Determination of the lipophilicity of some new thiosemicarbaside derivatives by reversed-phase thin-layer chromatography

Czasopismo : Acta Chromatographica
Tytuł artykułu : Determination of the lipophilicity of some new thiosemicarbaside derivatives by reversed-phase thin-layer chromatography

Autorzy :
Sajewicz, M.
University of Silesia Department of General Chemistry and Chromatography 9 Szkolna Street 40-006 Katowice Poland,
Kowalska, T.
University of Silesia Department of General Chemistry and Chromatography 9 Szkolna Street 40-006 Katowice Poland, teresa.kowalska@us.edu.pl,
Szalka, M.
ICN Polfa Rzeszów S.A. Product Development Department 35-959 Rzeszów Poland,
Kostka, J.
Rzeszów University of Technology Department of Chemical and Process Engineering 35-959 Rzeszów,
Rokaszewski, E.
ICN Polfa Rzeszów S.A. Product Development Department 35-959 Rzeszów Poland,
Kaczmarski, K.
Rzeszów University of Technology Department of Chemical and Process Engineering 35-959 Rzeszów, kkaczmarski@prz.edu.pl,
Belal, F.
University of Mansoura Department of Analytical Chemistry, Faculty of Pharmacy 35516 Mansoura Egypt,
El-Brashy, A. M.
University of Mansoura Department of Analytical Chemistry, Faculty of Pharmacy 35516 Mansoura Egypt,
El-Enany, N.
University of Mansoura Department of Analytical Chemistry, Faculty of Pharmacy 35516 Mansoura Egypt,
Tolba, M. M.
University of Mansoura Department of Analytical Chemistry, Faculty of Pharmacy 35516 Mansoura Egypt,
Cielecka-Piontek, J.
Poznan University of Medical Sciences Department of Pharmaceutical Chemistry, Faculty of Pharmacy Grunwaldzka 6 60-780 Poznań Poland, jpiontek@ump.edu.pl,
Krause, A.
PozLab Contract Research Organization Poznań Poland,
Zalewski, P.
Poznan University of Medical Sciences Department of Pharmaceutical Chemistry, Faculty of Pharmacy Grunwaldzka 6 60-780 Poznań Poland,
Lunzer, A.
Tanaka Laboratory in Hokkaido University W 7, Kita-ku Sapporo 060-8638 Japan,
Jelińska, A.
Poznan University of Medical Sciences Department of Pharmaceutical Chemistry, Faculty of Pharmacy Grunwaldzka 6 60-780 Poznań Poland,
Sarju, N.
Universiti Teknologi Malaysia Department of Industrial Biotechnology, Faculty of Biosciences and Bioengineering 81310 Skudai, Johor Bahru, Johor Malaysia,
Abd Samad, A.
Universiti Teknologi Malaysia Department of Industrial Biotechnology, Faculty of Biosciences and Bioengineering 81310 Skudai, Johor Bahru, Johor Malaysia,
Abd Ghani, M.
Universiti Kebangsaan Malaysia School of Chemical Sciences and Food Technology 43600 UKM Bangi, Selangor Malaysia,
Ahmad, F.
Universiti Teknologi Malaysia Department of Chemistry, Faculty of Science 81310 Skudai, Johor Bahru, Johor Malaysia, farediah@kimia.fs.utm.my,
Yang, G. J.
China Pharmaceutical University School of Pharmacy Nanjing 210009 P. R. China, yanggongjun888@163.com,
Lv, L.
Yangzhou University College of Chemistry and Chemical Engineering Yangzhou 225002 P. R. China,
O’sullivan, C.
Lafayette College Department of Chemistry Easton PA 18042 USA,
Sherma, J.
Lafayette College Department of Chemistry Easton PA 18042 USA, shermaj@lafayette.edu,
Nagaraju, P. M.
Forensic Science Laboratory Madivala, Bangalore 560068 Karnataka India,
Sanganalmath, P. U.
Forensic Science Laboratory Madivala, Bangalore 560068 Karnataka India,
Kemparaju, K.
Mysore University Department of Studies in Biochemistry, Manasa Gangothri Mysore Karnataka India,
Mohan, B. M.
Forensic Science Laboratory Madivala, Bangalore 560068 Karnataka India, praveen_usp@yahoo.com,
Kumbhalkar, B. B.
Agharkar Research Institute Botany Group, Plant Science Division G.G. Agarkar Road Pune 411 004 India,
Rajopadhye, A. A.
Agharkar Research Institute Botany Group, Plant Science Division G.G. Agarkar Road Pune 411 004 India,
Upadhye, A. S.
Agharkar Research Institute Botany Group, Plant Science Division G.G. Agarkar Road Pune 411 004 India, upadhye.anuradha@gmail.com,
Hawrył, A.
Medical University of Lublin Departments of Inorganic Chemistry and Organic Chemistry Chodźki 4a 20-093 Lublin Poland,
Kuśmierz, E.
Medical University of Lublin Departments of Inorganic Chemistry and Organic Chemistry Chodźki 4a 20-093 Lublin Poland,
Pisarczyk, P.
