• Bulletin of the Korean Chemical Society
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• 제32권5호
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• pp.1650-1656
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• 2011

A series of potent tricyclic derivatives with a non-aromatic amide as potent PARP-1 inhibitors were successfully synthesized and their PARP-1 inhibitory activity was evaluated. Among the derivatives, 2-(1-propylpiperidin-4-yloxy)-7,8,9,10-tetrahydrophenanthridin-6(5H)-one 23c displayed potent activity in a PARP-1 enzymatic assay and cell-based assay ($IC_{50}$ = 0.142 ${\mu}M$, $ED_{50}$ = 0.90 ${\mu}M$) with good water solubility. Further, molecular modeling studies confirmed the obtained biological results.

• Macromolecular Research
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• 제14권1호
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• pp.52-58
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• 2006

A novel fabrication of the patterned surfaces in the polymer films was demonstrated by using the self-organizing character of the block copolymers of polystyrene-b-oligothiophenes and polystyrene-b-aromatic amide dendron. Hexagonally arranged open pores with a micrometer-size were spontaneously formed by casting the polymer solutions under a moist air flow. The amphiphilic character of the block copolymers played the crucial role as a surfactant to stabilize the inverse emulsion of water in the organic solvent, and subsequently the aggregated structure of the hydrophilic oligothiophene or aromatic amide dendron segments remained on the interiors of the micropores. The chemical composition on the top of the surface of the microporous films was characterized by energy-filtering transmission electron microscopy (EFTEM) or a time-of-flight secondary ion mass spectrometer (ToF-SIMS). The characterizations clearly indicated that the patterned surfaces in the self-organized block copolymer films with the hexagonally ordered microporous structures were fabricated in a single step.

• 한국응용과학기술학회지
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• 제12권2호
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• pp.59-64
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• 1995

Two aromatic polysulfones, poly(PhC-co-SDA)-2 and poly(TPhC-co-SDA)-2, were synthesized by interfacial polycondensation of phthaoyl chloride(PhC) and terephthaloyl chloride(TPhC) with P, P'-sulfonyldianiline(SDA), respectively. The properties of the aromatic polysulfones synthesized were as follows : inherent viscosity, $0.32{\sim}0.35dL/g$:glass transition temperature, $220{\sim}240^{\circ}C$:tensile strength, $308{\sim}336Kg/cm^2$:and 5% weight loss temperature by TGA thermogram in the air, $500{\sim}530^{\circ}C$. As the result, thermal properties of the synthesized copolymers proved to be excellent.

• 공업화학
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• 제10권1호
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• pp.138-142
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• 1999

Imide 단위를 포함하는 diamine과 dicarboxylic acid 단량체들, N-(4-aminophenyl)-4-aminophthalimide(APAP), N-(4-carboxyphenyl)-4-carboxyphthalimide(CPCP), N,N'-oxydiphenylenebis(4-aminophthalimide)(ODPAP), 그리고 N,N'-oxydiphenylenebis(4-carboxy-phthalimide)(ODPCP)를 합성하였다. 상기 디아민을 포함한 단량체들과 디카르복시산을 포함한 단량체들을 서로 축합반응하여 imide 단위가 교대로 치환된 poly(imide-amide)s를 합성하였다. 또한 imide단위를 포함하는 diamine 단량체들과 terephthaloyl chloride, 그리고 isophthaloyl chloride를 축합하여 poly(imide-amide)s들도 합성하였다. 이렇게 합성된 중합체들은 NMP/LiCl용액에 매우 잘 용해하였으나 그밖에 극성 비양자성 극성 용매인 DMF, DMSO, 그리고 DMAc 등에는 $80^{\circ}C$에서도 작은 용해도를 보여주었다. 그밖에 고유점도는 0.18~0.67 dL/g를 보여주었으며 NMP/LiCl 용액으로부터 단단하고 부서지기 쉬운 막이 형성되었다. 중합체들은 $500^{\circ}C$ 이하에서 유리 전이 온도 및 융점은 관찰되지 않았으며 열 중량 분석에서 10% 중량 감량은 $500^{\circ}C$ 부근에서 나타나 우수한 열적 성질을 보여주었다.

