Abstract
Abstract
 The target derivative are gentamicin linked with L-Val- L-Ala by an ester linkage. These were synthesized by esterification method, which included the reaction of -OH hydroxyl group on (carbon No.5) of gentamicin with the acid chloride of the corresponding dipeptide, The preparation of new derivative of gentamicin involved protected the primary & secondary amine groups of Gentamicin, by Ethylchloroformate (ECF) to give N-carbomethoxy Gentamicin which was used for further chemical synthesis involving the free hydroxyl groups.
 Then prepared dipeptide (L-Val- L-Ala) by conventional solution method in present DCC & HoBt then reacted with thionyl chloride to prepared acid chloride of dipeptides, then after, linked by ester linkage to N-protection gentamicin in present pyridine as base, finally deportation the amino group of synthesized compound by using TFAA in present anisole.
 The characterization of the titled compounds were performed utilizing FTIR spectroscopy, CHNS elemental analysis, and by measurements of their physical properties.
Highlights
Gentamicin is an aminoglycoside antibiotic, used to treat many types of bacterial infections, those caused by Gramnegative bacteria
All chemicals and solvents used during synthesis were of analytical grade and used without further purification as follow ; Gentamicin Sulphate(Hyperchem, China), LAlanine, Acetone, Boc - L – Valine, Chloroform, Ethanol (98%),Methanol (98%) Thionyl chloride, and Trifluoroacetic acid (TFA) (Fluka AG, Germany), Acetyl Chloride, Acetic acid, Dichloromethane, methylene chloride, Hydrochloric acid (33%) Pyridine,and Tetrahydrofuran (THF)( BDH, England), Dimethylformamide (DMF)and Triethylamine (TEA)( Fluka AG, Switzerland), Ethyl chloroformate (ECF) and Silica gel F254 aluminum sheets,( Merck, Germany), Anisole(Gillard chem.,UK), Hydroxybenzotriazole (HOBt)( Sigma-Aldrich,USA), Petroleum ether (60 o -80 o C)(
The organic layer was dried using anhydrous magnesium sulfate filtered and methylene chloride was evaporated under vacuum leaving a white precipitate recrystallized using (70% methanol).The percentage yield, and Rf values are listed in table 1, The IR characteristic bands of Ncarboethoxy- gentamicin are listed in table 2, CHNO data are listed in table 3
Summary
Gentamicin is an aminoglycoside antibiotic, used to treat many types of bacterial infections, those caused by Gramnegative bacteria. Like all aminoglycosides, when gentamicin is given orally it is not systemically active. This is because it is not absorbed to any appreciable extent from the small intestine. Aminoglycosides are poorly absorbed from the gastrointestinal tract and are administered parenterally [4] Their high water solubility and low protein-binding facilitate distribution[5, 6]. Aciclovir major step forward toward molecular understanding of the physiological and pharmacological significance of peptide transporters [6] ,among various membrane transporters, peptide transporters are the most attractive targets in prodrug design to improve oral drug absorption[7]. The peptide transporter is a possible route for improving the intestinal absorption of pharmacologically active amino acid analogues. As examples of compounds without a peptide bond, the aminopeptidase inhibitor arphamenine, the antiviral agent valacyclovir and 4-aminophenylacetic acid were reported to be substrates for peptide transporter [8]
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Schedule a callMore From: Iraqi Journal of Pharmaceutical Sciences ( P-ISSN: 1683 - 3597 , E-ISSN : 2521 - 3512)
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