In:
Collection of Czechoslovak Chemical Communications, Institute of Organic Chemistry & Biochemistry, Vol. 69, No. 4 ( 2004), p. 833-849
Abstract:
The structure, fluorescence, biological properties and S(N)-methylation reactions of ten 1,1-alkyl/aryl-disubstituted 3-(acridin-9-yl)thioureas 4 have been studied. Various reaction conditions allowed to obtain corresponding S -methyl 5 and S , N -dimethyl derivatives 6 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 13 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. Z configuration in isothioureas 7 with secondary amino rest in relation to E configuration of isothioureas with primary amino rest is discussed. Of the obtained products, some isothiourea salts 6 exhibit more than 2 orders of magnitude higher intensity of fluorescence, using 9-isothiocyanatoacridine as a standard. The obtained isothiourea hydroiodides 5 and dimethylisothiourea iodides 6 show remarkable biological activity against Mycobacterium tuberculosis .
Type of Medium:
Online Resource
ISSN:
0010-0765
,
1212-6950
DOI:
10.1135/cccc20040833
Language:
English
Publisher:
Institute of Organic Chemistry & Biochemistry
Publication Date:
2004