Novel Analogues of 2-Pyrazoline: Synthesis, Characterization, and Antimycobacterial Evaluation
Fourteen new 1-[(N,N-disubstitutedthiocarbamoylthio)acetyl]- 3-(2-thienyl)-5-aryl-2-pyrazoline derivatives were synthesized by reacting 1-(chloroacetyl)-3-(2-thienyl)-5-aryl-2-pyrazolines and appropriate sodium salts of N,N-disubstituted dithiocarbamoic acids in acetone. The structures of the synthesized compounds were confirmed by UV, IR, 1H-NMR, and FAB+-MS spectral data. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The preliminary results showed that all of the tested compounds were inactive against the test organism.
Novel Analogues of 2-Pyrazoline: Synthesis, Characterization, and Antimycobacterial Evaluation
Fourteen new 1-[(N,N-disubstitutedthiocarbamoylthio)acetyl]- 3-(2-thienyl)-5-aryl-2-pyrazoline derivatives were synthesized by reacting 1-(chloroacetyl)-3-(2-thienyl)-5-aryl-2-pyrazolines and appropriate sodium salts of N,N-disubstituted dithiocarbamoic acids in acetone. The structures of the synthesized compounds were confirmed by UV, IR, 1H-NMR, and FAB+-MS spectral data. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The preliminary results showed that all of the tested compounds were inactive against the test organism.
___
- Levai, A. Chem. Heterocyclic Compd. 1997, 33, 647-659 .
- Turan-Zitouni, G.; ¨Ozdemir, A.; G¨uven, K. Arch. Pharm. 2005, 338, 96-104.
- Turan-Zitouni, G.; ¨Ozdemir, A.; Kaplancıklı, Z.A.; Chevallet, P.; Tunalı, Y. Phosphorus Sulfur 2005, 180, 2724 .
- Kaplancıklı, Z.A.; Turan-Zitouni, G.; ¨Ozdemir, A.; Revial, G.; G¨uven, K. Phosphorus Sulfur 2007, 182, 749-764
- Ozdemir, A.; Turan-Zitouni, G.; Kaplancıklı, Z.A.; Revial, G. and G¨uven, K. Eur. J. Med. Chem. 2007, 42, ¨ 409 .
- Shaharyar, M.; Siddiqui, A.A.; Ali, M.A.; Sriram, D.and Yogeeswari, P.; Bioorg. Med. Chem. Lett. 2006, 16, 3949.
- Nugent, R.A.; Murphy, M.; Schlachter, S.T.; Dunn, C.J.; Smith, R.J.; Staite, N.D.; Galinet, L.A.; Shields, S.K.; Aspar, D.G.; Richard, K.A., and Rohloff, N.A. J. Med. Chem. 1993, 36, 134-139 .
- Manna, F.; Chimenti, F.; Bolasco, A.; Cenicola, M.L.; D’Amico, M.; Parrillo, C.; Rossi, F. and Marmo, E. Eur. J. Med. Chem. 1992, 27, 633-639 .
- Bilgin, A.A.; Palaska, E.; Sunal, R. Arzneim. Forsch. Drug Res. 1993, 43, 1041-1044 .
- Bilgin, A.A.; Palaska, E.; Sunal, R.; G¨um¨usel, B. Pharmazie 1994, 49, 67- 69.
- Raiford, L.C.; Peterson, W.J. J. Org. Chem. 1937, 1, 544-551 .
- Raiford, L.C.; Gundy, G.V. J. Org. Chem. 1938, 3, 265-272 .
- Raiford, L.C.; Manley, R.H. J. Org. Chem. 1940, 5, 590-597 .
- Wiley, R.H.; Jarboe, C.H.; Hayes, F.N.; Hansbury, E.; Nielsen, J.T.; Callahan, P.X.; Sellars, M.C. J. Org. Chem. 1958, 23, 732-738 .
- Kabli, R.A.; Khalaf, A.A.; Zimaity, M.T.; Khalil, A.M.; Kaddah, A.M.; Al-Rifaie, H.A. J. Indian Chem. Soc. ,68, 47-51 . Mishriky, N.; Asaad, F.M.; Ibrahim, Y.A.; Girgis, A.S. Pharmazie 1996, 51, 544-548 .
- Manna, F.; Chimenti, F.; Bolasco, A.; Secci, D.; Bizzarri, B.; Befani, O.; Turini, P.; Mondovi, B.; Alcaro, S.; TaŞ, A. Bioorg. Med. Chem. Lett. 2002, 12, 3629-3633.
- Levai, A.; Patonay, T.; Silva, A.M.S.; Pinto, D.C.G.A.; Cavaleiro, J.A.S. J. Heterocyclic Chem. 2002, 39, 758.
- Levai, A. Heterocycl. Commun. 2003, 9, 287-292.
- Chimenti, F.; Bolasco, A.; Manna, F.; Secci, D.; Chimenti, P.; Befani, O.; Turini, P.; Giovannini, V.; Mondovi, B.; Cirilli, R.; Torre, F. J. Med. Chem. 2004, 47, 2071-2074 .
- Chimenti, F.; Bizzarri, B.; Manna, F.; Boalsco, A.; Secci, D.; Chimenti, P.; Granese, A.; Rivanera, D.; Lilli, D.; Scaltrito, M.M.; Brenciaglia, M.I. Bioorg. Med. Chem. Lett. 2005, 15, 603-607.
- Levai, A.; Jeko, J.; Brahmbhatt, D.I. J. Heterocyclic Chem. 2005, 42, 1231-1235.
- Levai, A. J. Heterocyclic Chem. 2005, 39, 1-13.
- Levai, A.; Jeko, J. J. Heterocyclic Chem. 2006, 43, 111-115.
- Khalaf, A.A.; Kabli, R.A.; Zimaity, M.T.; Khalil, A.M.; Kaddah, A.M.; Al-Rifaie, H.A. Indian J. Chem. 1993, B, 1125-1129.
- Karali, N.; Apak, I.; Ozkirimli, S.; G¨ursoy, A.; Do˘gan, S.U.; Eraslan, A.; Ozdemir, O. Arch. Pharm. 1999, 332, 426.
- Collins, L.; Franzblau, S.G. Antimicrob. Agents Chemother. 1997, 41, 1004-1009.
- G¨okhan, N.; Ye¸silada, A.; U¸car, G.; Erol, K. Arch. Pharm. 2003, 336, 362-371.