cas 22139-77-1, PINOSYLVIN | Articles data

Articles about 22139-77-1Total 26 be found

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Electro-Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes
Conventional methods carrying out C(sp2)?C(sp2) bond formations are typically mediated by transition-metal-based catalysts. Herein, we conceptualize a complementary avenue to access such bonds by exploiting the potential of electrochemistry in combination with organoboron chemistry. We demonstrate a transition metal catalyst-free electrocoupling between (hetero)aryls and alkenes through readily available alkenyl-tri(hetero)aryl borate salts (ATBs) in a stereoconvergent fashion. This unprecedented transformation was investigated theoretically and experimentally and led to a library of functionalized alkenes. The concept was then carried further and applied to the synthesis of the natural product pinosylvin and the derivatization of the steroidal dehydroepiandrosterone (DHEA) scaffold.
Baumann, Andreas N.,Dechent, Jonas,Didier, Dorian,Jagau, Thomas C.,Müller, Nicolas,Music, Arif
(2020/07/04)

Two resveratrol analogs, pinosylvin and 4,4′-dihydroxystilbene, improve oligoasthenospermia in a mouse model by attenuating oxidative stress via the Nrf2-ARE pathway
Two synthesized resveratrol analogs from our laboratory, namely pinosylvin (3,5-dihydroxy-trans-stilbene, PIN) and 4,4′-dihydroxystilbene (DHS), have been carefully evaluated for treatment of oligoasthenospermia. Recent studies have demonstrated that PIN and DHS improved sperm quality in the mouse. However, the mechanism of action of PIN and DHS on oligoasthenospermia remains unknown. Herein, we investigated the mechanistic basis for improvements in sperm parameters by PIN and DHS in a mouse model of oligoasthenospermia induced by treatment with busulfan (BUS) at 6 mg/kg b.w. Two weeks following busulfan treatment, mice were administered different concentrations of PIN or DHS daily for 2 consecutive weeks. Thereafter, epididymal sperm concentration and motility were determined, and histopathology of the testes was performed. Serum hormone levels including testosterone (T), luteinizing hormone (LH), and follicle stimulating hormone (FSH) were measured using corresponding specific enzyme-linked immunosorbent assay (ELISA) kits. Testicular mRNA expression profiles were determined by RNA sequencing analysis. These findings were validated by quantitative real-time PCR, western blotting and ELISA. Both PIN and DHS improved the epididymal sperm concentration and motility, enhanced testosterone levels, and promoted testicular morphological recovery following BUS treatment. PIN treatment was found to significantly reduce oxidative stress via the nuclear factor erythroid 2-related factor 2 (Nrf2)-antioxidant response element (ARE)-dependent antioxidant, glutathione peroxidase 3. DHS treatment significantly reduced oxidative stress via the Nrf2-ARE-dependent antioxidants glutathione S-transferase theta 2 and glutathione S-transferase omega 2. In summary, PIN and DHS ameliorated oligoasthenospermia in this mouse model by attenuating oxidative stress via the Nrf2-ARE pathway.
Cheng, C. Yan,Gong, Sheng-nan,Sang, Meng-meng,Sun, Fei,Wang, Cheng-niu,Yang, Jin-fei
(2020/10/02)

Pinosylvine, application of the pinosylvine and preparation method of same
The invention provides pinosylvine which is a crystal compound, and the temperature of the pinosylvine is 153-155 DEG C; EI-MS m/Z: 212(M+). The pinosylvine is used for preparing medicines for treating oligoasthenozoospermia, and can also be used for prep
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Paragraph 0020; 0021

(2020/10/21)

Ligand-controlled iridium-catalyzed semihydrogenation of alkynes with ethanol: highly stereoselective synthesis of E- and Z-alkenes
A ligand-controlled iridium-catalyzed semihydrogenation of alkynes to E- and Z-alkenes with ethanol was developed. Effective selectivity control was achieved by ligand regulation. The use of 1,2-bis(diphenylphosphino)ethane (DPPE) and 1,5-cyclooctadiene (COD) was critical for the stereoselective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 40 alkenes, with good stereoselectivities. The value of our approach in practical applications was investigated by studying the effects of pinosylvin and 4,4′-dihydroxystilbene (DHS) on zebrafish as a vertebrate model.
Yang., Jinfei,Wang, Chengniu,Sun, Yufeng,Man, Xuyan,Li, Jinxia,Sun, Fei
p. 1903 - 1906
(2019/05/02)

