61367-62-2Relevant articles and documents
Xylochemical synthesis and biological evaluation of shancigusin c and bletistrin g
Efferth, Thomas,Geske, Leander,Kauhl, Ulrich,Opatz, Till,Saeed, Mohamed E. M.,Schüffler, Anja,Thines, Eckhard
, (2021/06/16)
The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regiose-lective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.
Chain substituted cannabilactones with selectivity for the CB2 cannabinoid receptor
Alapafuja, Shakiru O.,Nikas, Spyros P.,Ho, Thanh C.,Tong, Fei,Benchama, Othman,Makriyannis, Alexandros
, (2019/10/11)
In earlier work, we reported a novel class of CB2 selective ligands namely cannabilactones. These compounds carry a dimethylheptyl substituent at C3, which is typical for synthetic cannabinoids. In the current study with the focus on the pharmacophoric side chain at C3 we explored the effect of replacing the C1′-gem-dimethyl group with the bulkier cyclopentyl ring, and, we also probed the chain's length and terminal carbon substitution with bromo or cyano groups. One of the analogs synthesized namely 6-[1-(1,9-dihydroxy-6-oxo-6H-benzo[c]chromen-3-yl) cyclopentyl] hexanenitrile (AM4346) has very high affinity (Ki = 4.9 nM) for the mouse CB2 receptor (mCB2) and 131-fold selectivity for that target over the rat CB1 (rCB1). The species difference in the affinities of AM4346 between the mouse (m) and the human (h) CB2 receptors is reduced when compared to our first-generation cannabilactones. In the cyclase assay, our lead compound was found to be a highly potent and efficacious hCB2 receptor agonist (EC50 = 3.7 ± 1.5 nM, E(max) = 89%). We have also extended our structure-activity relationship (SAR) studies to include biphenyl synthetic intermediates that mimic the structure of the phytocannabinoid cannabinodiol.
Total synthesis of (±)-kuwanol e
Iovine, Valentina,Benni, Irene,Sabia, Rocchina,D'Acquarica, Ilaria,Fabrizi, Giancarlo,Botta, Bruno,Calcaterra, Andrea
, p. 2495 - 2503 (2016/11/09)
The total synthesis of the Diels-Alder-type adducts (±)-kuwanol E and the heptamethyl ether derivative of (±)-kuwanon Y has been accomplished via a convergent strategy involving 2′-hydroxychalcone 6 or 9 and dehydroprenylstilbene 7, in nine steps. The syn
