• Archives of Pharmacal Research
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• 제19권3호
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• pp.246-247
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• 1996

In the previous reports (Park et al., 1991, and 1993), we described the synthesis and analgesic effects of various homovanillic amides as analogs of capsaicin. In the study, we tried to enhance the analgesic actvity of capsaicin by structural modification. Our study has been performed in three directions. First, the amide bond of capsaicin was transposed. Second, a phenyl ring was introduced to replace a double bond of capsaicin. Finally, aminoethylation was performed on 4-hydroxy group of capsaicin to improve oral bioavailability. These studies have led to N-(3-phenylpropyl)homovanillic amide 2 which has high analgesic activity. Our continuing efforts in this area have focused on the introduction of various substituents on the phenyl ring of 2 as well as their pharmacological studies. We report herein the synthesis of homovanillic amide derivatives and their analgesic activity.

• Korean Membrane Journal
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• 제3권1호
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• pp.9-16
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• 2001

The diamide-diamine having carboxylic acid was prepared by direct condensation of 1,2,4-benzenetricarboxylic acid with bits[4- (3-aminophenoxy ) phenyl] sulfone and bits(4-aminouhenyl)-1,4- diisopropylbenzene in medium consisting of triphenylphosphite, LiCl, and N-methyl-2-pyrrolidone. Copoly (amide-imide) derivatives with high molecular weight could be synthesized by one-step polycondensation of prepared diamide-diamine having carboxylic acid and various dianhydride compounds. Depending on the chemical structure and composition of polymer backbones, the viscosities of polymers were found to range between 0.87∼ 1.57 dL/B. All the polymers showed good thermal stability up to 320$\^{C}$ and the 10% weight loss temperature was observed in the range of 450∼540$\^{C}$ in a thermogravimetric traces. The glass transition was recorded in the temperature range of 200 ∼ 270$\^{C}$. All the polymers showed an amorphous nature on a differential scanning calorimetric thermograms. These polymers generally had good mechanical properties and readily soluble in various polar solvents. Further, it was proved that their properties could be determined from the composition.

• 공업화학
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• 제25권3호
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• pp.337-339
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• 2014

본 연구의 내용은 Dimethyl terephthalate의 생성 과정 중 필연적으로 생성되는 부산물인 Methyl 4-formylbenzoate를 이용해 one-pot reaction을 통한 p-Aminobenzoic acid를 얻는 방법이다. 이 방법은 Methyl 4-formylbenzoate에 chlorine gas와 methylene chloride를 이용해 acid chloride를 형성하고 ammonia gas를 통해 amide를 중간체로 가진다. 생성된 amide는 Hofmann degradation을 통해 p-Aminobenzoic acid로 전환된다. 이 방법은 폐기물인 Methyl 4-formylbenzoate를 재활용하여 기존의 p-Aminobenzoic acid를 수율 90%로 합성하였으며 이는 기존의 p-Aminobenzoic acid 생산과정을 대체할 수 있을 것으로 예상된다.

• Bulletin of the Korean Chemical Society
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• 제19권4호
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• pp.457-462
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• 1998

A chiral pentadentate bis-amide ligand, 1,9-bis(S)-pyrrolidinyl-2,5,8-triazanonane-1,9-dio ne$(S,S-prodienH_2)$ has been synthesized from the reaction of bis(2-aminoethyl)amine(dien) and S-proline, and the structure of $[Co(S,S-prodien)H_2O]ClO_4$ has be en determined by single crystal X-ray diffraction. The geometrical structure of the Co(III) complex has been an αβ -form, where the dien moiety of ligand chelates to a facial in metal center, and the aqua ligand coordinates a cis site to the secondary nitrogen of dien. The Co-N(1), Co-N(3) distances of two amide moiety in S,S-prodien are shorter than the other Co-N(2), Co-N(4), and Co-N(5) distances because of the increased basicity of nitrogen in amide. The complex crystallizes in the monoclinic space group $P2_1$(#4), with a=7.838(1), b=12.675(1), c=9.710(1) Å, β=100.39(1) and z=2. Refinement gives the final R and $R_w$ values of 0.045 and 0.057, respectively for 2130 observed reflections. Based upon the CD and X-ray data, it is identified that the absolute configuration of the αβ -$[Co(S,S-prodien)H_2O]ClO_4$ has a Λ-form.

• Bulletin of the Korean Chemical Society
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• 제19권10호
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• pp.1105-1109
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• 1998

A chiral stationary phase derived from (S)-N-(3,5-dinitrobenzoyl)leucine N-phenyl N-alkyl amide (CSP 2) was applied in separating the two enantiomers of various π-basic aromatic derivatives of leucine N-propyl amide in order to evaluate π-basic aromatic groups as an effective derivatizing group for the resolution of a-amino acids. Subsequently N-(3,5-dimethoxybenzoyl) group was found to be very effective as a π-basic aromatic derivatizing group. Based on these results, N-(3,5-dimethoxybenzoyl) derivatives of various a-amino N-propyl amides, N,N-diethyl amides and esters were resolved on the CSP derived from (S)-N-(3,5-dinitrobenzoyl) leucine N-phenyl N-alkyl amide (CSP 2) and the resolution results were compared with those on the CSP derived from (S)-N-(3,5-dinitrobenzoyl)leucine N-alkyl amide (CSP 1). The enantioselectivities exerted by CSP 2 were much greater than those exerted by CSP 1. In addition, racemic N-(3,5-dimethoxybenzoyl)-a-mino N,Ndiethyl amides were resolved much better than the corresponding N-(3,5-dimethoxybenzoyl)-a-mino N-propyl amides and esters on both CSPs. Based on these results, a chiral recognition mechanism utilizing the π-π donor-acceptor interaction and the two hydrogen bondings between the CSP and the analyte was proposed.

