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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

Year 2011, Issue: 1, 51 - 58, 01.01.2011

Abstract

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.

References

  • 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

Year 2011, Issue: 1, 51 - 58, 01.01.2011

Abstract

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.

References

  • 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.
There are 16 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Research Article
Authors

Miyase Gözde Gündüz This is me

Melike Ekizoğlu This is me

Didem Kart This is me

Rahime Şimşek

Cihat Şafak This is me

Publication Date January 1, 2011
Published in Issue Year 2011 Issue: 1

Cite

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.