106391-86-0Relevant articles and documents
Synthesis and biological evaluation of pyridine-modified analogues of 3-(2-aminoethoxy)pyridine as novel nicotinic receptor ligands
Lin, Nan-Horng,Dong, Liming,Bunnelle, William H,Anderson, David J,Meyer, Michael D
, p. 3321 - 3324 (2002)
Analogues of the potent nicotinic receptor agonist 3-(2-aminoethoxy)pyridine substituted at the 5′ and 6′-positions of the pyridine ring were synthesized and tested in vitro for nicotinic receptor binding activity (displacement of [3H](-)cytisine from whole rat brain synaptic membranes). The substituted analogues exhibited Ki values ranging from 0.076 to 319 nM compared to a Ki value of 26 nM for compound 1. Among the compounds tested, 5′-vinyl-6′-chloro substituted 1 was the most potent.
Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production
Reddy Guduru, Shiva Krishna,Chamakuri, Srinivas,Raji, Idris O.,MacKenzie, Kevin R.,Santini, Conrad,Young, Damian W.
, p. 11777 - 11793 (2018)
The piperazine heterocycle is broadly exploited in FDA-approved drugs and biologically active compounds, but its chemical diversity is usually limited to ring nitrogen substitutions, leaving the four carbon atoms underutilized. Using an efficient six-step synthesis, chiral amino acids were transformed into 3-substituted piperazine-2-acetic acid esters as diastereomeric mixtures whose cis and trans products (dr 0.56 a? 2.2:1, respectively) could be chromatographically separated. From five amino acids (both antipodes) was obtained a complete matrix of 20 monoprotected chiral 2,3-disubstituted piperazines, each as a single absolute stereoisomer, all but one in multigram quantities. In keeping with our overall purpose of constructing more Csp3-enriched compound libraries for drug discovery, these diverse and versatile piperazines can be functionalized on either nitrogen atom, allowing them to be used as scaffolds for parallel library synthesis and as intermediates for the production of novel piperazine compounds.
Exploring the dNTP -binding site of HIV-1 reverse transcriptase for inhibitor design
Das, Kalyan,De Jonghe, Steven,Gu, Weijie,Herdewijn, Piet,Martinez, Sergio,Nguyen, Hoai,Rozenski, Jef,Schols, Dominique,Singh, Abhimanyu K.
, (2021)
HIV-1 reverse transcriptase (RT) plays a central role in the viral life cycle, and roughly half of the FDA-approved anti-HIV drugs are targeting RT. Nucleoside analogs (NRTIs) require cellular phosphorylation for binding to RT, and to bypass this rate-limiting path, we designed a new series of acyclic nucleoside phosphonate analogs as nucleoside triphosphate mimics, aiming at the chelation of the catalytic Mg2+ ions via a phosphonate and/or a carboxylic acid group. Novel synthetic procedures were developed to access these nucleoside phosphonate analogs. X-ray structures in complex with HIV-1 RT/dsDNA demonstrated that their binding modes are distinct from that of our previously reported compound series. The impact of chain length, chirality and linker atom have been discussed. The detailed structural understanding of these new compounds provides opportunities for designing new class of HIV-1 RT inhibitors.
Pellasoren: Structure elucidation, biosynthesis, and total synthesis of a cytotoxic secondary metabolite from Sorangium cellulosum
Jahns, Christine,Hoffmann, Thomas,Mueller, Stefan,Gerth, Klaus,Washausen, Peter,Hoefle, Gerhard,Reichenbach, Hans,Kalesse, Markus,Mueller, Rolf
, p. 5239 - 5243 (2012)
Genetic analysis of biosynthetic gene clusters is becoming an accepted tool to predict the stereochemical outcome of a biosynthesis. However, in the case of pellasoren, one chiral center was not predicted correctly. The absolute configuration was verified by total synthesis, which also demonstrated that stereoselective protonations can be successfully applied to natural products synthesis. Copyright
Fluorinated Olefinic Lactams: The Case of Amino Acids - Preparation and Mechanistic Studies
Bartoszak-Adamska, El?bieta,Go?dyn, Mateusz,Koroniak, Henryk,Koroniak-Szejn, Katarzyna,Salamon-Krokosz, Katarzyna,Siod?a, Tomasz
, (2022/03/17)
Herein, we report the synthesis of analogues of amino acids with a monofluorovinyl moiety. Interestingly, we have found that cyclization of the obtained products proceeds easily in all cases. The cyclization process has not previously been observed at this reaction stage, and such fluorinated lactams derived from phenylalanine, valine, alanine have not been described before.
Urea based foldamers
Yoo, Sung Hyun,Li, Bo,Dolain, Christel,Pasco, Morgane,Guichard, Gilles
, p. 59 - 92 (2021/06/25)
N,N′-linked oligoureas are a class of enantiopure, sequence-defined peptidomimetic oligomers without amino acids that form well-defined and predictable helical structures akin to the peptide α-helix. Oligourea-based foldamers combine a number of features—such as synthetic accessibility, sequence modularity, and folding fidelity—that bode well for their use in a range of applications from medicinal chemistry to catalysis. Moreover, it was recently recognized that this synthetic helical backbone can be combined with regular peptides to generate helically folded peptide-oligourea hybrids that display additional features in terms of helix mimicry and protein-surface recognition properties. Here we provide detailed protocols for the preparation of requested monomers and for the synthesis and purification of homo-oligoureas and peptide-oligourea hybrids.
Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides
Steiman, Talia J.,Liu, Junyi,Mengiste, Amanuella,Doyle, Abigail G.
supporting information, p. 7598 - 7605 (2020/04/21)
A photoassisted Ni-catalyzed reductive cross-coupling between tosyl-protected alkyl aziridines and commercially available (hetero)aryl iodides is reported. This mild and modular method proceeds in the absence of stoichiometric heterogeneous reductants and uses an inexpensive organic photocatalyst to access medicinally valuable β-phenethylamine derivatives. Unprecedented reactivity was achieved with the activation of cyclic aziridines. Mechanistic studies suggest that the regioselectivity and reactivity observed under these conditions are a result of nucleophilic iodide ring opening of the aziridine to generate an iodoamine as the active electrophile. This strategy also enables cross-coupling with Boc-protected aziridines.
HETEROCYCLIC COMPOUNDS
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Paragraph 0224; 0281, (2020/12/29)
Provided herein are compounds of formula (I) which comprise a thiomorpholine 1,1-dioxide or 1-imino-thiomorpholine 1-oxide moiety, or pharmaceutically acceptable salts of any of the foregoing, pharmaceutical compositions that include a compound described herein (including salts of the compound) and methods of synthesizing the same. Also provided are methods of treating Hepatitis B viral (HBV) infections using a compound of formula (I), or pharmaceutically acceptable salts thereof.
NON-FUSED TRICYCLIC COMPOUNDS
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Paragraph 00691, (2018/11/26)
Provided herein are compounds and pharmaceutical compositions comprising said compounds that are useful for treating cancers. Specific cancers include those that are mediated by YAP/TAZ or those that are modulated by the interaction between YAP/TAZ and TEAD.
SHORT-ACTING BENZODIAZEPINE DERIVATIVES, PREPARATION METHOD THEREFOR, AND USE THEREOF
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Paragraph 0408-0409; 0461-0462, (2018/11/21)
The present invention relates to a benzodiazepine derivative of Formula I as a short-acting anesthetic, a pharmaceutical composition comprising the same, a kit comprising the same, a preparation method thereof, an method of anesthesia using the same and use thereof in the manufacture of an anesthetic medicament.
