4657-93-6Relevant academic research and scientific papers
Development and evaluation of a pharmacophore model for inhibitors of aldosterone synthase (CYP11B2)
Ulmschneider, Sarah,Negri, Matthias,Voets, Marieke,Hartmann, Rolf W.
, p. 25 - 30 (2006)
Recently, we proposed inhibition of aldosterone synthase (CYP11B2) as a novel strategy for the treatment of congestive heart failure and myocardial fibrosis and synthesized a large number of inhibitors. In this work, a pharmacophore model for CYP11B2 inhibitors was developed by superimposition of active and non-active compounds. This model was confirmed by the synthesis of two pyridyl substituted acenaphthene derivatives (A,B). This new class of compounds as well as the pharmacophore could be helpful for the discovery of novel inhibitors.
Cobalt-Catalyzed Direct Carbonylative Synthesis of Free (NH)-Benzo[ cd]indol-2(1 H)-ones from Naphthylamides
Ying, Jun,Fu, Lu-Yang,Zhong, Guoqiang,Wu, Xiao-Feng
supporting information, p. 5694 - 5698 (2019/07/08)
A cobalt-catalyzed C-H carbonylation of naphthylamides for the synthesis of benzo[cd]indol-2(1H)-one scaffolds has been developed. The reaction employs a traceless directing group and uses benzene-1,3,5-triyl triormate as the CO source, affording various free (NH)-benzo[cd]indol-2(1H)-ones in moderate to high yields (up to 88%). Using this protocol, the total synthesis of BET bromodomain inhibitors A and B was accomplished as well.
Synthesis and study of antiproliferative, antitopoisomerase II, DNA-intercalating and DNA-damaging activities of arylnaphthalimides
Quintana-Espinoza, Patricia,Garcia-Luis, Jonay,Amesty, Angel,Martin-Rodriguez, Patricia,Lorenzo-Castrillejo, Isabel,Ravelo, Angel G.,Fernandez-Perez, Leandro,Machin, Felix,Estevez-Braun, Ana
supporting information, p. 6484 - 6495 (2013/10/22)
A series of arylnaphthalimides were designed and synthesized to overcome the dose-limiting cytotoxicity of N-acetylated metabolites arising from amonafide, the prototypical antitumour naphthalimide whose biomedical properties have been related to its ability to intercalate the DNA and poison the enzyme Topoisomerase II. Thus, these arylnaphthalimides were first evaluated for their antiproliferative activity against two tumour cell lines and for their antitopoisomerase II in vitro activities, together with their ability to intercalate the DNA in vitro and also through docking modelization. Then, the well-known DNA damage response in Saccharomyces cerevisiae was employed to critically evaluate whether these novel compounds can damage the DNA in vivo. By performing all these assays we conclude that the 5-arylsubstituted naphthalimides not only keep but also improve amonafide's biological activities.
Reaction of substituted 5-bromoacenaphthenes with the catalytic reduction system NiCl2-2,2'-bipyridyl (or 1,10-phenanthroline)-Zn
Adonin,Ryabinin,Starichenko
, p. 913 - 915 (2007/10/03)
Transformations of substituted 5-bromoacenaphthenes under the action of a catalytic reduction system NiCl2-2,2'-bipyridyl (or 1,10-phenanthrolyne)-Zn in DMF and DMA was studied. Two types of transformation are shown to be characteristic for the studied compounds: reductive coupling with formation of the corresponding 5,5'-biacenaphthenyl and halogen elimination with hydrogen replacing the halogen. Yields of the coupling products and that of dehalogenation are found to depend substantially on the nature of the substituents in the nanhfhalene ring.
SUBSTITUTED GUANIDINES AND DERIVATIVES THEREOF AS MODULATORS OF NEUROTRANSMITTER RELEASE AND NOVEL METHODOLOGY FOR IDENTIFYING NEUROTRANSMITTER RELEASE BLOCKERS
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, (2008/06/13)
Modulators of neurotransmitter release including substituted guanidines, N"-aminoguanidines, and N,N'N",N"'-tetrasubstituted hydrazinedicarboximidamides, and pharmaceutical compositions thereof are disclosed. Also disclosed are methods involving the use of such neurotransmitter release modulators for the treatment or prevention of pathophysiologic conditions characterized by the release of excessive or inappropriate levels of neurotransmitters. Also disclosed are screening assays for compounds which selectively inhibit glutamate release. Also disclosed are methods of blocking voltage sensitive sodium and calcium channels in mammalian nerve cells. "
Condensed heterocycles: Part XXVI - Synthesis of cycloalkaazaphenanthrenes and cycloalkaaza-acephenanthrenes
Sharma, K. S.,Singh, S. P.,Kumari, Sharda
, p. 1191 - 1192 (2007/10/02)
Various 2-formylcycloalkanones on reaction with α-naphthylamine furnish the corresponding 2-(α-naphthylaminomethylene)cycloalkanones (1 and 3) which on PPA cyclisation afford the desired cycloalkaazaphenanthrenes (2 and 4). 5-Aminoacenaphthene on a similar treatment with 2-formylcycloalkanones give the corresponding 2-(5-acenaphthylaminomethylene)cycloalkanones (5, 7 and 9) which undergo smooth cyclisation to provide the desired cycloalkaaza-acephenanthrenes (6, 8 and 10).The structures of the products have been elucidated by elemental analyses, IR and 1H NMR spectral data.
Sterically Congested Polycyclic Hydrocarbons with Nonoptimal Geometries. 4,5-Didehydroacenaphthene as a Precursor for the Synthesis of 7,14-Diphenyl-8,9-(1',8'-naphthenylene)acephenanthrene
Plummer, Benjamin F.,Russell, Steven J.,Reese, W. Gregory,Watson, William H.,Krawiec, Mariusz
, p. 3219 - 3223 (2007/10/02)
A multistep synthetic route for the synthesis of the reactive intermediate 4,5-didehydroacenaphthene (15) is described.A mixture of N-1-, N-2-, and N-3-aminoacenaphthotriazoles is produced, which is oxidized by lead tetraacetate (LTA) to the corresponding aryne.The N-2-triazole is oxidized by LTA to 7-cyano-1-(cyanomethylene)indan (18), whose structure was verified by X-ray analysis.Intermediate 15 was trapped by 7,9-diphenyl-8H-cyclopentaacenaphthylen-8-one (acecyclone) to produce the congested hydrocarbon 7,14-diphenyl-8,9-(1',8'-naphthenylene)acephenanthrene (20).There is a small deviation from planarity for 20, and this is modeled by MMX calculations and verified by X-ray crystallographic analysis of the structure.
