931417-26-4Relevant articles and documents
The influence of ionic liquids on the Knoevenagel condensation of 1H-pyrrole-2-carbaldehyde with phenyl acetonitriles-cytotoxic 3-substituted-(1H-pyrrol-2-yl)acrylonitriles
Al Otaibi, Ahmed,Gordon, Christopher P.,Gilbert, Jayne,Sakoff, Jennette A.,McCluskey, Adam
, p. 19806 - 19813 (2014/05/20)
The Knoevenagel condensation of a series of substituted phenyl acetonitriles with 1H-pyrrole-2-carbaldehyde was examined in seven 1-butyl-3-methylimidazolium based ionic liquids and three protic ionic liquids. Of these [BMIM][Br] and [BMIM][OH], with cata
Discovery of acrylonitrile-based small molecules active against Haemonchus contortus
Gordon, Christopher P.,Hizartzidis, Lacey,Tarleton, Mark,Sakoff, Jennette A.,Gilbert, Jayne,Campbell, Bronwyn E.,Gasser, Robin B.,McCluskey, Adam
supporting information, p. 159 - 164 (2014/03/21)
We report the discovery of a series of acrylonitrile-containing molecules and α-amino amides which cause 99-100% lethality in H. contortus. Of the 22 acrylonitrile analogues investigated, the most active were 2-cyano-3-[1-(3-dimethylaminopropyl)-2-methyl-
Norcantharidin analogues with nematocidal activity in Haemonchus contortus
Campbell, Bronwyn E.,Tarleton, Mark,Gordon, Christopher P.,Sakoff, Jennette A.,Gilbert, Jayne,McCluskey, Adam,Gasser, Robin B.
supporting information; experimental part, p. 3277 - 3281 (2011/07/07)
With the major problems with resistance in parasitic nematodes of livestock to anthelmintic drugs, there is an urgent need to develop new nematocides. In the present study, we employed a targeted approach for the design of a series of norcantharidin analogues (n = 54) for activity testing against the barber's pole worm (Haemonchus contortus) of small ruminants in a larval development assay (LDA) and also for toxicity testing on nine distinct human cell lines. Although none of the 54 analogues synthesized were toxic to any of these cell lines, three of them (N-octyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboximide (B2), N-decyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboximide (B3) and 4-[(4-methyl)-3-ethyl-2-methyl-5-phenylfuran-10-oxa-4-azatricyclo[5.2.1] decane-3,5-dione (B21) reproducibly displayed 99-100% lethality to H. contortus in LDA, with LD50s of 25-40 μM. The high 'hit rate' (5.6%) indicates that the approach taken here has advantages over conventional drug screening methods. A major advantage of norcantharidin analogues over some other currently available anthelmintics is that they can be produced in one to two steps in large amounts at low cost and high purity, and do not require any additional steps for the isolation of the active isomer. This positions them well for commercial development.
A flow chemistry route to 2-phenyl-3-(1H-pyrrol-2-yl)propan-1-amines
Tarleton, Mark,McCluskey, Adam
experimental part, p. 1583 - 1586 (2011/04/26)
The Knoevenagel condensation of pyrrole-2-carboxaldehyde (1) with a range of substituted benzyl nitriles (2a-e) afforded rapid access to a family of α,β-unsaturated nitriles (3a-e) in good yields (67-78%). Flow hydrogenation (ThalesNano H-cube) at 60 °C, 50 bar H2 pressure, 1.0 mL/min through a 10% Pd-C catalyst selectively, and quantitatively, hydrogenated the olefin double bond (4a-e). Use of a Raney Nickel catalyst at 70 °C, 70 bar H2 pressure and flow rates of 0.5-1.0 mL/min afforded quantitative conversion into the corresponding saturated amines with the reduction of both the olefin and nitrile bonds (5a-e). The versatility of this approach was further exemplified by reaction of 5a and 5c with norcantharidin to afford acid amide norcantharidin analogues 7 and 8 as novel protein phosphatase 1 and 2A inhibitors.
Discovery of (Z)-2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile derivatives active against Haemonchus contortus and Ctenocephalides felis (cat flea)
Ali, Abdelselam,Bliese, Marianne,Rasmussen, Jo-Anne M.,Sargent, Roger M.,Saubern, Simon,Sawutz, David G.,Wilkie, John S.,Winkler, David A.,Winzenberg, Kevin N.,Woodgate, Ruth C.J.
, p. 993 - 997 (2007/10/03)
A series of 2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile derivatives were synthesized and evaluated for in vitro activity against the endoparasite Haemonchus contortus and the ectoparasite Ctenocephalides felis. Some compounds had significant in vitro activit
CONTROL OF PARASITES IN ANIMALS BY THE USE OF PARASITICIDAL 2-PHENYL-3-(1H-PYRROL-2-YL) ACRYLONITRILE DERIVATIVES
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Page/Page column 60, (2008/06/13)
2-Phenyl-3-(1H-pyrrol-2-yl)acrylonitrile compounds useful for controlling parasites in animals and methods of treatment of parasite infestation in animals using the compounds are disclosed.
