• Bulletin of the Korean Chemical Society
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• v.34 no.8
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• pp.2297-2304
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• 2013

A series of novel benzimidazole derivatives bearing a heterocyclic ring as oxadiazole (21-32), thiadiazole (33-34), triazole (35-36) were synthesized and evaluated for their activities against Coxsackie virus B3 and B6 in Vero cells. Compounds 21-26, 31-36 with moieties of 2'-pyridyl, 3'-pyridyl and 4'-pyridyl at the 2-position and oxadiazoles, thiadiazole, or triazole substituent at the 4- or 5-position generally displayed activities against CVB3 and CVB6. Especially compound 24 ($IC_{50}=1.08{\mu}g/mL$, SI = 61.7 against CVB3) was the promising candidate as lead compound for anti-enteroviral drug. It was observed in the incorporation of heterocyclic rings in benzimidazole at the 5-position could enhance their biological activities.

• Journal of the Korean Chemical Society
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• v.54 no.4
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• pp.414-418
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• 2010

Ethyl 1-aminotetrazole-5-carboxylate (1) reacted with hydrazine hydrate to give the corresponding aminohydrazide 2. Cyclization of 2 by carbon disulfide yielded 1,3,4-oxadiazole-5-thiol structure 3. Reaction of 3 with either chloroacetone or ethyl chloroacetate furnished S-acyl 1,3,4-oxadiazole derivatives 4 and 5, respectively. Also compound 3 reacted with hydrazine hydrate afforded 4-amino-1,2,4-triazole-5-thiol derivative 6. 6-Methyl-1,3,4-triazolo[3,4-b]-1,3,4-thiadiazole structure 7 was synthesized by reaction of aminothiol 6 with glacial acetic acid. Diazotization of 1 with sodium nitrite in presence of hydrochloric acid yielding the diazonium salt which on treating with hippuric acid, oxazolone derivative 8 was obtained. Furthermore, tetrazolo[5,1-f]-1,2,4-triazine 9 was constructed via cyclization of aminoester 1 with formamide. Compound 9 reacted with carbon disulfide to furnish 8-thione derivative 10 which reacting with chloroacetone, ethyl chloroacetate, and hydrazine hydrate, the corresponding chemical structures 11, 12, and 13 were synthesized. 1,2,4-Triazolo[4,3-d]tetrazolo[5,1-f]-1,2,4-triazines 14 and 15 were resulted by treating of compound 13 with triethyl orthoformate, and glacial acetic acid, respectively. The structures of the newly synthesized products were elucidated according to elemental analyses and spectroscopic evidences. Some of the representative members of the prepared compounds were screened for antimicrobial activity.

• The Korean Journal of Pesticide Science
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• v.7 no.2
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• pp.108-116
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• 2003

A series of new quinclorac family, herbicidal 3-phenyl-5-(3,7-dichloro-8-quinolinyl)-1,2,4-oxadiazole derivatives as substrate were synthesized and their growth inhibition activity $(pI_{50})$ against root and shoot of rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli) were determined. And then comparative molecular field analysis (CoMFA) and molecular holographic quantitative structure- activity relationship (HQSAR) were compared in terms of their potential for predictiability. The statistical results were suggested that HQSAR based model had better predictability than CoMFA model. The selective factors to remove barnyard grass take electron withdrawing groups which can be created positive charge and steric bulky on the phenyl ring. Results revealed that the unknown 2,6-dichloro-substituent, U5 and 2,4,6-trichloro-substituent, U6(${\Delta}pI_{50}$=CoMFA: 1.18 & HQSAR: 1.82) were predicted as compound with higher activity and selectivity.

• The Korean Journal of Pesticide Science
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• v.6 no.4
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• pp.279-286
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• 2002

To improve the growth inhibition activities and selectivities for quinclorac family, novel 3-substituted phenyl-5-(3,7-dichloro-8-quinolinyl)-1,2,4-oxadiazole derivatives as the substrate were synthesized and their the activities ($pI_{50}$) against shoot and root of rice plant (Oryza sativa L.) and barn-yard grass (Echinochloa crus-galli) were measured. And the quantitative structure-activity relationships (QSARs) between physicochemical parameters of the substitutents (R) on phenyl group and the activities ($pI_{50}$) were analyzed quantitatively. According to the SAR analyses, the substrates of planar conformation showed higher herbicidal activities against barnyard grass than rice plant. The activities against rice plant depend on the electronic effect (shoots: ${\sigma}_{opt.}=0.49$ & root: $R_{opt.}=-0.15$) of substituents, whereas the activities against shoots and roots of barnyard grass depend on hydrophobicity (${\pi}_{opt.}=0.37{\sim}2.40$). There were conditions of selective growth inhibition activity against barnyard grass when such a ortho-substituted electron donating substituents showing the hydrophobicity value, ${\pi}=2.40$ were introduced on the phenyl ring. The 2-tolyl substituent predicted from SAR equations was expected to have better growth inhibition activity and selectivity (${\Delta}pI_{50}=1.26$) for barnyard grass.