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Exploration of Novel 2-Alkylimino-1,3-thiazolines: T-Type Calcium Channel Inhibitory Activity
Han, Minsoo,Nam, Kee Dal,Shin, Dongyun,Jeong, Nakcheol,Hahn, Hoh-Gyu American Chemical Society 2010 Journal of combinatorial chemistry Vol.12 No.4
<P>We have developed combinatorial libraries of new 2-alkylimino-1,3-thiazolines with four diversity points, consisting of more than 500 compounds, in a parallel synthetic fashion. The synthetic strategy was based on the construction of a large library aimed at the discovery of new compounds with T-type calcium channel inhibitory activity through structure modifications of hit compound <B>2</B>. The syntheses of the compounds of Chemset A with four diversity points were accomplished by the condensation of thioureas <B>5</B> with α-haloketones <B>6</B>{<I>1−66</I>} having two diversity points each. A library of phthalimidyl 1,3-thiazolines <B>24</B> was synthesized to provide Chemset B, which allowed the introduction of other diversity points through the nucleophilic character of the amino nitrogen. A sublibrary, Chemset C, was constructed from the libraries of Chemset A and Chemset B by functionalization of the C-4 position of the 1,3-thiazoline ring. The products containing ester or acid groups at the C-4 position of the 1,3-thiazoline ring were used in amide synthesis to give a new sublibrary within Chemset C. Deprotection of the phthalimidyl moiety of <B>24</B> followed by the reaction with benzoyl chloride gave the corresponding sublibrary in Chemset C. Another sublibrary which includes secondary amino derivatives was obtained by reduction of the amide moiety or reductive amination of <B>23</B> with phenyl aldehyde. The selected compounds from the generated libraries were evaluated with respect to inhibition of T-type calcium channels, where some of them have exhibited promising activity.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jcchff/2010/jcchff.2010.12.issue-4/cc100041m/production/images/medium/cc-2010-00041m_0022.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/cc100041m'>ACS Electronic Supporting Info</A></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/cc100041m'>ACS Electronic Supporting Info</A></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/cc100041m'>ACS Electronic Supporting Info</A></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/cc100041m'>ACS Electronic Supporting Info</A></P>
The Design and Synthesis of 1,4-Substituted Piperazine Derivatives as Triple Reuptake Inhibitors
Han, Min-Soo,Han, Young-Hue,Song, Chi-Man,Hahn, Hoh-Gyu Korean Chemical Society 2012 Bulletin of the Korean Chemical Society Vol.33 No.8
Novel 1,4-substituted piperazine derivatives 5, Series A and B were designed by fragment analysis and molecular modification of 4 selected piperazine-containing compounds which possess antidepressant activity. We synthesized new 39 analogues of Series A and 10 compounds of Series B, respectively. The antidepressant screening against DA, NE, and serotonin neurotransmitter uptake inhibition was carried out using the Neurotransmitter Transporter Uptake Assay Kit. The compounds in Series B showed relatively higher reuptake inhibitory activity for SERT, NET, and DAT than those in Series A. The length of spacer between the central piperazine core and the terminal phenyl ring substituted at the piperazine ring in Series B seems to exert an important role in the activity.
Han, Won-Seok,Lee, Jin-Kak,Lee, Jun-Seok,Hahn, Hoh-Gyu,Yoon, Chang-No Korean Chemical Society 2012 Bulletin of the Korean Chemical Society Vol.33 No.5
Rice blast is the most serious disease of rice due to its harmfulness and its world wide distribution. $Magnaporthe$ $grisea$ is the cause of rice blast disease and destroys rice enough to feed several tens of millions of people each year. Fungicides are commonly used to control rice blast. But $M.$ $grisea$ acquires resistance to chemical treatments by genetic mutations. 2-Phenylimino-1,3-thiazolines were proposed as a novel class of fungicides against $M.$ $grisea$ in the previous study. To develop compounds with a higher biological activity, a new series of 2-phenylimino-1,3-thiazolines was synthesized and its fungicidal activity was determined against $M.$ $grisea$. The QSAR analysis was carried out on a series of 2-phenylimino-1,3-thiazolines. The QSAR results showed the dependence of fungicidal activity on the structural and physicochemical features of 2-phenylimino-1,3-thiazolines. Our results could be used as guidelines for the study of the mode of action and further design of optimal fungicides.
2-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranosyl) imino-1,3-thiazoline 유도체의 합성
한호규 ( Hoh Gyu Hahn ),신동윤 ( Dong Yun Shin ),한민수 ( Min Soo Han ),허정회 ( Jeong Hoe Heo ),남기달 ( Kee Dal Nam ) 한국키틴키토산학회 2010 한국키틴키토산학회지 Vol.15 No.2
2-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranosyl) imino-1,3-thiazoline 유도체 5를 N-methyl-N`-(β-D-glucopyranosyl) thiourea 3과 phenyl 4-chloroacetamide 유도체 4로 부터 합성하였다. N-methyl-N`-(-D-glucopyranosyl)thiourea 3는 β-D-glucosamine 염산염 1과 methyl isothiocyanate 2를 반응시켜 합성하였으며, 생성된 thiourea를 phenyl 4-chloroacetamide 4와 반응시켜 생성물을 합성하였다. 본 연구에서는 β-D-glucopyranose의 C-2 위치에 2-imino-1,3-thiazoline을 도입할 수 있는 방법을 제시 하였다. 2-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranosyl)imino-1,3-thiazoline deri vatives 5 were synthesized from a reaction of N-methyl-N`-(β-D-glucopyranosyl)thiourea 3 with phenyl 4-chloroacetamide derivatives 4. N-methyl-N`-(β-D-glucopyranosyl) thiourea 3 was obtained by a dehydrochlorination of β-D-glucosamine hydrogenchloride salt 1 followed by the reaction of methyl isothiocyanate 2 of which structures were confirmed by their 1H NMR spectra. thus, the protons of 3-methyl, methylene, 5- vinyl showed in range of δ 2.9-3.1 ppm, 4.6-4.7 ppm and 6.9-7.1 ppm respectvely without influence of functional group of the side stereochemistry of the compounds. The synthesized compounds would be contributed a chemical library for an exploration of new biological active material.