17094-21-2Relevant articles and documents
Prenylated β-diketones, two new additions to the family of biologically active Hypericum perforatum L. (Hypericaceae) secondary metabolites
Radulovi?, Niko S.,Gen?i?, Marija S.,Stojanovi?, Nikola M.,Randjelovi?, Pavle J.,Baldovini, Nicolas,Kurteva, Vanya
, p. 505 - 513 (2018)
Two novel β-diketones, 2,6,9-trimethyl-8-decene-3,5-dione (A) and 3,7,10-trimethyl-9-undecene-4,6-dione (B), were identified from the renowned medicinal plant Hypericum perforatum L. The structures of β-diketones A and B were corroborated by syntheses (4 steps starting from methyl acetoacetate, overall yields 30% and 23%, respectively). In solution, these β-diketones predominantly exist as two rapidly interconverting β-keto-enol tautomers. The structures of A and B show some common fragments with the molecules of hyperforin and adhyperforin, respectively, the acknowledged multi-target secondary metabolites from St. John's wort. It is therefore not surprising that A displayed a noteworthy biological activity profile as well (including brine shrimp toxicity, antinociceptive, antidepressant and acetylcholinesterase inhibitory activity). β-Diketone A manifested the most outstanding potency as an acetylcholinesterase inhibitor with IC50 value of 1.51 μM pointing again to the β-keto-enol moiety as a promising lead structure for the development of drugs that could lessen symptoms of Alzheimer's disease (such as dementia, depression and pain).
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Tai,A.,Imaida,M.
, p. 1114 - 1117 (1978)
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Total Synthesis of Oridamycins A and B
Trotta, Adam H.
, p. 3358 - 3361 (2015)
(Chemical Equation Presented) The total synthesis of both oridamycin A and oridamycin B was accomplished starting from a common synthetic intermediate readily prepared from geranyl acetate. The sequence utilizes an oxidative radical cyclization to construct the trans-decalin ring system, setting three of four contiguous stereocenters in one operation. The carbazole nucleus was forged through a one-pot process entailing acid-promoted dehydration followed by 6π-electrocyclization/aromatization.
Method for preparing pentazocine intermediate
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Paragraph 0044-0045, (2021/02/13)
The invention belongs to the technical field of chemical synthesis, and provides a method for preparing a pentazocine intermediate, which comprises the following steps: by using low-price methyl acetoacetate as a raw material, carrying out methylation, methoxyformylation and removal of one methoxyformyl group, reducing by using a reducing agent, and reacting the reduction product with alkyl sulfonyl chloride to obtain the pentazocine intermediate; generating a compound with a dialkyl sulfonyl group; reacting a compound with dialkyl sulfonyl with phthalimide potassium salt, removing one alkyl sulfonyl, and grafting phthalimide; carrying out dehydrogenation reaction on the phthalimido product under an alkaline condition to generate a vinyl compound, and reacting the vinyl compound with hydrazine hydrate to obtain the pentazocine intermediate. Cheap compounds are used as initial raw materials, the whole route avoids high-pressure and high-temperature dangerous reactions, and industrial production is facilitated.
Synthesis method of pirimicarb intermediate 2-methyl acetoacetate
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Paragraph 0040; 0044-0047; 0050-0052; 0055-0057; 0060-0062, (2020/12/10)
The invention relates to a synthesis method of a pirimicarb intermediate 2-methyl acetoacetate, comprising the following steps of: in the presence of tertiary amine and a polymerization inhibitor, carrying out an addition reaction on raw materials methyl acrylate and acetyl chloride to obtain 2-acetyl-methyl acrylate, and carrying out hydrogenation reduction to obtain the product 2-methyl acetoacetate. The synthetic method of the pirimicarb intermediate 2-methyl acetoacetate has the advantages of high yield, high purity and few byproducts.