Use and preparation method of pinosylvi
The invention provides use and preparation method of pinosylvin. The pinosylvin is used for preparing a medicine for inhibiting nerve activity, and is also used for preparing an antipsychotic drug. Itis found through the study of the pinosylvi that the pi
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Paragraph 0032-0034; 0039-0041

(2019/06/13)

Novel Carbazole-Based N-Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd-Catalyzed Coupling Processes
A series of new carbazole-based N-heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole-based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale-up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double-tandem chemoselective Heck reaction followed by Miyaura borylation in a one-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple-tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one-pot modification of biologically relevant molecules.
Girase, Tejpalsingh Ramsingh,Kapdi, Anant R.
supporting information
p. 2611 - 2619
(2019/07/05)

Method for synthesizing artificially all-trans-resveratrol and derivative thereof
The invention discloses a method for synthesizing artificially all-trans-resveratrol and a derivative thereof. In the method, the precursors of all-trans-resveratrol and the derivative thereof are prepared by means of constructing a conjugated fused ring, thus the all-trans-spatial structure of resveratrol and the derivative thereof is restricted completely, to prepare all-trans-resveratrol and the derivative thereof. The resulting product of the preparation method of 1,2-stilbene or the derivative thereof in the invention is of all-trans configuration, so as to meet the demand of biologically active substance chemicals. Compared to the previous processes, the method provided by the invention has the advantages of simple processes and mild conditions, thereby meeting the green chemistry concept.
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Paragraph 0074; 0075

(2017/08/31)

A method for the synthesis of hydroxy [...] composition of the new method (by machine translation)
The present invention discloses a new method for the synthesis of hydroxy [...] compound. The claimed method is: in the organic solvent, under a certain temperature, ammonium formate/through the palladium catalytic removal of benzyl protecting group system, to obtain hydroxyl [...] compound. The method has the mild reaction conditions, the operation is simple, small reagent toxicity, safety, high yield, wide range of application, low cost, relatively suitable for mass production and the like. (by machine translation)
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Paragraph 0081-0082

(2017/08/27)

Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor
A series of 31 resveratrol derivatives was designed, synthesized and evaluated for activation and inhibition of the TRPA1 channel. Most acted as activators and desensitizers of TRPA1 channels like resveratrol or allyl isothiocyanate (AITC). Compound 4z (HUHS029) exhibited higher inhibitory activity than resveratrol with an IC50 value of 16.1?μM. The activity of 4z on TRPA1 was confirmed in TRPA1-expressing HEK293 cells, as well as in rat dorsal root ganglia neurons by a whole cell patch clamp recording. Furthermore, pretreatment with 4z exhibited an analgesic effect on AITC-evoked TRPA1-related pain behavior in vivo.
Nakao, Syuhei,Mabuchi, Miyuki,Wang, Shenglan,Kogure, Yoko,Shimizu, Tadashi,Noguchi, Koichi,Tanaka, Akito,Dai, Yi
p. 3167 - 3172
(2017/06/13)

A facile and rapid access to resveratrol derivatives and their radioprotective activity
A facile and rapid access to resveratrol derivatives has been achieved based on palladium-catalyzed oxidative Heck reaction of aryl boronic acids with styrenes followed by demethylation in moderate to good yields. A series of resveratrol derivatives with various functional groups has been synthesized easily. The radioprotective activity of synthesized compounds has also been evaluated using rat thymocytes. The results revealed that some resveratrol derivatives efficiently protected the thymocytes from radiation-induced apoptosis.
Uzura, Saori,Sekine-Suzuki, Emiko,Nakanishi, Ikuo,Sonoda, Motohiro,Tanimori, Shinji
supporting information
p. 3886 - 3891
(2016/08/01)

MOLECULARLY IMPRINTED POLYMERS
The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.
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(2012/03/12)

Modified approach for preparing (E)-Stilbenes related to resveratrol, and evaluation of their potential immunobiological effects
Resveratrol and closely related stilbenoids belong to the most intensively studied biologically active compounds. This interest evoked several attempts to prepare such compounds in a convenient synthetic way. Our approach allowed obtaining largely methoxystilbenes, formed as E-isomers only (using Wittig-Horner synthesis as the key step), which were further demethylated by boron tribromide. The hydroxymethoxystilbenes (e.g. pterostilbene) were prepared using isopropyl protection, later selectively deprotected by boron trichloride. The method is suitable for preparing such compounds in a large amount. Effects of the obtained stilbene derivatives on immunobiological responses triggered by lipopolysacharide and interferon-a were tested under in vitro conditions. Namely production of nitric oxide (NO) was investigated, and relation between the molecular structure and immunobiological activity was assessed.
Smidrkal, Jan,Harmatha, Juraj,BudiSinsky, Milo,Vokae, Karel,ZIDEKc, Zdenik,Kmoniekova, Eva,Merkl, Roman,Filip, Vladimir
experimental part
p. 175 - 186
(2010/07/10)

