Pretražite po imenu i prezimenu autora, mentora, urednika, prevoditelja

Napredna pretraga

Pregled bibliografske jedinice broj: 988885

Synthesis and antiplasmodial evaluation of novel mefloquine-based fumardiamides


Beus, Maja; Fontinha, Diana; Held, Jana; Rajić, Zrinka, Prudêncio, Miguel; Zorc, Branka
Synthesis and antiplasmodial evaluation of novel mefloquine-based fumardiamides // Acta pharmaceutica, 69 (2019), 2; 233-248 doi:10.2478/acph-2019-0019 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 988885 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Synthesis and antiplasmodial evaluation of novel mefloquine-based fumardiamides

Autori
Beus, Maja ; Fontinha, Diana ; Held, Jana ; Rajić, Zrinka, Prudêncio, Miguel ; Zorc, Branka

Izvornik
Acta pharmaceutica (1330-0075) 69 (2019), 2; 233-248

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Mefloquine ; 2, 8-bis(Trifluoromethyl)quinoline ; Fumardiamide, Halogenaniline, Antiplasmodial activity

Sažetak
The paper is focused on synthesis and screening of the antiplasmodial activity of novel fumardiamides 5–10 with the mefloquine pharmacophore and a Michael acceptor motif. Multi-step reactions leading to the title compounds included two amide bond formations. The first amide bond was achieved by the reaction of (E)-ethyl 4-chloro-4-oxobut-2-enoate (1) and N1-(2, 8-bis(trifluoromethyl)quinolin-4-yl)butane-1, 4-diamine (2). Basic hydrolysis of the obtained ester 3 afforded acid 4, which then reacted with the selected halogenanilines in the presence of HATU/DIEA and formed products 5–10. The title compounds showed significant, dose dependent activity in vitro against hepatic stages of Plasmodium berghei. IC50 values of the most active compounds 5, 7 and 9 bearing 3-fluoro, 3-chloro and 3-trifluoromethyl substituents were 3.04–4.16 µmol L–1, respectively. On the other hand, the compounds exerted only weak activity against the erythrocytic stages of two P. falciparum strains (Pf3D7 and PfDd2) in vitro, with the exception of compound 5 (IC50 = 2.9 µmol L–1).

Izvorni jezik
Engleski

Znanstvena područja
Farmacija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2014-09-1501 - Dizajniranje, sinteza i evaluacija derivata primakina, vorinostata i sorafeniba kao potencijalnih citostatika (HRZZ)

Ustanove
Farmaceutsko-biokemijski fakultet, Zagreb

Profili:

Avatar Url Zrinka Rajić (autor)

Avatar Url Branka Zorc (autor)

Avatar Url Maja Beus (autor)

Citiraj ovu publikaciju

Beus, Maja; Fontinha, Diana; Held, Jana; Rajić, Zrinka, Prudêncio, Miguel; Zorc, Branka
Synthesis and antiplasmodial evaluation of novel mefloquine-based fumardiamides // Acta pharmaceutica, 69 (2019), 2; 233-248 doi:10.2478/acph-2019-0019 (međunarodna recenzija, članak, znanstveni)
Beus, M., Fontinha, D., Held, J., Rajić, Zrinka, Prudêncio, Miguel & Zorc, B. (2019) Synthesis and antiplasmodial evaluation of novel mefloquine-based fumardiamides. Acta pharmaceutica, 69 (2), 233-248 doi:10.2478/acph-2019-0019.
@article{article, year = {2019}, pages = {233-248}, DOI = {10.2478/acph-2019-0019}, keywords = {Mefloquine, 2, 8-bis(Trifluoromethyl)quinoline, Fumardiamide, Halogenaniline, Antiplasmodial activity}, journal = {Acta pharmaceutica}, doi = {10.2478/acph-2019-0019}, volume = {69}, number = {2}, issn = {1330-0075}, title = {Synthesis and antiplasmodial evaluation of novel mefloquine-based fumardiamides}, keyword = {Mefloquine, 2, 8-bis(Trifluoromethyl)quinoline, Fumardiamide, Halogenaniline, Antiplasmodial activity} }

Časopis indeksira:


  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


Citati





    Contrast
    Increase Font
    Decrease Font
    Dyslexic Font