02335nas a2200229 4500008004100000022001400041245017300055210006900228260007100297300001400368490000700382520140600389100002101795700002601816700002301842700002201865700002301887700002601910700002601936700002301962856012001985 2012 eng d a0022-326300aAlpha-geminal dihydroxymethyl piperidine and pyrrolidine iminosugars: synthesis, conformational analysis, glycosidase inhibitory activity, and molecular docking studies0 aAlphageminal dihydroxymethyl piperidine and pyrrolidine iminosug a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcSEP a7873-78820 v773 a

The Jocic-Reeve and Corey-Link type reaction of dichloromethyllithium with suitably protected 5-keto-hexofuranoses followed by treatment with sodium azide and sodium borohydride reduction gave 5-azido-5-hydroxylmethyl substituted hexofuranoses 7a-c with required geminal dihydroxymethyl group. Removal of protecting groups and converting the C-1 anomeric carbon into free hemiacetal followed by intramolecular reductive aminocyclization with in situ generated C5-amino functionality afforded corresponding 5C-dihydroxymethyl piperidine iminosugars 2a-c. Alternatively, removal of protecting groups in 7b and 7c and chopping of C1-anomeric carbon gave C2-aldehyde that on intramolecular reductive aminocyclization with CS-amino gave 4C-dihydroxyrnethyl pyrrolidine iminosugars 1b and 1c, respectively. On the basis of the H-1 NMR studies, the conformations of 2a/2b were assigned as C-4(1) and that of 2c as C-1(4). The glycosidase inhibitory activities of all five iminosugars were studied with various glycosidase enzymes and compared with natural o-g/uco-l-deoxynojirimycin (DNJ). All the five compounds were found to be potent inhibitors of rice alpha-glucosidase with K-i and IC50 values in the nanomolar concentration range. Iminosugars 2b and 1b were found to be more potent inhibitors than their parent iminosugar. These results were substantiated by in silico molecular docking studies.

1 aPawar, Nitin, J.1 aParihar, Vijay, Singh1 aChavan, Sanjay, T.1 aJoshi, Rakesh, S.1 aJoshi, Pranaya, V.1 aSabharwal, Sushma, G.1 aPuranik, Vedavati, G.1 aDhavale, Dilip, D. uhttps://library.ncl.res.in/content/alpha-geminal-dihydroxymethyl-piperidine-and-pyrrolidine-iminosugars-synthesis-002321nas a2200289 4500008004100000022001400041245013600055210006900191260011100260300001200371490000700383520126500390653002001655653003401675653001401709653001601723653001601739100001401755700001801769700001501787700001401802700002201816700002601838700002301864700001801887856012601905 2012 eng d a1566-524000aAndrographolide inhibits osteopontin expression and breast tumor growth through down regulation of PI3 Kinase/Akt signaling pathway0 aAndrographolide inhibits osteopontin expression and breast tumor aEXECUTIVE STE Y-2, PO BOX 7917, SAIF ZONE, 1200 BR SHARJAH, U ARAB EMIRATESbBENTHAM SCIENCE PUBL LTDcSEP a952-9660 v123 a

Breast cancer is one of the most common cancers among women in India and around the world. Despite recent advancement in the treatment of breast cancer, the results of chemotherapy to date remain unsatisfactory, prompting a need to identify natural agents that could target cancer efficiently with least side effects. Andrographolide (Andro) is one such molecule which has been shown to possess inhibitory effect on cancer cell growth. In this study, Andro, a natural diterpenoid lactone isolated from Andrographis paniculata has been shown to inhibit breast cancer cell proliferation, migration and arrest cell cycle at G2/M phase and induces apoptosis through caspase independent pathway. Our experimental evidences suggest that Andro attenuates endothelial cell motility and tumor-endothelial cell interaction. Moreover, Andro suppresses breast tumor growth in orthotopic NOD/SCID mice model. The anti-tumor activity of Andro in both in vitro and in vivo model was correlated with down regulation of PI3 kinase/Akt activation and inhibition of pro-angiogenic molecules such as OPN and VEGF expressions. Collectively, these results demonstrate that Andro may act as an effective anti-tumor and anti-angiogenic agent for the treatment of breast cancer.

10aAndrographolide10aangiogenesis and breast tumor10amigration10aosteopontin10aPI 3 kinase1 aKumar, S.1 aPatil, H., S.1 aSharma, P.1 aKumar, D.1 aDasari, Sreekanth1 aPuranik, Vedavati, G.1 aThulasiram, H., V.1 aKundu, G., C. uhttps://library.ncl.res.in/content/andrographolide-inhibits-osteopontin-expression-and-breast-tumor-growth-through-down-001219nas a2200193 4500008004100000022001400041245006400055210006400119260007100183300001400254490000700268520054200275100002500817700002100842700002600863700001900889700002100908856009600929 2013 eng d a0163-386400aAntimycobacterial labdane diterpenes from leucas stelligera0 aAntimycobacterial labdane diterpenes from leucas stelligera a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcOCT a1836-18410 v763 a

Phytochemical investigation of the acetone extract of the aerial parts of Leucas stelligera afforded four new compounds (1-4) belonging to the labdane diterpene series as well as two known flavones, velutin (5) and chrysoeriol (6). Structure elucidation of the new compounds was carried out using ID and 2D NMR spectroscopic data and single-crystal X-ray crystallography of compound 1. Compounds 1-4 exhibited selective antimycobacterial activity against Mycobacterium tuberculosis with IC50 values in the range 5.02-9.80 mu g/mL.

1 aKulkarni, Roshan, R.1 aShurpali, Ketaki1 aPuranik, Vedavati, G.1 aSarkar, Dhiman1 aJoshi, Swati, P. uhttps://library.ncl.res.in/content/antimycobacterial-labdane-diterpenes-leucas-stelligera-002655nas a2200325 4500008004100000022001400041245008700055210006900142260007700211300001400288520149300302653001301795653002001808653002001828653002301848100002701871700002401898700003301922700002101955700002201976700002501998700002102023700002602044700002402070700002302094700002602117700003502143700002802178856012302206 2013 eng d a1434-193X00aAnt-pro reverse-turn motif. structural features and conformational characteristics0 aAntpro reverseturn motif structural features and conformational  aBOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANYbWILEY-V C H VERLAG GMBHcJUN a3529-35423 a

This article details the characteristic conformational features of the Ant-Pro reverse turn ? a folded pseudo -turn motif that displays a closed nine-membered-ring hydrogen-bonded network involving just two amino acid residues, namely anthranilic acid (Ant; a constrained -amino acid), and proline (Pro; a constrained -amino acid). The results from the extensive investigation of ten crystal structures and their NMR conformations in the solution state provide a clear idea about the conformational characteristics of the Ant-Pro reverse turn. The Ant and Pro residues, which form the turn segment, maintain a perfect antiperiplanar orientation throughout, leaving little possibility for the formation of the otherwise possible six-membered hydrogen-bonding that requires a coplanar disposition of the two amino acid residues, as clearly evident from investigation of several crystal structures. The closed hydrogen-bonded network observed in the Ant-Pro reverse turn motif, formed in the forward direction of the sequence (12 amino acid interactions) involving only two amino acid residues, is in stark contrast to the native -turns that involve four residues to form hydrogen-bonded network featuring backward 14 amino acid interactions. The readily available two-residue Ant-Pro motif raises the possibility of a practical utility, particularly in the application of rigidifying flexible peptide backbones by inserting the robust Ant-Pro reverse turn motifs into their backbone.

10aPeptides10aPeptidomimetics10aProtein folding10aProtein structures1 aThorat, Vijaykumar, H.1 aIngole, Tukaram, S.1 aVijayadas, Kuruppanthara, N.1 aNair, Roshna, V.1 aKale, Sangram, S.1 aRamesh, Veera, V. E.1 aDavis, Hilda, C.1 aPrabhakaran, Panchami1 aGonnade, Rajesh, G.1 aGawade, Rupesh, L.1 aPuranik, Vedavati, G.1 aRajamohanan, Pattuparambil, R.1 aSanjayan, Gangadhar, J. uhttps://library.ncl.res.in/content/ant-pro-reverse-turn-motif-structural-features-and-conformational-characteristics-000793nas a2200217 4500008004100000022001400041245010500055210006900160260000800229300000900237490000700246653003400253653003200287653002100319100002600340700002300366700003100389700002600420700002000446856010900466 2014 eng d a2053-273300aAdditive induced capture of elusive polymorphs of conformationally flexible Sulfonamides/Sulfoesters0 aAdditive induced capture of elusive polymorphs of conformational cMAY aC7760 v7010aadditive induced polymorphism10aintermolecular interactions10aphase transition1 aShaikh, Samir, Rashid1 aGawade, Rupesh, L.1 aChakravarty, Debamitra, K.1 aPuranik, Vedavati, G.1 aGonnade, Rajesh uhttps://library.ncl.res.in/content/additive-induced-capture-elusive-polymorphs-conformationally-flexible04280nas a2200277 4500008004100000022001400041245018000055210006900235260007100304300001400375490000700389520321000396100002303606700003103629700001803660700001903678700002303697700001703720700002003737700001703757700001703774700003503791700002603826700002403852856012603876 2016 eng d a1528-748300aAdditive mediated syn-anti conformational tuning at nucleation to capture elusive polymorphs: remarkable role of extended pi-stacking interactions in driving the self-assembly0 aAdditive mediated synanti conformational tuning at nucleation to a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcAPR a2416-24280 v163 a

