Araştırma Makalesi
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2-Metil-3-Acil-4-Aril-2,6,6 ve/veya 2,7,7-Trimetil-1,4,5,6,7,8-Hekzahidrokinolin Türevlerinin Antimikrobiyal Etkilerinin Araştırılması

Yıl 2011, Sayı: 1, 51 - 58, 01.01.2011

Miyase Gözde Gündüz Melike Ekizoğlu Didem Kart Rahime Şimşek , Cihat Şafak

Öz

Bu çalışmada metil etil 2,6,6- veya 2,7,7-trimetil-5-okso-4- difluorosübstitüe fenil -1,4,5,6,7,8-hekzahidrokinolin-3-karboksilat ve N,N-dietil-2,6,6- veya 2,7,7-trimetil-5-okso-4- difluorosübstitüe fenil -1,4,5,6,7,8-hekzahidrokinolin-3-karboksamit yapısına sahip otuz bileşiğin antimikrobiyal aktivitesi taranmıştır. Bakteri ve funguslara karşı antimikrobiyal aktiviteleri broth mikrodilüsyon yöntemi kullanılarak minimum inhibitör konsantrasyonu MIC olarak saptanmıştır.

Anahtar Kelimeler

1 4-dihydropyridine hexahydroquinoline antimicrobial activity

Kaynakça

  • Edraki, N., Mehdipour, A. R., Khoshneviszadeh, M., Ramin, M.; Dihydropyridines: Evaluation of Their Current and Future Pharmacological Applications, Drug Discov. To- day, 14(21-22), 1058 (2009).
  • Şafak, C., Şimşek, R.; Fused 1,4-Dihydropyridines as Potential Calcium Modulatory Compounds, Mini Rev. Med. Chem., 6, 747 ( 2006).
  • Peri, R., Padmanabhan, S., Rutledge, A., Singh, S., Triggle, D.J.; Permanently Charged Chiral 1,4-Dihydropyridines: Molecular Probes of L-Type Calcium Channels. Synthesis and Pharmacological Characterization of Methyl (ω-Trimethylalkylammonium) 1,4-Di- hydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5- pyridinedicarboxylate Iodide, Calcium Channel Antagonists, J. Med. Chem, 43(15), 2906 ( 2000).
  • Coburn, R. A., Wierzba, M., Suto, M. J., Solo, A. J., Triggle, A. M., Triggle, D.J.; 1,4-Di- hydropyridine Antagonist Activities at the Calcium Channel: A Quantitative Structure- Activity Relationship Approach, J. Med. Chem., 31(11), 2103 (1988).
  • Wojewodzka, M., Gradzka, I., Buraczewska, I., Brzoska, K., Sochanowicz, B., Goncha- rov, R., et al.; Dihydropyridines Decrease X-ray-induced DNA Base Damage in Mam- malian Cells, Mutat. Res., 671(1-2), 45 (2009).
  • Mehdipour, A. R., Javidnia, K., Hemmateenejad, B., Amirghofran, Z., Miri, R.; Dihy- dropyridine Derivatives to Overcome Atypical Multidrug Resistance: Design, Synthesis, QSAR Studies, and Evaluation of Their Cytotoxic and Pharmacological Activities, Chem. Biol. Drug Res., 70(4), 337 (2007).
  • Samzadeh-Kermani, A., Shafaroodi, H., Miri, R., Mirkhani, H., Vosooghi, M., Shafiee, A.; Lipophilic 2-(4-chlorophenyl)-4-thiazolyl-1,4-dihydropyridines: Synthesis, Calcium Channel Antagonist Activity, and Protection Against Pentylenetetrazole-induced Seizu- re, Med. Chem. Res., 18, 112 (2009).
  • Sirisha, K., Achaiah, G., Reddy, V.M.; Facile Synthesis and Antibacterial, Antitubercu- lar, and Anticancer Activities of Novel 1,4-Dihydropyridines, Arch. Pharm. Chem. Life Sci., 343, 342 (2010).
  • Sirisha, K., Bikshapathi, D., Achaiah, G., Reddy, V.M.; Synthesis, Antibacterial and Antimycobacterial Activities of Some New 4-Aryl/heteroaryl-2,6-dimethyl-3,5-bis-N- (aryl)-carbamoyl-1,4-dihydropyridines, Eur. J. Med. Chem., 46, 1564 (2011).
  • Desai, B., Sureja, D., Naliapara, Y., Shah, A., Saxena, A.K.; Synthesis and QSAR Stud- ies of 4-Substituted phenyl-2,6-dimethyl-3, 5-bis-N-(substituted phenyl)carbamoyl- 1,4-dihydropyridines as Potential Antitubercular Agents, Bioorg. Med. Chem., 9(8), 1993 (2001).
  • Kumar, R. S., Idhayadhulla, A., Abdul Nasser, A.J., Selvin, J.; Synthesis and Antimi- crobial Activity of a New Series of 1,4-Dihydropyridine Derivatives, J. Serb. Chem. Soc., 76(1), 1 (2011).
  • Pattan, S. R., Butle, S.R. Bhat, A.R., Purohit, S.S.; Synthesis & Evaluation of Some 1,4-Dihydropyridine Derivatives as Anti-microbial Agents, Indian J. Heterocyc. Chem., 14(1), 79 (2004).
  • Mithlesh, P., Pawan, K., Kant, R., Shukla, S.K., Ojha, K.G.; Rapid Synthesis and Bio- logical Evaluation of 1, 4-Dihydropyridine Derivatives Containing A Benzothiazolyl Moi- ety, Cent. Eur. J. Chem., 8(1), 163 (2010).
  • Şimşek, R., Gündüz, M.G., Sırmagül, B., Şafak, C., Erol, K, Linden, A.; 4-Difluoro- substituted phenyl-5-oxohexahydroquinoline Derivatives and Their Effects on Calcium Channels, Arzneim. Forsch. Drug Res., 56(7), 527 (2006).
  • Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Sus- ceptibility Tests for Bacteria That Grow Aerobically, Approved Standard 8th ed., M 07- A8, 2008.
  • Clinical and Laboratory Standards Institute, Reference Method for Broth Dilution An- tifungal Susceptibility Testing of Yeasts: Approved Standard 3rd ed., M 27-A3, 2008.

