188404-16-2Relevant articles and documents
Original antileishmanial hits: Variations around amidoximes
Tabélé, Clémence,Fai?es, Viviane dos S.,Grimaud, Fabien,Torres-Santos, Eduardo Caio,Khoumeri, Omar,Curti, Christophe,Vanelle, Patrice
, p. 154 - 164 (2018/02/20)
In continuation to our previous findings on amidoximes' antiparasitic activities, a new series of 23 original derivatives was designed and obtained by convergent synthesis. First, new terminal alkenes were synthesized by cross-coupling reaction. Then, cyclization was performed between terminal alkenes and β-ketosulfones using manganese(III) acetate reactivity. Twenty-three amidoximes were tested for their in vitro activity against Leishmania amazonensis promastigotes and their toxicity on murine macrophages. Seven of the tested compounds exhibited an antileishmanial activity at lower than 10 μM with moderate to low toxicity. Six of these molecules showed activity at lower than 10 μM against promastigotes and toxicity at higher than 50 μM were selected and evaluated for their activity against intracellular Leishmania amazonensis amastigotes. Modulating chemical substituents in position 2 of dihydrofuran highly influenced their antileishmanial activities. The introduction of a methyl or trifluoromethyl group on the benzene ring of the benzyl group had a positive influence on activity without significantly increasing toxicity (52, 59, 60).
Palladium-catalyzed desulfinylative C-C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters
Rao Volla, Chandra M.,Dubbaka, Srinivas Reddy,Vogel, Pierre
experimental part, p. 504 - 511 (2009/04/07)
2-Methylprop-2-ene-, prop-2-ene-, 1-methylprop-2-ene-, and (E)-but-2-enesulfonyl chlorides have been used as electrophilic partners in desulfinylative palladium-catalyzed C-C coupling with Grignard reagents and sodium salts of dimethyl malonate and methyl
Ligandless iron-catalyzed desulfinylative C-C allylation reactions using Grignard reagents and alk-2-enesulfonyl chlorides
Volla, Chandra M. R.,Markovic, Dean,Dubbaka, Srinivas Reddy,Vogel, Pierre
experimental part, p. 6281 - 6288 (2011/02/28)
Alk-2-enesulfonyl chlorides 1-4 were synthesized by the BCl3-promoted ene reaction of alkenes with SO2. These sulfonyl chlorides were then used as electrophilic partners in iron-catalyzed desulfinylative cross-coupling reactions with different Grignard reagents (aromatic, aliphatic, and heteroaromatic). The reaction can be catalyzed with even 2 mol-% of the simple iron salt Fe(acac)3. The regioselectivity of these allylations was studied by using sulfonyl chlorides 3 and 4 with aryl Grignard reagents. The scope of these allylations was further extended by the coupling of ester-substituted alk-2-enesulfonyl chloride 10 with aromatic Grignard reagents. Symmetrical products were synthesized by double C-C allylation with the use of 2-methylidenepropane-1,3-disulfonyl chloride (12). Wiley-VCH Verlag GmbH & Co. KGaA.
Palladium-catalyzed desulfinylative Negishi C-C bond forming cross-couplings of sulfonyl and organozinc chlorides
Dubbaka, Srinivas Reddy,Vogel, Pierre
, p. 3345 - 3348 (2007/10/03)
Arene-, phenylmethane- and alkenesulfonyl chlorides are suitable electrophilic reagents in desulfinylative carbon-carbon bond formation cross-coupling reactions with organozinc reagents.
Molybdenum- and tungsten-catalyzed allylation of aromatic compounds with allylic esters and alcohols
Shimizu, Isao,Sakamoto, Toshiaki,Kawaragi, Saeko,Maruyama, Yooichiro,Yamamoto, Akio
, p. 137 - 138 (2007/10/03)
A novel method to substitute aromatic compounds with allylic groups using oxygen-containing allylic compounds in the presence of molybdenum or tungsten carbonyls under neutral conditions has been developed. The method is applicable to one step synthesis of methyl eugenol.
