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

Abstract

It is noteworthy that the reaction of (III) with methyl iodide under alkaline conditions to compounds such as (IV) fails. -(BERNAT, J.; BALENTOVA, E.; KRISTIAN*, P.; IMRICH, J.; SEDLAK, E.; DANIHEL, I.; BOEHM, S.; PRONAYOVA, N.; PIHLAJA, K.; KLIKA, K. D.; Collect. Czech.

Tautomerism, regioisomerism, and cyclization reactions of acridinyl thiosemicarbazides

“…The likely explanation for this is that H-bonding to the sulfur atom by one of these Hs is occurring with resultant formation of a stable five-membered ring (see Scheme 1). Firm confirmation for the presence of an NH 2 group in the major species, and thus the formation of the N-13 methylated product 2, was provided by an 15 N INEPT experiment whereby two hydrogen-bearing nitrogen atoms were readily observed, one of which was discerned to be NH and the other NH 2 . The distinctiveness of the two Hs bound to the same nitrogen was further emphasized by their disparate exchangeability evident from NOESY spectra, thus realizing their assignment.…”

“…(Atomic charges were also calculated at this same level of theory.) The isotropic magnetic shieldings ( ) so obtained were evaluated as chemical shifts ( ) based on their difference from the shieldings of TMS (for both 13 This methodology has been found [32,33,34] to be a reliable and useful method for the calculation of chemical shifts for 15 N, 13 To a solution of acridin-9-yl isothiocyanate [36] (1, 1 g, 4.2 mmol) in methanol (15 mL), methylhydrazine (0.194 g, 0.223 mL, 4.2 mmol) was added dropwise at 0 ºC. The mixture was allowed to stir at room temperature in an atmosphere of nitrogen for 2 h until completion of the reaction as indicated by TLC (benzene/ acetone 5:2).…”

A review on acridinylthioureas and its derivatives: biological and cytotoxic activity

“…Bernát et al () reported the synthesis of 9‐acridinyl disubstituted thioureas 5a–j by refluxing appropriate amines with 9‐isothiocyanatoacridine in anhydrous ethanol or at room temperature in chloroform (Fig. ).…”

“…1-Acridin-9-yl-phenylthiourea was prepared from 9isothiocyanatoacridine and aniline/butylamine by Sinsheimer et al (1975) and 1-acridin-yl-butylthiourea by Deleenheer et al (1973). Bernát et al (2004) reported the synthesis of 9-acridinyl disubstituted thioureas 5a-j by refluxing appropriate amines with 9-isothiocyanatoacridine in anhydrous ethanol or at room temperature in chloroform ( Fig. 4).…”

Regiospecific synthesis, structure and electron ionization mass spectra of 1,3‐thiazolidin‐4‐ones containing the acridine skeleton

“…For some time our group has been interested to study the synthesis, structure, fluorescence and biological activity of acridine derivatives [7,8,9]. We found it interesting to prove the possible biological synergetic effect by combining the acridine skeleton with other biologically active moieties.…”