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酸촉매하의 Monoterpenone과 Formaldehyde의 反應硏究
柳忠珪,朴善惠 梨花女子大學校 韓國生活科學硏究院 1988 韓國生活科學硏究院 論叢 Vol.42 No.-
α 위치에 alkyl 기가 치환된 monoterpenone (thujan-3-one, pinan-3-one, p-menthan-2-one, p-menthan-3one)을 산촉매하에서 formaldehyde와 반응시켜 hydroxymethyl-monoterpenone, 4β-hydroxymethyl-thujan-3-one(Ⅰ), 2α-hydroxym-ethyl-pinan-3-one(Ⅱ), 1β-hydroxymethy1-p-menthan-2-one(Ⅲ), 1α-hydroxymethy1-menthan-2-one(Ⅳ), 4α-hydroxymethy1-p-menthan-3one(Ⅶ), 4β-hydroxymethy1-p-menthan-3-one(Ⅷ)을 합성했다. 이 반응은 Prins 반응과 유사한 alkali 촉매하의 반응과 동일함을 알았다. Hydroxymethylation이 일어나는 반응기전은 α-위치에 alkyl기가 치환된 탄소원자에서 proton이 탈리하여 먼저 enol이 regioselective 하게 형성되고, formaldehyde는 입체장해가 적은 α-alky1-substituted ketone에 우선적으로 공격함으로써 hydroxymethylation이 alkyl기가 치환된 탄소에서 regioselective 하게 일어났다. 산촉매하에서 monoterpenone과 formaldehyde의 hydroxymethylation은 bicyclic monoterpenone에서는 regio, stereoselective 하게, monocyclic monoterpenone에서는 regioselective하게 진행된다는 결론을 얻었다. The synthetic product of hydroxymethyl-monoterpenone was afforded by the acid-catalyzed reaction between α-alkyl substituted monoterpenone(thujan-3-one, pinan-3-one, p-menthan-2-one, p-menthan-3-one, etc) and formaldehyde. This reactions involve the aldol condensation analogous to the Prins reaction. The preferential position of formaldehyde is alkyl substituted α-carbon atom where these enols are regioselectively formed. The hydroxymethylation of monoterpenone was also proved to happen regioselectively in the position of α-alkyl substituted ketone, whose conformation has less steric hindrance. The hydroxymethylation with formaldehyde proceeds regio-and stereoselectively with the bicyclic monoterpenone, whereas regioselectively only with the monocyclic monoterpenone.
Synthesis and Antifungal Activity of Naphthalene-1,4-diones Modified at Positions 2, 3, and 5
유충규,Mi Jin Chae 대한약학회 2005 Archives of Pharmacal Research Vol.28 No.7
A series of 2-arylamino-5-hydroxy-naphthalene-1,4-diones, 3-arylamino-5-methoxy-naphthalene- 1,4-diones, and 2-arylamino-3chloro-5-hydroxy-naphthalene-1,4-diones were synthesized and tested for in vitro antifungal activity against the species Candida and Aspergillus niger. Among those tested, 3-arylamino-5-methoxy-naphthalene-1,4-diones exhibited potent antifungal activity. In general, the 3- arylamino-5-methoxy-naphthalene-1,4-diones showed more potent antifungal activity than the 2-arylamino-5-hydroxy-naphthalene-1,4-diones and the 2-arylamino-3-chloro-5-hydroxy-naphthalene-1,4-diones.
