Benzothiazolyl Biguanides의 합성

임철부,이인숙,임채욱 중앙대학교 약학연구소 1996 약학 논총 Vol.10 No.-

In order to find new antimicrobial agents, twelve new alkylene bis benzothiazolyl biguanides and eight benzothiazoly biguanides were synthesized. The treatment of alkylenediamines·2HCI with sodium dicyanamide afforded alkylene bis cyanoguanidines. Alkylene bis benzothiazolyl biguanides were synthesized by the reaction of alkylene bis cyanoguanidines with 2-aminobenzothiazole. Benzothiazolyl biguanides were obtained from N-cyanoheterocyclylamidines and 2-aminobenzothiazoles through the similar procedures.

N-치환 Piperazino Ciprofloxacin 誘導體의 合成 및 抗菌作用

任哲夫,韓完植 중앙대학교 약학연구소 1993 약학 논총 Vol.7 No.-

In order to find more potent antimicrobial agents, fourteen new 1-clyclo-propyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(N-substituted)-1-piperazinyl]-3-quinoline carboxylic acid derivatives(R=methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, phenyl, 2,4-dimethoxy phenyl) and their pivaloyloxymethyl esters were synthesized and evaluated for their antimirobial activities. Treatment of isocynates with 1-cyclopropyl-6-fluoro-1,4-digydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid[Ciprofloxacin]afforded N-substitued carbamoyl piperazino quinoline carboxylic [acids(1)-(8)]. Their pivaloyloxymethyl esters were obtained by the reaction of N-substitued ciprofloxacins with pivaloyloxymethyl chloride in the presence of potassium carbonate and potassium iodide[(9)-(14)]. The synthesized compounds were examined their antimicrobial activities in vitro against Streptococus pyogenes 77 A, Streptococcus faecium MD 8, b, Staphylococcus aureus SG 511, Escherichia coli 1507 E, Pseudomonas aeruginosa 1711 M, Pseudomonas aeruginosa 1592 E, Salmonella typhimurium, Klebsiella oxytoca 1082 E, Klebsiel la aerogenes 1522 E, Enterobacter cloacae 1321 E. 1. The most active compound [12], 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(N-isopropyl carbamoyl)-1-piperazinyl]-3-quinoline, carboxylic acid pivaloyoxymethyl ester, exhibited the growth inhibitory activity at a concentration of 0.5㎍/ml against St.pyogenes 77 A, 1.0㎍/ml against St.faecium MD 8b, 1.0㎍/ml against Staphylococcus aureus SG 511, 0.06㎍/ml against Escherichia coli 1507 E, 0.25㎍/ml aginst Peudomanas aeruginosa 1711 M, 0.25㎍/ml against Pseudomonas aeruginosa 1592 E, 0.25㎍/ml against Salmonella typhimurium, 0.06㎍/ml against Klebsiella oxytoca 1082 E, 0.06㎍/ml against Klebsiella aerogenes 1522 E, 0.25㎍/ml against Enterobacter cloacae 1321 E. 2. Most synthesized carbamoyl piperazino ciprofloxacins showed more potent antimicrobial activities than those their pivaloyloxymethyl esters.

Benzothiazolyl Biguanides의 항미생물작용

임철부,이인숙,임채욱 중앙대학교 약학연구소 1996 약학 논총 Vol.10 No.-

The twenty benzothiazolyl biguanides synthesized were evaluated for their antimicrobial activities against Staphylococcus aureus. Bacillus subtilis, Mycobacterium phlei, Escherichia coli, Microsporium canis, Candida albicans, Sporothrix schenkii and Trichophyton mentagrophytes. The results obtained were as follow : The most active compound, 1,6-bis{N^5-(6-chlorobenzothiazol-2-yl)-N^1-biguanido} hexane·2HCI (14) showed the growth inhibitory activity against S. aureus at the concentration of 7.81ug/mL, against B.subtilis at 15.63ug/mL and against M. phlei at 31.25ug/mL. 1,6-Bis {N^5-(6-chlorobenzothiazol-2-yl)-N^1-biguanido} hexane·2HCI(14), 1,6-Bis{N^5-(6-bromobenzothiazol-2-yl)-N^1-biguanido) hexane·2HCI (15) and N-(6-chlorobenzothiazol-2-yl)-1-piperidinylamidinoamidine·HCI (24) inhibited the growth of M. phlei at the concentration of 31.25ug/mL respectively. 1,4-Bis{N^5-(6-methylbenzothiazol-2yl)-N^1-biguanido}butane·2HCI(9) and 1,4-bis{N^5-(6-bromobenzothiazol-2-yl)-N^1-biguanido}butane·2HCI(11) exhibited the antimicrobial activity against B.subtilils at the concentration of 31.25ug/mL. Twelve new biguanide compounds showed growth inhibitory activities against C. albicans at the concentration of 400ug/mL.

(4-Nicotinate-2-yl)thiobutyl 6-Exomethylene Penam의 합성

임채욱,박희석,임철부 중앙대학교 약학연구소 1996 약학 논총 Vol.10 No.-

The synthesis of new 6-exomethylene penam containing triazole ring was described. 1, 3-Dipolar cycloaddition of 4-azidobutanol with propargyl aldehyde gave 1-(4-hydroxybutyl)-1,2,3-triazole-4-carboxaldehyde, which reacted with 6,6-dibromopenicillanate to yield the stereoisomeric mixture of 6-bromo -6-〔hydroxy-1-(triazol-4-yl)methyl〕 penicillanate compound. This hydroxy compound was treated with acetic anhydride and zinc to afford the 6-exomethylene penam compound.