Radical-scavenging activity and mechanism of resveratrol-oriented analogues: Influence of the solvent, radical, and substitution
(Chemical Equation Presented). Resveratrol (3,5,4′-trihydroxy-trans- stilbene, 3,5,4′-THS) is a well-known natural antioxidant and cancer chemopreventive agent that has attracted much interest in the past decade. To find a more active antioxidant and investigate the antioxidative mechanism with resveratrol as the lead compound, we synthesized 3,5-dihydroxy-trans-stilbene (3,5-DHS), 4-hydroxy-trans-stilbene (4-HS) 3,4-dihydroxy-trans-stilbene (3,4-DHS), 4,4′-dihydroxy-trans-stilbene (4,4′-DHS), 4-hydroxy-3-methoxy-trans-stilbene (3-MeO-4-HS), 4-hydroxy-4′-methoxy- trans-stilbene (4′-MeO-4-HS), 4-hydroxy-4′-methyl-trans-stilbene (4′-Me-4-HS), 4-hydroxy-4′-nitro-trans-stilbene (4′-NO 2-4-HS), and 4-hydroxy-4′-trifluoromethyl-trans-stilbene (4′-CF3-4-HS). The radical-scavenging activity and detailed mechanism of resveratrol and its analogues (ArOHs) were investigated by the reaction kinetics with galvinoxyl (GO?) and 2,2-diphenyl-1- picrylhydrazyl (DPPH?) radicals in ethanol and ethyl acetate at 25°C, using UV-vis spectroscopy. It was found that the reaction rates increase with increasing the electron-rich environment in the molecules, and the compound bearing o-dihydroxyl groups (3,4-DHS) is the most reactive one among the examined resveratrol analogues. The effect of added acetic acid on the measured rate constant for GO?-scavenging reaction reveals that in ethanol that supports ionization solvent besides hydrogen atom transfer (HAT), the kinetics of the process is partially governed by sequential proton loss electron transfer (SPLET). In contrast to GO?, DPPH ? has a relatively high reduction potential and therefore enhances the proportion of SPLET in ethanol. The relatively low rate constants for the reactions of ArOHs with GO? or DPPH? in ethyl acetate compared with the rate constants in ethanol prove that in ethyl acetate these reactions occur primarily by the HAT mechanism. The contribution of SPLET and HAT mechanism depends on the ability of the solvent to ionize ArOH and the reduction potential of the free radical involved. Furthermore, the fate of the ArOH-derived radicals, i.e., the phenoxyl radicals, was investigated by the oxidative product analysis of ArOHs and GO? in ethanol. The major products were dihydrofuran dimers in the case of resveratrol, 4,4′-DHS, and 4-HS and a dioxane-like dimer in the case of 3,4-DHS. It is suggested from the oxidative products of these ArOHs that the hydroxyl group at the 4-position is much easier to subject to oxidation than other hydroxyl groups, and the dioxane-like dimer is formed via an o-quinone intermediate.
Shang, Ya-Jing,Qian, Yi-Ping,Liu, Xiao-Da,Dai, Fang,Shang, Xian-Ling,Jia, Wen-Qiang,Liu, Qiang,Fang, Jian-Guo,Zhou, Bo
supporting information; experimental part
p. 5025 - 5031
(2009/10/17)

Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol
Resveratrol is a well-known natural antioxidant and cancer chemopreventive agent that has attracted much nterest in the past decade. Resveratrol-directed compounds were synthesized, and their antioxidant effects gainst reactive oxygen species (ROS)-induced DNA damage, their prooxidant effects on DNA damage in he presence cupric ions, and their cytotoxic and apoptosis-inducing effects on human promyelocytic leukemia(HL-60) cells were investigated in vitro. It was found that the compounds bearing o-diphenoxyl groups exhibited remarkably higher activities in inhibiting ROS-induced DNA damage, accelerating DNA damage in the presence cupric ions, and inducing apoptosis of HL-60 cells compared with the ones bearing no such groups. The detail mechanism of the structure-activity relationship was also studied by the oxidative product analysis of resveratrol and its analogues with galvinoxyl radical or cupric ions and UV-visible spectra change in the presence cupric ions. This study reveals a good and interesting correlation between antioxidant and prooxidant activity, as well as cytotoxicity and apoptosis-inducing activity against HL-60 cells, and provides an idea for designing antioxidant-based cancer chemoprevention agents. ?2009 American Chemical Society.
Qian, Yi-Ping,Cai, Yu-Jun,Fan, Gui-Juan,Wei, Qing-Yi,Jie, Yang,Zheng, Li-Fang,Li, Xiu-Zhuang,Fang, Jian-Guo,Bo, Zhou
supporting information; experimental part
p. 1963 - 1974
(2009/12/31)

