129354-77-4Relevant academic research and scientific papers
Original TDAE strategy using α-halocarbonyl derivatives
Since, Marc,Terme, Thierry,Vanelle, Patrice
experimental part, p. 6128 - 6134 (2011/03/19)
We report herein the selective C-C bond formation by the reaction of nitrobenzyl carbanions, formed via the TDAE strategy, with α-haloesters and α-haloamides. This reaction, extended in benzodioxole and dimethoxybenzene series provides new potentially CNS
Structure-activity relationships for the antileishmanial and antitrypanosomal activities of 1'-substituted 9-anilinoacridines
Gamage, Swarna A.,Figgitt, David P.,Wojcik, Stanley J.,Ralph, Raymond K.,Ransijn, Adriana,Mauel, Jacques,Yardley, Vanessa,Snowdon, Diane,Croft, Simon L.,Denny, William A.
, p. 2634 - 2642 (2007/10/03)
Members of the class of 9-anilinoacridine topoisomerase II inhibitors bearing lipophilic electron-donating 1'-aniline substituents are active against both the promastigote and amastigote forms of the parasite Leishmania major. A series of analogues of the known 1'-NHhexyl lead compound were prepared and evaluated against L. major in macrophage culture to further develop structure-activity relationships (SAR). Toxicity toward mammalian cells was measured in a human leukemia cell line, and the ratio of the two IC50 values (IC50(J)/IC50(L)) was used as a measure of the in vitro therapeutic index (IVTI). A 3,6-diNMe2 substitution pattern on the acridine greatly increased toxicity to L. major without altering mammalian toxicity, increasing IVTIs over that of the lead compound. The 2-OMe, 6-C1 acridine substitution pattern used in the antimalarial drug mepacrine also resulted in potent antileishmanial activity and high IVTIs. Earlier suggestions of the utility of 2'-OR groups in lowering mammalian cytotoxicity were not borne out in this wider study. A series of very lipophilic 1'-NRR (symmetric dialkylamino)-substituted analogues showed relatively high antileishmanial potency, but no clear trend was apparent across the series and none were superior to the 1'-NH(CH2)5Me subclass. Subsets of the most active 1'- N(R)(CH2)5Me- and 1'-N(alkyl)2-substituted compounds against L. major were also evaluated against Leishmania donovani, Trypanosoma cruzi, and Trypanosoma brucei, but no consistent SAR could be discerned in these physiologically diverse test systems. The present study has confirmed earlier conclusions that lipophilic electron-donating groups at the 1'-position of 9- anilinoacridines provide high activity against L. major, but the SAR patterns observed do not carry over to the other parasites studied.
A One Step General Synthesis of 3-Benzylcoumarins
Deshmukh, Sanjay Y.,Kelkar, Shriniwas L.,Wadia, Murzban S.
, p. 855 - 863 (2007/10/02)
Reaction od a preformed complex of the amides (2a-c) and POCl3 with substituted salicylaldehydes yielded 3-benzylcoumarins in one step and in good yields.
