Naftaleniloksipropanol türevi bazı bileşiklerin çok ilaca dirençli bakterilere karşı in vitro etkinliklerinin incelenmesi
Abstract
Çoklu ilaca dirençli bakterilerin tedavisi bütün
dünya için ciddi bir problem teşkil etmekte ve yeni antibakteriyellere olan
ihtiyaç gün geçtikçe artmaktadır. 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. Bu bileşiklerin ÇİD bakterilere karşı in vitro etkinlikleri Kirby-Bauer metodu
ile CLSI standartlarına göre belirlenmiştir. 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.
References
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- G. Sabitha, K. Arundhathi, K. Sudhakar, B. S. Sastry ve J.S. Yadav, "Sabitha, G., Arundhathi, K., Sudhakar, K., Sastry, B. S., ve Yadav, J. S. "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, 2010.
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Examination of in vitro activities of some naphthalenyloxypropanol derivatives against multi-drug resistant bacteria
Abstract
Treatment
of multi-drug resistant bacteria is a growing problem for the whole World and
the need for new antibacterial drug is increasing day by day. 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 Gram-pozitif 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. in vitro activities of these compounds against MDR bacteria were
determined by the Kirby-Bauer method according to CLSI standards. 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.
References
- 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, 1984.
- H. Bercher, W. Siegmud ve A. Grisk, "Correlations between chemical structure and cardiac effectivity of a group of beta-receptor blockaders" Acta Biol. Med. Ger., cilt 37, no. 7, pp. 1081-1090, 1978.
- 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, 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, 1972.
- 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, 1977.
- G. Bazylak ve . L.J. Nagels, "A novel potentiometric approach for detection of beta-adrenergics and beta-adrenolytics in high-performance liquid chromatography" Il Farmaco, cilt 58, no. 8, pp. 591-603, 2003.
- J. B. Wechsler, C.L. Hsu ve P.J. Bryce, "IgE-mediated mast cell responses are inhibited by thymol-mediated, activation-induced cell death in skin inflammation" J. Allergy. Clin. Immunol., cilt 133, no. 6, pp. 1735-1743, 2014.
- V. Cecchetti, A. Fravolini, . F. Schiaffella, O. Tabarrini, G. Bruni ve G. Segre, "o-Chlorobenzenesulfonamidic derivatives of (aryloxy)propanolamines as .beta.-blocking/diuretic agents" J. Med. Chem., cilt 36, no. 1, pp. 157-161, 1993.
- J.E. OatisJr, M.P. Russell, D.R. Knapp ve T. Walle, "Ring-hydroxylated propranolol: synthesis and .beta.-receptor antagonist and vasodilating activities of the seven isomers" J. Med. Chem., cilt 24, no. 3, pp. 309-314, 1981.
- 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, 2003.
- T. Nishizaki, T. Kanno, A. Tsuchiya, Y. Kaku, T. Shimizu ve A. Tanaka, "1-[2-(2-Methoxyphenylamino)ethylamino]-3-(naphthalene-1-yloxy)propan-2-ol May Be a Promising Anticancer Drug" Molecules, cilt 19, no. 12, pp. 21462-21472, 2014.
- G. Sabitha, K. Arundhathi, K. Sudhakar, B. S. Sastry ve J.S. Yadav, "Sabitha, G., Arundhathi, K., Sudhakar, K., Sastry, B. S., ve Yadav, J. S. "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, 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, 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, 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, 1991.
- M.A. Wikler, "Performance standards for antimicrobial susceptibility testing: eighteenth informational supplement" Clinical and Laboratory Standards Institute (CLSI), WAYNE, PA, 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 or interim standard definitions for acquired resistance" Clin. Microbiol. Infect., cilt 18, pp. 268-281, 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 , 1997.
Details
| Subjects | Chemical Engineering |
|---|---|
| Journal Section | Research Articles |
| Authors | |
| Publication Date | June 1, 2017 |
| Submission Date | September 8, 2016 |
| Acceptance Date | January 23, 207 |
| Published in Issue | Year 2017 Volume: 21 Issue: 3 |
Cite
Sakarya University Journal of Science (SAUJS)