19894-97-4Relevant articles and documents
New inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 7-hydroxycoumarin and monoterpenoid moieties
Khomenko, Tatyana,Zakharenko, Alexandra,Odarchenko, Tatyana,Arabshahi, Homayon John,Sannikova, Victoriya,Zakharova, Olga,Korchagina, Dina,Reynisson, Jóhannes,Volcho, Konstantin,Salakhutdinov, Nariman,Lavrik, Olga
, p. 5573 - 5581 (2016)
A number of derivatives of 7-hydroxycoumarins containing aromatic or monoterpene substituents at hydroxy-group were synthesized based on a hit compound from a virtual screen. The ability of these compounds to inhibit tyrosyl-DNA phosphodiesterase I (Tdp 1), important target for anti-cancer therapy, was studied for the first time. It was found that the 7-hydroxycoumarin derivatives with monoterpene pinene moiety are effective inhibitors of Tdp 1 with the most active derivative (+)-25c with IC50value of 0.675?μM. This compound has low cytotoxicity (CC50?>100?μM) when tested against human cancer cells which is crucial for presupposed application in combination with clinically established anticancer drugs. The ability of the new compounds to enhance the cytotoxicity of camptothecin, an established topoisomerase 1 poison, was demonstrated.
New monoterpene glycosides from sunflower seeds and their protective effects against H2O2-induced myocardial cell injury
Fei, Yonghe,Zhao, Jianping,Liu, Yanli,Li, Xiaoran,Xu, Qiongming,Wang, Taoyun,Khan, Ikhlas A.,Yang, Shilin
, p. 385 - 390 (2015)
Three new monoterpene glycosides (1-3) and eleven known compounds (4-14) were isolated from seeds of Helianthus annuus L. (sunflower). Their structures were determined by spectroscopic and chemical methods. All the compounds were isolated from sunflower seeds for the first time. Protective effects of compounds 1-14 against H2O2-induced H9c2 cardiomyocyte injury were evaluated, and compounds 1 and 2 showed some cell-protective effects. No significant DPPH radical scavenging activity was observed for compounds 1-14.
Selective C-H Allylic Oxygenation of Cycloalkenes and Terpenoids Photosensitized by [Cu(Xantphos)(neoc)]BF4
Kallitsakis, Michael G.,Gioftsidou, Dimitra K.,Tzani, Marina A.,Angaridis, Panagiotis A.,Terzidis, Michael A.,Lykakis, Ioannis N.
, p. 13503 - 13513 (2021/09/13)
We present herein for the first time the use of the [Cu(Xantphos)(neoc)]BF4 as a photocatalyst for the selective C-H allylic oxygenation of cycloalkenes into the corresponding allylic hydroperoxides or alcohols in the presence of molecular oxygen. The proposed methodology affords the products at good yields and has also been applied successfully to several bioactive terpenoids, such as geraniol, linalool, β-citronellol, and phytol. A mechanistic study involving also kinetic isotope effects (KIEs) supports the proposed singlet oxygen-mediated reaction. On the basis of the high chemoselectivity and yields and the fast and clean reaction processes observed, the present catalytic system, [Cu(Xantphos)(neoc)]BF4, has also been applied to the synthesis, at a laboratory scale, of the cis-Rose oxide, a well-known perfumery ingredient used in rose and geranium perfumes.
