Yıl: 2016 Cilt: 40 Sayı: 3 Sayfa Aralığı: 510 - 534 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine

Öz:
A series of 38 new acylhydrazones [3{40], derived from (2S)-4-(methylsulfanyl)-2-[[(4-methylphenyl)sulfonyl]amino]butanoic acid hydrazide [2], were synthesized and evaluated for their anti-HIV and antimicrobial activity withthe further aim to develop acylhydrazones carrying an amino acid side chain. All tested compounds possess strongeractivity against gram (+) bacteria. Compound23was found active against methicillin-resistantStaphylococcus aureus(MRSA) with a MIC value of 3.9 g/mL. The MIC value of compound30againstEnterococcus faecalis,Listeriamonocytogenes, andBacillus cereuswas 8 g/mL. A computational study for prediction of ADME and drug-likeproperties (solubility, drug-likeness, and drug score) as well as potential toxicity pro les of compounds2{40wasperformed using the Molinspiration online property calculation toolkit and Osiris Property Explorer. As most of ourcompounds meet Lipinski's rule of ve, they promise good solubility and permeability. According to Osiris calculations,the majority of our compounds are supposed to be nonmutagenic and nonirritating.
Anahtar Kelime:

Konular: Mühendislik, Kimya
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
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  • 1.Rai, J.; Randhawa, G. K.; Kaur, M.Int. J. Appl. Basic Med. Res.2013,3, 3-10.
  • 2.Rollas, S.; Gulerman, N.; Erdeniz, H.Farmaco2002,57, 171-174.
  • 3.Kucukguzel, S. G.; Mazi, A.; Sahin, F.;Ozturk, S.; Stables, J.Eur. J. Med. Chem.2003,38, 1005-1013.
  • 4.Cukuroval, A.; Ylmaz,_I.; Gur, S.; Kazaz, C.Eur. J. Med. Chem.2006,41, 201-207.
  • 5.Kumar, D.; Judge, V.; Narang, R.; Sangwan, S.; De Clercq, E.; Balzarini, J.; Narasimhan, B.Eur. J. Med. Chem.2010,45, 2806-2816.
  • 6.Kumar, N. S.; Amandoron, E. A.; Cherkasov, A.; Finlay, B. B.; Gong, H.; Jackson, L.; Kaur, S.; Lian, T.; Moreau,A.; Labriere, C.; et al.Bioorg. Med. Chem.2012,20, 7069-7082.
  • 7.7Kocyigit-Kaymakcoglu, B.; Oruc, E.;Unsalan, S.; Kandemirli, F.; Shvets, N.; Rollas, S.; Dimoglo, A.Eur. J.Med. Chem.2006,41, 1253-1261.
  • 8.Rollas, S.; Kucukguzel, S. G.Molecules2007,12, 1910-1939.
  • 9.Eswaran, S.; Adhikari, A. V.; Pal, N. K.; Chowdhury, I. H.Bioorg. Med. Chem. Lett.2010,20, 1040-1044.
  • 10.Kumar, P.; Narasimhan, B.; Yogeeswari, P.; Sriram, D.Eur. J. Med. Chem.2010,45, 6085-6089.
  • 11.Pavan, P. I.; da S Maia, F. R.; Leite, S. R.; De on, V. M.; Batista, A. A.; Sato, D. N.; Franzblau, S. G.; Leite, C.Q.Eur. J. Med. Chem.2010,45, 1898-1905.
  • 12.Bairwa, R.; Kakwani, M.; Tawari, N. R.; Lalchandani, J.; Ray, M. K.; Rajan, M. G.; Degani, M. S.Bioorg. Med.Chem. Lett.2010,20, 1623-1625.
  • 13.Nordfelth, R.; Kauppi, A. M.; Norberg, H. A.; Wolf-Watz, H.; Elofsson, M.Infect. Immun.2005,73, 3104-3114.
  • 14.Lee, J. Y.; Jeong, K. W.; Lee, J. U.; Kang, D. I.; Kim, Y.Bioorg. Med. Chem.2009,17, 1506-1513.
  • 15.Lee, J. Y.; Jeong, K. W.; Shin, S.; Lee, J. U.; Kim, Y.Eur. J. Med. Chem.2012,47, 261-269.
  • 16.Wang, X. L.; Zhang, Y. B.; Tang, J. F.; Yang, Y. S.; Chen, R. Q.; Zhang, F.; Zhu, H. L.Eur. J. Med. Chem.2012,57, 373-382.
