178551-80-9Relevant academic research and scientific papers
Design, synthesis, and monoamine transporter binding site affinities of methoxy derivatives of indatraline
Gu,Yu,Jacobson,Rothman,Dersch,George,Flippen-Anderson,Rice
, p. 4868 - 4876 (2000)
A series of methoxy-containing derivatives of indatraline 13a-f and 17 were synthesized, and their binding affinities for the dopamine, serotonin, and norepinephrine transporter binding sites were determined. Introduction of a methoxy group to indatraline
Chalcone derivatives targeting mitosis: synthesis, evaluation of antitumor activity and lipophilicity
Pinto, Patricia,Machado, Carmen Mariana,Moreira, Joana,Almeida, José Diogo P.,Silva, Patrícia M.A.,Henriques, Ana C.,Soares, José X.,Salvador, Jorge A.R.,Afonso, Carlos,Pinto, Madalena,Bousbaa, Hassan,Cidade, Honorina
, (2019/10/14)
This study describes the synthesis of a series of chalcones, including pyrazole and α,β-epoxide derivatives, and evaluation of their cell growth inhibitory activity in three human tumor cell lines, as well as their lipophilicity using liposomes as a biomi
Synthesis and structural elucidation of pyrimido-[1,2-a]benzimidazoles and fused derivatives. I. Dihydropyrimido[1,2-a]benzimidazoles
El Ella, Dalal Abou,Goessnitzer, Edith,Wendelin, Winfried
, p. 373 - 382 (2007/10/03)
The condensation of 2-benzimidazolamine (4, BIA) with α,β-unsaturated ketones 1 affords, according to Desenko, Orlov et al. [12,13], 1,4-dihydropyrimido[1,2-a]benzimidazoles (1,4-DHPBI, 51). However, the described ring closure reactions could a priori also yield isomeric 1,2-DHPBI 81 or tautomers of DHPBIs 5I and 8I. An unequivocal proof for the postulated structures 5I was not presented. We prepared, as described [12,13], BIA-chalcone- and BIA-benzalacetone-condensate X and Y, 5a,e or 8a,e, and additionally, their hydrochlorides. One and two dimensional high resolution nmr analyses showed that only isomers 5a,e and salts 5a,e·HCl were generated. In DMSO-d6 these isomers exclusively exist as 1,4-dihydro tautomers 5a,eI and 5a,eI·HCl. In trifluoroacetic acid 3,4-dihydro tautomers 5a,eIII-CF3COOH besides of tautomers 5a,eI·CF3COOH (≈1:4) were ascertained. Action of ethanolic hydrochloric acid on base 5eI afforded, besides of 5eI·HCl as main product, a small amount of 2-methyl-4-phenyltetrahydropyrim-ido[1,2-a]benzimidazol-2-ol hydrochloride 9e·HCl. The reaction of BIA 4 with α,β-unsaturated ketones 1b-d and f yielded 1,4-DHPBI 5b-dI and 5fI and their hydrochlorides, respectively The stereochemistry of bases 5a,eI, of salts 5a-eI-HCl and 5a,eIII·CF3COOH, and of addition product 9e·HCl was elucidated by nmr (stereoformulae in Figures 1-3 and Scheme 5). The accomplished nmr-analyses are documented in detail and discussed.