• Macromolecular Research
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• 제17권11호
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• pp.912-918
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• 2009

An optically active diacid containing the L-histidine moiety was prepared by reacting pyromellitic dianhydride (1,2,4,5-benzenetetracarboxylic acid 1,2,4,5-dianhydride) 1 with L-histidine 2 in acetic acid, and was polymerized with several aromatic diamines 5a-g to obtain a new series of optically active poly(amide-imide)s (PAIs) using two different methods, such as direct polycondensation in a medium consisting of N-methyl-2-pyrrolidone (NMP)/triphenyl phosphite (TPP)/calcium chloride ($CaCl_2$)/pyridine (Py) and direct polycondensation in a tosyl chloride (TsCl)/pyridine (Py)/N,N-dimethylformamide (DMF) system as a condensation agent. The resulting new polymers 6a-g with inherent viscosity was obtained in good yield. The polymers were readily soluble in polar organic solvents, such as N,N-dimethyacetamide (DMAc), N,N-dimethyformamide (DMF), and dimethyl sulfoxide (DMSO). The obtained polymers were characterized by FTIR, specific rotation, elemental analysis as well as $^1$H-NMR spectroscopy and gel permeation chromatography (GPC). The thermal stability of the resulting PAIs was evaluated with thermogravimetric analysis techniques under a nitrogen atmosphere.

• Macromolecular Research
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• 제17권11호
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• pp.901-906
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• 2009

Several aromatic optically active polyamides (PA)s were synthesized from 5-(2-phthalimidiylpropanoylamino)isophthalic acid with various aromatic diamines via direct polycondensation with triphenyl phosphite and pyridine in the presence of calcium chloride and N-methyl-2-pyrrolidone under microwave irradiation and conventional heating conditions. Under the optimized conditions, the reaction mixture was irradiated for 2 min. with a 100% irradiation power (900 W). The resulting polymers were obtained in high yield and moderate inherent viscosity ranging from 0.35 to 0.60 dL/g. All synthesized polymers showed excellent solubility in amide-type solvents. Thermogravimetric analysis revealed a 10% weight loss temperature and char yield at $600^{\circ}C$ in a nitrogen atmosphere of > $350^{\circ}C$ and > 58%, respectively, which suggests that the resulting PAs have good thermal stability.

• Bulletin of the Korean Chemical Society
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• 제23권9호
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• pp.1208-1254
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• 2002

Photoreaction of N-(o-halophenyl)acetamide in basic acetonitrile produces an intramolecular substituted product, 2-methylbenzoxazole in addition to reduced product, acetanilide, whereas photoreaction of N-(o-halobenzyl) acetamide affords a reduced product, N-benzylacetamide only. On the basis of preparative reaction, kinetics, and UV/vis absorption behavior, an electrophilic aromatic substitution of aryl halide with oxygen of its amide bond are proposed.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1993년도 제2회 신약개발 연구발표회 초록집
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• pp.71-71
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• 1993

