Öz
Heterosiklik hidrazon yapısı antitüberküloz aktiviteleri nedeniyle medisinal kimyacıların dikkatini çeken, cazip biyolojik olarak aktif önemli bir ilaç sınıfıdır. Bu amaçla, yeni hidrazon türevleri sentezlendi ve antitüberküloz etkinlikleri değerlendirilmiştir. (5,6,7,8-Tetrahidronaftalen-1-il) asetik asit hidraziti ile çeşitli benzaldehitlerin reaksiyonu, 5,6,7,8-tetrahidronaftalen asetik asit benziliden hidrazit türevlerini verdi. Bileşiklerin kimyasal yapıları 1H-NMR, EI-MS spectral verileri ve elemental analiz metodları ile aydınlatıldı. BACTEC 460 radyometrik sistem ve BACTEC 12B ortamından yararlanılarak Mycobacterium tuberculosis H37Rv (ATCC 27294)’e karşı bileşiklerin antitüberküloz aktiviteleri değerlendirilmiştir. Bileşik A10 yüksek antitüberküloz etkinlik (IC50: 3.072 μg/mL ve IC90: 3.358 μg/mL) ve düşük sitotoksisite (CC50: >40 μg/mL) gösterdi
Kaynakça
- Meng Q, Luo H, Chen Y, Wang T, Yao Q. Synthesis of novel [1,2]-diamines with antituberculosis activity. Bioorg Med Chem Lett, 19: 5372-5375, 2006.
- Kaymakçıoğlu BK, Oruç E, Unsalan S, Kandemirli F, Shvets N, Rollas S, Dimoglo A. Synthesis and charac- terization of novel hydrazide-hydrazones and the study of their structure-antituberculosis activity. Eur J Med Chem, 44: 1253-1261, 2006.
- Kaymakçıoğlu BK, Rollas S. Synthesis, characterization and evaluation of antituberculosis activity of some hy- drazones. Farmaco, 57: 595-599, 2002.
- Swamy BN, Suma TK, Rao GV and Reddy GC. Synthe- sis of isonicotinoylhydrazones from anacardic acid and their in vitro activity against Mycobacterium smegmatis. Eur J Med Chem, 42: 420-424, 2007.
- Küçükgüzel SG, Rollas S. Synthesis, characterization of novel coupling products and 4-arylhydrazono-2-pyra- zoline-5-ones as potential antimycobacterial agents. Far- maco, 57: 583-587, 2002.
- Sriram D, Yogeeswari P, and Madhu K. Synthesis and in vitro and in vivo antimycobacterial activity of isonicoti- noyl hydrazones. Bioorg Med Chem Lett, 15: 4502-4505, 2005.
- Sriram D, Yogeeswari P, and Devakaram RV. Synthe- sis, in vitro and in vivo antimycobacterial activities of diclofenac acid hydrazones and amides. Bioorg Med Chem, 14: 3113-3118, 2006.
- Patole J, Sandbhor U, Padhye S, Deobagkar DN, Anson CE, Powell A, Structural chemistry and in vitro antitu- bercular activity of acetylpyridine benzoyl hydrazone and its copper complex against Mycobacterium smeg- matis. Bioorg Med Chem Lett, 13: 51-55, 2003.
- Maccari R, Ottana R, and Vigorita MG, In vitro advanced antimycobacterial screening of isoniazid-related hydra- zones, hydrazides and cyanoboranes: Part 14. Bioorg Med Chem Lett, 15: 2509-2513, 2005.
- Turan-Zitouni G, Özdemir A, Kaplancıklı ZA, Benkli K, Chevallet P and Akalın G, Synthesis and antituberculo- sis activity of new thiazolylhydrazone derivatives. Eur J Med Chem, 43: 981-985, 2008.
- Çukurovalı A, Yılmaz I, Gür S, Kazaz C, Synthesis, anti- bacterial and antifungal activity of some new thiazolyl- hydrazone derivatives containing 3-substituted cyclobu- tane ring. Eur J Med Chem, 41: 201-207, 2006.
- Hamzacebi MC, Rollas S, Küçükgüzel SG, Kaymakçıoğlu BK, Synthesis and structure elucidation of hydrazones derived from N-(2,4-dimethylphenyl)-3-oxobutanamide. Arkivoc, 12: 188-194, 2008.
- Karalı N, Kocabalkanlı A, Gürsoy A, Ateş Ö, Synthesis and antitubercular activity of 4-(3-coumarinyl)-3-cy- clohexyl-4-thiazolin-2-one benzylidenehydrazones. Far- maco, 57: 589-593, 2002.
- Yale HL, Losee K, Martins J, Holsing M, Perry FM, Bern- stein J, Chemotherapy of experimental tuberculosis. VIII. The synthesis of acid hydrazides, their derivatives and related compounds. J Am Chem Soc, 75: 1933-1942, 1953.
- Collins LA, Franzblau SG, Microplate alamar blue assay versus BACTEC 460 system for high-throughput screen- ing of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob Agents Chem- other, 41: 1004-1009, 1997.
- Lara-Díaz VJ, Gaytán-Ramos AA, Dávalos-Balderas AJ, Santos-Guzmán J, Mata-Cárdenas BD, Vargas-Vil- larreal J, Barbosa-Quintana A, Sanson M, López-Reyes AG, Moreno-Cuevas JE. Microbiological and toxicologi- cal effects of perla black bean (Phaseolus vulgaris L.) extracts:in vitro and in vivo studies. Basic Clin Pharma- col Toxicol, 104: 81-86, 2009.
- CellTiter-Glo® Luminescent Cell Viability Assay, Promega Corporation’s, http://www.promega.com/ tbs/tb288/tb288.html June 2009.
