A-4; N-(3-(alkylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide (alkyl = methyl to butyl). Crystal structures of B-3, A-1 to A-3 and I-2 to I-4 were obtained through single crystal X-ray diffraction experiments. Electronic structure and charge distribution have further been characterized with the use of Density Functional Theory. Seven of these derivatives display a broad spectrum of antibacterial activity against few selected bacterial strains (Gram-positive and Gram-negative). As demonstrated MIC values with B-2 and B-3 against bacterial isolates were 8-64 mu g ml(-1) and those against pathogenic yeast, C. albicans, were observed in the range of 128-256 mu g ml(-1). MIC data of these derivatives suggest them to be promising against pathogens.

1 aChoudhari, Dinkar1 aSalunke-Gawali, Sunita1 aChakravarty, Debamitra1 aShaikh, Samir, R.1 aLande, Dipali, N.1 aGejji, Shridhar, P.1 aRao, Pradeep, Kumar1 aSatpute, Surekha1 aPuranik, Vedavati, G.1 aGonnade, Rajesh uhttps://library.ncl.res.in/content/synthesis-and-biological-activity-imidazole-based-14-naphthoquinones04103nas a2200253 4500008004100000022001400041245015900055210006900214260000800283300001000291490000700301520318700308100002003495700002703515700002403542700002003566700002703586700002303613700002803636700002003664700001903684700002603703856012003729 2021 eng d a2576-989800aReactions of 2,3-dibromonaphthalene-1,4-dione and pyridyl amines: X-ray structures, DFT investigations, and selective detection of the Hg2+ and Ni2+ ions0 aReactions of 23dibromonaphthalene14dione and pyridyl amines Xray cFEB a78-930 v143 a

In this work, the products formed by the reaction between 2,3-dibromonaphthalene-1,4-dione with (pyridine-2-yl)methanamine and (pyridine-4-yl)methanamine are discussed in detial. The products 2-amino-3-bromonaphthalene-1,4-dione (A) and 2-aminonaphthalene-1,4-dione (B(1)) obtained are characterized through 1H and 13C-NMR, FTIR, mass spectrometry, single-crystal X-ray diffraction experiments, which are in conjunction with wB97X based density functional theory. compound A can effectively and selectively detect Hg2+ and Ni2+ ions, and proposes a potential mechanism of action.

1 aAggrwal, Gunjan1 aSalunke-Gawali, Sunita1 aGejji, Shridhar, P.1 aNikalje, Milind1 aChakravarty, Debamitra1 aVerma, Prakash, L.1 aGosavi-Mirkute, Prajkta1 aHarihar, Shital1 aJadhav, Mahesh1 aPuranik, Vedavati, G. uhttps://library.ncl.res.in/content/reactions-23-dibromonaphthalene-14-dione-and-pyridyl-amines-x-ray-structures-dft02379nas a2200349 4500008004100000022001400041245013700055210006900192260000900261300001100270490000900281520118000290653000601470653002701476653003701503653003301540653003001573653002801603653003701631100002601668700001801694700001701712700002401729700001801753700002201771700002401793700002101817700002001838700002101858700002101879856012901900 2026 eng d a0022-286000aStructural characterisation, anticancer properties, and BSA binding of 2,6-dipyrazinylpyridines: Insights from experiment and theory0 aStructural characterisation anticancer properties and BSA bindin cFEB  a1442250 v13513 a

The phenyl-(2,6-di-2-pyrazinyl)pyridine derivatives (L1, L2) were synthesized using a one-pot Krohnke-type method, starting from 2-acetylpyrazine and substituted benzaldehydes. Their structures were characterized using a combination of spectroscopic (NMR, HRMS) and single-crystal X-ray diffraction techniques, complemented by density functional theory (DFT). Single-crystal X-ray diffraction reveals that L1 crystallizes in the C2/c space group (T = 296 K) with its supramolecular assembly being stabilized by C-H & ctdot;N and pi-pi stacking interactions, whereas L2 facilitates C-H & ctdot;N, N-H & ctdot;pi bifurcated, and pi-pi* interactions. The bio-interaction properties of L1 were studied using fluorescence spectroscopy with bovine serum albumin (BSA) as a model protein. Fluorescence studies demonstrated L1 induces static quenching of BSA, with a binding constant of 5.15 x 104 mol & sdot;dm-3. Synchronous and three-dimensional fluorescence spectra further demonstrated that L1 brings forth significant conformational changes in BSA. The compounds were evaluated for cytotoxicity against the HCT-116 human colorectal cancer cell line.

10a210a6-dipyrazinylpyridines10aBovine serum albumin interaction10aCytotoxicity (HCT-116 cells)10aDensity functional theory10aHalogenated derivatives10aSingle-crystal X-ray diffraction1 aEnumula, Sreenivasulu1 aShaikh, Javed1 aShaikh, Amin1 aSheikh, Kounsar, N.1 aTambe, Pranav1 aLande, Dipali, N.1 aGejji, Shridhar, P.1 aShaligram, Parth1 aGonnade, Rajesh1 aBhadbhade, Mohan1 aAhmed, Khursheed uhttps://library.ncl.res.in/content/structural-characterisation-anticancer-properties-and-bsa-binding-26-dipyrazinylpyridines