Naftaleniloksipropanol türevi bazı bileşiklerin çok ilaca dirençli bakterilere karşı in vitro etkinliklerinin incelenmesi
Bu çalışmada, α-Naftol bileşiğinden oksipropanolamin türevleri sentezlenmiş ve ÇİD (çoklu ilaca dirençli) bakterilere karşı aktiviteleri değerlendirilmiştir. Gram-pozitif bakterilerden Staphylococcus aureus ve Gram-negatif bakterilerden A. baumannii, P. aeruginosa, E. coli suşları kullanılmıştır. Çalışmada kullanılan 2a-d bileşiklerinin sentezi için ilk olarak α-naftol ile epiklorohidrin reaksiyona sokularak 2-((naftelen-1-iloksi)metil)oksiran (1) bileşiği elde edilmiş ve ardından dört değişik amin türevi ile reaksiyona sokularak 2a-d türevleri elde edilmiştir. Elde edilen bileşiklerden 2a, 2b ve 2c her bir bakteri türüne karşı test edilen diğer antibakteriyellerden daha fazla antibakteriyel etkiye sahipken, 2d bileşiği Gram-negatif bakterilere karşı ortalama veya altında bir etkinlik göstermiş, Gram-pozitif bakteri olan S. aureus’ a karşı yüksek bir etkinlik sergilemiştir.
Examination of in vitro activities of some naphthalenyloxypropanol derivatives against multi-drug resistant bacteria
Herein, oxipropanolamine derivatives from α-naphthol compound were synthesized and the activities against MDR (multi-drug resistant) bacteria were evaluated. Strains of S. aureus which is one of Gram-positive bacteria and A. baumannii, P. aeruginosa, E. coli which are of Gram-negative bacteria were used.The tested bacteria are Grampozitif stain of S. aureus and Gram-negatif stains of A. baumannii, P. aeruginosa, E. coli. For the synthesis of compounds 2a-d which were used in the study, firstly 2-((naphthalen-1-yloxy)methyl) oxirane was obtained with the reaction of α-naphthol with epichlorohydrin and then reacted with four diffrent amine groups to obtain 2a-d derivatives. While the obtained compounds 2a, 2b and 2c have more antibacterial activity than other tested antibacterials, the compound 2d has shown moderate or blow antibacterial activity against Gram-negative bacteria, but has a high activity against gram-positive bacteria S. aureus.
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- M. C. Carre, A. Youlassani ve P. Caubere,
“Synthesis of a novel series of
(aryloxy)propanolamines: new selective .beta.2-
blocking agents” J. Med. Chem., cilt 27, no. 6, pp.
792-799, Haz. 1984.
- D. Mauleón, M. D. Pujol, ve G. Rosell. "BAdrenergic
antagonists: N-alkyl and N-amidoethyl
(arylalkoxy) propanolamines related to
propranolol." Eur. J. Med. Chem., cilt 23. no. 5, pp.
421-426, Eyl.1988.
- P. J. Machin, D. N. Hurst, R. M. Bradshaw, L. C.
Blaber, D. T. Burden ve M. A. Rosemary, “.beta.1-
Selective adrenoceptor antagonists. 3. 4-Azolyl
linked phenoxypropanolamines” J. Med. Chem.,
cilt 27, no. 4, pp. 503-509, Nis 1984.
- A. F. Crowther, R. Howe, B. J. McLoughlin, K. B.
Mallion, B. S. Rao, L. H. Smith ve R. W. Turner,
“.beta.-Adrenergic blocking agents. 12.
Heterocyclic compounds related to propranolol” J.
Med. Chem., cilt 15, no. 3, pp. 260-266, Mar 1972.
- G., Bazylak ve L.J. Nagels, “A novel
potentiometric approach for detection of betaadrenergics
and beta-adrenolytics in high performance liquid chromatography” II Farmaco,
cilt 58, no. 8, pp. 591-603, Agu 2003.
- J. B. Wechsler, C. L. Hsu ve P. J. Bryce, “IgEmediatedmastcellresponsesareinhibitedbythymolmediated,
activation-inducedcelldeath in skin
inflammation” J. Allergy Clin. Immunol., cilt 133,
no. 6, pp. 1735-1743, Haz 2014.
- V. Cecchetti, A. Fravolini, F. Schiaffella, O.
Tabarrini, G. Bruni, ve G. Segre, “oChlorobenzenesulfonamidicderivatives
of
(aryloxy) propanolamines as. beta.-
blocking/diureticagents” J Med. Chem. cilt 36, no.