• 대한화학회지
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• 제56권1호
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• pp.92-101
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• 2012

The degradation of one of the commercially important hydrogel based on acrylic acid and acryl amide, (acrylic acid-co-acryl amide) hydrogels, by means of ultrasound irradiation and its combination with heterogeneous ($TiO_2$) was investigated. 24 kHz of ultrasound irradiation was provided by a sonicator, while an ultraviolet source of 16 W was used for UV irradiation. The extent of sonolytic degradation increased with increasing ultrasound power (in the range 30-80 W). $TiO_2$ sonophotocatalysis led to complete (acrylic acid-co-acryl amide) hydrogels degradation with increasing catalyst loading, while, the presence of $TiO_2$ in the dark generally had little effect on degradation. Therefore, emphasis was totally on the sonolytic and sonophotocatalytic degradation of hydrogels and a synergy effect was calculated for combined degradation procedures (Ultrasound and Ultraviolet) in the presence of $TiO_2$ nanoparticles. $TiO_2$ sonophotocatalysis was always faster than the respective individual processes due to the enhanced formation of reactive radicals as well as the possible ultrasound-induced increase of the active surface area of the catalyst. A kinetics model based on viscosity data was used for estimation of degradation rate constants at different conditions and a negative order for the dependence of the reaction rate on total molar concentration of (acrylic acid-co-acryl amide) hydrogels solution within the degradation process was suggested.

• 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.

• 폴리머
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• 제31권6호
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• pp.550-554
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• 2007

최근 ATRP를 이용하여 단백질에 조절된 구조의 고분자를 연결시키는 연구가 활발히 진행되고 있다. 이때, ATRF 개시제는 단백질에 있는 일차아민에 아미드화 반응을 통하여 도입할 수 있다. 그런데, 형성되는 $\alpha$-할로 아미드의 경우, 상대적으로 늦은 개시 속도를 나타내는 것으로 알려져 있어 원하는 구조의 고분자를 얻는 것이 쉽지 않다. 따라서 본 연구에서는 아미드기를 가지고 있는 개시제를 이용한 [poly(ethylene glycol)methyl ether] methacrylate(PEGMA)의 ATRP 반응에 대한 적절한 반응 조건을 찾고자 하였다. PEGMA는 FEG를 가지로 가지는 단량체로서 고분자로 만들어졌을 때, 물에 잘 녹고 단백질과의 비특이적 상호작용이 적어 단백질과의 결합을 통한 바이오 응용에 널리 사용되고 있다. 아미드기를 가지는 개시제를 이용하여 PEGMA를 성공적으로 중합하기 위한 최적의 중합 조건은 할로겐 교환 반응과 활성 감소제를 사용해서 얻을 수 있었다.

• 폴리머
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• 제38권5호
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• pp.596-601
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• 2014

방향족 구조를 포함하고 분자량이 조절된 polyamide(PA) 올리고머를 4-aminobenzoic acid와 12-aminododecanoic acid의 축합반응으로 합성하였다. 이 올리고머를 여러 분자량의 polytetramethylene glycol(PTMG)과 축합하여 PA를 hard segment로 하고 PTMG를 soft segment로 하는 열가소성 탄성체로서 poly(ether-b-amide)(PEBA)를 제조하였다. 합성된 PEBA의 구조는 FTIR과 $^1H$ NMR로 확인하였으며 DSC와 UTM을 사용하여 hard segment의 구조변화에 따른 열적특성과 기계적 성질의 변화를 비교해 본 결과 방향족 구조를 30%까지 포함할 때 결정성의 변화 없이 PEBA들의 용융온도는 높아졌고 초기 modulus와 strength는 더 크게 나타났다.

• 한국산학기술학회논문지
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• 제16권2호
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• pp.1563-1570
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• 2015

본 연구는 올리고펩티드의 연쇄성장 과정에서의 배좌의 변화를 조사하기 위하여 알라닌 올리고머 모델의 2량체 부터 5량체 까지 양자화학 계산(QCC)에 의한 구조최적화 계산을 하였다. 말단기의 영향을 확인하기 위하여 N말단 및 C말단이 공히 amide 구조를 갖는 "amide type" ($CH_3CONH-and-CONHCH_3$)과 N말단만이 methyl 구조를 갖는 "methyl type" ($CH_3NH-and-CONHCH_3$)의 2종류 모델을 준비하였다. 5량체 까지의 구조 최적화 계산 결과 3종류의 형태이성질체로 수렴이 되었다. 안정성이 높은 순서로 각각 ${\alpha}$ 나선형, PPII 유사형, ${\beta}$ 확장형으로 나타났으며, 사슬회전 방향이 서로 반대인 형태이성질체간의 에너지 값은 동일하게 나타났다 (5량체, "amide type" 좌 우회전형: ${\Delta}E=-1.05$, "methyl type" 좌 우회전형: ${\Delta}E=-1.62$). ${\alpha}$ 나선형의 모노머 단위당 에너지변화(${\Delta}E$)는 모노머의 증가와 함께 감소하였다.