  • 17.Zoraghi, R.; See, R. H.; Axerio-Cilies, P.; Kumar, N. S.; Gong, H.; Moreau, A.; Hsing, M.; Kaur, S.; Swayze, R.D.; Worrall, L.; et al.Antimicrob. Agents Chemother.2011,55, 2042-2053.
  • 18.Hughes, R. A.; Moody, C. J.Angew. Chem. Int. Ed. Engl.2007,46, 7930-7954.
  • 19.Karp, C. L.; Auwaerter, P. G.Clin. Infect. Dis.2007,45, 1214-1220.
  • 20.Arion, D.; Sluis-Cremer, N.; Min, K. L.; Abram, M. E.; Fletcher, R. S.; Parniak, M. A.J. Biol. Chem.2002, 277,1370-1374.
  • 21.Schultz, S. J., Champoux, J. J.Virus Res.2008,134, 86-103.
  • 22.Tian, B.; He, M.; Tang, S.; Hewlett, I.; Tan, Z.; Li, J.; Jin, Y.; Yang, M.Bioorg. Med. Chem. Lett.2009,19,2162-2167.
  • 23.Sara anos, S. G.; Marchand, B.; Das K; Himmel, D. M.; Parniak, M. A.; Hughes, S. H.; Arnold, E.J. Mol. Biol.2009,385, 693-713.
  • 24.Jin, Y.; Tan, Z.; He, M.; Tian, B.; Tang, S.; Hewlett, I.; Yang, M.Bioorg. Med. Chem.2010,18, 2135-2140.
  • 25.Gong, Q.; Menon, L.; Ilina, T.; Miller, L. G.; Ahn, J.; Parniak, M. A.; Ishima, R.Chem. Biol. Drug Des.2011,77, 39-47.
  • 26.Tian, B.; He, M.; Tan, Z.; Tang, S.; Hewlett, I.; Chen, S.; Jin, Y.; Yang, M.Chem. Biol. Drug Des.2011,77,189-198.
  • 27.Felts, A. K.; Labarge, K.; Bauman, J. D.; Patel, D. V.; Himmel, D. M.; Arnold, E.; Parniak, M. A.; Levy, R. M.J. Chem. Inf. Model.2011,51, 1986-1998.
  • 28.Bocanegra, R.; Rodrguez-Huete, A.; Fuertes, M.A.; DelAlamo, M.; Mateu, M. G.Virus Res.2012,169, 388-410.
  • 29.Tatar, E.; Kucukguzel, I.; Daelemans, D.; Talele, T. T.; Kaushik-Basu, N.; De Clercq, E.; Pannecouque, C.Arch.Pharm. Chem. Life Sci.2013,346, 140-153.
  • 30.Zareef, M.; Iqbal, R.; Al-Masoudi, N.; Zaidi, J. H.; Arfan, M.; Shahzad, S. A.Phosphorus, Sulfur, Silicon Relat.Elem.2007,182, 281-298.
  • 31.Hill, R. R.; Moore, S. A.; Roberts, D. R.Photochem. Photobiol.2005,81, 1439-1446.
  • 32.Nechab, M.; Vanthuyne,N. Org. Lett.2012,14, 3974-3977.
  • 33.Ckla, P.; Kucukguzel, S. G.; Kucukguzel,_I.; Rollas, S.; Pannecouque, C.; Andrei, G.; Snoeck, R.; Sahin, F.; Bayrak,O. F.Marmara Pharm. J.2010,14, 13-20.
  • 34.Ckla, P.;Ozsavc, D.; Bingol-Ozakpnar,O.; Sener, A.; Cevik,O.;Ozbas-Turan, S.; Akbuga, J.; Sahin, F.;Kucukguzel, S. G.Arch. Pharm. Chem. Life Sci.2013,346, 367-379.
  • 35.Ckla, P.; Tatar, E.; Kucukguzel,_I.; Sahin, F.; Yurdakul, D.; Basu, A.; Krishnan, R.; Nichols, D. B.; Kaushik-Basu,N.; Kucukguzel, S. G.Med. Chem. Res.2013,22, 5685-5699.
  • 36.Aydn, S.; Kaushik-Basu, N.; Arora, P.; Basu, A.; Nichols, D. B.; Talele, T. T.; Akkurt, M.; Celik,_I.; Buyukgungor,O.; Kucukguzel, S. G.Marmara Pharm. J.2013,17, 26-34.
  • 37.Salgin-Goksen, U.; Gokhan-Kelekci, N.; Goktas, O.; Koysal, Y.; Kilic, E.; Isik, S.; Aktay, G.; Ozalp, M.Bioorg.Med. Chem.2007,15, 5738-5751.
  • 38.Rutavichyus, A.; Valiulene, S.; Kuodis, Z. Chem.Heterocycl. Comp.2000,36, 851-856.
  • 39.Easmon, J.; Purstinger, G.; Thies, K. S.; Heinisch, G.; Hofmann, J.J. Med. Chem.2006,49, 6343-6350.
  • 40.Lipinski, C. A ; Lombardo, F.; Dominy, B. W.; Feeney, P. J.Adv. Drug Deliv. Rev.2001,46, 3-26.
  • 41.Molinspiration Cheminformatics, Bratislava, Slovak Republic, Available at:http://www.molinspiration.com/services/properties.html [accessed 18.08.2015].
  • 42.Jarrahpour, A.; Fathi, J.; Mimouni, M.; Ben Hadda, T.; Sheikh, J.; Chohan, Z.; Parvez A.Med. Chem. Res.2012,21, 1984-1990.
  • 43.Rauf, A.; Ahmed, F.; Qureshi, A.M.; Aziz-ur-Rehman, K. A.; Qadir, M. I.; Choudhary, M. I.; Chohan, Z. H.;Youssou , M. H.; Ben Hadda T.J. Chin. Chem. Soc.2011,58, 528-537.
  • 44.Sheikh, J.; Parvez, A.; Ingle, V.; Juneja, H.; Dongre, R.; Chohan, Z. H.; Youssou , M. H.; Ben Hadda, T.Eur. J.Med. Chem.2011,46, 1390-1399.
  • 45.Parvez, A.; Jyotsna, M.; Youssou , M.H.; Ben Hadda, T.Phosphorus, Sulfur, Silicon Relat. Elem.2010,7, 1500-1510.
  • 46.Parvez, A.; Meshram, J.; Tiwari, V.; Sheikh, J.; Dongre, R.; Youssou , M. H.; Ben Hadda, T.Eur. J. Med. Chem.2010,45, 4370-4378.
  • 47.Chohan, Z. H.; Youssou , M. H.; Jarrahpour, A.; Ben Hadda, T.Eur. J. Med. Chem.2010,45, 1189{1199.
  • 48.Jarrahpour, A.; Motamedifar, M.; Zarei1, M.; Youssou , M. H.; Mimouni, M.; Chohan, Z. H.; Ben Hadda, T.Phosphorus, Sulfur, Silicon Relat. Elem.2010,185, 491-497.
  • 49.Ben Hadda, T.; Ali, M. A.; Masand, V.; Gharby, S.; Fergoug, T.; Warad, I.Med. Chem. Res.2013,22, 1438-1449.
  • 50.Osiris Property Explorer. Avaliable at: http://www.organic-chemistry.org/prog/peo/ [accessed 18.08.2015].
  • 51.Perez, C.; Pauli, M.; Bazerque, P.Acta Biol. Med. Exp.1990,15, 113-115.
  • 52.Ahmad, I.; Mehmood, Z.; Mohammad, F.J. Ethnopharmacol.1998,62, 183-193.
  • 53.Clinical Laboratory Standards Instutitute (CLSI). Susceptibility Testing of Mycobacteria, Nocardiae, and otherAerobic Actinomyces; Approved Standard. Second Ed. CLSI document. M24-A.2011,31, 3-26.
  • 54.Clinical Laboratory Standards Instutitute (CLSI). Performance Standards for Antimicrobial Susceptibility Testing,Twentieth Information Supplement. CLSI document. M100-S20.2010,3, 108-114.
  • 55.Pannecouque, C.; Daelemans, D.; De Clercq, E.Nat. Protoc.2008,3, 427-434.
  • 56.Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.J. Virol. Methods1988,20, 309-321.
  • 57.Popovic, M.; Sarngadharan, M. G.; Read, E.; Gallo, R. C.Science1984,224, 497-500.
  • 58.Barre-Sinoussi, F.; Chermann, J. C.; Rey, F.; Nugeyre, M. T.; Chamaret, S.; Gruest, J.; Dauguet, C.; Axler-Blin,C.; Vezinet-Brun, F.; Rouzioux, C.; et al.Science1983,220, 868-871.
  • 59.Miyoshi, I.; Taguchi, H.; Kobonishi, I.; Yoshimoto, S.; Ohtsuki, Y.; Shiraishi, Y.; Akagi, T.Gann. Monogr. CancerRes.1982,28, 219-228.
APA Tatar E, şenkardeş s, SELLİTEPE H, Küçükgüzel Ş, Alpay Karaoğlu Ş, BOZDEVECİ A, DE CLERCQ E, Pannecouque C, BEN HADDA T, KÜÇÜKGÜZEL İ (2016). Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine. , 510 - 534.