Deep eutectic solvents as H2-sources for Ru(II)-catalyzed transfer hydrogenation of carbonyl compounds under mild conditions
Cavallo, Marzia,Arnodo, Davide,Mannu, Alberto,Blangetti, Marco,Prandi, Cristina,Baratta, Walter,Baldino, Salvatore
supporting information, (2021/02/22)
The employment of easily affordable ruthenium(II)-complexes as pre-catalysts in the transfer hydrogenation of carbonyl compounds in deep eutectic media is described for the first time. The eutectic mixture tetrabutylammonium bromide/formic acid = 1/1 (TBABr/HCOOH = 1/1) acts both as reaction medium and hydrogen source. The addition of a base is required for the process to occur. An extensive optimization of the reaction conditions has been carried out, in terms of catalyst loading, type of complexes, H2-donors, reaction temperature and time. The combination of the dimeric complex [RuCl(p-cymene)-μ-Cl]2 (0.01–0.05 eq.) and the ligand dppf (1,1′-ferrocenediyl-bis(diphenylphosphine)ferrocene) in 1/1 molar ratio has proven to be a suitable catalytic system for the reduction of several and diverse aldehydes and ketones to their corresponding alcohols under mild conditions (40–60 °C) in air, showing from moderate to excellent tolerability towards different functional groups (halogen, cyano, nitro, phenol). The reduction of imine compounds to their corresponding amine derivatives was also studied. In addition, the comparison between the results obtained in TBABr/HCOOH and in organic solvents suggests a non-innocent effect of the DES medium during the process.
Molecular Chirality and Cloud Activation Potentials of Dimeric α-Pinene Oxidation Products
Bé, Ariana Gray,Bellcross, Aleia,Geiger, Franz M.,Thomson, Regan J.
supporting information, p. 16653 - 16662 (2021/10/20)
The surface activity of ten atmospherically relevant α-pinene-derived dimers having varying terminal functional groups and backbone stereochemistry is reported. We find ～10% differences in surface activity between diastereomers of the same dimer, demonstrating that surface activity depends upon backbone stereochemistry. Octanol-water (KOW) and octanol-ammonium sulfate partitioning coefficient (KOAS) measurements of our standards align well with the surface activity measurements, with the more surface-active dimers exhibiting increased hydrophobicity. Our findings establish a link between molecular chirality and cloud activation potential of secondary organic aerosol particles. Given the diurnal variations in enantiomeric excess of biogenic emissions, possible contributions of such a link to biosphere:atmosphere feedbacks as well as aerosol particle viscosity and phase separation are discussed.
New hybrid compounds combining fragments of usnic acid and monoterpenoids for effective tyrosyl-dna phosphodiesterase 1 inhibition
Dyrkheeva, Nadezhda S.,Filimonov, Aleksandr S.,Luzina, Olga A.,Zakharenko, Alexandra L.,Ilina, Ekaterina S.,Malakhova, Anastasia A.,Medvedev, Sergey P.,Reynisson, Jóhannes,Volcho, Konstantin P.,Zakian, Suren M.,Salakhutdinov, Nariman F.,Lavrik, Olga I.
, (2021/07/02)
Usnic acid (UA) is a secondary metabolite of lichens that exhibits a wide range of biological activities. Previously, we found that UA derivatives are effective inhibitors of tyrosyl-DNA phosphodiesterase 1 (TDP1). It can remove covalent complex DNA-topoisomerase 1 (TOP1) stabi-lized by the TOP1 inhibitor topotecan, neutralizing the effect of the drugs. TDP1 removes damage at the 3′ end of DNA caused by other anticancer agents. Thus, TDP1 is a promising therapeutic target for the development of drug combinations with topotecan, as well as other drugs for cancer treatment. Ten new UA enamino derivatives with variation in the terpene fragment and substituent of the UA backbone were synthesized and tested as TDP1 inhibitors. Four compounds, 11a-d, had IC50 values in the 0.23–0.40 μM range. Molecular modelling showed that 11a-d, with relatively short aliphatic chains, fit to the important binding domains. The intrinsic cytotoxicity of 11a-d was tested on two human cell lines. The compounds had low cytotoxicity with CC50 ≥ 60 μM for both cell lines. 11a and 11c had high inhibition efficacy and low cytotoxicity, and they enhanced topotecan’s cyto-toxicity in cancerous HeLa cells but reduced it in the non-cancerous HEK293A cells. This “protec-tive” effect from topotecan on non-cancerous cells requires further investigation.