Antimicrobial Screening of 2-Methyl-3- Acyl-4-Aryl-2,6,6 and / or 2,7,7-Trimethyl1,4,5,6,7,8-Hexahydroquinoline Derivatives

Yıl 2011, Sayı: 1, 51 - 58, 01.01.2011

Miyase Gözde Gündüz Melike Ekizoğlu Didem Kart Rahime Şimşek , Cihat Şafak

Öz

In this study, thirty compounds having methyl ethyl 2,6,6- or 2,7,7-trimethyl-5-oxo-4- difluorosubstituted phenyl -1,4,5,6,7,8-hexahydroquinoline- 3-carboxylate and N,N-diethyl-2,6,6- or 2,7,7-trimethyl- 5-oxo-4- difluorosubstituted phenyl -1,4,5,6,7,8-hexahydroquinoline-3- carboxamide structure, have been screened for their antimicrobial activities. Antimicrobial activities were determined as minimum inhibitory concentration MIC values by broth microdilution method against bacteria and fungi.

Anahtar Kelimeler

1 4-dihidropiridin hekzahidrokinolin antimikrobiyal aktivite

Kaynakça

  • Edraki, N., Mehdipour, A. R., Khoshneviszadeh, M., Ramin, M.; Dihydropyridines: Evaluation of Their Current and Future Pharmacological Applications, Drug Discov. To- day, 14(21-22), 1058 (2009).
  • Şafak, C., Şimşek, R.; Fused 1,4-Dihydropyridines as Potential Calcium Modulatory Compounds, Mini Rev. Med. Chem., 6, 747 ( 2006).
  • Peri, R., Padmanabhan, S., Rutledge, A., Singh, S., Triggle, D.J.; Permanently Charged Chiral 1,4-Dihydropyridines: Molecular Probes of L-Type Calcium Channels. Synthesis and Pharmacological Characterization of Methyl (ω-Trimethylalkylammonium) 1,4-Di- hydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5- pyridinedicarboxylate Iodide, Calcium Channel Antagonists, J. Med. Chem, 43(15), 2906 ( 2000).
  • Coburn, R. A., Wierzba, M., Suto, M. J., Solo, A. J., Triggle, A. M., Triggle, D.J.; 1,4-Di- hydropyridine Antagonist Activities at the Calcium Channel: A Quantitative Structure- Activity Relationship Approach, J. Med. Chem., 31(11), 2103 (1988).
  • Wojewodzka, M., Gradzka, I., Buraczewska, I., Brzoska, K., Sochanowicz, B., Goncha- rov, R., et al.; Dihydropyridines Decrease X-ray-induced DNA Base Damage in Mam- malian Cells, Mutat. Res., 671(1-2), 45 (2009).
  • Mehdipour, A. R., Javidnia, K., Hemmateenejad, B., Amirghofran, Z., Miri, R.; Dihy- dropyridine Derivatives to Overcome Atypical Multidrug Resistance: Design, Synthesis, QSAR Studies, and Evaluation of Their Cytotoxic and Pharmacological Activities, Chem. Biol. Drug Res., 70(4), 337 (2007).
  • Samzadeh-Kermani, A., Shafaroodi, H., Miri, R., Mirkhani, H., Vosooghi, M., Shafiee, A.; Lipophilic 2-(4-chlorophenyl)-4-thiazolyl-1,4-dihydropyridines: Synthesis, Calcium Channel Antagonist Activity, and Protection Against Pentylenetetrazole-induced Seizu- re, Med. Chem. Res., 18, 112 (2009).