Understanding the process of prenucleation clustering at supersaturating stage is of significant importance to envisage the polymorphism in crystalline materials. Preferential formation of a thermodynamically stable crystal form suggests energetically favored patterns of interactions which control molecular aggregation during nucleation. Introduction of additives during crystallization is sometimes used as a suitable strategy to obtain metastable polymorphs in cases where it is not easy to capture the same by conventional crystallization methods. Comparative analysis of energy relationships and intermolecular interactions between thermodynamically stable and metastable crystal forms provides valuable clues about the nature of growth synthons at prenucleation clustering and preferential crystallization of the thermodynamic form. Conformationally flexible sulfonamide/sulfoester derivatives constituting electron rich and electron deficient aromatic rings were synthesized to study the interplay between pi-stacking and hydrogen bonding synthons. We have identified and characterized the thermodynamically stable and metastable elusive polymorphs of aromatic sulfonamides 1 and 2 and sulfoesters 3 and 4. However, these compounds eluded polymorphism during crystallisation from various common solvents/conditions and only produced thermodynamically stable crystals forms (form I crystals). Surprisingly, exploitation of pyrazinamide as an additive in different stoichiometric ratios during crystallization gave elusive polymorphs [three for 1 (form 1II, form 1III, and form 1IV) and one each for 2 (form 2II), 3 (form 3II), and 4 (form 4II)]. Molecules in stable crystal forms of these compounds are linked via extended chains of parallel displaced pi...pi stacking interactions that seem to play a vital role in driving the self-assembly of molecules and subsequently governing the nucleation process. In contrast, molecules in metastable polymorphs are devoid of such extended pi-stacking assemblies. Interestingly, differential scanning calorimetry, hot stage microscopy, and X-ray crystallographic studies confirmed the thermal crystal-to-crystal transition of all three metastable polymorphs of 1 (form 1II, form 1III, and form 1IV) to its thermodynamically stable crystal form (form 1I). Conformational analysis of molecule 1 using density functional theory calculations also validated higher stability for syn conformation (observed in Form 1I crystals) over anti and midway conformations (seen in metastable polymorphs). Melt crystallization of form 1I crystals of 1 on the larger face (001) of delta-pyrazinamide and lattice matching analysis (GRACE) revealed that the layered arrangement of molecules of delta-pyrazinamide (on 001 face) during heterogeneous nucleation acts as a template (heteroepitaxy) to provide a preferential site for the nucleation of new metastable polymorphs by selectively inhibiting the most preferred crystal form from growing into the nucleus. Solution state one- and two-dimensional (NOESY) H-1 NMR, scanning electron microscopy, and a Cambridge Structural Database survey were conducted to substantiate the role of additives during crystallization.

1 aGawade, Rupesh, L.1 aChakravarty, Debamitra, K.1 aKotmale, Amol1 aSangtani, Ekta1 aJoshi, Pranaya, V.1 aAhmed, Awais1 aMane, Manoj, V.1 aDas, Susanta1 aVanka, Kumar1 aRajamohanan, Pattuparambil, R.1 aPuranik, Vedavati, G.1 aGonnade, Rajesh, G. uhttps://library.ncl.res.in/content/additive-mediated-syn-anti-conformational-tuning-nucleation-capture-elusive-polymorphs01147nas 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-aggregation