Öz
ABSTRACT: The heterocyclic hydrazone constitute an important class of biologically active
drug molecules which have attractive attention of medicinal chemists due to their antituberculosis
activities. For this purpose, new hydrazone derivatives were synthesized and evaluated
for antituberculosis activity. The reaction of (5,6,7,8-tetrahydronaphthalen-1-yl) acetic
acid hydrazide with various benzaldehydes gave 5,6,7,8-tetrahydronaphtalen acetic acid
benzylidene hydrazide derivatives. The chemical structures of the compounds were elucidated
by 1H-NMR, EI-MS spectral data and Elemental Analysis. The compounds were evaluated
for antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC 27294)
using the BACTEC 460 radiometric system and BACTEC 12B medium. The preliminary results
indicated that all of the tested compounds showed low activity against the test organism.
The compound A10 showed high antituberculosis activity (IC50: 3.072
Anahtar Kelimeler
Hydrazone Antituberculosis activity Mycobacterium tuberculosis
Kaynakça
- Meng Q, Luo H, Chen Y, Wang T, Yao Q. Synthesis of novel [1,2]-diamines with antituberculosis activity. Bioorg Med Chem Lett, 19: 5372-5375, 2006.
- Kaymakçıoğlu BK, Oruç E, Unsalan S, Kandemirli F, Shvets N, Rollas S, Dimoglo A. Synthesis and charac- terization of novel hydrazide-hydrazones and the study of their structure-antituberculosis activity. Eur J Med Chem, 44: 1253-1261, 2006.
- Kaymakçıoğlu BK, Rollas S. Synthesis, characterization and evaluation of antituberculosis activity of some hy- drazones. Farmaco, 57: 595-599, 2002.
- Swamy BN, Suma TK, Rao GV and Reddy GC. Synthe- sis of isonicotinoylhydrazones from anacardic acid and their in vitro activity against Mycobacterium smegmatis. Eur J Med Chem, 42: 420-424, 2007.
- Küçükgüzel SG, Rollas S. Synthesis, characterization of novel coupling products and 4-arylhydrazono-2-pyra- zoline-5-ones as potential antimycobacterial agents. Far- maco, 57: 583-587, 2002.
- Sriram D, Yogeeswari P, and Madhu K. Synthesis and in vitro and in vivo antimycobacterial activity of isonicoti- noyl hydrazones. Bioorg Med Chem Lett, 15: 4502-4505, 2005.
- Sriram D, Yogeeswari P, and Devakaram RV. Synthe- sis, in vitro and in vivo antimycobacterial activities of diclofenac acid hydrazones and amides. Bioorg Med Chem, 14: 3113-3118, 2006.
- Patole J, Sandbhor U, Padhye S, Deobagkar DN, Anson CE, Powell A, Structural chemistry and in vitro antitu- bercular activity of acetylpyridine benzoyl hydrazone and its copper complex against Mycobacterium smeg- matis. Bioorg Med Chem Lett, 13: 51-55, 2003.
- Maccari R, Ottana R, and Vigorita MG, In vitro advanced antimycobacterial screening of isoniazid-related hydra- zones, hydrazides and cyanoboranes: Part 14. Bioorg Med Chem Lett, 15: 2509-2513, 2005.
- Turan-Zitouni G, Özdemir A, Kaplancıklı ZA, Benkli K, Chevallet P and Akalın G, Synthesis and antituberculo- sis activity of new thiazolylhydrazone derivatives. Eur J Med Chem, 43: 981-985, 2008.
- Çukurovalı A, Yılmaz I, Gür S, Kazaz C, Synthesis, anti- bacterial and antifungal activity of some new thiazolyl- hydrazone derivatives containing 3-substituted cyclobu- tane ring. Eur J Med Chem, 41: 201-207, 2006.
- Hamzacebi MC, Rollas S, Küçükgüzel SG, Kaymakçıoğlu BK, Synthesis and structure elucidation of hydrazones derived from N-(2,4-dimethylphenyl)-3-oxobutanamide. Arkivoc, 12: 188-194, 2008.
- Karalı N, Kocabalkanlı A, Gürsoy A, Ateş Ö, Synthesis and antitubercular activity of 4-(3-coumarinyl)-3-cy- clohexyl-4-thiazolin-2-one benzylidenehydrazones. Far- maco, 57: 589-593, 2002.
- Yale HL, Losee K, Martins J, Holsing M, Perry FM, Bern- stein J, Chemotherapy of experimental tuberculosis. VIII. The synthesis of acid hydrazides, their derivatives and related compounds. J Am Chem Soc, 75: 1933-1942, 1953.
- Collins LA, Franzblau SG, Microplate alamar blue assay versus BACTEC 460 system for high-throughput screen- ing of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob Agents Chem- other, 41: 1004-1009, 1997.
- Lara-Díaz VJ, Gaytán-Ramos AA, Dávalos-Balderas AJ, Santos-Guzmán J, Mata-Cárdenas BD, Vargas-Vil- larreal J, Barbosa-Quintana A, Sanson M, López-Reyes AG, Moreno-Cuevas JE. Microbiological and toxicologi- cal effects of perla black bean (Phaseolus vulgaris L.) extracts:in vitro and in vivo studies. Basic Clin Pharma- col Toxicol, 104: 81-86, 2009.
- CellTiter-Glo® Luminescent Cell Viability Assay, Promega Corporation’s, http://www.promega.com/ tbs/tb288/tb288.html June 2009.
Ayrıntılar
| Birincil Dil | İngilizce |
|---|---|
| Bölüm | Makaleler |
| Yazarlar | |
| Yayımlanma Tarihi | 3 Mart 2014 |
| Yayımlandığı Sayı | Yıl 2010 Cilt: 14 Sayı: 2 |