• Archives of Pharmacal Research
• /
• 제23권4호
• /
• pp.302-309
• /
• 2000

Based on (-)-neplanocin A with the 5'-hydroxyl substituted with fluoro, azido, or amino group, the corresponding xylo- and arabino derivatives were synthesized from D-ribose using the Mit-sunobu reaction as a key step. None of the final nucleosides did show either significant antiviral activities or cytotoxicities.

• Bulletin of the Korean Chemical Society
• /
• 제31권6호
• /
• pp.1643-1648
• /
• 2010

Adenosine 5'-phosphonates have been reported as potential chain terminators against Hepatitis C virus (HCV); therefore, we developed convenient sequences for synthesis of modified adenosine 5'-phosphonates in which the hydroxyl group at 2' or 3'-position of the sugar moiety is substituted with the azido or amino group and the oxymethyl group at the 4'-position is modified by the ethylene or vinyl group. This synthetic sequence can provide six adenosine 5'-phosphonates via one protocol, and is considered to be very efficient and a convenient route of synthesis. An assay of adenosine 5'-phosphonate analogues (1, 2, 3, 4, 5, and 6) against HCV infection is now in progress.

• Journal of Pharmaceutical Investigation
• /
• 제28권1호
• /
• pp.1-5
• /
• 1998

The effect of synthetic polymer membranes on the permeation rate of dideoxynucleoside-type anti-HIV drugs through hairless rat skin was studied using ethylene/vinyl acetate copolymer (EVA) and ethylene/methyl acrylate copolymer (EMA) membranes fabricated by solvent casting method. In vitro skin permeation kinetics study of DDC (2',3'-dideoxythymidine), DDI (2',3'-dideoxyinosine) and AZT (3'-azido-3'-deoxythymidine) across the (membrane/skin) composite was conducted for 24 hours at $37^{\circ}C$ using the Valia-Chien skin permeation system. The results showed that skin permeation rate of each drug across the (skin/membrane) composite was mainly dependent on the property of the membrane. Proper selection of the polymeric membrane which resembles hydrophilicity/lipophilicity of the delivering drug was important in controlling the skin permeation rate.

• 통합자연과학논문집
• /
• 제5권3호
• /
• pp.175-181
• /
• 2012

Oxepane high explosives substituted to explosive group such as azido, nitrato and hydrazino are investigated theoretically the acid catalyzed reaction using the semiempirical MINDO/3, MNDO and AM1 methods to use as the guidelines of high explosives. The nucleophilicity and basicity of oxepane high explosives can be explained by the value of negative charge on oxygen atom of oxepane and the reactivity in propagation step can be represented by the value of positive charge on carbon atom and low electrophile LUMO energy. It was known that carbenium ion was favorable due to the stable energy (19.507~32.101 Kcal/mol) between oxonium ion and carbenium ion in the process of cyclic oxonium ion of oxepane high explosives being converted to open carbenium ion in oxepane high explosives. The value of concentration of cyclic oxonium ion and open carbenium ion in equilibrium status was found to be a major determinant of mechanism, it was expected to react faster in the prepolymer propagation step in SN1 mechanism than in that of $S_N2$.

• 대한약학회:학술대회논문집
• /
• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
• /
• pp.341.1-341.1
• /
• 2002

Apio nucleosides belong to unique classes of nucleosides in that 4'-hydroxymethyl group moves to 3'-position. Among thse compounds. we found that apio dideoxyadenosine (apio-ddA) exhibited potent antiviral activity and apio-d4A showed potent anti-HCMV activity. Based on thse findings. it was of great interest to design and synthesize Anio nucleoside anlogues with various substituents such as fluorn or azido group. In order to synthesize apio analogues. the glyxosyl dondr. D-. and L-apio sugar acetates were first synthesized. starting from D-gallas. condensed whth silylated N4-benzoylcytosine. and then convenged to the linal D-andL-nucleosides. Synthesist of the D-and-apio nucieosides will be prssented in detail aht th the meeting.

• 공업화학전망
• /
• 제23권6호
• /
• pp.14-24
• /
• 2020

최근 우수한 발광 특성을 갖는 양자점을 고해상도 디스플레이의 발광 소재로 도입하고자 하는 노력이 활발하다. 양자점을 활용한 디스플레이의 실현을 위해서는 콜로이드 상태인 다색의 양자점을 고해상도로 패터닝하는 기술의 확립이 필요하다. 본 연구에서는 ethane-1,2-diyl bis(4-azido-2,3,5,6-tetrafluorobenzoate)를 양자점용 가교제로 활용하여 용액공정을 기반으로 형성된 양자점 박막을 고해상도로 패터닝한 기술을 소개하고자 한다. 위 양자점용 가교제의 양 말단에는 아지드 그룹을 포함한 작용기가 존재한다. 아지드 기는 자외선에 의해 광 활성화되어 양자점 표면의 알킬 리간드와 가교 결합을 형성함으로써, 양자점 박막에 화학적 내구성을 부여한다. 본 기술을 기반으로, 적색, 녹색, 청색의 카드뮴 기반 양자점을 고해상도로 패터닝하고 정밀하게 배열하여 인치 당 화소 수 1400 이상의 픽셀 형성에 성공하였다. 또한 가교 반응 후에도 성능 저하가 없는 양자점 박막 및 자발광 양자점 다이오드를 개발하였다.

