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Article

Purine and Purine Isostere Derivatives of Ferrocene: An Evaluation of ADME, Antitumor and Electrochemical Properties

1
Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Zagreb 10000, Croatia
2
Fidelta d.o.o., Zagreb 10000, Croatia
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Department of Biotechnology, Center for High-Throughput Technologies, University of Rijeka, Rijeka 51000, Croatia
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International Relations Office, Faculty of Chemical Engineering and Technology, University of Zagreb, Zagreb 10000, Croatia
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Division for Marine and Environmental Research, Ruđer Bošković Institute, Zagreb 10000, Croatia
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Faculty of Medicine, Juraj Dobrila University of Pula, Pula 52100, Croatia
*
Author to whom correspondence should be addressed.
Academic Editor: Paula B. Andrade
Molecules 2020, 25(7), 1570; https://doi.org/10.3390/molecules25071570
Received: 13 March 2020 / Revised: 25 March 2020 / Accepted: 26 March 2020 / Published: 29 March 2020
(This article belongs to the Special Issue Translational Approach to Antitumor Drugs)
Novel purine and purine isosteres containing a ferrocene motif and 4,1-disubstituted (11a11c, 12a12c, 13a13c, 14a14c, 15a15c, 16a, 23a23c, 24a24c, 25a25c) and 1,4-disubstituted (34a34c and 35a35c) 1,2,3-triazole rings were synthesized. The most potent cytotoxic effect on colorectal adenocarcinoma (SW620) was exerted by the 6-chloro-7-deazapurine 11c (IC50 = 9.07 µM), 6-chloropurine 13a (IC50 = 14.38 µM) and 15b (IC50 = 15.50 µM) ferrocenylalkyl derivatives. The N-9 isomer of 6-chloropurine 13a containing ferrocenylmethylene unit showed a favourable in vitro physicochemical and ADME properties including high solubility, moderate permeability and good metabolic stability in human liver microsomes. View Full-Text
Keywords: purine; ferrocene; cytostatic activity; permeability; microsomal stability purine; ferrocene; cytostatic activity; permeability; microsomal stability
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MDPI and ACS Style

Rep, V.; Piškor, M.; Šimek, H.; Mišetić, P.; Grbčić, P.; Padovan, J.; Gabelica Marković, V.; Jadreško, D.; Pavelić, K.; Kraljević Pavelić, S.; Raić-Malić, S. Purine and Purine Isostere Derivatives of Ferrocene: An Evaluation of ADME, Antitumor and Electrochemical Properties. Molecules 2020, 25, 1570. https://doi.org/10.3390/molecules25071570

AMA Style

Rep V, Piškor M, Šimek H, Mišetić P, Grbčić P, Padovan J, Gabelica Marković V, Jadreško D, Pavelić K, Kraljević Pavelić S, Raić-Malić S. Purine and Purine Isostere Derivatives of Ferrocene: An Evaluation of ADME, Antitumor and Electrochemical Properties. Molecules. 2020; 25(7):1570. https://doi.org/10.3390/molecules25071570

Chicago/Turabian Style

Rep, Valentina, Martina Piškor, Helena Šimek, Petra Mišetić, Petra Grbčić, Jasna Padovan, Vesna Gabelica Marković, Dijana Jadreško, Krešimir Pavelić, Sandra Kraljević Pavelić, and Silvana Raić-Malić. 2020. "Purine and Purine Isostere Derivatives of Ferrocene: An Evaluation of ADME, Antitumor and Electrochemical Properties" Molecules 25, no. 7: 1570. https://doi.org/10.3390/molecules25071570

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