  • Sirisha, K., Achaiah, G., Reddy, V.M.; Facile Synthesis and Antibacterial, Antitubercu- lar, and Anticancer Activities of Novel 1,4-Dihydropyridines, Arch. Pharm. Chem. Life Sci., 343, 342 (2010).
  • Sirisha, K., Bikshapathi, D., Achaiah, G., Reddy, V.M.; Synthesis, Antibacterial and Antimycobacterial Activities of Some New 4-Aryl/heteroaryl-2,6-dimethyl-3,5-bis-N- (aryl)-carbamoyl-1,4-dihydropyridines, Eur. J. Med. Chem., 46, 1564 (2011).
  • Desai, B., Sureja, D., Naliapara, Y., Shah, A., Saxena, A.K.; Synthesis and QSAR Stud- ies of 4-Substituted phenyl-2,6-dimethyl-3, 5-bis-N-(substituted phenyl)carbamoyl- 1,4-dihydropyridines as Potential Antitubercular Agents, Bioorg. Med. Chem., 9(8), 1993 (2001).
  • Kumar, R. S., Idhayadhulla, A., Abdul Nasser, A.J., Selvin, J.; Synthesis and Antimi- crobial Activity of a New Series of 1,4-Dihydropyridine Derivatives, J. Serb. Chem. Soc., 76(1), 1 (2011).
  • Pattan, S. R., Butle, S.R. Bhat, A.R., Purohit, S.S.; Synthesis & Evaluation of Some 1,4-Dihydropyridine Derivatives as Anti-microbial Agents, Indian J. Heterocyc. Chem., 14(1), 79 (2004).
  • Mithlesh, P., Pawan, K., Kant, R., Shukla, S.K., Ojha, K.G.; Rapid Synthesis and Bio- logical Evaluation of 1, 4-Dihydropyridine Derivatives Containing A Benzothiazolyl Moi- ety, Cent. Eur. J. Chem., 8(1), 163 (2010).
  • Şimşek, R., Gündüz, M.G., Sırmagül, B., Şafak, C., Erol, K, Linden, A.; 4-Difluoro- substituted phenyl-5-oxohexahydroquinoline Derivatives and Their Effects on Calcium Channels, Arzneim. Forsch. Drug Res., 56(7), 527 (2006).
  • Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Sus- ceptibility Tests for Bacteria That Grow Aerobically, Approved Standard 8th ed., M 07- A8, 2008.
  • Clinical and Laboratory Standards Institute, Reference Method for Broth Dilution An- tifungal Susceptibility Testing of Yeasts: Approved Standard 3rd ed., M 27-A3, 2008.
Toplam 16 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Eczacılık ve İlaç Bilimleri
Bölüm Research Article
Yazarlar

Miyase Gözde Gündüz Bu kişi benim

Melike Ekizoğlu Bu kişi benim

Didem Kart Bu kişi benim

Rahime Şimşek

Cihat Şafak Bu kişi benim

Yayımlanma Tarihi 1 Ocak 2011
Yayımlandığı Sayı Yıl 2011 Sayı: 1

Kaynak Göster

Vancouver Gündüz MG, Ekizoğlu M, Kart D, Şimşek R, Şafak C. Antimicrobial Screening of 2-Methyl-3- Acyl-4-Aryl-2,6,6 and / or 2,7,7-Trimethyl1,4,5,6,7,8-Hexahydroquinoline Derivatives. HUJPHARM. 2011(1):51-8.