• 폴리머
• /
• 제39권1호
• /
• pp.165-168
• /
• 2015

하이드록시 그룹을 지닌 온도민감형 고분자들이 원자전이라디칼중합법(ATRP)과 클릭반응(click reaction)에 의해 합성되어졌다. 고분자들의 분자량과 분자량 분포도는 gel permeation chromatography(GPC)에 의하여 얻어졌고, 고분자들의 분자량은 잘 제어되었으며 분자량 분포도도 낮게 유지되었다. 클릭반응의 효율은 $^1H$ NMR spectroscopy에 의해 얻어졌으며, 높은 효율을 나타내었다. 고분자 사슬 곁가지의 아민 그룹의 종류와, 치환된 알코올 그룹의 종류에 따라 저임계 용액 온도(LCST)의 제어가 가능했다.

• Bulletin of the Korean Chemical Society
• /
• 제35권9호
• /
• pp.2694-2698
• /
• 2014

A multisegmented polystyrene (PS) with pH-cleavable ester and carbamate linkages was successfully synthesized by a combination of atom transfer radical polymerization (ATRP) and Cu(I)-catalyzed 1,3-dipolar cycloaddition of azide and alkynes (click chemistry). ATRP was employed to synthesize polystyrene from hydroxyl-terminated initiator using CuBr/N,N,N',N",N"-pentamethyldiethylenetriamine (PMDETA) as the catalyst. The reaction of the resulting PS with sodium azide yielded the azido-terminated polymer. The hydroxyl group in the other end of the polymer was reacted with 4-nitrophenyl chloroformate (NPC), followed by reaction with propargylamine to produce an alkyne end group with a carbamate linkage. The PS with an alkyne group in one end and an azide group in the other end was then self-coupled in the presence of CuBr/2,2'-bipyridyl (bpy) in DMF to yield a desired multisegmented PS. Molecular weight and molecular weight distribution of the self-coupled polymer increased with time, as in the typical step-growth-type polymerization processes. Finally, we demonstrated that the ester and carbamate linkages of the multisegmented PS were hydrolyzed in the presence of HCl to yield individual PS chains.

• 자연과학논문집
• /
• 제9권1호
• /
• pp.95-104
• /
• 1997

본 연구에서는 thymidine으로부터 시작하여 3'-OH과 5'-OH의 각각의 변형, 동시의 변형을 통해 크게 5종의 amino thymidine 골격의 촉매를 합성하였다. 다양한 thymidine 화합물들이 새로운 키랄 보조체로서의 촉매효과를 위해 우선 3'-OH 자리에 mono-methylamino thymidine과 dimethylamino thymidine을 합성하고, 이들의 합성과정을 응용하여 5'-OH을 Ac-O로 변환한 5'-acetyl-3'-dimethylamino thymidine과 5'-OH를 TBS로 변환하고 up위치의 azido화합물인 5'-TBS-3'-Up-tBOC methylamino thymidine을 합성하였다. 그리고, 5'-OH를 amino group으로 변환하고 3'-OH를 -Me로 변환한 화합물 3'-acetyl-5'-tBOC-amino thymidine을 합성하였다.

• 한국응용약물학회:학술대회논문집
• /
• 한국응용약물학회 1994년도 춘계학술대회 and 제3회 신약개발 연구발표회
• /
• pp.222-222
• /
• 1994

목적하는 화합물인 2',5'-dihydroxy-3'-무치환 유도체(1)는 uridine을 sodium metaperiodate로 산화하여 dialdehyde를 얻은다음 1,2-dianilinoethane으로 3'-aldehyde만을 선택적으로 보호, 2'-aldehyde를 NaBH$_4$로 환원, alcohol로 하여 deprotection 하므로서 hemiacetal율 얻는다. 이 hemiacetal을 TsSNHHNH$_2$로 처리하여 목적하는(1) 화합물을 얻었으며 2-azido-5-Hydroxy-3'-무치환 유도체(2)는 (1)화합물 합성시 얻은 hemiactal을 출발 물질로 하여 먼저 TBDPSCl로 silyaltion하여 5'-hydroxyl group을 보호하고 TsNHNH$_2$로 3'-위치를 hydrazone으로 한다음 NaB(CNH$_3$로 처리하여 얻은 hydrazide를 NaOAc를 반응시켜 2'-hydroxy-3'-무치환-5'-silyl 유도체를 얻고 또한 2',3'-dihydroxy group을 tosyl화, azido화, 5'-silyl group을 deprotection 하므로서 (2)를 얻었다. 또한 2',3'-dihydroxy-5'-무치환 유도체(4)는 uridine의 2',3'-위치를 먼저 protection, 5'-위치를 benzoyl화 2',3'-deprotection, periodate oxidation하여 얻은 diol을 silyl화 한 다음 5'-위치를 benzoyl화, 2',3'-deprotection, 산화하여 얻은 hemiacetal의 silyl group을 제거한후 primary hydroxyl group만을 선택적으로 silyl화, TsNHNH$_2$, NaB(CN)H$_3$ 및 NaOAc로 처리하므로서 얻은 2'-hydroxy-3'-0-silyl group-5'-무치환 화합물을 tosyl, azido화 한다음 desilylation하여 얻었다. 목적하는(1) 화합물의 diasteromer 인 2',3'-dihydroxy-5'-무치환 유도체(3)는 (4)화합물 합성시 얻은 hemiactal을 key intermediate로 하여 TsNHNH$_2$, NaB(CN)H$_3$ 및 NaOAc로 처리하므로서 얻을수 있었다. 이들 화합물들의 각종 DNA 및 RNA virus에 대한 항 바이러스작용을 검토한 결과 현저한 항 바이러스 작용을 나타내지 않았다.