500-67-4Relevant academic research and scientific papers
Phenolic glycosides from the filamentous fungus Acremonium sp. BCC 14080
Bunyapaiboonsri, Taridaporn,Yoiprommarat, Seangaroon,Khonsanit, Artit,Komwijit, Somjit
, p. 891 - 894 (2008)
New phenolic mono- and digalactopyranosides (1 and 2), their aglycone KS-501a (3), and a new phenolic 4-O-methylglucopyranoside (4) were isolated from the filamentous fungus Acremonium sp. BCC 14080. Structures of these compounds were elucidated by extensive MS and NMR spectroscopic analyses. Compound 1 displayed anti-HSV-1 activity with an IC50 value of 7.2 μM. Compound 3 exhibited activity against Plasmodium falciparum K1 with an IC 50 value of 9.9 μM.
Using (+)-carvone to access novel derivatives of (+)-ent-cannabidiol: The first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV
Golliher, Alexandra E.,Tenorio, Antonio J.,Dimauro, Nina O.,Mairata, Nicolas R.,Holguin, F. Omar,Maio, William
supporting information, (2021/02/20)
(?)-Cannabidiol [(?)-CBD] has recently gained prominence as a treatment for neuro-inflammation and other neurodegenerative disorders; interest is also developing in its synthetic enantiomer, (+)-CBD, which has a higher affinity to CB1/CB2 receptors than the natural stereoisomer. We have developed an inexpensive, stereoselective route to access ent-CBD derivatives using (+)-carvone as a starting material. In addition to (+)-CBD, we report the first syntheses of (+)-cannabidivarin, (+)-cannabidiphorol as well as C-6/C-8 homologues.
Cannabidiol derivative as well as preparation method and medical application thereof
-
Paragraph 0298; 0301; 0308-0313, (2021/07/10)
The invention relates to a cannabidiol derivative and application thereof in medicine, in particular to a pyrimidine derivative as shown in a general formula (I), or a stereoisomer, a solvate, a metabolite, a prodrug, a pharmaceutically acceptable salt or a co-crystal thereof, and definition of each substituent in the general formula (I) is the same as that in the specification.
Alkylresorcylic acid synthesis by type III polyketide synthases from rice Oryza sativa
Matsuzawa, Miku,Katsuyama, Yohei,Funa, Nobutaka,Horinouchi, Sueharu
experimental part, p. 1059 - 1067 (2011/03/20)
Alkylresorcinols, produced by various plants, bacteria, and fungi, are bioactive compounds possessing beneficial activities for human health, such as anti-cancer activity. In rice, they accumulate in seedlings, contributing to protection against fungi. Alkylresorcylic acids, which are carboxylated forms of alkylresorcinols, are unstable compounds and decarboxylate readily to yield alkylresorcinols. Genome mining of the rice Oryza sativa identified two type III polyketide synthases, named ARAS1 (alkylresorcylic acid synthase) and ARAS2, that catalyze the formation of alkylresorcylic acids. Both enzymes condensed fatty acyl-CoAs with three C2 units from malonyl-CoA and cyclized the resulting tetraketide intermediates via intramolecular C-2 to C-7 aldol condensation. The alkylresorcylic acids thus produced were released from the enzyme and decarboxylated non-enzymatically to yield alkylresorcinols. This is the first report on a plant type III polyketide synthase that produces tetraketide alkylresorcylic acids as major products.
C1′-cycloalkyl side chain pharmacophore in tetrahydrocannabinols
Papahatjis, Demetris P.,Nahmias, Victoria R.,Nikas, Spyros P.,Andreou, Thanos,Alapafuja, Shakiru O.,Tsotinis, Andrew,Guo, Jianxin,Fan, Pusheng,Makriyannis, Alexandros
, p. 4048 - 4060 (2008/02/09)
In earlier work we have provided evidence for the presence of a subsite within the CB1 and CB2 cannabinoid receptor binding domains of classical cannabinoids. This putative subsite corresponds to substituents on the C1-position of the C3-alkyl side chain, a key pharmacophoric feature in this class of compounds. We have now refined this work through the synthesis of additional C1′-cycloalkyl compounds using newly developed approaches. Our findings indicate that the C1′-cyclopropyl and C1′-cyclopentyl groups are optimal pharmacophores for both receptors while the C1′-cyclobutyl group interacts optimally with CB1 but not with CB2. The C1′-cyclohexyl analogs have reduced affinities for both CB1 and CB2. However, these affinities are significantly improved with the introduction of a C2′-C3′ cis double bond that modifies the available conformational space within the side chain and allows for a better accommodation of a six-membered ring within the side chain subsite. Our SAR results are highlighted by molecular modeling of key analogs.
Synthesis and pharmacology of the isomeric methylheptyl-Δ8-tetrahydrocannabinols
Huffman, John W.,Liddle, John,Duncan Jr., Sammy G.,Yu, Shu,Martin, Billy R.,Wiley, Jenny L.
, p. 2383 - 2396 (2007/10/03)
The synthesis of the 3-heptyl, and the eleven isomeric 3-methylheptyl-Δ8-tetrahydrocannabinols (3-7, R and S methyl epimers, and 8) has been carried out. The synthetic approach entailed the synthesis of substituted resorcinols, which were subjected to acid catalyzed condensation with trans-para-menthadienol to provide the Δ8-THC analogue. The 1'-, 2'- and 3'-methylheptyl analogues (3-5) are considerably more potent than Δ8-THC. The 4'-, 5'- and 6'-methylheptyl isomers (6-8) are approximately equal in potency to Δ8-THC. Copyright (C) 1998 Elsevier Science Ltd.
Synthesis of inhibitors of calmodulin-mediated enzymes including KS-501, KS-502 and their enantiomers
-
, (2008/06/13)
The total synthesis of a group of compounds with inhibitory effects on calmodulin-mediated enzyme activities has been accomplished. Among these synthesized compounds are KS-501 and KS-502. Other compounds that have been synthesized by the described scheme are ent-KS-501 and ent-KS-502 which are enantiomers of KS-501 and KS-502 and which also have inhibitory effects on calmodulin-mediated enzyme activities.
Thermal Decomposition of Lichen Depsides
Huneck, Siegfried,Schmidt, Juergen,Tabacchi, Raffaele
, p. 1283 - 1289 (2007/10/02)
The thermal decomposition of the following lichen depsides has been described: lecanoric acid, gyrophoric acid, evernic acid, perlatolic acid, planaic acid, confluentic acid, atranorin, 4-O-demethylbarbatic acid, and sekikaic acid.Main reaction products are decarboxylated compounds, phenolic units, rearranged depsides, and xanthones.Triethylammonium salts of depside carboxylic acids decompose at reasonably lower temperature than the corresponding free acids. - Keywords: Lichen Depsides, Thermal Decomposition
