http://chineseinput.net/에서 pinyin(병음)방식으로 중국어를 변환할 수 있습니다.
변환된 중국어를 복사하여 사용하시면 됩니다.
α-D-glucopyranosyl isothiocyanate의 기능화에 의한 2-Phenylimino-1,3-thiazoline 유도체의 합성
한호규,마혜덕,신동윤,한민수,남기달 한국키틴키토산학회 2009 한국키틴키토산학회지 Vol.14 No.4
As a part of fuctionalization of α-D-glucopyranosyl isothiocyanate 15, 2-(2-phenylimino-4-thioureido-1,3-thiazoline)-α-D-glucopyranose derivatives 16 were synthesized by the reaction of α-D-glucopyranosyl isothiocyanate 15 with 4-aminomethyl-1,3-thiazoline derivatives 6. An optimal reaction condition for a synthesis of α-D-glucosamine hydrogen chloride 12 was established by the reaction of D-glucosamine sequentially with diethylethoxymethylene malonate, acetic anhydride, and chlorine. α-D-glucopyranosyl isothiocyanate 15 was prepared from the dehydrochlorination of α-D-glucosamine hydrogen chloride 12 and then treated with thiophogene. Bromination of 2-keto phthalimide which was obtained from the reaction of phthalimide potassium salts with chloroacetone gave 2-keto bromophthalimide 3 in high yield. This was reacted with an equal molar equivalent of N-methyl-N'-phenylthiourea derivatives 4, which were prepared independently to give the corresponding 4-phthalimidyl-1,3-thiazoline 5 in over 80% yield. 4-Aminomethyl-1,3-thiazoline intermediates 6 were synthesized by a deprotection of phthalimidyl moiety of 5 by the action of hydrazine, methylamine or ethanolamine, of which structures were confirmed by their 1H NMR spectra. Thus, the protons of amino methylene, 3-methyl and 5-vinyl showed in range of δ 1.3-1.8 ppm, 3.4-3.7 ppm and 5.7-5.8 ppm respectively without influence of functional group of the side chain. The characteristic doublet at 6.36 ppm with J1,2 3.3Hz in the 1H NMR of the target molecule α-anomer 16 confirmed the sterochemistry of the compound. The synthesized compounds would be contributed a combinatorial chemistry or a chemical library for an exploration of new biological active material.
Identification of Phenylureidoglucosamines as a Novel T-type Calcium Channel Blocker
한호규,신동윤,남기달,배수열,강호원,Jung-Sup Lim 한국키틴키토산학회 2006 한국키틴키토산학회지 Vol.11 No.1
We have found phenylureidoglucosamines as a novel scaffold for T-type Ca2+channel blocker and evaluated for the inhibitoryactivities against α1H, one of the isoforms of the T-type Ca2+channel subfamily. Among them, 3,4-dichlorophenylureidoglucosamineshowed the most potent blocking activity.
Glucosamine 유도체의 입체선택적 합성(V) : 환원성 알킬화 반응에 의한 3차 아민의 생성
한호규,마혜덕,신동윤,한민수,남기달 한국키틴키토산학회 2007 한국키틴키토산학회지 Vol.12 No.2
N-Benzylamino-N-ethyl-β-D-glucopyranose 3 β-D-glucopyranose 2by a reaction of N-benzylidene-β-D-glucopyranose 5 with sodium borohydride in a mixture of acetic acid and methanol solution inhigh yield as a side product. The product of alkylated tertiary amine 3 was obtained in high yield in comparable if the reaction wascarried out at high reaction temperature and longer reaction time while the benzylated product 2 was synthesized in high yield if thereaction proceeded in short reaction time at low temperature. Therefore, it is conceivable that the compound 2 was the product ofreductive benzylation and the tertiary amine 3 was the outcome of reductive alkylation of the secondary amine of the intermediate 2.The formation mechanism of 3 was proposed in three steps. First, triacyloxyborohydride was formed as an intermediate by the reactionhydederivative. Third, the reaction of N-benzylamino-β-D-glucopyranose 2 with the aldehyde afforded immonium ion 6 which was prone toreduction and then it was converted to N-benzylamino-N-ethyl-β-D-glucopyranose 3. The produced mixtures were separated andpurified by the medium pressure liquid chromatography(MPLC) and the yields were 34-55%. The structures of N-benzylamino-N-ethyl-β-D-glucopyranose derivatives 3 were identified by their 1H NMR; the H-1 proton showed at 5.7ppm with J value of 6.6-8.9 Hz,the methylene protons of benzyl moiety were resonated at 3.7ppm with AB splitting pattern with coupling constant of 13-14 Hz and theprotons of the N-ethyl group were confirmed. Little biological anti-fungal effect was showed in the screening of the compounds 3 at100ppm in vivo against 6 kinds of typical plant fungi including rice last.