• Bulletin of the Korean Chemical Society
• /
• 제30권2호
• /
• pp.435-440
• /
• 2009

19 Aromatic ring and L-amino acid ester contained rupestonic acid amide derivatives 2a~2l, 3a~3g were synthesized and preliminarily evaluated in vitro against influenza virus $A_3$,B and herpes simplex virus type 1 (HSV-1), 2(HSV-2) by the national center for drug screening of China. The rusults showed that 2i possessed the highest inhibition against both influenza virus $A_3\;(TC_{50}\;=\;120.6\;{\mu}mol/L,\;IC_{50}=\;19.2\;{\mu}$mol/L, SI = 6.3) and B (T$C_{50}\;=\;120.6\;{\mu}mol/L,\;IC_{50}=\;29.9\;{\mu}$mol/L, SI = 4.0); 2g was more active against influenza $A_3$ virus at very low cytotoxicity ($TC_{50}\;>\;2092.1\;{\mu}mol/L,\;IC_{50}=\;143.7\;{\mu}mol/L,$ SI > 14.6) than the parent compound; Compounds 2b, 2c, 2f showed higher activities both against HSV-1 and HSV-2 than that of the parent compound, and 2f was the most potent inhibitor of HSV-1 ($TC_{50}\;=\;200.0\;{\mu}mol/L,\;IC_{50}\;=\;11.3\;{\mu}mol$/L, SI = 17.7 ) and HSV-2 ($TC_{50}\;=\;200.0\;{\mu}mol/L,\;IC_{50}\;=\;20.7\;{\mu}mol$/L , SI = 9.7).

• Archives of Pharmacal Research
• /
• 제28권11호
• /
• pp.1205-1212
• /
• 2005

2-Thiouracil-5-sulphonic acid N-(4-acetylphenyl) Amide (1) was reacted with a series of aromatic aldehydes giving chalcones 2 (Claisen-Schemidt reaction), some of these chalcones were reacted with urea and thiourea giving pyrimidine-2-one and pyrimidine-2 thione derivatives respectively of the type 3a,b and 4a,b. In addition many chalcones were reacted with hydroxylamine hydrochloride giving isoxazoline derivatives 5a,b. They could also reacted with phenylhydrazine to give pyrazoline derivatives 5a,b, chalcones also were reacted withethylcyano acetate and/or malononitryl in pyridine giving pyran derivatives 7a,c and 8a,c. In another pathway chalcones were epoxidised by $H_{2}O_{2}$ giving epoxides 9a,c which in turn were reacted with phenylhydrazine giving 4-hydroxypyrazoline derivatives 10a,c. In another reaction chalcones were reacted with ethylcyanoacetate in presence of amm.acetate giving pyridone derivatives 11a,d which could be prepared also in exellent yield from compound 1 by its reaction with certain aromatic aldehydes and ethylcyanoacetate in presence of ammonium acetate. Finally, compound 1 was reacted with semicarbazide giving semicarbazone intermediate 12 which in turn was reacted with thionyl chloride giving thiadiazole derivative 13. The biological effects of some of the new synthesized compounds were also investigated.

• 공업화학
• /
• 제3권4호
• /
• pp.694-700
• /
• 1992

Palladium 촉매에 의한 CO Insertion Heck reaction을 고분자 중합에 응용하여 가공성이 좋은 고강도 엔지니어링 플라스틱으로 응용 가능한 flexible spacer를 가진 aromatic polyamide와 Polyester를 합성할 수 있었다. 촉매로서 dichlorobis(triphenyl phosphine) palladium(II) $(PdCl_2(PPh_3)_2)$와 Palladium chloride($PdCl_2$)를 사용하였고, 이 중합 시스템은 똑같은 조건에서 polyamide와 polyester를 합성 할 수 있는 장점이 있으므로 그 중합체의 열적성질을 DSC, TGA 등으로 조사하였는데 곁사슬이 있지 않은 aromatic polyamide와 Polyester는 amide와 ester 결합의 차이에도 불구하고 전이온도등이 거의 같았다. Hexyl부터 hexadecyl까지 alkyl 곁사슬을 2,5 위치에 이중으로 가진 phenylene dibromide와 Phenylene diamine으로부터 중합체를 합성하였는데 치환기가 없는 경우에 비하여 전이온도가 감소하였고, alkyl side chain이 hexadecyl인 경우는 뚜렷한 융점을 확인할 수 있었다.

• 폴리머
• /
• 제34권4호
• /
• pp.369-375
• /
• 2010

용융 중합법을 이용하여 말단에 메틸 말레이미드(methyl maleimide) 반응성기를 가지며 방향족 에스터와 아 미드 결합을 포함하는 액정(liquid crystal, LC)을 합성하였다. 합성된 액정은 용액 캐스팅과 열처리를 거쳐 열경화 성 액정(liquid crystalline thermoset, LCT) 필름으로 제조되었다. 합성된 LC 및 LCT는 적외선 분광기(FTIR), 시차주사 열량계(DSC), 열중량 분석기(TGA), 열-기계 분석기(TMA), X-선 회절기(XRD) 및 가열판이 부착된 편광 현미경(POM) 등을 이용해서 각각 특성 분석을 하였다. 합성된 모든 액정은 스멕틱(smectic) 상을 보였으며 LC와 LCT들의 열적 성질은 주로 주사슬에 포함된 메소젠 구조에 영향을 받았다. 열팽창 계수(coefficients of thermal expansion, CTE)는 27.72~50.95 ppm/$^{\circ}C$ 사이의 값을 보였다.

