1968-71-4Relevant academic research and scientific papers
Synthesis of natural urolithin M6, a galloflavin mimetic, as a potential inhibitor of lactate dehydrogenase A
Rupiani, Sebastiano,Guidotti, Laura,Manerba, Marcella,Ianni, Lorenza Di,Giacomini, Elisa,Falchi, Federico,Stefano, Giuseppina Di,Roberti, Marinella,Recanatini, Maurizio
, p. 10981 - 10987 (2016/12/06)
Glycolysis is the main route for energy production in tumors. LDH-A is a key enzyme of this process and its inhibition represents an attractive strategy to hamper cancer cell metabolism. Galloflavin is a reliable LDH-A inhibitor as previously identified b
Enantioselective synthesis of α-benzylated lanthionines and related tripeptides for biological incorporation into E. coli peptidoglycan
Denol, Thibaut,Zervosen, Astrid,Lemaire, Christian,Joris, Bernard,Herv, Mireille,Blanot, Didier,Zaragoza, Guillermo,Luxen, Andr
supporting information, p. 9853 - 9863 (2015/01/09)
The synthesis of modified tripeptides (S)-Ala-γ-(R)-Glu-X, where X = (R,S) or (R,R) diastereomers of α-benzyl or α-(4-azidobenzyl)lanthionine, was carried out. The chemical strategy involved the enantioselective alkylation of a 4-MeO-phenyloxazoline. The reductive opening of the alkylated oxazolines, followed by cyclization and oxidation, led to four PMB-protected sulfamidates. Subsequent PMB removal, Boc protection and regioselective opening with cysteine methyl ester led to protected lanthionines. These compounds were further converted in a one pot process to the corresponding protected tripeptides. After ester and Boc deprotection, the four tripeptides were evaluated as potential analogues of the natural tripeptide (S)-Ala-γ-(R)-Glu-meso-A2pm. These compounds were evaluated for introduction, by means of the biosynthetic recycling pathway, into the peptidoglycan of Escherichia coli. A successful in vitro biosynthesis of UDP-MurNAc-tripeptides from the tripeptides containing α-benzyl lanthionine was achieved using purified murein peptide ligase (Mpl). Bioincorporation into E. coli W7 did not occur under different tested conditions probably due to the bulky benzyl group at the Cα carbon of the C-terminal amino acid. This journal is
Aryl-β-C-glucosidation using glucal boronate: Application to the synthesis of tri-O-methylnorbergenin
Sakamaki, Shigeki,Kawanishi, Eiji,Nomura, Sumihiro,Ishikawa, Tsutomu
experimental part, p. 5744 - 5753 (2012/09/08)
Novel aryl-β-C-glucosidation method using glucal boronate was developed. This protocol can offer several advantages including use of non-toxic, easily handling glucal boronate as a crystalline solid and storable at room temperature for several months. Tri-O-methylnorbergenin (8,10-di-O-methylbergenin), an anti-HIV active bergenin derivative, was concisely synthesized by application of the aryl-β-C-glucosidation method.
Synthesis of unsymmetrical biphenyls as potent cytotoxic agents
Wu, Gang,Guo, Huan-Fang,Gao, Kun,Liu, Yi-Nan,Bastow, Kenneth F.,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung,Xie, Lan
scheme or table, p. 5272 - 5276 (2009/05/07)
Twenty-six unsymmetrical biphenyls were synthesized and evaluated for cytotoxic activity against DU145, A549, KB and KB-Vin tumor cell lines. Three compounds 27, 35 and 40 showed very potent activity against the HTCL panel with an IC50 value range of 0.04-3.23 μM. In addition, fourteen active compounds were all more potent against the drug-resistant KB-Vin cell line than the parental KB cell line. Preliminary SAR analysis indicated that two bulky substituents on the 2,2′-positions of unsymmetrical biphenyl skeleton are necessary and crucial for in vitro anticancer activity, thus providing a good starting point to develop unsymmetrical biphenyls as novel anticancer agents.
Buttressing and Electronic Effects of meta- and para-Methoxy Substituents on the Configurational Stability of 5,7-Dihydro-1,11-dimethoxydibenzoxepine
Insole, Joan M.
, p. 2831 - 2867 (2007/10/02)
Three methoxy-substituted 5,7-dihydrodibenzoxepines have been prepared, each in both enantiomeric forms: (-)- and (+)-5,7-dihydro-1,3,9,11-tetramethoxydibenzoxepine (12) starting from, respectively, (+)- and (-)-4,4',6,6'-tetramethoxydiphenic acid (16); (+)- and (-)-5,7-dihydro-1,2,10,11-tetramethoxydibenzoxepine (13) from, respectively, (+)- and (-)-5,5',6,6'-tetramethoxydiphenic acid (25); and (R)-(+)- and (S)-(-)-5,7-dihydro-1,2,3,9,10,11-hexamethoxydibenzoxepine (14) from, respectively, (R)-(+)- and (S)-(-)-4,4',5,5',6,6'-hexamethoxydiphenic acid (30).The previously unpublished resolutions of 4,4',6,6'-tetramethoxydiphenic acid (16) and 5,5',6,6'-tetramethoxydiphenic acid (25) are described.Racemisation parameters for the three 5,7-dihydrodibenzoxepines have been determined and are compared with those for 5,7-dihydro-1,11-dimethoxydibenzoxepine (11).The buttressing effects of the meta-methoxy substituents, and the electronic effects of the para-methoxy substituents on the optical stabilities of the 5,7-dihydrodibenzoxepines are discussed, as are the u.v., and 1H and 13C n.m.r. spectra of these bridged biphenyls.