Promising new inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 4- arylcoumarin and monoterpenoid moieties as components of complex antitumor therapy
Ayine-tora, Daniel M.,Chand, Raina,Chepanova, Arina A.,Ilina, Ekaterina S.,Kaledin, Vasily I.,Khomenko, Tatyana M.,Korchagina, Dina V.,Lavrik, Olga I.,Leung, Ivanhoe K. H.,Nikolin, Valeriy P.,Patel, Jinal,Popova, Nelly A.,Reynisson, Jóhannes,Salakhutdinov, Nariman F.,Volcho, Konstantin P.,Zakharenko, Alexandra L.,Zakharova, Olga D.
, (2020/01/08)
Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is an important DNA repair enzyme in humans, and a current and promising inhibition target for the development of new chemosensitizing agents due to its ability to remove DNA damage caused by topoisomerase 1 (Top1) poisons such as topotecan and irinotecan. Herein, we report our work on the synthesis and characterization of new Tdp1 inhibitors that combine the arylcoumarin (neoflavonoid) and monoterpenoid moieties. Our results showed that they are potent Tdp1 inhibitors with IC50 values in the submicromolar range. In vivo experiments with mice revealed that compound 3ba (IC50 0.62 μM) induced a significant increase in the antitumor effect of topotecan on the Krebs-2 ascites tumor model. Our results further strengthen the argument that Tdp1 is a druggable target with the potential to be developed into a clinically-potent adjunct therapy in conjunction with Top1 poisons.
Application of sulfonate ester compound in preparation of cervical cancer resistant drug
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Paragraph 0044; 0046-0047; 0051; 0056-0058; 0061, (2018/03/13)
The invention provides an application of a (1R,5S)-(6,6-dimethyl-bicyclo[3,1,1]hept-2-ene-2-base) sulfonate ester compound in preparation of a cervical cancer resistant drug. The (1R,5S)-(6,6-dimethyl-bicyclo[3,1,1]hept-2-ene-2-base) sulfonate ester compound is one of the following chemical formulas, namely, (1R,5S)-(6,6-dimethyl-bicyclo[3,1,1]hept-2-ene-2-base) benzene sulfonate and (1R,5S)-(6,6-dimethyl-bicyclo[3,1,1]hept-2-ene-2-base)p-toluene sulfonate. The effects of the compound are verified by combining cell cycle detection, cell apoptosis detection and inhibition of the activity of cervical cancer cell lines. According to the result, it is shown that the compound has the significant effect of inhibiting the activity of the cervical cancer cell lines, and is low in toxicity, efficient and stable, the anticancer compound library is enriched, and the powerful technical support is provided for preparation of the anticancer drug or a drug composition.
A α-pinene derivatives and its preparation method and application (by machine translation)
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Paragraph 0138; 0139; 0152; 0166; 0173; 0180, (2016/10/09)
This invention has offered a kind of α-pinene derivatives, the derivatives of formula I such as a structural formula shown in formula II. Said α-pinene derivatives by the reduction, the organic acid ester and the like introduced into the α-pinene in the molecule skeleton to obtain new derivatives. Research shows that in vitro anti-tumor activity, the present invention provides the α-pinene derivatives to liver cancer cells has significant inhibition function, as the preparation of anti-tumor compound or its pharmaceutically acceptable salt, hydrate, solvate or prodrug, has good application prospect. Type I ;? ? ? Type II. (by machine translation)
Biomass to value added chemicals: Isomerisation of β-pinene oxide over supported ionic liquid catalysts (SILCAs) containing Lewis acids
Salminen, Eero,Rujana, Luis,M?ki-Arvela, P?ivi,Virtanen, Pasi,Salmi, Tapio,Mikkola, Jyri-Pekka
, p. 318 - 321 (2015/09/28)
The isomerisation of β-pinene oxide was studied over supported ionic liquid catalysts (SILCAs) consisting of Lewis acids in immobilized ionic liquid. SILCAs were demonstrated as efficient catalysts for the transformation of β-pinene oxide to myrtanal with the product distribution and activity being dependent on the nature of the ionic liquid and Lewis acid strength of catalytic species. With the catalyst ZnCl2/[N(3-OH-Pr)Py][NTf2]/ACC, the highest myrtanal molar yield obtained was 68%.
