Methylation of Acridin-9-ylthioureas. Structure, Fluorescence and Biological Properties of Products

[img]PDF - Authorized users only
Language: English
201Kb
Title:Methylation of Acridin-9-ylthioureas. Structure, Fluorescence and Biological Properties of Products
Creators:
Bernát, Juraj
Balentová, Eva
Kristian, Pavol
Imrich, Ján
Sedlák, Erik
Danihel, Ivan
Böhm, Stanislav
Prónayová, Naďa
Pihlaja, Kalevi
Klika, Karel D.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 4, pp. 833-849
Uncontrolled Keywords:<i>Ab initio</i> calculations, NOE, Fluorescence, INEPT, Acridines, DFT, Isothioureas, PDQF COSY, NMR spectroscopy, Antimycobacterial activity

Abstract

The structure, fluorescence, biological properties and S(N)-methylation reactions of ten 1,1-alkyl/aryl-disubstituted 3-(acridin-9-yl)thioureas <strong>4</strong> have been studied. Various reaction conditions allowed to obtain corresponding <i>S</i>-methyl <strong>5</strong> and <i>S</i>,<i>N</i>-dimethyl derivatives <strong>6</strong> in good yields. Structure and stereochemistry of the synthesized products are demonstrated by ab initio quantum chemical calculations and NMR techniques including PDQF-COSY, selective INEPT and NOE-difference experiments. Remarkable upfield <sup>13</sup>C shifts of resonance signals of carbons C-4a, C-10a adjacent to acridine N-10 are characteristic of hydroiodides in contrast to free bases. <i>Z</i> configuration in isothioureas <strong>7</strong> with secondary amino rest in relation to <i>E</i> configuration of isothioureas with primary amino rest is discussed. Of the obtained products, some isothiourea salts <strong>6</strong> exhibit more than 2 orders of magnitude higher intensity of fluorescence, using 9-isothiocyanatoacridine as a standard. The obtained isothiourea hydroiodides <strong>5</strong> and dimethylisothiourea iodides <strong>6</strong> show remarkable biological activity against <i>Mycobacterium tuberculosis</i>. <p>

Title:Methylation of Acridin-9-ylthioureas. Structure, Fluorescence and Biological Properties of Products
Creators:
Bernát, Juraj
Balentová, Eva
Kristian, Pavol
Imrich, Ján
Sedlák, Erik
Danihel, Ivan
Böhm, Stanislav
Prónayová, Naďa
Pihlaja, Kalevi
Klika, Karel D.
Uncontrolled Keywords:<i>Ab initio</i> calculations, NOE, Fluorescence, INEPT, Acridines, DFT, Isothioureas, PDQF COSY, NMR spectroscopy, Antimycobacterial activity
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:4
Page Range:pp. 833-849
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20040833UNSPECIFIED
ID Code:2246
Item Type:Article
Deposited On:06 Feb 2009 17:16
Last Modified:06 Feb 2009 16:17

Citation

Bernát, Juraj; Balentová, Eva; Kristian, Pavol; Imrich, Ján; Sedlák, Erik; Danihel, Ivan; Böhm, Stanislav; Prónayová, Naďa; Pihlaja, Kalevi; Klika, Karel D. (2004) Methylation of Acridin-9-ylthioureas. Structure, Fluorescence and Biological Properties of Products. Collection of Czechoslovak Chemical Communications, 69 (4). pp. 833-849. ISSN 0010-0765

Repository Staff Only: item control page