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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.
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.
새로운 2,4-Diimino-1,3-thiazoles 유도체의 합성과 구조 결정
한호규,임철수,마혜덕,Hoh-Gyu Hahn,Chul-soo Lim,Heduck Mah 대한화학회 2003 대한화학회지 Vol.47 No.1
신농약 개발을 목적으로 isosterism 이론을 근거로 하여 선도화합물, 2-imino-1,3-thiazoline의 분자 수정을 통하여 분자내에 1,3-thiazole과 urea기가 포함된 새로운 화합물 2를 디자인하였다. N-Methylthiourea 5와 bromoacetonitrile을 에탄올 용액 중에서 반응시켜 위치 선택적으로 생성된 2,4-diimino-1,3-thiazole 4를 phenylisocyanate 유도체와 반응하여 화합물 2의 tautomer인 7을 얻었고 이것의 구조를 여러 가지 스펙트럼(<TEx>$^1H$ NMR, $^{13}C$ NMR, FT-IR, HRMS)과 X-ray 결정 데이터로부터 확인하였다. 화합물 7의 구조이성질체 8은 열역학적으로 불안정한 중간체 2,4-diimino-1,3-thiazole 6을 통하여 생성되었다. For the purpose of developing new agrochemical fungicides, compound 2 possessing 1,3-thiazole scaffold as well as urea moiety in the structure was designed through molecular modification of lead compound, 2-imino-1,3-thiazoline based on isosterism. The reaction of N-methylthiouea 5 and bromoacetonitrile in ethanol gave 2,4-diimino-1,3-thiazole 4 regioselectively, which was treated with phenyl isocyanates to give the corresponding 7 which is tautomer of 2. The structural assignment of 7 was confirmed by various spectra(<TEx>$^1H$ NMR, $^{13}C$ NMR, FT-IR, HRMS), and X-ray crystallographic data. Compound 8 which is a structural isomer of 7 was formed through thermodynamically unstable intermediate 2,4-diimino-1,3-thiazole 6.
한호규,장기혁,이화석,마혜덕,Hahn, Hoh Gyu,Chang, Kee Hyuk,Lee, Wha Suk,Ma, He Duck 대한화학회 1996 대한화학회지 Vol.40 No.5
아세톡시 1,3-옥사티올란 1의 이성체들의 입체화학을 두 가지 방법에 의해 결정하였다. 첫째, 산촉매하에서 디히드로옥사티인 2로의 전환되는 반응속도 차이에 의해 알파이성체 7과 베타이성체 9의 구조를 결정하였다. 이탈기인 아세톡시기가 황원자와 트랜스 위치에 있을 때 1,3-옥사티올란 고리에 대한 입체장애가 적은 이성체가 알파이성체 7이며 반응속도가 느린 이성체가 베타이성체 9이었다. 둘째, 술폭시드의 각각의 diastereomer들의 중수소 치환반응에서, methine 수소가 중수소로 치환된 화합물은 시스이성체 15, 17, 그리고 메틸기의 수소가 중수소로 치환된 화합물은 트랜스이성체 16, 18이었다. Methine 또는 메틸기의 수소의 중수소로의 치환은 [2,3] 시그마트로픽 전위에 의한 입체특이적 개환 및 폐환의 결과였다. Stereochemistries of acetoxy 1,3-oxathiolane 1 were determined by two methods. First, the structures of $\alpha$ isomer 7 and $\beta$ isomer 9 were confirmed by the difference of their conversion rates to dihydrooxathiin 2 under acid catalysis. When the acetoxy leaving group is located in trans relationship to sulfur, a isomer in which carboxanilide is less hindered sterically against the 1,3-oxathiolane ring is $\beta$ isomer 7, and the other isomer of which the reaction rate is slower than 7 is $\beta$ isomer 9. Second, in the deuterium reactions of diastereomeric sulfoxides, the isomers of which methine hydrogen is substituted to deuterium were cis isomers 15 and 17, and another isomers of which methyl hydrogen is substituted to deuterium were trans isomers 16 and 18. Substitution of either methine or methyl hydrogen to deuterium resulted from stereospecific ring opening followed by recyclization by [2,3] sigmatropic rearrangement.