1860-39-5Relevant articles and documents
Synthesis and Inhibitory Properties of Pheromone Analogues for the Epoxide Hydrolase of the Gypsy Moth
Graham, Steven M.,Prestwich, Glenn D.
, p. 2956 - 2966 (1994)
A series of analogues of disparlure, the gypsy moth (Lymantria dispar) sex attractant, was synthesized, and the potency of these inhibitors in suppressing the metabolism of disparlure by the L. dispar epoxide hydrolase (EH) was determined.The analogues substituted at the 6-position (6-hydroxy-, 6-oxo-, and 6,6-difluorodisparlure; (+/-)-threo,cis-11, (+/-)-13, and (+/-)-17, respectively), along with 9,9-difluorodisparlure , were the most potent inhibitors (IC 50 values of 4-9 μM).Two other 9-substituted analogues, 9-hydroxydisparlure and 9-oxodisparlure , were slightly less potent (IC 50 values of 18 and 30 μM, respectively).Analogues substituted at both the 6- and 9-positions (threo,erythro-6,9-dihydroxy-, threo,threo-6,9-dihydroxy-, and 6,9-dioxodisparlure; (+/-)-threo,erythro-32, (+/-)-threo,threo-32, and (+/-)-33, respectively) were generally the least potent inhibitors (IC 50 values of 27-200 μM).On the basis of a model of the EH active site, a hypothesis is advanced to rationalize the higher potencies of the 6-substituted analogues.Pheromone metabolism plays a key role in pheromone perception, and the potential consequences of inhibition of pheromone metabolism are discussed.
First total synthesis of (-)-(3S,6R)-3,6-dihydroxy-10-methylundecanoic acid
Zhang, Xianshu,Da, Shijun,Zhang, Chaoxin,Xie, Zhixiang,Li, Ying
, p. 507 - 509 (2006)
The first total synthesis of (3S,6R)-3,6-dihydroxy-10-methylundecanoic acid was accomplished from commercially available 1-bromo-3-methylbutane in 11 steps and 25.8% overall yield. The key steps were asymmetric allylic alkylations via allyldiisopinocampheylborane and hydroboration-oxidation.
Synthesis of Optically Active N -(4-Hydroxynon-2-enyl)pyrrolidines: Key Building Blocks in the Total Synthesis of Streptomyces coelicolor Butanolide 5 (SCB-5) and Virginiae Butanolide A (VB-A)
Donges, Jonas,Hofmann, Sandra,Walter, Johannes C.,Reichertz, Julia,Brüggemann, Moritz,Frank, Andrea,Nubbemeyer, Udo
, p. 2632 - 2642 (2021/04/27)
Starting from 5-methylhexanal and (S)-configured N -propargylprolinol ethers, coupling delivered N -(4-hydroxynon-2-ynyl)prolinol derivatives as mixtures of C4 diastereomers. Resolution of the epimers succeeded after introduction of an (R)-mandelic ester derivative and subsequent HPLC separation. Alternatively, suitable oxidation gave the corresponding alkynyl ketone. Midland reagent controlled diastereoselective reduction afforded a defined configured propargyl alcohol with high selectivity. LiAlH 4reduction and Mosher analyses of the allyl alcohols enabled structure elucidation. The suitably protected products are used as key intermediates in enantioselective Streptomyces γ-butyrolactone signaling molecule total syntheses.
PROTEIN KINASE C AGONISTS
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Paragraph 0353, (2020/09/12)
The present disclosure relates generally to certain diacylglycerol lactone compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions disclosed herein may be used for the treatment or prevention of diseases, disorders, or infections modifiable by protein kinase C (PKC) agonists, such as HIV.