1, pp. 157-161, Haz 1993.
- J. E. Oatis, M. P. Russell, D. R. Knapp ve T.
Walle, “ Ring-Hydroxylated Propranolol: Synthesis
and P-Receptor Antagonist and Vasodilating
Activities of the Seven Isomers, » J. Med.
Chem.cilt 24, no 3, pp. 299-354, Mar 1981.
- C. Kaiser, T. Jen, E. Garvey, W. D. Bowen, . D. F.
Colella ve . J. R. WardellJr., “Adrenergic agents. 4.
Substituted phenoxypropanolamine derivatives as
potential .beta.-adrenergic agonists” J. Med.
Chem., cilt 20, no. 5, pp. 687-692, Eki 1977.
- X. Wang ve C. B. Ching, “Determination of the
Competitive Adsorption Isotherms of Nadolol
Enantiomers by an Improved h-Root Method” Ind.
Eng. Chem. Res., cilt 42, no. 24, pp. 6171-6180,
Eki 2003.
- T. Nishizaki, T. Kanno, A. Tsuchiya, Y. Kaku, T.
Shimizu ve A. Tanaka, “1-[2-(2-
Methoxyphenylamino)ethylamino]-3-(naphthalene1-yloxy)propan-2-ol
May Be a Promising
Anticancer Drug” Molecules, cilt 19, no. 12, pp.
21462-21472, Kas 2014.
- G. Sabitha, K. Arundhathi, K. Sudhakar, B. S.
Sastry ve J. S. Yadav, “A novel three‐component
one‐pot reaction involving β‐naphthol, aldehydes,
and urea promoted by TMSCl/NaI” J. Heterocyclic
Chem., cilt 47, no. 2, pp. 272-275, Haz 2010.
- P. K. Sahu, P. K. Sahu, D. Thavaselvam, . A. M.
Alafeefy ve D. D. Agarwal, “Synthesis and
evaluation of antimicrobial activity of 2-
aminobenzothiazolomethyl naphthol derivatives”
Med. Chem. Res., cilt 24, no. 2, pp. 725-736, Şub
2015.
- Y. B. Rokade ve R. Z. Sayyed, “Naphthalene
derivatives: A new range of antimicrobials with
high therapeutic value” Rasayan J. Chem, cilt 2,
no. 4, pp. 972-980, Eki 2009.
- H. S. Bevinakatti ve A. A. Banerji, “Practical
chemoenzymic synthesis of both enantiomers of
propranolol” J. Org. Chem, cilt 56, no. 18, pp.
5372-5375, Agu 1991.
- M. A. Wikler, “Performance standards for
antimicrobial susceptibility testing: eighteenth
informational supplement” Clinical and Laboratory
Standards Institute (CLSI), WAYNE, PA, Haz
2008.
- A. P. Magiorakos, A. Srinivasan, R. B. Carey, Y.
Carmeli, M. E. Falagas, C. G. Giske, S. Harbarth,
J. F. Hindler, G. Kahlmeter, D. L. Peterson, L. B.
Rice, J. Stelling, M. J. Struelens, A. Vatopoulos, J.
T. Webwr ve D. L. Monnet, “Multidrug-resistant,
extensively drug-resistant and pandrug-resistant
bacteria: an international expert proposal for
interim standard definitions for acquired
resistance” Clin. Microbio.l Infect., cilt 18, pp.
268-281, Tem 2012.
- E. N. Nen, “Chemical disinfectants and
antisepticsquantitative suspension test for the
evaluation of bactericidal activity of chemical
disinfectants and antiseptics used in food,
industrial, domestic, and institutional areas-test
method and requirements (phase 1)” European
committee for standardization, Brussels , Haz
1997.
- World Health Organization, “Antimicrobial
resistance: 2014 global report on surveillance”
Geneva, Switzerland,
2014 pp. xxii - 232.
- U. Theuretzbacher, “Global antibacterial
resistance: The never-ending story” Journal of
Global Antimicrobial Resistance, cilt 1, no. 2, pp.
63-69, Mar 2013.
- S.N. Louis, T.L. Nero, D. Iakovidis, G.P. Jackman
ve W.J. Louis, “LK 204–545, a highly selective β
1-adrenoceptor antagonist at human βadrenoceptors”
Eur. J. Pharmacol., cilt 367, no. 2,
pp. 431-435, Şub 1999.