دورية أكاديمية
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Synthesis of Novel Biologically Active Proflavine Ureas Designed on the Basis of Predicted Entropy Changes.

التفاصيل البيبلوغرافية
العنوان: Synthesis of Novel Biologically Active Proflavine Ureas Designed on the Basis of Predicted Entropy Changes.
المؤلفون: Janovec L; Department of Organic Chemistry, Faculty of Science, P. J. Safarik University in Kosice, Moyzesova 11, 040 01 Kosice, Slovakia., Kovacova E; Department of Organic Chemistry, Faculty of Science, P. J. Safarik University in Kosice, Moyzesova 11, 040 01 Kosice, Slovakia., Semelakova M; Department of Medical Biology, Faculty of Medicine, P. J. Safarik University in Kosice, Trieda SNP1, 040 11 Kosice, Slovakia., Kvakova M; Department of Experimental Medicine, Faculty of Medicine, P. J. Safarik University in Kosice, Trieda SNP1, 040 11 Kosice, Slovakia., Kupka D; Institute of Geotechnics, Slovak Academy of Sciences, Watsonova 45, 040 01 Kosice, Slovakia., Jager D; Institute of Geotechnics, Slovak Academy of Sciences, Watsonova 45, 040 01 Kosice, Slovakia., Kozurkova M; Department of Biochemistry, Faculty of Science, P. J. Safarik University in Kosice, Moyzesova 11, 040 01 Kosice, Slovakia.; Biomedical Research Center, University Hospital Hradec Kralove, Sokolovska 581, 500 05 Hradec Kralove, Czech Republic.
المصدر: Molecules (Basel, Switzerland) [Molecules] 2021 Aug 11; Vol. 26 (16). Date of Electronic Publication: 2021 Aug 11.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI, c1995-
مواضيع طبية MeSH: Entropy*, Proflavine/*chemical synthesis , Urea/*chemical synthesis, Chemical Phenomena ; Fibroblasts/cytology ; Fibroblasts/drug effects ; Humans ; Inhibitory Concentration 50 ; Kinetics ; Male ; Models, Molecular ; Proflavine/chemistry ; Proflavine/pharmacology ; Urea/chemistry ; Urea/pharmacology
مستخلص: A novel series of proflavine ureas, derivatives 11a - 11i , were synthesized on the basis of molecular modeling design studies. The structure of the novel ureas was obtained from the pharmacological model, the parameters of which were determined from studies of the structure-activity relationship of previously prepared proflavine ureas bearing n -alkyl chains. The lipophilicity (Log P ) and the changes in the standard entropy (Δ S °) of the urea models, the input parameters of the pharmacological model, were determined using quantum mechanics and cheminformatics. The anticancer activity of the synthesized derivatives was evaluated against NCI-60 human cancer cell lines. The urea derivatives azepyl 11b , phenyl 11c and phenylethyl 11f displayed the highest levels of anticancer activity, although the results were only a slight improvement over the hexyl urea, derivative 11j , which was reported in a previous publication. Several of the novel urea derivatives displayed GI 50 values against the HCT-116 cancer cell line, which suggest the cytostatic effect of the compounds azepyl 11b -0.44 μM, phenyl 11c -0.23 μM, phenylethyl 11f -0.35 μM and hexyl 11j -0.36 μM. In contrast, the novel urea derivatives 11b , 11c and 11f exhibited levels of cytotoxicity three orders of magnitude lower than that of hexyl urea 11j or amsacrine.
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معلومات مُعتمدة: 1/0016/18 Agentúra Ministerstva Školstva, Vedy, Výskumu a Športu SR; 00179906 Ministerstvo Zdravotnictví Ceské Republiky
فهرسة مساهمة: Keywords: cytostatic activity; cytotoxicity; molecular design; proflavine ureas
المشرفين على المادة: 8W8T17847W (Urea)
CY3RNB3K4T (Proflavine)
تواريخ الأحداث: Date Created: 20210827 Date Completed: 20210915 Latest Revision: 20210915
رمز التحديث: 20221213
مُعرف محوري في PubMed: PMC8398074
DOI: 10.3390/molecules26164860
PMID: 34443446
قاعدة البيانات: MEDLINE
الوصف
تدمد:1420-3049
DOI:10.3390/molecules26164860