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Lpophilicity vs. Antitumor Activity of Carboxylatoplatinum(lV) Complexes
송리타,김관묵,손윤수,Song, Ri Ta,Kim, Gwan Muk,Son, Yun Su Korean Chemical Society 2000 Bulletin of the Korean Chemical Society Vol.21 No.10
Acylation of an intermediate tetrahydroxoplatinum(IV) complex, $[Pt(OH)_4(dach)]$ (dach = $trans-(\pm)-12-di-aminocyclohexane)$, with one or two kinds of carboxylic anhydrides in stepwise manner afforded various car-boxylatoplatinum(IV) complexes, $[Pt(O_2CR)\chi(OR’)4-\chi(dach)]$ (R = $(CH_2)_3CH_3$ or $C(CH_3)_3$, R’ = H or $OCCH_3$, and $\chi$ = 1-4) with a wide range of lipophilicity. The title complexes were subjected to bioassay using the murine leukemia L1210 cell line, and in particular, their in vivo oral antitumor activity was attempted to correlate with their lipophilicity and water solubility. The most orally active complex exhibited intermediate lipophilicity and water solubility, but it has been found that an exact relationship between the lipophilicity and oral anticancer activity could not be established, since the lipophilicity of the complexes is not the sole parameter to determine the oral activity. One of the important intermediate complexes partially substituted was subjected to X-ray anal-ysis for positit of the substituted group: $[Pt(OPiv)_3(OH)(dach)]$ crystallizes in the tetragonal sys-tem, space group $P42_1c$ with a = 21.161(3) $\AA$, b = 21.161(6) $\AA$, c = 12.816(3) $\AA$, $\alpha=\beta=$ r $=90^{\circ}$, V = 5739(2) $\AA^3$ and Z = 8.
최미선,전무진,김관묵 대한화학회 2015 Bulletin of the Korean Chemical Society Vol.36 No.7
A binaphthol aldehyde with phenyl ether linkage, compound 2, has been synthesized starting from binaphthol-3-carboxylic acid. The axially chiral binaphthol ring was racemized during the synthesis due to high temperatures required in O-phenylation reaction. The enantiomerically pure form of 2 was obtained from the resolution of the diastereomeric imine of 2. Optically pure compound (S)-2 was applied to the enantioselective liquid–liquid extraction of amino acid between CH2Cl2 and aqueous layers. The stereoselectivities, that is, d/l ratio of the amino acid extracted, ranged from 3.57 to 11.1. One carbon was absent in compound (S)-2 compared to the compound (S)-1 with benzyl ether linkage, which differentiated the conformations of their imines formed with amino acids.
Jiyoung Kim,Raju Nandhakumar,김관묵 대한화학회 2011 Bulletin of the Korean Chemical Society Vol.32 No.4
Novel binol-based uryl and guanidinium receptors having higher ring conjugation at the periphery of the hydrogen bonding donor sites have been synthesized and utilized to study the enantioselective recognition of 1,2-aminoalcohols and chirality conversion of natural amino acids via imine bond formation. There is a remarkable decrease in the stereoselectivites as the conjugation increases at the periphery of hydrogen bonding donor sites. The guanidinium-based receptors show more selectivity towards the amino alcohol than that of the uryl based ones due to its charge reinforced hydrogen bonds. The conversion efficiency of L-amino acids to Damino acids by the uryl-based receptors is higher than that of the guanidinium-based ones.
Jang-Hoon Cho,노동윤,김관묵,이홍인 대한화학회 2011 Bulletin of the Korean Chemical Society Vol.32 No.11
A new octahedral Ru(III) complex with a tripodal tetraamine ligand, tpea = tris[2-(1-pyrazoyl)ethyl]amine, has been prepared and characterized. The single crystal X-ray crystallographic study of the complex revealed that the complex has a near octahedral geometry with the tetradentate ligand and two chloride ions. Peroxidase activity was examined by observing the oxidation of 2,2'-azinobis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) with hydrogen peroxide in the presence of the complex. Amount of ABTS^(+•) generated during the reaction was monitored by UV/VIS and EPR spectroscopies. After the initiation of the peroxidase reaction,ABTS^(+•) concentration increases and then decreases after certain time, indicating that both ABTS and ABTS+•are the substrates of the peroxidase activity of the Ru(III) complex.
Hyunjung Park,Jooyeon Hong,함시현,Raju Nandhakumar,김관묵 대한화학회 2009 Bulletin of the Korean Chemical Society Vol.30 No.2
Novel binol aldehydes derivatized at 2' hydroxy position with both uryl and acetamide groups (2), and diuryl groups (3) have been synthesized. Both were designed for streospecific binding and chirality conversion of general dipeptides with support of multiple hydrogen bonding donor sites in the receptors. The receptors, 2 and 3, converted the chirality of N-terminal amino acids of peptides such as Ala-Gly, Met-Gly, Leu-Gly and His-Gly with stereoselectivity on D-form over L-form. The stereoselectivity ratios were in the range of 5-11, somewhat higher than those of the binol receptor with mono uryl group (1). The DFT calculation at the B3LYP/6-31G*//MPWB1K/6-31G* level revealed that 3-D-Ala-Gly was 2.2 kcal/mol more stable than 3-L-Ala-Gly. The considerable steric hindrance between the methyl group of the alanine and the imine CH moiety of the receptor seems to be the main contributing factor for the thermodynamic preference.
The Chirality Conversion Reagent for Amino Acids Based on Salicyl Aldehyde
윤호진,Hein Jung,안윤수,Raju Nandhakumar,김준수,김관묵 대한화학회 2012 Bulletin of the Korean Chemical Society Vol.33 No.5
2-Hydroxy-6-(1-(3-phenylurylphenyl)ethoxy)-benzaldehyde (2) has been synthesized in racemic form from 1,3-Dihydroxybenzene via formylation and reaction with 3-phenyluryl-methylbenzylbromide. The optically pure form of 2 was separated by normal silica column chromatography from the imine diastreomer which was obtained by the reaction of racemic mixture of 2 with optically pure leucinol. The absolute configuration of the separated enantiomer of 2 was decided from the energy calculation of the corresponding imine diastereomers. The activity of 2 as a chirality conversion reagent (CCR) for amino acids was determined by 1H NMR analysis. The efficiency of 2 is not better than the previous CCRs based on binaththol. Compound 2, however, has lower molecular weight compared to other CCRs. This work demonstrates that asymmetric carbon can control the selectivity of amino acids.