Medical University of Lublin Departments of Inorganic Chemistry and Organic Chemistry Chodźki 4a 20-093 Lublin Poland,
Wujec, M.
Medical University of Lublin Departments of Inorganic Chemistry and Organic Chemistry Chodźki 4a 20-093 Lublin Poland,
Waksmundzka-Hajnos, M.
Medical University of Lublin Departments of Inorganic Chemistry and Organic Chemistry Chodźki 4a 20-093 Lublin Poland, monika.hajnos@am.lublin.pl,
Abstrakty : In this study, the chromatographic behavior of a newly synthesized series of 1,4-disubstituted thiosemicarbazide derivatives and products of their dehydrocyclization is presented. These compounds have been subjected to this study because they exhibit antimicrobial activity. The compounds have been chromatographed on RP-18 and on cyano-bonded silica chromatographic phases with eluents containing water and an organic modifier (methanol, dioxane, acetone, acetonitrile or tetrahydrofuran) of various concentrations. Statistically proved linear relationships between the retention parameter (RM) and the concentration of organic modifier in the mobile phase allow the extrapolation procedure to obtain RM0 for investigated compounds. The correlations between both the values of the intercept (RM0 ) and the slope (S) from the linear equation, taken as a measure of the lipophilicity, were calculated. The experimentally established parameters of lipophilicity (RM0 ) were compared with the log P values calculated by use of four different software packages. The values of the correlation coefficients of these relationships are higher for the cyanopropyl phase than for RP-18. Moreover, in this work the influences of different mobile phase modifiers and adsorbent layers on experimentally obtained lipophilicity parameters were analyzed and compared. Generally, the best correlations were obtained for systems with the cyanopropyl-bonded stationary phase in comparison with RP-18.

Słowa kluczowe : lipophilicity, TLC, CN-propyl-silica, RP-18, log P calculated,
Wydawnictwo : University of Silesia in Katowice
Rocznik : 2012
Numer : Vol. 24, no. 2
Strony : 271 – 290
Bibliografia : 1 U. Salgın-Gökşen, N. Gökhan-Kelekçi, Ö. Göktaş, Y. Köysal, E. Kılıç, Ş. Işık, G. Aktay, and M. Özalp, Bioorg. Med. Chem., 15, 5738–5751 (2007)
2 S. Tehranchian, T. Akbarzadeh, M.R. Fazeli, H. Jamalifar, and A. Shafiee, Bioorg. Med. Chem. Lett., 15, 1023–1025 (2005)
3 G. Turan-Zitouni, Z.A. Kaplancıklı, M.T. Yıldız, P. Chevallet, and D. Kaya, Eur. J. Med. Chem., 40, 607–613 (2005)
4 N. Demirbas, S.A. Karaoglu, A. Demirbas, and K. Sancak, Eur. J. Med. Chem., 39, 793–804 (2004)
5 A. Demirbas, S. Deniz, N. Demirbas, and S.A. Karaoglu, Eur. J. Med. Chem., 44, 2896–2903 (2009)
6 H. Bayrak, A. Demirbas, S.A. Karaoglu, and N. Demirbas, Eur. J. Med. Chem., 44, 1057–1066 (2009)
7 H. Bayrak, A. Demirbas, N. Demirbas, and S.A. Karaoglu, Eur. J. Med. Chem., 44, 4362–4366 (2009)
8 M.S. Karthikeyan, D.J. Prasad, B. Poojary, K.S. Bhat, B.M. Holla, and N.S. Kumari, Bioorg. Med. Chem., 14, 7482–7489 (2006)
9 N.C. Desai, A.M. Bhavsar, M.D. Shah, and A.K. Saxena, Indian J. Chem., 47B, 579–589 (2008)
10 A. Shafiee, A. Sayadi, M.H. Roozbahani, A. Foroumadi, and F. Kamal, Arch. Pharm. Pharm. Med. Chem., 10, 495–499 (2002)
11 T. Plech, M. Wujec, A. Siwek, U. Kosikowska, and A. Malm, Eur. J. Med. Chem., 46, 241–248 (2011)
12 M.C. Sarvà, G. Romeo, F. Guerrera, M. Siracusa, L. Salerno, F. Russo, A. Cagnotto, M. Goegan, and T. Mennini, Bioorg. Med. Chem., 10, 313–323 (2002)
13 G. Turan-Zitouni, Z.A. Kaplancikli, F.S. Kiliç, and K. Erol, Boll. Chim. Farm., 141, 192–196 (2002)
