22739-29-3Relevant articles and documents
IR-Raman, NMR and density functional methods in the examination of tautomerism and features of N-methyl substituted 9-acridinamine derivatives
Rak, Janusz,Krzyminski, Karol,Skurski, Piotr,Jozwiak, Ludwika,Blazejowski, Jerzy
, p. 45 - 55 (1999)
Four N-methyl substituted derivatives of amino or imino forms of 9- acridinamine were synthesized and subjected to detailed IR-Raman and NMR (1H and 13C) investigations. Harmonic frequencies predicted at the density functional (DFT) level enabled certain modes to be assigned to bands in IR or Raman spectra and those characteristic of either the amino or imino tautomeric forms of 9-acridinamine. Theoretical 1H and 13C chemical shifts, particularly the latter, fit the relevant NMR spectra only qualitatively; both demonstrate a unique pattern for each of the compounds studied. The derivatives examined seem to exhibit their own identity and features, reflected in unique vibrational and NMR spectra, rather than retain those of the parent tautomeric forms of 9-acridinamine. Both experimental and theoretical investigations reveal that two tautomeric forms of N-methyl-9- acridinamine, in similar to 9-acridinamine, should co-exist at room temperature. The polarity of the compounds, expressed by dipole moments, as well as distribution of relative atomic partial charges and electrostatic potential around the molecules, are unique for each of the compounds but generally similar in the groups of derivatives originating from the amino or imino tautomers of 9-acridinamine.
Syntheses of acridines and quinazoline-2,4(1H,3H)-dithiones by rearrangements of N-Heterocyclic carbenes of indazole
Guan, Zong,Gjikaj, Mimoza,Schmidt, Andreas
, p. 2356 - 2367 (2014/12/11)
N-Heterocyclic carbenes of indazole which are arylated at N1 (1-aryl-indazol-3-ylidenes) have been generated by deprotonation of the corresponding indazolium salts. On deprotonation with potassium carbonate, potassium phosphate or tert-butanolate in dioxane or toluene at reflux temperature, a rearrangement to acridines took place. Deprotonation with n-butyllithium in THF at room temperature in the presence of carbon disulfide gave quinazoline-2,4(1H,3H)-dithiones by a new rearrangement reaction.
Design, synthesis, and biological activity of a novel non-cisplatin-type platinum-acridine pharmacophore
Martins,Baruah,Kramarczyk,Saluta,Day,Kucera,Bierbach
, p. 4492 - 4496 (2007/10/03)
Platinum-acridine conjugates were prepared from [PtCl2(ethane-1,2-diamine)] and the novel acridinylthioureas MeHNC(S)NMeAcr (6) and MeHNC(S)NMe(CH2CH2)NHAcr (15) by replacing one chloro leaving group in the cisplatin analogue with thiourea sulfur. In HL-60 leukemia cells, IC50 values for 7 (Pt-tethered 6) and 16 (Pt-tethered 15) were 75 and 0.13 μM, respectively. In the ovarian cell lines 2008 and C13*, 16 was active at micromolar concentrations and showed only partial cross-resistance with clinical cisplatin. Possible structure-activity relationships are discussed.