112348-45-5Relevant academic research and scientific papers
Oxidative radical cyclizations of diketopiperazines bearing an amidomalonate unit. Heterointermediate reaction sequences toward the asperparalines and stephacidins
Amatov, Tynchtyk,Gebauer, Martin,Pohl, Radek,Cisa?ová, Ivana,Jahn, Ullrich
, p. S6 - S17 (2016)
A novel approach to the diazabicyclo[2.2.2]octane core of prenylated bridged diketopiperazine alkaloids is described by direct oxidative cyclizations of functionalized diketopiperazines mediated by ferrocenium hexafluorophosphate or the Mn(OAc)3?2H2O/Cu(OTf)2 system. Divergent reaction pathways take place depending on the substitution pattern of the substrates and the oxidation conditions such as temperature or the presence or absence of persistent radical TEMPO. For ester-substituted diketopiperazines, the ester group exerts a significant influence on the reaction outcome and stereochemistry of the radical cyclizations.
Anti-tumor diazo dicyclic apoptosis protein inhibitor
-
Paragraph 0099-103, (2019/08/01)
The invention provides a novel apoptosis protein inhibitor or pharmaceutically acceptable salts and isomers as well as preparation methods thereof and a pharmaceutical composition. The definition of each group is shown in the description. The invention further provides application of the compound and pharmaceutically acceptable salts and isomers thereof to preparation of medicines for treating IAP(Immimmunosuppressive Acidic Protein) related diseases. The compound disclosed by the invention has high binding affinity to XIAP, cIAP1 and cIAP2 proteins, has an excellent inhibiting effect on cellgrowth in MDA-MB-231 breast cancer and PC-3 pancreatic cancer cell lines, and also has high medicinal value and wide market prospects.
A Convergent Synthesis of Enantiopure Open-Chain, Cyclic, and Fluorinated α-Amino Acids
Li, Shi-Guang,Portela-Cubillo, Fernando,Zard, Samir Z.
, p. 1888 - 1891 (2016/05/19)
A radical based synthesis of a broad variety of protected enantiopure α-amino acids, including fluorinated derivatives, is described. The radical addition furnishes naturally latent mercapto-α-amino acids ideally equipped for native chemical ligation.
A systematic approach to diverse, lead-like scaffolds from α,α-disubstituted amino acids
Foley, Daniel J.,Doveston, Richard G.,Churcher, Ian,Nelson, Adam,Marsden, Stephen P.
supporting information, p. 11174 - 11177 (2015/07/07)
A powerful strategy for the efficient lead-oriented synthesis of novel molecular scaffolds is demonstrated. Twenty two scaffolds were prepared from just four α-amino acid-derived building blocks and a toolkit of six connective reactions. Importantly, each individual scaffold has the ability to specifically target lead-like chemical space.
Synthesis and evaluation of C8-substituted 4.5-spiro lactams as Glycogen Phosphorylase a inhibitors
Loughlin, Wendy A.,Schweiker, Stephanie S.,Jenkins, Ian D.,Henderson, Luke C.
supporting information, p. 1576 - 1582 (2013/03/29)
An effective synthesis of 4.5-spiro lactams 28/29, has been completed in nine steps with an overall yield of 5.8%. The 4.5-spiro lactams were made from 2-allyl-Cbz-Pro-OMe 21, which was converted into the corresponding alcohol 22 via a hindered borane reaction with (2-methylbutyl)2borane. Subsequent Swern oxidation of 22 gave novel aldehyde 23. Aldehyde 23 was treated under Bucherer-Bergs reaction conditions to give hydantoin 26, which was opened to the corresponding amino acid 30 using di-tert-butyl dicarbonate and DMAP followed by hydrolysis. Treatment of amino acid 30 with acidic methanol gave 4.5-spiro lactams 28/29. Only 4.5-spiro lactam 29 displayed moderate activity against GPa with an IC50 of 241 μM.
Design, synthesis, and biological evaluation of new monoamine reuptake inhibitors with potential therapeutic utility in depression and pain
Lucas, Matthew C.,Weikert, Robert J.,Carter, David S.,Cai, Hai-Ying,Greenhouse, Robert,Iyer, Pravin S.,Lin, Clara J.,Lee, Eun Kyung,Madera, Ann Marie,Moore, Amy,Ozboya, Kerem,Schoenfeld, Ryan C.,Steiner, Sandra,Zhai, Yansheng,Lynch, Stephen M.
scheme or table, p. 5559 - 5566 (2011/02/22)
Two new series of monoamine triple reuptake inhibitors (TRIs) have been discovered through scaffold homologation of our recently reported series of 3,3-disubstituted pyrrolidine TRIs. The regioisomeric 2- and 3-ketopyrrolidines demonstrated high levels of
Design, synthesis, and in vitro activity of peptidomimetic inhibitors of myeloid differentiation factor 88
Fantò, Nicola,Gallo, Grazia,Ciacci, Andrea,Semproni, Mauro,Vignola, Davide,Quaglia, Marco,Bombardi, Valentina,Mastroianni, Domenico,Zibella, M. Pia,Basile, Giancarlo,Sassano, Marica,Ruggiero, Vito,De Santis, Rita,Carminati, Paolo
, p. 1189 - 1202 (2008/09/20)
We describe the design and synthesis of a peptidomimetic library derived from the heptapeptide AC-RDVLPGT-NH2, belonging to the Toll/IL-1 receptor (TIR) domain of the adaptor protein MyD88 and effective in inhibiting its homodimerization. The a
Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines
Kelleher, Fintan,Kelly, Sinead,McKee, Vickie
, p. 9235 - 9242 (2008/02/10)
The syntheses of racemic and homochiral [4.4]-spirolactams, starting from l-proline, in good yields are described. Reduction of the lactam carbonyl group of spirolactams, containing chiral substituents on the lactam nitrogen, with lithium aluminium hydride, gives?a series of homochiral [4.4]-spirodiamines. The crystal structure of one of these spirodiamines on complexation with zinc chloride was obtained. Interestingly it showed a hydrogen-bonded dimeric structure, where the monomers are diastereoisomeric diamines.
Spirobicyclic diamines 1: synthesis of proline-derived spirolactams via thermal intramolecular ester aminolysis
Kelleher, Fintan,Kelly, Sinead
, p. 3005 - 3008 (2007/10/03)
Proline-derived [4.4]-spirolactams have been synthesised in good yields by a reductive-amination reaction followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. The synthesis of the corresponding [4.5]-spirolactams by the same method gave much reduced yields.