A short total synthesis for biologically interesting (+)- and (-)-machaeriol A
This paper describes a new and efficient synthetic approach for biologically interesting natural (+)-machaeriol A and its unnatural enantiomer (-)-machaeriol A. The key strategies involve stilbene formation through a Horner-Wadsworth-Emmons reaction and t
Xia, Likai,Lee, Yong Rok
body text
p. 1643 - 1646
(2009/04/10)

Algicidal activity of stilbene analogues
Continuing our search for natural product and natural product-based compounds for the control of off-flavor in catfish, 29 stilbene analogues were synthesized and evaluated for algicidal activity against the 2-methylisoborneol (MIB)-producing cyanobacteri
Mizuno, Cassia S.,Schrader, Kevin K.,Rimando, Agnes M.
experimental part
p. 9140 - 9145
(2010/04/23)

Synthesis and inhibitory effects of pinosylvin derivatives on prostaglandin E2 production in lipopolysaccharide-induced mouse macrophage cells
The inhibitory effects of pinosylvin analogues on the production of COX-2 mediated PGE2 were evaluated in a cell culture system. A new series of potential inhibitors, including 3-hydroxy-5-benzyloxy-trans-stilbene and 3,5-dimethoxy-trans-stilbene, have been identified. A series of natural stilbenoids, pinosylvin and its derivatives, were synthesized and evaluated for the inhibitory activity of prostaglandin E2 production in lipopolysaccharide-induced RAW 264.7 cells. Potential inhibitors, including 3,5-dimethoxy-trans-stilbene and 3-hydroxy-5-benzyloxy-trans-stilbene, have been newly identified, and thus providing chemical leads for the further development of anti-inflammatory or cancer chemopreventive agents.
Park, Eun-Jung,Min, Hye-Young,Ahn, Yong-Hyun,Bae, Cheol-Man,Pyee, Jae-Ho,Lee, Sang Kook
p. 5895 - 5898
(2007/10/03)

Hydroxystilbene compounds used as microbicidal active substances
The use of hydroxystilbene compounds of formula wherein A is a radical of formula ?or a radical of formula ?and R1, R2, R3, R4and R5are each independently of the others hydrogen, halogen, hydroxy, Cs
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(2008/06/13)

Efficiency and structure-activity relationship of the antioxidant action of resveratrol and its analogs
Resveratrol and its analogs, six other polyhydroxystilbenes, were synthesized and their antioxidative activities were evaluated in vitro by determination of the levels of malondialdehyde and hydrogen peroxide. Results clearly exhibited that resveratrol and its analogs had various potencies in inhibiting lipid peroxidation in rat brain, kidney, and liver homogenates and rat erythrocyte hemolysis. Several polyhydroxystilbenes were found to be more active than resveratrol in these models, and structure-activity relationship studies on polyhydroxystilbenes are described in this paper.
Lu,Cai,Fang,Zhou,Liu,Wu, Longmin M.
p. 474 - 478
(2007/10/03)

Evaluation of resveratrol derivatives as potential antioxidants and identification of a reaction product of resveratrol and 2,2-diphenyl-1- picryhydrazyl radical
Resveratrol (3,4',5-trihydroxy-trans-stilbene), an antioxidant from grapes, and five other polyhydroxystilbenes were synthesized. Their antioxidative properties were evaluated in two model systems [pure lipid oxidation using the Rancimat method and 2,2-diphenyl-1-picryhydrazyl (DPPH) free radical scavenging model.] 3,3',4,5'-Tetrahydroxystilbene, 3,3',4,5,5'- pentahydroxystilbene, and 3,4,4',5-tetrahydroxystilbene were found to be more active than resveratrol in both models. A dimer of resveratrol was identified as the major radical reaction product when resveratrol was reacted with DPPH radicals.
Wang, Mingfu,Jin, Yi,Ho, Chi-Tang
p. 3974 - 3977
(2007/10/03)

Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules
The reaction of 3,5-dimethoxybenzyl trimethylsilyl ether (3) with different aldehydes (n-PrCHO, n-C11H23CHO, MeCHO, PhCHO) in the presence of lithium powder and a catalytic amount of naphthalene (4 mol %) gave, after hydrolysis, the expected alcohols 4 in moderate yields. The dehydroxylation of these compounds through the corresponding mesylates 5 or directly from benzylic derivatives by catalytic hydrogenation, afforded compounds 6, which are finally demethylated to yield 5-alkyl-3,5-dihydroxyresorcinols, such as olivetol (7a), grevillol (7b), 1,3-dihydroxy-5-propylbenzene (7c), or dihydropinosilvine (7d). Dehydration of alcohol derivatives 4 followed by demethylation led to hydroxylated stilbene-type structures, such as pinosilvine (9d), resveratrol (9e), or piceatannol (9f), which in some cases can be hydrogenated to give saturated molecules such as combretastanin B-4 tetramethyl ether (6f) or chrysotobibenzyl (6g). Finally, when the naphthalene-catalyzed lithiation of compound 3 was performed in the presence of other electrophiles [Me3SiCl, t-BuCHO, CH3(CH2)4CHO, 4-Me3SiOC6H4CHO, (CH2)5CO, PhN = C = O, PhN = CHPh], the expected reaction products 12 were isolated, after hydrolysis.
Alonso, Emma,Ramon, Diego J.,Yus, Miguel
p. 417 - 421
(2007/10/03)

ENDOGENEOUS PINE WOOD NEMATICIDAL SUBSTANCES IN PINES, PINUS MASSONIANA, P. STROBUS AND P. PALUSTRIS
The presence of the repellents and nematicides to the pine wood nematode, Bursaphelenchus xylophilus, was found in the heartwood and bark of Pinus massoniana, P. strobus and P. palustris, which have a resistance to the pine wood nematode.The heartwood of P. massoniana contained a repellent, α-humulene and two nematicidal substances, pinosylvin monomethylether (PMS) and (-)-nortrachelogenin for the nematode.The bark of the pine contained two nematicides, methyl ferulate and (+)-pinoresinol.PMS, which showed the highest nematicidal activity (LD 50 was 4 ppm), was also contained in the heartwood of P. strobus and the heartwood and bark of P. palustris.The resistance of these pines to the pine wood nematode is considered to be attributed to the presence of these endogenously defending substances.Further, the relationship between the structure and the nematicidal activity was elucidated for PSM and methyl ferulate.Moreover, PSM showed little anti-acetylcholinesterase activity.
Suga, Takayuki,Ohta, Shinji,Munesada, Kiyotaka,Ide, Nagatoshi,Kurokawa, Masako,et al.
p. 1395 - 1402
(2007/10/02)

Synthesis and Protein-Tyrosine Kinase Inhibitory Activity of Polyhydroxylated Stilbene Analogues of Piceatannol
A series of hydroxylated trans-stilbene related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxy stilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function.A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product.Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly.The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.
Thakkar, Kshitij,Geahlen, Robert L.,Cushman, Mark
p. 2950 - 2955
(2007/10/02)

Synthesis and nematocidal activity of hydroxystilbenes
Various (E)-hydroxystilbenes were synthesized from (E)/(Z) mixtures of methoxystilbenes through a new (Z)-(E) isomerization method followed by demethylation. The nematocidal activity appears when methoxystilbenes are demethylated to hydroxystilbenes. For this activity, a hydroxy group at the C-2 or C-3 position is necessary. Thus, 2-hydroxy-, 3-hydroxy-, 2,6-dihydroxy-, 3,4-dihydroxy-, 3,5-dihydroxy-, 2,2'-dihydroxy-, 3,3'-dihydroxy-, 3,4'dihydroxy-, 2-hydroxy-4-methoxy-, 5-hydroxy-2-methoxy-, 2-hydroxy-6-methoxy-, 6-allyloxy-2-hydroxy-, 3-hydroxy-5-methoxy-, and 5-allyloxy-3-hydroxystilbenes showed rather potent nematocidal activity. The activity of 5-allyloxy-3-hydroxystilbene was the strongest [minimal lethal concentration (MLC) = 30 μM]. The activities of the (E) and (Z) isomers were comparable. The activities were also retained, though they were weaker, in the dihydro derivatives, hydroxybibenzyls.
Ali,Kondo,Tsuda
p. 1130 - 1136
(2007/10/02)

New method for isomerization of (Z)stilbenes into the (E)-isomers catalyzed by diaryl disulfide
A new method for isomerization of (Z)-stilbenes into the (E)-isomers, catalyzed by diaryl disulfide, has been developed. Diphenyl disulfide is the most versatile catalyst, smoothly effecting the isomerization of stilbene, methoxystilbenes, and hydroxystil
Ali,Tsuda
p. 2842 - 2844
(2007/10/02)