• Archives of Pharmacal Research
• /
• 제27권4호
• /
• pp.371-375
• /
• 2004

The silicon linker is the foremost traceless linker used in solid-phase reactions. Hydrogen fluo-ride (HF) or trifluoroacetic aicd (TFA) can remove the silicon linker with the silicon atom being replaced by a hydrogen atom. In this experiment, the linkers 1c and 2d, which are the most useful in solid-phase reactions, were synthesized, Linker 1c is composed of seven linearly linked carbons and linker 2d includes an oxygen atom in the linear carbon chain to increase the solvation capacity. The carboxylic acid component of linker 1c and 2d forms an amide or ester bond with resin. The synthesized linkers 1c and 2d could be utilized in constructing a chemical compound library that includes indole, benzodiazepine and phenothiazine (aromatic ring compounds).

• Bulletin of the Korean Chemical Society
• /
• 제35권7호
• /
• pp.2025-2028
• /
• 2014

Anion receptor 1 based on acylhydrazone has been designed and synthesized. UV-vis and $^1H$ NMR titration showed that receptor 1 is selective receptor for dihydrogen phosphate ($H_2PO_4{^-}$). Dihydrogen phosphate was complexed by the receptor 1 via at least 4 hydrogen bonding interactions, contributing from two amide N-Hs and two imine C-Hs. In addition, nitrogen in the aromatic ring could make 2 additional hydrogen bondings with OH groups in the dihydrogen phosphate. However, the receptor 1 could make only 4 hydrogen bonds with halides. Therefore, receptor 1 could bind anions through hydrogen bonds with a selectivity in the order of $H_2PO_4{^-}$ > $Br^-$ > $Cl^-$ in highly polar solvent such as DMSO.

• 약학회지
• /
• 제49권1호
• /
• pp.60-67
• /
• 2005

Nonclassical aminobenz[cd]indole antifolates 4, 5 and 6, in which the glutamic acid moiety of the classical antifolates is substituted by 2-phenylglycinamide or 3-aminobenzamide, were synthesized and their in vitro antitumor activity was evaluated. The purpose of this substitution is that the lipophilicity is enhanced due to the aromatic ring of the target compounds for the passive transport through lipid membrane of cells while the hydrogen bonding of the amide is retained in the active site of the enzyme, thymidylate synthase, where the glutamate is originally present. The target compounds were highly cytotoxic against tumor cell lines of murine and human origin with micromolar to nanomolar $IC_{50}$ values. Most effective was compound 4 ($N^6-methyl-N^6$-[4-[(${\alpha}$(S)-aminocarbonylbenzyl) aminocarbonyl]benzyl]-2,6-diaminobenz[cd]indole)with $IC_{50}$ of 2 nM against SW480, human colon adenocarcinoma cell line, which is 650-fold more potent than the reference compound 3.

• Bulletin of the Korean Chemical Society
• /
• 제11권4호
• /
• pp.333-339
• /
• 1990

A series of new dimesogenic compounds whose mesogens are of aromatic ester or amide type having a trifluoromethyl $(CF_3)$ substituent at the para-position of each terminal phenolic rings were prepared and their liquid crystalline properties were studied by differential scanning calorimetry (DSC) and on a cross-polarizing microscope. The compounds have two identical mesogenic units bracketing a central decamethylene spacer. Trifluoromethyl group appears to favor the formation of smectic phases when it is attached to a phenoxy or anilide terminal. Its group efficiency for mesophase formation seems to be inferior to other common substituents. A thermodynamic analysis of the phase transitions was made and the results were explained in relation to the structures of the compounds.

• 대한약학회:학술대회논문집
• /
• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
• /
• pp.341.2-341.2
• /
• 2002

An efficient process for the solution-phase synthesis of biaryl amides has been developed. Girard's reagent T. an inexpensive scanvenger. was found to be very efficient in trapping excess aromatic acid chlorides. resulting in water soluble by-products. which were easily removed from the products by liquid-liquid extraction. The ease of use. and the excellent purity of the amide libraries obtained are important features of this protocol. (omitted)

• 대한화학회지
• /
• 제17권4호
• /
• pp.275-285
• /
• 1973

유기화합물의 선택환원에 필요한 자료를 얻기 위하여 수소화붕소나트륨과 염화알루미늄의 3:1 혼합물의 테트라히드로푸란 용액에서의 환원성을 규명하였다. 49개의 대표적 유기화합물을 골라 이시약과 실온에서 작용하여 대략의 반응속도와 정량관계를 알아보았다. 테트라히드로푸란 용액에서 염화알루미늄 1몰에 수소화붕소나트륨 3몰을 가하면 현탁용액이 생기는데 수소화붕소나트륨 보다는 훨씬 환원성이 강하다. 알데히드와 케톤은 한시간 이내에 빨리 환원되고 아실유도체는 서서히 그러나 카르복시산은 매우 느리게 환원되었다. 에스테르, 락톤, 에폭시드는 수소화붕소나트륨이나 보란보다 훨씬 빨리 환원되었다. 삼차 아미드는 서서히 환원되었으나 일차 아미드는 수소는 발생하지만 환원은 거의 일어나지 않았다. 벤조니트릴은 30분에 환원이 완결되었으나 카프로니트릴은 느리게 환원되었다. 니트로화합물, 이황화물, 술폰등은 이 시약과 반응하지 않으나 아조, 아족시, 옥심기는 서서히 반응하고 이소시안산페닐은 도중단계까지만 환원되었다 올레핀은 쉽게 수소화붕소화 반응을 하였다.