Carboxylesterase is widely distributed in the tissues of vertebrates, insects, plants and mycobacteria. Among various tissues of animals and humans, the highest esterase activity with various substrates is found in the liver. Kidney has moderate carboxylesterase activity in the proximal tubules. Considerable esterase activity is also found in the small intestine epithet elial cells and serum of mammals. Besides these tissues, carboxylesterase has been found in the lung, testis, adipose tissue, nasal mucosa and even in the central nervous system. Hepatic microsomal carboxylesterase catalyzes the hydrolysis of a wide variety of endogenous and exogenous compounds such as carboxylester, thioester and aromatic amide. Since carboxylesterases are important for metabolic activation of prodrugs and detoxification of xenobiotics, differences in substrate specificity and immunological properties of this enzyme are important in connection with choosing a suitable laboratory animal for the evaluation of biotransformation and toxicity of drugs. On the other hand, liver, kidney, intestine and serum were found to contain multiple forms of carboxylesterases in animal species and humans. In fact, we have purified more than fifteen isoforms of carboxylesterases from microsomes of liver, kidney and intestinal mucosa of nine animal species and humans. and characteristics of these isoforms were compared each other in terms of their physical and immunochemical properties. On the other hand, we have reported that hepatic microsomal carboxylesterases are induced by many exogenous compounds such as phenobarbital, polycyclic aromatic hydrocarbons, Aroclor 1254, aminopyrine and clofibrate. Later, we showed that some isoforms of hepatic carboxylesterase were induced by glucocorticoids such as dexamethasone and 16 ${\alpha}$-carbonitrile, but other isoforms were rather inhibited by these compounds. These findings indicate that involvement of carboxylesterases in the metabolism and toxicity of drugs should be explained by the isoforms involved. Since 1991, we have carried out detailed research investigating the types of carboxylesterases involved in the metabolic activation of CPT-11, a derivative of camptothecin, to the active metabolite, SN-38. The results obtained strongly suggest that some isoforms of carboxylesterase of liver microsomes and intestinal mucosal membrane are exclusively involved in CPT-11 metabolism. In this symposium, the properties of carboxylesterase isoforms purified from liver, kidney and intestine of animal species and humans are outlined. In addition, metabolism of CPT-11, a novel antitumor agent, by carboxylesterases in relation to the effectiveness will also be discussed.

• Bulletin of the Korean Chemical Society
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• 제32권1호
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• pp.162-168
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• 2011

Many ligands have been experimentally designed and tested for their activities as inhibitors against bacterial enoyl-ACP reductase (FabI), ENR. Here the binding energies of the reported ligands with the E. coli ENR-$NAD^+$ were calculated, analyzed and compared, and their molecular dynamics (MD) simulation study was performed. IDN, ZAM and AYM ligands were calculated to have larger binding energies than TCL and IDN has the largest binding energy among the considered ligands (TCL, S54, E26, ZAM, AYM and IDN). The contribution of residues to the ligand binding energy is larger in E. coli ENR-NAD+-IDN than in E. coli ENR-$NAD^+$-TCL, while the contribution of $NAD^+$ is smaller for IDN than for TCL. The large-size ligands having considerable interactions with residues and $NAD^+$ have many effective functional groups such as aromatic $\pi$ rings, acidic hydroxyl groups, and polarizable amide carbonyl groups in common. The cation-$\pi$ interactions have large binding energies, positively charged residues strongly interact with polarisable amide carbonyl group, and the acidic phenoxyl group has strong H-bond interactions. The residues which have strong interactions with the ligands in common are Y146, Y156, M159 and K163. This study of the reported inhibitor candidates is expected to assist the design of feasible ENR inhibitors.

• 한국응용과학기술학회지
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• 제25권2호
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• pp.144-150
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• 2008

The polyamide-amide-imide (PAAI) was synthesized by reacting 4,4'-diaminobenzanilide (DBA) with trimellitic anhydride chloride using a two-stage heating. The precursor of polyamide-acids was formed at first stage and followed by the formation of imide of PAAI. Two polyamide-imides (PAIs) were prepared from benzidine (BZ) or 4,4'-diaminodiphenylether (DPE) with trimellitic anhydride chloride. These three polymers had glass transition temperature in the temperature range of $240-250^{\circ}C$. X-ray data were obtained on thin film specimens cured at $250^{\circ}C$. There was a minimal kind of short-range order consisting of the most probable distances between neighboring chains. The average segmental spacing of short-range order decreased in the order of polymers obtained from 4,4'-diaminobenzanilide (DBA), polyamide-imide, and 4,4'-diaminodiphenylether (DPE). The imidization of three polyamide-imides was confirmed by $^{15}N$ MAS NMR and FT-IR spectroscopy. $^{15}N$ NMR spectrum of cured polyamide-imide showed imide $^{15}N$ peak, thereby providing an evidence for the imidization of three polyamide-imides.