14 P.B. Wingrove, K.A. Wafford, C. Bain, and P.J. Whiting, Proc. Natl. Acad. Sci. USA, 91, 4569–4573 (1994)
15 N. Siddiqui and W. Ahsan, Eur. J. Med. Chem., 45, 1536–1543 (2010)
16 C.h.X. Wei, L.P. Guan, J.H. Jia, K.Y. Chai, and Z.S. Quan, Arch. Pharm. Res., 32, 23–31 (2009)
17 C. Hansch, A. Leo, and D. Elkins, Chem. Revs., 71, 525–616 (1971)
18 C. Hansch and T. Fujita, J. Am. Chem. Soc., 86, 1616–1626 (1964)
19 K. Jóźwiak, H. SzumiŁo, and E. Soczewiński, Wiad. Chem., 55, 1047–1074 (2001) (in Polish)
20 L.R. Snyder, J.W. Dolan, and J.R. Gant, J. Chromatogr., 165, 3 (1979)
21 E. Soczewiński and C.A. Wachtmeister, J. Chromatogr., 7, 311–320 (1962)
22 HyperChem Release 8.0. for Windows Molecular Modeling System
23 www.molinspiration.com 24 www.organic-chemistry.org
24 www.vcclab.org
25 N. Perišić-Janjić and S.O. Podunavac-Kuzmanović, J. Planar Chromatogr., 21, 135–141 (2008)
26 A. Zięba and W. Prus, Acta Chromatogr., 21, 369–378 (2009)
27 N. Perišić-Janjić, T. Djaković-Sekulić, L.R. Jevrić, and B. Jovanović, J. Planar Chromatogr., 18, 212–216 (2005)
28 J. Sochacka and A. Kowalska, J. Planar Chromatogr., 19, 307–312 (2006)
29 B. Malawska, K. Kulig, and E. Bendieck, J. Planar Chromatogr., 16, 390–395 (2003)
30 K. Więckowski, A. Czaja, A. Woźniak, A. MusiaŁ, and B. Malawska, J. Planar Chromatogr., 20, 101–106 (2007)
31 J. Obniska and K. Kamiński, J. Planar Chromatogr., 18, 240–243 (2005)
32 N. Perišić-Janjić, G. Vastag, J. Tomić, and S. Petrović, J. Planar Chromatogr., 20, 353–359 (2007)
33 Ł. Komsta, K. Sztanke, P. Mączka, M. Ucherek, R. Skibiński, and A. Gumieniczek, J. Planar Chromatogr., 22, 327–331 (2009)
34 G. Cimpan, M. Hadaruga, and V. Miclaus, J. Chromatogr., A, 869, 49–55 (2000)
35 E.C. Bate-Smith and R.G. Westall, Biochim. Biophys. Acta, 4, 427 (1950)
36 A.K. Ghose, A. Pritchett, and G.M. Crippen, J. Comput. Chem., 9, 80 (1988)
37 V.N. Viswanadhan, A.K. Ghose, G.N. Revankar, and R.K. Robins, J. Chem. Inf. Comput. Sci., 29, 163 (1989)
38 H.H. Jaffe, Chem. Rev., 53, 191–261 (1953)
39 R.D. Briciu, A. Kot-Wasik, A. Wasik, J. Namieśnik, and C. Sârbu, J. Chromatogr. A, 1217, 3702–3706 (2010)
40 J.H. Park, M.H. Yoon, Y.K. Ryu, B.E. Kim, J.W. Ryu, and M.D. Jang, J. Chromatogr. A, 796, 249–258 (1998)
41 M.M. Acanski, Chromatographia, 62, 475–482 (2005)
42 R.D. Briciu, A. Kot-Wąsik, A. Wąsik, J. Namieśnik, and C. Sârbu, J. Chromatography A, 1217, 3702–3706 (2010)
43 D. Casoni, J. Petre, V. David, and C. Sarbu, J. Sep. Sci., 34, 247–254 (2011)
44 C. Sarbu, D. Casoni, A. Kot-Wąsik, A. Wąsik, and J. Namieśnik, J. Sep. Sci., 33, 2219–2229 (2010)
45 D. Casoni, A. Kot-Wąsik, J. Namieśnik, and C. Sârbu, J. Chromatogr. A, 1216, 2456–2465 (2009)
46 G.L. Biagi, A.M. Barbaro, and A. Sapone, J. Chromatogr. A, 662, 341–361 (1994)
47 C. Horváth, W. Melander, and I. Molnár, J. Chromatogr., 125, 129 (1976)
DOI :
Cytuj : Sajewicz, M. ,Kowalska, T. ,Szalka, M. ,Kostka, J. ,Rokaszewski, E. ,Kaczmarski, K. ,Belal, F. ,El-Brashy, A. M. ,El-Enany, N. ,Tolba, M. M. ,Cielecka-Piontek, J. ,Krause, A. ,Zalewski, P. ,Lunzer, A. ,Jelińska, A. ,Sarju, N. ,Abd Samad, A. ,Abd Ghani, M. ,Ahmad, F. ,Yang, G. J. ,Lv, L. ,O’sullivan, C. ,Sherma, J. ,Nagaraju, P. M. ,Sanganalmath, P. U. ,Kemparaju, K. ,Mohan, B. M. ,Kumbhalkar, B. B. ,Rajopadhye, A. A. ,Upadhye, A. S. ,Hawrył, A. ,Kuśmierz, E. ,Pisarczyk, P. ,Wujec, M. ,Waksmundzka-Hajnos, M. , Determination of the lipophilicity of some new thiosemicarbaside derivatives by reversed-phase thin-layer chromatography. Acta Chromatographica Vol. 24, no. 2/2012
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