- Effect of substituents on the configurational stability of the stereogenic nitrogen in metal(II) complexes of α-amino acid Schiff bases
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Herein, we report a general method for quantitative measurement of the configurational stability of the stereogenic nitrogen coordinated to M (II) in the corresponding square planar complexes. This stereochemical approach is quite sensitive to steric and electronic effects of the substituents and shown to work well for Ni(II), Pd(II), and Cu(II) complexes. Structural simplicity of the compounds used, coupled with high sensitivity and reliability of experimental procedures, bodes well for application of this approach in evaluation of chemical stability and stereochemical properties of newly designed chiral ligands for general asymmetric synthesis of tailor-made amino acids.
- Mei, Haibo,Jean, Marion,Albalat, Muriel,Vanthuyne, Nicolas,Roussel, Christian,Moriwaki, Hiroki,Yin, Zizhen,Han, Jianlin,Soloshonok, Vadim A.
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supporting information
p. 401 - 409
(2019/04/01)
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- Design, synthesis and evaluation of aminobenzophenone derivatives containing nitrogen mustard moiety as potential central nervous system antitumor agent
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A series of novel substituted aminobenzophenone derivatives containing nitrogen mustard moiety (5a-f) were synthesized and characterized on the basis of their IR, 1H NMR, 13C NMR, CHN, and mass spectral data. All the compounds when evaluated for chemical 4-(4-nitrobenzyl) pyridine alkylating activity proved to be active alkylating agents. All the synthesized compounds were subjected to physicochemical parameters determination required for central nervous system (CNS) activity through computational, online software, and QikProp 3.2. The log P values and other in silico ADME physicochemical descriptors analyzed lay between the ranges those are required for good BBB penetration. The in vitro antiproliferative activity against human cancer cell lines viz. A 549 (lung), COLO 205 (colon), U 87 (glioblastoma), and IMR-32 (neuroblastoma) was investigated. Most of the test compounds showed potent antitumor activity, especially compound (5f) which displayed the highest activity against CNS cancer cell line comparable to that of chlorambucil and docetaxel. The preliminary structure-activity relationship (SAR) revealed that 5-chloroaminobenzophenone-mustard series (5a-c) exhibited better antitumor activity than 5-nitroaminobenzophenone-mustard series (5d-f).
- Singh, Rajesh K.,Prasad,Bhardwaj
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p. 5901 - 5911
(2013/11/06)
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- Synthesis of 3-O-methylviridicatin analogues with improved anti-TNF-α properties
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We synthesized 3-O-methylviridicatin 1 and several analogues of this fungal metabolite. We showed that replacement of the methoxy moiety by a thiomethyl enhanced dramatically its ability to inhibit TNF-α secretion. These results strongly suggest that 4-phenyl-3-methylthioquinolinone 3 may provide the basis for the development of new anti-inflammatory agents.
- Ribeiro, Nigel,Tabaka, Helena,Peluso, Jean,Fetzer, Ludivine,Nebigil, Can,Dumont, Serge,Muller, Christian D.,Desaubry, Laurent
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p. 5523 - 5524
(2008/03/13)
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