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Information Journal Paper

Title

CORRELATION BETWEEN LIPOPHILICITY AND ANTIMICROBIAL ACTIVITY OF SOME 2-(4-SUBSTITUTED PHENYL)-3(2H)-ISOTHIAZOLONES

Pages

  256-263

Keywords

3(2H)-ISOTHIAZOLONES 
LOG PO/W 

Abstract

 Background and purpose of the study. 3(2H)-Isothiazolones have shown antimicrobial activity and have been used as preservative in different products. However, reports on their structure-antimicrobial activity relationship are scanty. The aim of this study was to determine the relationship between lipophilicity and antimicrobial activity of several 2- (4-substituted phenyl) -3(2H)-isothiazolones of which some have shown antibacterial activities similar or higher than gentamycin, ceftazidime, ceftriaxone, ciprofloxacin , and antifungal activites similar or higher than itraconazole and ketoconazole as reference drugs.Methods. Partition coefficient (log Po/w) of the tested compounds was determined experimentally by a reversed- phase high performance liquid chromatography method using octadecyl-poly(vinyl alcohol) (ODP) column and methanol-water gradient as mobile phase and theoretically by CLOG P and ALOGPS computer programs. Results. The HPLC and theoretical log Po/wvalues showed potential correlations which indicate that both experimental and theoretical methods are equally suitable to predict lipophilicity of 3(2H)-isothiazolones. There were also significant correlations between MICs (minimum inhibitory concentrations) of 5-chloro substituted 3(2H)- isothiazolnes against Salmonella typhimurium and Escherichia coli and experimentally determined log Po/w values, as well as MICs of 5-unsubstituted 3(2H)- isothiazolnes against E. coli and ALOGPS values. The antifungal activity of the tested compounds against Tricophyton. mentagrophytes and M.canis increased with increase in the experimental and theoretical log P values , but this increase was only significant for the activity against Microsporum. canis.v

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    • Cite

    APA: Copy

    REZAEI, SAEID, KHALAJ, A., ADIBPOUR, N., & SAFARI, M.. (2009). CORRELATION BETWEEN LIPOPHILICITY AND ANTIMICROBIAL ACTIVITY OF SOME 2-(4-SUBSTITUTED PHENYL)-3(2H)-ISOTHIAZOLONES. DARU JOURNAL OF PHARMACEUTICAL SCIENCE, 17(4), 256-263. SID. https://sid.ir/paper/275528/en

    Vancouver: Copy

    REZAEI SAEID, KHALAJ A., ADIBPOUR N., SAFARI M.. CORRELATION BETWEEN LIPOPHILICITY AND ANTIMICROBIAL ACTIVITY OF SOME 2-(4-SUBSTITUTED PHENYL)-3(2H)-ISOTHIAZOLONES. DARU JOURNAL OF PHARMACEUTICAL SCIENCE[Internet]. 2009;17(4):256-263. Available from: https://sid.ir/paper/275528/en

    IEEE: Copy

    SAEID REZAEI, A. KHALAJ, N. ADIBPOUR, and M. SAFARI, “CORRELATION BETWEEN LIPOPHILICITY AND ANTIMICROBIAL ACTIVITY OF SOME 2-(4-SUBSTITUTED PHENYL)-3(2H)-ISOTHIAZOLONES,” DARU JOURNAL OF PHARMACEUTICAL SCIENCE, vol. 17, no. 4, pp. 256–263, 2009, [Online]. Available: https://sid.ir/paper/275528/en

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