First Total Synthesis of 锠?Phenyl 铻? Fatty Acids and their Leishmanicidal and Anticancer Properties was written by Carballeira, Nestor M.;Morales-Guzman, Christian;Alvarez-Benedicto, Ester;Torres-Martinez, Zally;Delgado, Yamixa;Griebenow, Kai H.;Tinoco, Arthur D.;Reguera, Rosa M.;Perez-Pertejo, Yolanda;Carbajo-Andres, Ruben;Balana-Fouce, Rafael. And the article was included in Current Topics in Medicinal Chemistry (Sharjah, United Arab Emirates) in 2018.Formula: C10H13BrO This article mentions the following:
The first total synthesis of 锠?Ph 铻? fatty acids (FA), e.g., 10-cyclohexyl-6-decynoic acid, 16-phenylhexadecanoic acid, and (Z)-10-Phenyl-6-decenoic acid, and their cytotoxicity (A549) and leishmanicidal (L. infantum) activities are described. The novel 16-phenyl-6-hexadecynoic acid and the known 16-phenylhexadecanoic acid were synthesized in 7-8 steps with overall yields of 46% and 41%, resp. The syntheses of the unprecedented 10-phenyl-6-decynoic acid, 10-cyclohexyl-6-decynoic acid and 10-(4-methoxyphenyl)-6-decynoic acid was also performed in 3 steps with 73-76% overall yields. The use of lithium acetylide coupling enabled the 4-step synthesis of 10-phenyl-6Z-decenoic acid with a 100% cis-stereochem. The cytotoxicity of these novel FA was determined against A549 cells and L. infantum promastigotes and amastigotes. Among the 锠?phenylated FA, the best cytotoxicity towards A549 was displayed by 16-phenyl-6-hexadecynoic acid, with an IC50 of 18 鍗?1 娓璏. On the other hand, among the C10 acids, 10-cyclohexyl-6-decynoic acid presented the best cytotoxicity (IC50 = 40 鍗?2 娓璏) towards A549. Based on caspase-3/7 studies, neither of the FA induced apoptosis in A549, thus implying other mechanisms of cell death. The antileishmanial studies were performed with the top Leishmania donovani topoisomerase IB (LdTopIB) inhibitors, namely 16-phenyl-6-hexadecynoic acid and 16-phenylhexadecanoic acid (EC50 between 14 and 36 娓璏, resp.), acids that did not stabilize the cleavage complexes between LdTopIB and DNA. Acids 16-phenyl-6-hexadecynoic acid and 16-phenylhexadecanoic acid displayed cytotoxicity towards L. infantum amastigotes (IC50 = 3-6 娓璏) and L. infantum promastigotes (IC50 = 60-70 娓璏), but low toxicity towards murine splenocytes. This results identified 16-phenyl-6-hexadecynoic acid as the optimum 锠?phenylated acid of the series. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Formula: C10H13BrO).
1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Formula: C10H13BrO
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary