10385-78-1Relevant articles and documents
Simple Plug-In Synthetic Step for the Synthesis of (?)-Camphor from Renewable Starting Materials
Calderini, Elia,Drienovská, Ivana,Myrtollari, Kamela,Pressnig, Michaela,Sieber, Volker,Schwab, Helmut,Hofer, Michael,Kourist, Robert
, p. 2951 - 2956 (2021/06/18)
Racemic camphor and isoborneol are readily available as industrial side products, whereas (1R)-camphor is available from natural sources. Optically pure (1S)-camphor, however, is much more difficult to obtain. The synthesis of racemic camphor from α-pinene proceeds via an intermediary racemic isobornyl ester, which is then hydrolyzed and oxidized to give camphor. We reasoned that enantioselective hydrolysis of isobornyl esters would give facile access to optically pure isoborneol and camphor isomers, respectively. While screening of a set of commercial lipases and esterases in the kinetic resolution of racemic monoterpenols did not lead to the identification of any enantioselective enzymes, the cephalosporin Esterase B from Burkholderia gladioli (EstB) and Esterase C (EstC) from Rhodococcus rhodochrous showed outstanding enantioselectivity (E>100) towards the butyryl esters of isoborneol, borneol and fenchol. The enantioselectivity was higher with increasing chain length of the acyl moiety of the substrate. The kinetic resolution of isobornyl butyrate can be easily integrated into the production of camphor from α-pinene and thus allows the facile synthesis of optically pure monoterpenols from a renewable side-product.
Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process
Baev, Dmitriy S.,Maksyutov, Rinat A.,Mordvinova, Ekaterina D.,Pyankov, Oleg V.,Salakhutdinov, Nariman F.,Shcherbakov, Dmitriy N.,Shcherbakova, Nadezhda S.,Sokolova, Anastasiya S.,Tolstikova, Tatyana G.,Yarovaya, Olga I.,Zaykovskaya, Anna V.,Zybkina, Anastasiya V.
, (2020/09/09)
In this study, we screened a large library of (+)-camphor and (?)-borneol derivatives to assess their filovirus entry inhibition activities using pseudotype systems. Structure-activity relationship studies revealed several compounds exhibiting submicromolar IC50 values. These compounds were evaluated for their effect against natural Ebola virus (EBOV) and Marburg virus. Compound 3b (As-358) exhibited the good antiviral potency (IC50 = 3.7 μM, SI = 118) against Marburg virus, while the hydrochloride salt of this compound 3b·HCl had a strong inhibitory effect against Ebola virus (IC50 = 9.1 μM, SI = 31) and good in vivo safety (LD50 > 1000 mg/kg). The results of molecular docking and in vitro mutagenesis analyses suggest that the synthesized compounds bind to the active binding site of EBOV glycoprotein similar to the known inhibitor toremifene.
Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water
Barata-Vallejo, Sebastián,Ferreri, Carla,Golding, Bernard T.,Chatgilialoglu, Chryssostomos
supporting information, p. 4290 - 4294 (2018/07/29)
Hydrogen sulfide (H2S) was evaluated for its peculiar sulfur radical species generated at different pHs and was used under photolytical conditions in aqueous medium for the reduction of 1,2-diols to alcohols. The conversion steps of 1,2-cyclopentanediol to cyclopentanol via cyclopentanone were analyzed, and it was proven that the reaction proceeds via a dual catalytic/radical chain mechanism. This approach was successfully adapted to the reduction of a variety of carbonyl compounds using H2S at pH 9 in water. This work opens up the field of environmental friendly synthetic processes using the pH-driven modulation of reactivity of this simple reagent in water.