Thiocarbamyl Norfloxacin 유도체의 합성 및 항균작용

이강수,임철부 중앙대학교 약학연구소 1989 약학 논총 Vol.3 No.-

Eleven new l-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-N-(substituted)-thiocarbamyl-piperazin- yl]-3-quinolinecarboxylic acid derivatives (R- methyl, n-propyl, isopropyl, n-butyl, isobutyl, phenyl, 4-chorophenyl, 4-methylphenyl,4-methylphenyl, 4-ethoxyphenyl, m-naphthyl) and their pivaloyloxyme-thyl esters were synthesized and evaluated for their antimicrobial activities. 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-N-(substiuted)-thiocarbamyl-1-piperazinyl]-3-quino-linecarboxylic acid derivatives were prepared by the reaction of alkyl-and arylisothiocyanates with 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperainyl)-3-quinolinecarboxylic acid (Norfloxa-cin). Treatment of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-N-(substituted)-thiocarbamyl-1-piper-azinyl]-3-quinolinecarboxylic acids with pivaloyloxymethy]chloride afforded eleven 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-N-(substiuted)-thiocarbamyl-1-piperazinyl]-3-quinolinecarboxylic acid pivaloyoxymethyl esters. The synthesized compounds were examined their antimicrobial activities against Escheri-chia coli 6-PE-4, Staphylococcus aureus CHA 79110, Bacillus subtilis 74-51, Klebsiella pneumo-niae. Proteus vulgaris 78615, and Pseudomonas aeruginosa /8765-1P_2, in vitro. The results obtained were as follows; 1. The most active ester compound[23], 1-ethyl-6-fluoro-1-4-dihydro-4-oxo-7-[4-N-(methyl)-thiocarbamyl-1-piperazinyl]-3-quinolinecarboxylic acid pivaloyoxymethyl ester, inhibited the growth of Escherichia coli at the concentration of 3.90㎍/mℓ, Staphylococcus aureus at 7.81㎍/mℓ, Bacillus subtilis at 0.06㎍/mℓ, Klebsiella pneumoniac at 1.95㎍/mℓ, Proteus vul-garis at 15.63㎍/mℓ, and Pseudomonas aeruginosa at 15.63㎍/mℓ, respectively. 2.In general, aliphatic substituted thiocarbamyl norfloxacin pivaloyloxymethyl esters showed more potent antimicrobial activities than those of aromatic substituted thiocarbamyl norflox-acin esters.

6-Exomethylene penamsulfone 유도체의 β-lactamase 저해작용

김해종,여성현,임채욱,임철부,김미영 중앙대학교 약학연구소 1996 약학 논총 Vol.10 No.-

6-Exomethylene penam derivatives were tested as possible β-lactamase inhibitors. The in vitro β-lactamase inhibitory activities were determined by a spectrophotometric assay using Type Ⅰ, Ⅱ, Ⅲ, Ⅳ and TEM β-lactamase. Their activities were compared with sulbactam, tazobactam and clavulanic acid. The 6-exomethylene sulfone derivatives were more potent than clavulanic acid and sulbactam against Type Ⅳ β-lactamase. The Z-isomers showed stronger activities than the E-isomers against TEM and Type Ⅳ β-lactamase.

Adenosine 수용체 길항제인 플라보노이드 유도체의 3D-QSAR

임채욱,최세경,민지홍,유재학,임철부 중앙대학교 약학연구소 2000 약학 논총 Vol.14 No.-

3D-QSAR of flavonoid derivatives as adenosine receptor antagonist was performed with the comparative molecular field analysis (CoMFA). Their activities were well correlated with their steric field, electrostatic field, and lipophilicities.

Thiocarbamyl Enoxacin 유도체의 합성 및 항균작용

신화우,고무수,정동훈,최광식,임철부 원광대학교 식품약품안전성연구소 1991 食品藥品安全性硏究 Vol.4 No.-

Treatment of 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7-(1-piperazinyl)-1, 8-naphthyridine-3-carboxylic acid (Enoxacin) with alkyl(or aryl) isothiocyanates which obtained from alkyl(or aryl) amines afforded six 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7-(1-alkylthiocarbamylpiperazinyl)-1, 8-naphthyridine-3-carboxylic acids and five 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7-(1-arylthiocarbamyl piperazinyl)-1, 8-naphthyridine-3-carboxylic acids. The compounds synthesized were evaluated for their antimicrobial activities, in vitro, against Escherichia coli 6-PE-4, Bacillus subtilis 74-51, Proteus vulgaris 78645, Klebsiella pneumoniae JYA-78314, Staphylococcus aureus 79110 and Pseudomonas aeruginosa 8765-1 p_2.

p-Aminosalicylate 유도체의 향미생물작용

임채욱,이극선,오옥희,이현수,임철부 중앙대학교 약학연구소 2000 약학 논총 Vol.14 No.-

The 15 synthesized p-aminosalicylate esters derivatives were evaluated for their antimicrobial activities, in vitro, against Mycobacterium phlei (CACC 75432), Staphylococcus aureus (CHA 78311), Bacillus subtilis (CAUCC 310) and Escherichia coli (P32). Bivalent ligand derivatives (1-6) showed weaker activities than their parent p-aminosalicylate(PAS) in vitro. But some of thiouera derivatives (8 and 10) gave stronger activities against Mycobacterium phlei and Staphylococcus aureus than their parent p-aminosalicylate.

Synthesis and β-lactamase inhibitory activity of 6-exomethylene penamsulfone derivatives - III ( In vitro β-lactamase Ingibitory activity of 6-exomethylene penamsulfone derivatives )

(Chul Bu Yim),(Chae Uk Im),(Sung Hyun Yeo),(Mie Young Kim) 한국응용약물학회 1996 학술대회 Vol.1996 No.1