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에폭시드 고리 개환에 의한 옥사졸리딘티온의 합성 및 항바이러스 활성
황규자,이희경,한호규 숙명여자대학교 약학연구소 1998 약학논문집-숙명여자대학교 Vol.15 No.-
A synthesis and antiviral actvity of new oxazolidinthiones are discribed. Based on the structure-activity relationship from UC38 and UC84, 4-chloro-3-isopropyloxycarbonylphenylamino moiety is found to be a essential pharmacophore for activity. The oxazolidines, which are cyclic thiocarbamate of a 5-membered ring were designed by molecular modification of UC38. Nucleophilic attack of substituted aniline to epoxide by using lithiumperchlorate as a catalyst gave 2-aminoalcohols in good yields. Treatment of 2-aminoalcohol either with thiophosgen or with thionyl chloride gave oxazolidinthiones and 5-chloromethyl-N-phenyl-1,2,3-oxathiazolidin-2-oxide, respectively. Screening results of the 8 oxazolidinthiones against the typical three kinds of viruses(HSV-l, VSV, HIV-1) showed lower activity than those of the UC84 and UC38.
성낙도,유성재,남기달,장기혁,한호규 충남대학교 생물공학연구소 1999 생물공학연구지 Vol.7 No.-
기질(S) 화합물로 30종의 5,6-dihydro-2-trifluoromethyl-1,4-oxathiin carboxanilide 유도체들을 합성하고 벼 잎집무늬 마름병균(Rhizoctonia solani)과 밀 붉은 녹병균(Puccinia recondita)에 대한 항균활성(in vivo) 값(pI_50)을 측정하였다. (S)는 잘록병균보다 밀 붉은녹병균에 대하여 보다 큰 항균활성을 나타내었으며 두 종의 균에 대하여 3-methoxy, 11, 3-iso-propyloxy, 13 및 3-iso-propyl 치환체, 25가 제일 큰 활성을 보였다. 그리고 치환(X)-phenylcarbamoyl group의 변화에 따른 물리-화학 파라미터와 항균활성(pI_50)으로부터 구조-활성관계(SAR)를 검토 한 결과, 벼 잎집무늬 마름병균에 대하여는 공명효과에 따른 전자밀게(R<0)의 소수성이 큰(π>0) m-alkyl 치환기(X)가, 그리고 밀 붉은녹병균에 대하여는 분자 분극율(Sp.Po1.)과 분자의 음하전(ABSQ<0)을 위시하여 HOMO에너지(e.v.)가 클수록(HOMO<0) 높은 항균활성을 나타내었다. 또한, 전하-조절 반응에 의한 수용체-(S)간의 상호작용과 높은 활성발현 조건들이 검토되었다.(1998년 2월 3일 접수, 1998년 12월 1일 수리) New thirty derivatives of 5,6-dihydro-2-trifluoromethyl-1,4-oxathiin carboxanilide as substrate(S) were synthesized and their fungicidal activities in vivo against rice sheath blight(Rhizoctonia solani) and wheat leaf rust(Puccinia recondita) were examined. The structure activity relationships(SAR) between the activities(pI_50) and a physicochemical parameters of substituents(X) at the phenylcarbamoyl group were analyzed using the adaptive regression analysis method. The 3-methoxy, 11, 3-isopropyloxy, 13 and 3-isopropyl substituent, 25 as X on the phenylcarbamoyl group exhibited the most highest fungicidal activity against the two fungi. The fungicidal potency of the (S) against Puccinia recondita was higher than Rhizoctonia solani. In case of Rhizoctonia solani, the molecular hydrophobicity(π>0) and resonance effect(R<0) by meta-alkyl substitutents with electron donating were important factors in determining fungicidal activity. And the HOMO energy(HOMO>0), ABSQ, sum of absolute values of the atomic charges on each atom and specific polarizability(Sp.Pol<0) of (S) were significantly influential towards fungicidal activity against Puccinia recondita. The interaction between (S) and receptor against from the based on SAR studies proceeds through charge-control reaction, and conditions to show higher activity has been also discussed.
Designs and Syntheses of Oxathiin Carboxanilide Analogues and their Antiviral Activities
Hahn, Hoh-Gyu,Rhee, Hee-Kyung,Lee, Chong-Kyo,Whang, Kyu-Ja The Pharmaceutical Society of Korea 2000 Archives of Pharmacal Research Vol.23 No.4
Syntheses of new analogues of oxathiin carboxanilide (UC84) and their antiviral activities were described. The heterocyclic carboxylic acids including oxathiins (4), thiazines (9) and dithiins (13) in which the methyl was replaced either by lipophilic trifluoromethyl- or bulky phenylgroup were synthesized starting from $\beta$-keto esters (5). Reaction of 4, 9 and 13 with thionyl chloride followed by treatment of the substituted aniline 22 gave the corresponding carboxanilides (24a~24f). The carboxanilides were subjected to Laweson's reagent the corresponding thiocarboxanilides (24g~24k). The antiviral activities of the synthesized compounds against human immunodeficiency virus type 1 (HIV-1), poliovirus type 1 (PV-1 ), coxsackie B virus type 3 (CoxB-3), vesicular stomatitis virus (VSV) and herpes simplex virus type 1 (HSV-1) were presented. The antiviral activity against HIV-1 of dithiin carboxanilide (24e) was similar with that of UC84 (24a). The corresponding thiocarboxanilides (24g~24k) showed higher inhibitory activity against HIV-1 than the carboxanilides (24a, 24b, 24d, 24e). The compounds in which ether the lipophilic trifluorormethyl substituents (24d, 24f, 24i ,24k) or bulky phenyl substituent is present in the heterocyclic compounds showed lower inhibitory activity than that of the methyl substituents is present in the compounds against the HIV-1. But the trifluoromethylated dithiin (24f) showed higher inhibitory activity against PV-1 and CoxB-3 virus than commercial antiviral agents, ribavirin (RV).
Hahn, Hoh-Gyu,Oh, Heong-Sub,Cheon, Seung-Hoon,Oak, Min-Ho,Kim, Young-Ran,Kim, Kyeong-Man The Pharmaceutical Society of Korea 2004 Archives of Pharmacal Research Vol.27 No.5
An allergic reaction ensues after antigen binds to mast cell or basophil high affinity IgE receptor, Fc$\varepsilon$RI, resulting in degranulation of various inflammatory mediators that produce various allergic symptoms. In this study, i) we isolated the active component for the inhibition of mast cell degranulation from the extract of leaves of Castanea crenata and identified it as quercetin; ii) we established the total synthesis procedure of quercetin; iii) using quercetin as positive control, we excavated some lead compounds that possess inhibitory activities for mast cell degranulation by screening the chemical libraries of 1,3-oxazolidine derivatives prepared by solid phase combinatorial chemistry. Some of 1,3-oxazolidine compounds possessing acetyl and 3',4'-dichlorophenyl group displayed strong inhibitory activities on Fc$\varepsilon$RI-mediated mast cell degranulation, suggesting that they can be used as lead compounds for the development of anti-allergic agents.