2556-46-9Relevant articles and documents
Direct, Late-Stage Mono-N-arylation of Pentamidine: Method Development, Mechanistic Insight, and Expedient Access to Novel Antiparastitics against Diamidine-Resistant Parasites
Robertson, Jack,Ungogo, Marzuq A.,Aldfer, Mustafa M.,Lemgruber, Leandro,McWhinnie, Fergus S.,Bode, Bela E.,Jones, Katherine L.,Watson, Allan J. B.,de Koning, Harry P.,Burley, Glenn A.
supporting information, p. 3396 - 3401 (2021/09/06)
A selective mono-N-arylation strategy of amidines under Chan-Lam conditions is described. During the reaction optimization phase, the isolation of a mononuclear Cu(II) complex provided unique mechanistic insight into the operation of Chan-Lam mono-N-arylation. The scope of the process is demonstrated, and then applied to access the first mono-N-arylated analogues of pentamidine. Sub-micromolar activity against kinetoplastid parasites was observed for several analogues with no cross-resistance in pentamidine and diminazene-resistant trypanosome strains and against Leishmania mexicana. A fluorescent mono-N-arylated pentamidine analogue revealed rapid cellular uptake, accumulating in parasite nuclei and the kinetoplasts. The DNA binding capability of the mono-N-arylated pentamidine series was confirmed by UV-melt measurements using AT-rich DNA. This work highlights the potential to use Chan-Lam mono-N-arylation to develop therapeutic leads against diamidine-resistant trypanosomiasis and leishmaniasis.
Access to Amidines and Arylbenzimidazoles: Zinc-Promoted Rearrangement of Oxime Acetates
Zhu, Zhongzhi,Cen, Jinghe,Tang, Xiaodong,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
, p. 2020 - 2031 (2018/04/09)
An efficient and straightforward zinc-promoted rearrangement of oxime acetates with arylamines for the synthesis of amidines has been developed under mild conditions. This process involves N?O/C?C bond cleavages and C?C/C?N bond formations. Various oxime
Solvent/oxidant-switchable synthesis of multisubstituted quinazolines and benzimidazoles via metal-free selective oxidative annulation of arylamidines
Lin, Jian-Ping,Zhang, Feng-Hua,Long, Ya-Qiu
supporting information, p. 2822 - 2825 (2014/06/23)
A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp3)-C(sp2) and C(sp 2)-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp3C-H/sp2C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.