13743-90-3

Upstream product

• 289893-35-2 (2S)-[(1R-cis)-1-Hydroxy-7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydro-2-naphthyl]propionohydrazide 
• 14794-71-9 (-)-α-desmotroposantonin acetate 
• 74-83-9 methyl bromide 
• 13743-88-9 (-)-α-desmotroposantonin 
• 481-06-1 santonin 
• 1121-60-4 pyridine-2-carbaldehyde 
• 74-88-4 methyl iodide 

Downstream Products

• 13744-04-2 (+/-)-Dihydroartemisiasaeure-methylaether 

Relevant academic research and scientific papers

T- and B-cell immunosuppressive activity of novel α-santonin analogs with humoral and cellular immune response in Balb/c mice

In continuation of our endeavours to synthesize immunosuppressive agents from α-santonin, we report herein the design and synthesis of a new series of α-santonin derived O-aryl/aliphatic ether, ester and amide analogs and the evaluation of their immunosuppressive activities. The in vitro studies led to several analogs with significant immunosuppressive effects by inhibiting ConA and LPS stimulated T- and B-cell proliferation in a dose dependent manner. The more significant compounds 4d, 4e, 4f, 4h, 6a and 6b displayed potent inhibitory activity on the mitogen-induced T- and B-cell proliferation in comparison to α-santonin 1. Compound 4e displayed stupendous in vitro immunosuppressive effects with ～80% suppression of B and ～75% suppression of T lymphocyte proliferation, respectively. The in vivo investigation on BALB/c mice revealed that non-cytotoxic compound 4e suppresses both humoral and cellular immunity.

Identification of natural-product-derived inhibitors of 5-lipoxygenase activity by ligand-based virtual screening

A natural product collection and natural-product-derived combinatorial libraries were virtually screened for potential inhibitors of human 5-lipoxygenase (5-LO) activity. We followed a sequential ligand-based approach in two steps. First, similarity searc

Synthesis of nitrogen-containing derivatives of (-)-α-methyldesmotroposantonin

Transformations of (-)-α-methyldesmotroposantonin into hydrazides and amines of the tetrahydronaphthalene series were studied. The latter were brought into reactions with salicylaldehyde and 2-pyridinecarbaldehyde with the goal of obtaining the corresponding Schiff bases.

Relative Stabilities of the Desmotroposantonins

Equilibration of (-)-α-desmotroposantonin methyl ether (6), (+)-β-desmotroposantonin methyl ether (7), and isohyposantonin (8) with K2CO3 in xylene gives the same 56:44 mixture of isomers at C-11.Although acid-catalyzed isomerization of (-)-α-desmotroposantonin (2) affords (+)-β-desmotroposantonin (3) in good yield, the deoxy analogue of 2, isohyposantonin (8), gives an approximately 1 to 1 mixture of 8 and β-desmotroposantonin analogue (11) with acid 10 as the major product.These results indicate that the published data which indicate that the β-isomers are significantly more stable than their α-epimers are based on reactions in which equilibrium was not reached.NMR studies at 200 MHz show that the conformation of the lactone ring in the α- and β-isomers is not the same.A conformation is suggested for α-desmotroposantonin on the basis of the NMR data, and an explanation is offered for the stability relationships in the desmotroposantonin series.