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

ABSTRACT: Novel purine and purine isosteres containing a ferrocene motif and 4,1-disubstituted (11a-11c, 12a-12c, 13a-13c, 14a-14c, 15a-15c, 16a, 23a-23c, 24a-24c, 25a-25c) and 1,4-disubstituted (34a-34c and 35a-35c) 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.

SUBMITTER: Rep V 

PROVIDER: S-EPMC7180452 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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

Rep Valentina V   Piškor Martina M   Šimek Helena H   Mišetić Petra P   Grbčić Petra P   Padovan Jasna J   Gabelica Marković Vesna V   Jadreško Dijana D   Pavelić Krešimir K   Kraljević Pavelić Sandra S   Raić-Malić Silvana S  

Molecules (Basel, Switzerland) 20200329 7

Novel purine and purine isosteres containing a ferrocene motif and 4,1-disubstituted (<b>11a</b>-<b>11c</b>, <b>12a</b>-<b>12c</b>, <b>13a</b>-<b>13c</b>, <b>14a</b>-<b>14c</b>, <b>15a</b>-<b>15c</b>, <b>16a</b>, <b>23a</b>-<b>23c</b>, <b>24a</b>-<b>24c</b>, <b>25a</b>-<b>25c</b>) and 1,4-disubstituted (<b>34a</b>-<b>34c</b> and <b>35a</b>-<b>35c</b>) 1,2,3-triazole rings were synthesized. The most potent cytotoxic effect on colorectal adenocarcinoma (SW620) was exerted by the 6-chloro-7-deazapu  ...[more]

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