156150-59-3Relevant academic research and scientific papers
3-Hydroxypyrrolidine and (3,4)-dihydroxypyrrolidine derivatives: Inhibition of rat intestinal α-glucosidase
Carreiro, Elisabete P.,Louro, Patrícia,Adriano, Gizé,Guedes, Romina A.,Vannuchi, Nicholas,Costa, Ana R.,Antunes, Célia M.M.,Guedes, Rita C.,Burke
, p. 81 - 88 (2014/06/09)
Thirteen pyrrolidine-based iminosugar derivatives have been synthesized and evaluated for inhibition of α-glucosidase from rat intestine. The compounds studied were the non-hydroxy, mono-hydroxy and dihydroxypyrrolidines. All the compounds were N-benzylated apart from one. Four of the compounds had a carbonyl group in the 2,5-position of the pyrrolidine ring. The most promising iminosugar was the trans-3,4-dihydroxypyrrolidine 5 giving an IC50 of 2.97 ± 0.046 and a KI of 1.18 mM. Kinetic studies showed that the inhibition was of the mixed type, but predominantly competitive for all the compounds tested. Toxicological assay results showed that the compounds have low toxicity. Docking studies showed that all the compounds occupy the same region as the DNJ inhibitor on the enzyme binding site with the most active compounds establishing similar interactions with key residues. Our studies suggest that a rotation of ～90° of some compounds inside the binding pocket is responsible for the complete loss of inhibitory activity. Despite the fact that activity was found only in the mM range, these compounds have served as simple molecular tools for probing the structural features of the enzyme, so that inhibition can be improved in further studies.
FUSED BENZENE DERIVATIVE AND USE
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Page/Page column 56, (2010/02/12)
The present invention provides a compound represented by the general formula: [wherein Ring A represents an optionally substituted 5- to 8-membered ring, Ring B represents a further optionally substituted 4- to 10-membered ring, Ring C represents a further optionally substituted benzene ring, X1 represents carbon atom, X2 represents a carbon atom, an oxygen atom, etc., W represents a nitrogen atom, etc., Y11 represents a group represented by the formula CR2R3' (wherein R2 represents a hydrogen atom, a cyano group, a nitro group, etc., and R3' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), Y21 represents a group represented by the formula CR4R5' (wherein R4 represents a hydrogen atom, a cyano group, a nitro group, etc., and R5' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), etc., and R1 represents an electron-withdrawing group, respectively. The formula represents a single bond or a double bond] or a salt thereof, which is useful as an androgen receptor modulator.
Practical synthesis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its acetate from L-tartaric acid
Tomori, Hiroshi,Maruyama, Hiroshi,Ogura, Katsuyuki
, p. 415 - 423 (2007/10/03)
An efficient method for preparing (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its acetate is described starting from L-tartaric acid, which affords the desired compounds with 99% ee in good overall yields (63-74%).
4-[(Alkylamino)methyl]furo[3,2-c]pyridines: A new series of selective κ- receptor agonists
Naylor,Judd,Scopes,Hayes,Birch
, p. 2138 - 2144 (2007/10/02)
The synthesis of 5-(arylacetyl)-4-[(alkylamino)methyl]furo[3,2- c]pyridines (16-23, 26, 27) and their activities as κ-opioid receptor agonists are described. κ-Agonist potency was particularly sensitive to the nature of the basic moiety. In particular, in the rabbit vas deferens (κ- specific tissue), the 3-pyrrolidinol analogue 17 (IC50 = 2.7 nM) was found to be approximately 5-fold more potent than the corresponding pyrrolidine analogue 16 (IC50 = 15 nM). In the rat and hamster vasa deferentia (μ- specific and δ-specific tissues, respectively), 17 showed only weak antagonist activity (pK(B) > 5.5), underlining its selectivity for the κ- opioid receptor. The major activity for 17 is resident in the 4S,3'S-isomer 26 (rabbit vas deferens IC50 = 1.1 nM). Compound 26 displays excellent antinociceptive activity, as determined in the mouse acetylcholine-induced abdominal constriction test (ED50 = 0.001 mg/kg, sc).
