1228015-35-7Relevant articles and documents
Hydroxylated di- and tri-styrylbenzenes, a new class of antiplasmodial agents: Discovery and mechanism of action
Sharma, Naina,Mohanakrishnan, Dinesh,Shard, Amit,Sharma, Abhishek,Sinha, Arun K.,Sahal, Dinkar
, p. 49348 - 49357 (2016/07/06)
The first systematic evaluation of the antiplasmodial activity of the hydroxystilbene family of natural products and di/tristyrylbenzenes is described. A library of 27 diversely substituted hydroxy stilbenoids was rapidly synthesized using modified Knoevenagel-Perkin-decarboxylation-Heck sequences from readily available starting materials (i.e. hydroxybenzaldehyde-phenylacetic acid-arylhalide). These compounds were evaluated for in vitro antiplasmodial activity against three different strains of Plasmodium falciparum. Notably, 4,4′4′′-((1E,1′E,1′′E)-benzene-1,3,5-triyltris(ethene-2,1-diyl))tris(2,6-dimethoxyphenol) (27), an octupolar stilbenoid, showed IC50 (μM) values of 0.6, 0.5 and 1.36 while a distyrylbenzene (11) showed IC50 values of 0.9, 2.0 and 2.7 against 3D7 (chloroquine sensitive), Dd2 and Indo (chloroquine resistant) strains of Plasmodium falciparum respectively. Moreover, 27 and 11, which exhibited selectivity indices of 40 and >111 were also found to be nontoxic to the HeLa cell line. Microscopic studies revealed that the rings and trophozoites obtained from the 27 and 11 (an octupolar tristyrylbenzene and distyrylbenzene respectively) treated cultures were growth inhibited and morphologically deformed. These cultures also showed DNA fragmentation and loss of mitochondrial membrane potential (ΔΨm), suggestive of apoptotic death of the parasite. Together, these studies introduce di/tristyrylbenzenes as a new class of antimalarial agents.
Direct olefination of benzaldehydes into hydroxy functionalized oligo (p-phenylenevinylene)s via Pd-catalyzed heterodomino Knoevenagel- decarboxylation-Heck sequence and its application for fluoride sensing π-conjugated units
Sharma, Abhishek,Sharma, Naina,Kumar, Rakesh,Shard, Amit,Sinha, Arun K.
supporting information; experimental part, p. 3283 - 3285 (2010/07/13)
A new approach for one step olefination of benzaldehydes into hydroxy functionalized OPVs is achieved through the first domino Knoevenagel- decarboxylation-Heck sequence using a single catalyst system. The methodology also led to new oxygen based OPV scaffolds capable of selective and visible fluoride recognition in organic or aqueous medium.
