Preparation and Biological Activity of Novel Twin-Drug Type C2-Symmetrical Cyclic Phenylboronic Acid Derivatives

Anti-proliferative Activities towards Human Brain Glioma U251 Cells and Human Carcinoma Cells (KB3-1) of Some Twin-Drug Type Bivalent <i>C</i>₂-Symmetrical Phenylboronic Acid Derivatives

“…Chemical shifts are expressed in δ ppm relative to the solvent peaks for 1 H-NMR [(DMSO-d 6 ) (2.50 ppm)] and 13 C-NMR [DMSO-d 6 (39.52 ppm)]. The signal assignments were confirmed by 1 H-1 H two-dimensional (2D) correlation spectroscopy (COSY), 1 H- 13 C heteronuclear multiple-quantum coherence (HMQC), and 1 H- 13 C heteronuclear multiple-bond connectivity (HMBC) spectra. High-resolution FAB-MS spectra [HR-MS (FAB)] were obtained by a JEOL JMS-700T mass spectrometer.…”

“…1 have already been reported. 7,12,13) Thioamide analogue 1e and new mode C 2 -symmetrical compound 1h were prepared by a procedure described below in good yields.…”

“…19,20) The anti-herpes simplex virus (HSV)-1 activities (EC 50 ) of the synthesized boronic acid derivatives were determined by using a plaque reduction assay 21) and their cytotoxicity against Vero cells (IC 50 ) was also determined by our previously described method. 7,12,13) The cytotoxic activities against Vero cells (IC 50 ) are shown in Table 1.…”

“…In connection with the above projects, we have recently reported some C 2 -or C 3 -symmetrical phenylboronic acid derivatives and the results of biological evaluation of the synthesized symmetrical phenylboronic acid derivatives. 12,13) Among previously targeted C 2 -or C 3 -symmetrical phenylboronic acid derivatives (so-called boronolectins), we found that a few C 2 -or C 3 -symmetrical derivatives showed a considerable level of cytotoxic activity against Vero cells. These compounds are considered to be potential leads in the search for preferred anticancer activity.…”

“…6) We have been interested in molecules that interfere with carbohydrate recognition stages by directing a controlled biological response in order to find new bioactive leads. [7][8][9][10][11][12][13][14][15] From the viewpoint of molecular geometry, many host receptors that consist of homo-oligometric units often constitute symmetric macromolecule architectures such as C 2 -or C 3 -symmetrical geometric systems. 1) These phenomena of bio-macromolecules have encouraged us to develop new oligovalent C 2 -or C 3symmetrical synthetic molecules to find new bioactive leads.…”