56083-03-5Relevant articles and documents
Synthesis and biological evaluation of chalcones as potential antileishmanial agents
Gupta, Shweta,Shivahare, Rahul,Korthikunta, Venkateswarlu,Singh, Rohit,Gupta, Suman,Tadigoppula, Narender
, p. 359 - 366 (2014/06/09)
Antileishmanial activities of thirty-five synthetic chalcones have been examined. Among them, ten compounds (4, 6, 16, 22, 23, 24, 25, 29, 35 and 37) exhibited potent in vitro activity (IC50 range from 1.70 to 8 μM) against extracellular promastigotes and intracellular amastigotes form of Leishmania donovani. Two promising compounds 22 and 37 were tested in vivo in L. donovani/hamster model. Chalcone 37 showed 83.32% parasite inhibition at a dose of 50 mg/kg for 10 days whereas, 75.89% parasite inhibition at 100 mg/kg dose for 5 days by intraperitoneal route at day 7 post-treatment.
Synthesis and biological evaluation of pyranoisoflavone derivatives as anti-inflammatory agents
Wei, Zhe,Yang, Youzhe,Xie, Caifeng,Li, Chunyan,Wang, Guangcheng,Ma, Liang,Xiang, Mingli,Sun, Jian,Wei, Yuquan,Chen, Lijuan
, p. 172 - 183 (2014/07/21)
In this paper, barbigerone (1a) and its twenty-seven related structural analogues were synthesized via complementary synthetic routes and their anti-inflammatory effects on the expression of TNF-α in LPS-stimulated splenocytes were evaluated. Among these compounds, 1a, 1d, 1f and 1g were found to remarkably inhibit TNF-α production. Furthermore, 1g showed the most potent and dose-dependent manner inhibitory effect on TNF-α release, with better IC50 value (3.58 μM) than barbigerone (8.46 μM). Oral administration of 1g at 20 mg/kg/day for two weeks obviously demonstrated protective effect in adjuvant-induced arthritis models as evaluated by clinical score of paws, and histological examination of joint tissues from rats. Mechanism studies on mRNA and protein level suggested that 1g inhibited the TNF-α production via depressing TNF-α converting enzyme (TACE) mRNA expression. In conclusion, these data show 1g with potential therapeutic effects as an anti-inflammatory agent.
A new route to the synthesis of pyranoflavone and pyranochalcone natural products and their derivatives
Lee, Yong Rok,Kim, Do Hoon
, p. 603 - 608 (2007/10/03)
The total synthesis of biologically active pyranoflavone natural products 1 and 2 was carried out starting from 2H-pyran. The synthesis of pyranochalcone natural products, lonchocarpin (9) and 4-hydroxylonchocarpin (10), and their derivatives 30-32 is des
A convenient and biogenetic type synthesis of few naturally occurring chromeno dihydrochalcones and their in vitro antileishmanial activity
Narender, Tadigoppula,Shweta,Gupta, Suman
, p. 3913 - 3916 (2007/10/03)
2′,2′-Dimethyl chromeno dihydrochalcones are very rare in nature as plant secondary metabolites. Recently we have reported three such compounds from the plant Crotalaria ramosissima. Chromeno dihydrochalcones contain a 2′,2′-dimethyl benzopyran system, which are frequently encountered in many natural products and exhibit a variety of biological activities. We here report the strategy to conveniently synthesize naturally occurring chromeno dihydrochalcones by biogenetic type pyridine or Amberlyst-15 catalyzed chromenylation of dihydrochalcones and in vitro antileishmanial activity of chromeno dihydrochalcones and their intermediates.
Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans
Nicolaou,Pfefferkorn,Roecker,Cao,Barluenga,Mitchell
, p. 9939 - 9953 (2007/10/03)
Herein we report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran moiety is selected as an inaugural template for the construction of natural product-like libraries via this strategy. Initially, a novel solid-phase synthesis of the benzopyran motif is developed employing a unique cycloloading strategy that relies on the use of a new, polystyrene-based selenenyl bromide resin. Once the loading, elaboration, and cleavage of these benzopyrans was established, this new solid-phase method was then thoroughly validated through the construction of six focused combinatorial libraries designed around natural and designed molecules of recent biological interest.