Chicago Tatar Esra,şenkardeş sevil,SELLİTEPE Hasan Erdinç,Küçükgüzel Ş.Güniz,Alpay Karaoğlu Şengül,BOZDEVECİ ARİF,DE CLERCQ Erik,Pannecouque Christophe,BEN HADDA Taibi,KÜÇÜKGÜZEL İLKAY Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine. (2016): 510 - 534.
MLA Tatar Esra,şenkardeş sevil,SELLİTEPE Hasan Erdinç,Küçükgüzel Ş.Güniz,Alpay Karaoğlu Şengül,BOZDEVECİ ARİF,DE CLERCQ Erik,Pannecouque Christophe,BEN HADDA Taibi,KÜÇÜKGÜZEL İLKAY Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine. , 2016, ss.510 - 534.
AMA Tatar E,şenkardeş s,SELLİTEPE H,Küçükgüzel Ş,Alpay Karaoğlu Ş,BOZDEVECİ A,DE CLERCQ E,Pannecouque C,BEN HADDA T,KÜÇÜKGÜZEL İ Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine. . 2016; 510 - 534.
Vancouver Tatar E,şenkardeş s,SELLİTEPE H,Küçükgüzel Ş,Alpay Karaoğlu Ş,BOZDEVECİ A,DE CLERCQ E,Pannecouque C,BEN HADDA T,KÜÇÜKGÜZEL İ Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine. . 2016; 510 - 534.
IEEE Tatar E,şenkardeş s,SELLİTEPE H,Küçükgüzel Ş,Alpay Karaoğlu Ş,BOZDEVECİ A,DE CLERCQ E,Pannecouque C,BEN HADDA T,KÜÇÜKGÜZEL İ "Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine." , ss.510 - 534, 2016.
ISNAD Tatar, Esra vd. "Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine". (2016), 510-534.
APA Tatar E, şenkardeş s, SELLİTEPE H, Küçükgüzel Ş, Alpay Karaoğlu Ş, BOZDEVECİ A, DE CLERCQ E, Pannecouque C, BEN HADDA T, KÜÇÜKGÜZEL İ (2016). Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine. Turkish Journal of Chemistry, 40(3), 510 - 534.
Chicago Tatar Esra,şenkardeş sevil,SELLİTEPE Hasan Erdinç,Küçükgüzel Ş.Güniz,Alpay Karaoğlu Şengül,BOZDEVECİ ARİF,DE CLERCQ Erik,Pannecouque Christophe,BEN HADDA Taibi,KÜÇÜKGÜZEL İLKAY Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine. Turkish Journal of Chemistry 40, no.3 (2016): 510 - 534.
MLA Tatar Esra,şenkardeş sevil,SELLİTEPE Hasan Erdinç,Küçükgüzel Ş.Güniz,Alpay Karaoğlu Şengül,BOZDEVECİ ARİF,DE CLERCQ Erik,Pannecouque Christophe,BEN HADDA Taibi,KÜÇÜKGÜZEL İLKAY Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine. Turkish Journal of Chemistry, vol.40, no.3, 2016, ss.510 - 534.
AMA Tatar E,şenkardeş s,SELLİTEPE H,Küçükgüzel Ş,Alpay Karaoğlu Ş,BOZDEVECİ A,DE CLERCQ E,Pannecouque C,BEN HADDA T,KÜÇÜKGÜZEL İ Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine. Turkish Journal of Chemistry. 2016; 40(3): 510 - 534.
Vancouver Tatar E,şenkardeş s,SELLİTEPE H,Küçükgüzel Ş,Alpay Karaoğlu Ş,BOZDEVECİ A,DE CLERCQ E,Pannecouque C,BEN HADDA T,KÜÇÜKGÜZEL İ Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine. Turkish Journal of Chemistry. 2016; 40(3): 510 - 534.
IEEE Tatar E,şenkardeş s,SELLİTEPE H,Küçükgüzel Ş,Alpay Karaoğlu Ş,BOZDEVECİ A,DE CLERCQ E,Pannecouque C,BEN HADDA T,KÜÇÜKGÜZEL İ "Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine." Turkish Journal of Chemistry, 40, ss.510 - 534, 2016.
ISNAD Tatar, Esra vd. "Synthesis, and prediction of molecular properties and antimicrobial activity ofsome acylhydrazones derived fromN-(arylsulfonyl)methionine". Turkish Journal of Chemistry 40/3 (2016), 510-534.