항산화제의 면역억제 및 항진연구 II - 항산화제인 Propyl gallate가 세포 면역기능에 미치는 영향 -
유충규,황미경 한국식품위생안전성학회 1990 한국식품위생안전성학회지 Vol.5 No.1
황산화제인 Propyl gallate가 in vivo에서 정상 웅성 마우스이 세포 면역기능에 미치는 영향에 관한 실험 결과, 1. Propyl gallate는 지연형과민증을 용량의존적으로 감소시켰다. 2. Phagocitic index와 corrected phagocytic index는 Propyl gallate의 영향을 볼수 없었다. 3. Propyl gallate는 혈중 백혈구 수를 용량의존적으로 감소시켰다. Propyl gallate used as an antioxidant was examined for its effects on murine immune system. As immunotoxicology assay parameters, we adopted circulating leukocytes and immunoorgan weights for pathotoxicology, delayed hypersensitivity and colloidal carbon clearance for cell mediated immuntity. Propyl gallate's effects were observed as follows; 1) Propyl gallate decreased circulating leukocyte counts, dose dependently. 2) Propyl gallate decreased delayed hypersensitivity reaction. 3) Phagocytic index were similar in the test and control groups.
유충규,류재천,정세영,김동현 梨花女子大學校 藥學硏究所 1992 藥學硏究論文集 Vol.- No.2
In order to evaluate the antimicrobial effect of 2,3-substituted-1.4-naphthoquinone derivatives, we newly synthesized several 2-chloro, 2-bromo and 2-hydroxy-1, 4-naphthoquinones and subjected to antibacterial and antifungal activites, in vitro, against Escherichia coli NIHJ, Staphylococcus aureus ATCC6538p, Candida albicans 10231, Aspergillus niger 1231 and Tricophyton mentagrophytes 6085. Among these derivatives 3, 9, 18 and 23 showed the potent antibacterial activities. 18, 23 and 28 have the antifungal activities. However, these compounds have no significant hemolytic activity at concentrations higher than that required for showing the antibacterial and antifungal activities.
항응고성의 3-(N-Arylamino)-1,4-Naphthoquinone 유도체 합성(Ⅲ)
유충규 梨花女子大學校 藥學硏究所 1991 藥學硏究論文集 Vol.- No.1
2.3-Dibromo-1.4-naphthoquinone was reacted with p-aminobenzoic acid. 2-aminopyridine, 2-amino-4-metylpyridine, m-nitroaniline, sulfathiazol, p-chloroaniline, phenetidine and 2-bromo-3-(N-aryl-amino)-1.4-naphthoquinones (1~8) 2.3-Epoxy-2.3-dihydro-1.4-naphthoquinone was also reacted with p-amonobenzoic acid, p-toluidine, p-chloroaniline, m-chloroaniline, m-nitroaniline, p-phenetidine, N, N-dimethyl-1.4-pheylenediamine as a ring opening and dehydogenation to form 2-hydroxy-3-(N-arylamino)-naphthoquinones ((~16) in good yield. These new compounds (1~16) are expected to have a biological activities such as anticoagulant and cytotoxic.
Monoterpene 향료의 화학구조와 Olfaction과의 구조활성 상관작용
유충규 한국식품위생안전성학회 1987 한국식품위생안전성학회지 Vol.2 No.2
Bifunctional monoterpene 유도체의 향의 유무는 분자내에 존재하는 두 개의 관능기인, proton donor(AH)와 proton acceptor(B)가 olfaction과 구조활성 상호작용(SAR)과 밀접한 관계가 있다. 일반적으로 Ohloff가설에 의하면, p-menthane monoterpene 분자내의 AH와 B의 입체배위적 최소거리가 3${\AA}$ 이하인 경우 향을 갖고, 3${\AA}$ 이상인 경우는 향을 갖지 않는다. Bifunctional pinanone, thujane, carane, carvomenthone 및 기타 menthone 유도체 등을 이용하여 이 가설을 확대 연구하였다. Bifunctional monoterpene인 (원문이미지참조) 등은 분자내에 각각 AH (OH 혹은 COOH)와 B (C=O)의 입체배위적 최소 거리가 항상 3${\AA}$ 이하여서 향을 가지며, 이들은 olfactory three point attachment에 의한 구조활성 상관관계를 가지는 것으로 사료된다. 상기 화합물의 proton donor인 OH, 혹은 COOH가 각각 acetylation이나 methylation되는 경우에는 proton donor로서의 기능 상실로 향이 사라지게 되었다.