138490-94-5Relevant academic research and scientific papers
Total Synthesis of (±)-Thebainone A by Intramolecular Nitrone Cycloaddition
Hahn, Christian,Hennig, André,J?ger, Anne,Küttler, Thomas,Metz, Peter,Wang, Yuzhou
, (2020/04/21)
Using an intramolecular nitrone cycloaddition and a Heck cyclization as the crucial transformations, a total synthesis of the racemic morphine alkaloid thebainone A was accomplished in 22 steps commencing with isovanillin.
Synthesis, biological evaluation and molecular modeling studies of substitutedN-benzyl-2-phenylethanamines as cholinesterase inhibitors
Carmona-Viglianco, Florencia,Enriz, Ricardo D.,Feresin, Gabriela E.,Garro, Adriana,Kurina-Sanz, Marcela,Orden, Alejandro A.,Parravicini, Oscar,Zaragoza-Puchol, Daniel
, p. 9466 - 9476 (2020/06/17)
In this work, we report the synthesis of a series of derivatives ofN-benzyl-2-phenylethanamine which is the framework of norbelladine, the natural common precursor of the Amaryllidaceae alkaloids. These compounds were assessed in the inhibition of both AChE and BChE which are the enzymes responsible for the breakdown of acetylcholine and hence they constitute targets in the palliative treatment of Alzheimer's disease. In particular, brominated derivatives exhibited the lowest IC50values against AChE. Interestingly, the presence of iodine in one of the aromatic rings highly increased the inhibition of BChE compared to its analogues, with an IC50value similar to that of galantamine, which is the reference compound currently used in the treatment of AD. A possible mechanism of action for these compounds was determined by molecular modeling studies using combined techniques of docking and molecular dynamics simulations.
Enantioselective Synthesis and Racemization of (?)-Sinoracutine
Volpin, Giulio,Vep?ek, Nynke A.,Bellan, Andreas B.,Trauner, Dirk
supporting information, p. 897 - 901 (2017/01/14)
Sinoracutine is a recently isolated alkaloid with unusual stereochemical and biological properties. It features an unprecedented tetracyclic 6/6/5/5 skeleton that bears an N-methylpyrrolidine ring fused to a cyclopentenone. Interestingly, both enantiomers
Synthesis of 2,3,9,10-Tetraoxygenated benzo[c]phenanthridine derivatives via palladiummediated aryl-Aryl coupling reaction
Abe, Hitoshi,Kobayashi, Naoko,Kadoshima, Yutaka,Takeuchi, Yasuo,Harayama, Takashi,Horino, Yoshikazu
, p. 673 - 684 (2017/04/10)
Two 2,3,9,10-Tetraoxygenated benzo[c]phenanthridine alkaloids, 1 2, originally reported as zanthoxyline and broussonpapyrine, respectively, were synthesized using the Pd-mediated intramolecular aryl-Aryl coupling reaction as the key step.
Synthesis of a functionalized benzofuran as a synthon for salvianolic acid C analogues as potential LDL Antioxidants
López-Frías, Gabriela,Camacho-Dávila, Alejandro A.,Chávez-Flores, David,Zaragoza-Galán, Gerardo,Ramos-Sánchez, Víctor H.
, p. 8654 - 8665 (2016/09/04)
A palladium mediated synthesis of a common synthon for the syntheses of antioxidant analogues of naturally occurring salvianolic acids is presented. The synthetic route may be used to obtain analogues with a balanced lipophilicity/hydrophilicity which may
AMPHIPATHIC AND OTHER DOUBLE-SIDED ALPHA-HELIX MIMETICS BASED ON A 1,2-DIPHENYLACETYLENE SCAFFOLD
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Page/Page column, (2014/09/29)
Small-molecule scaffolds based on 1,2-diphenylacetylene that accurately replicate the spatial and angular projections of several side chains on both faces of an α-helix, specifically the i and i+7 side chains on one face, and the i and i+2 side chains on the other. The amphipathic α-helix mimetic can be used to disrupt disease-promoting protein-protein interactions that are mediated by α-helices.
Amphipathic α-helix mimetics based on a 1,2-diphenylacetylene scaffold
Jung, Kwan-Young,Vanommeslaeghe, Kenno,Lanning, Maryanna E.,Yap, Jeremy L.,Gordon, Caryn,Wilder, Paul T.,Mackerell, Alexander D.,Fletcher, Steven
supporting information, p. 3234 - 3237 (2013/07/26)
In order to mimic amphipathic α-helices, a novel scaffold based on a 1,2-diphenylacetylene was designed. NMR and computational modeling confirmed that an intramolecular hydrogen bond favors conformations of the 1,2-diphenylacetylene that allow for accurat
A concise route to dihydrobenzo[b]furans: Formal total synthesis of (+)-lithospermic acid
Fischer, Joshua,Savage, G. Paul,Coster, Mark J.
supporting information; experimental part, p. 3376 - 3379 (2011/09/12)
A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH4Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan- 3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.
Synthetic applications of the nickel-catalyzed cyclization of alkynes combined with addition reactions in a domino process
Durandetti, Muriel,Hardou, Lucie,Lhermet, Rudy,Rouen, Mathieu,Maddaluno, Jacques
supporting information; experimental part, p. 12773 - 12783 (2011/12/04)
Carbonickelations of alkynes and functionalization of the resulting vinylnickel moiety have been performed efficiently in a nickel-catalyzed domino cyclization-condensation process. This reaction, which does not require the preparation of any other organometallic reagent, proceeds only by exo-dig cyclization. This convenient and mild method constitutes a one-pot synthesis of substituted dihydrobenzofurans, chromans, isochromans, indoles, or indanes. Theses valuable products are generally obtained in good yields and high stereoselectivity. They are shown to be useful synthons for rapid access to functionalized polycyclic skeletons. Yes nickel can! Carbonickelation of alkynes and functionalization of the resulting vinylnickel moiety occurs efficiently. Overall, a domino cyclization-condensation process propagated by substoichiometric nickel catalysis takes place (see scheme). This one-pot synthesis provides substituted polyheterocyclic compounds in good yields and high stereoselectivity.
Total synthesis of (±)-Galanthamine via a C3-selective stille coupling and IMDA cycloaddition cascade of 3,5-dibromo-2-pyrone
Chang, Jay Hyok,Kang, Ho-Ung,Jung, In-Hak,Cho, Cheon-Gyu
supporting information; experimental part, p. 2016 - 2018 (2010/06/21)
Figure presented A new efficient synthetic route to (±)-galanthamine was devised by using a tandem C3-selective Stille coupling-IMDA cascade of 3,5-dibromo-2-pyrone as a key strategy.
