Day: February 22, 2023

Synthesis of long-chain fatty acid derivatives as a novel anti-Alzheimer’s agent was written by Zhang, Hong-Yan;Yamakawa, Yu-ichiro;Matsuya, Yuji;Toyooka, Naoki;Tohda, Chihiro;Awale, Suresh;Li, Feng;Kadota, Shigetoshi;Tezuka, Yasuhiro. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2014.Safety of 2-(But-3-yn-1-yloxy)tetrahydro-2H-pyran This article mentions the following:

In order to develop new drugs for Alzheimer’s disease, we prepared 17 fatty acid derivatives with different chain lengths and different numbers and positions of double bonds by using Wittig reaction and stereospecific hydrogenation of triple bonds as key reactions. Among them, (4Z,15Z)-octadecadienoic acid (10) and (23Z,34Z)-heptatriacontadienoic acid (16) showed the most potent neurite outgrowth activities on A尾(25-35)-treated rat cortical neurons, which activities were comparable to that of a pos. control, NGF. Both fatty acids 10 and 16 possess two (Z)-double bonds at the n-3 and n-14 positions, which might be important for the neurite outgrowth activity. In the experiment, the researchers used many compounds, for example, 2-(But-3-yn-1-yloxy)tetrahydro-2H-pyran (cas: 40365-61-5Safety of 2-(But-3-yn-1-yloxy)tetrahydro-2H-pyran).

2-(But-3-yn-1-yloxy)tetrahydro-2H-pyran (cas: 40365-61-5) belongs to tetrahydropyran derivatives. Tetrahydropyran is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. 2-(Arylmethylene)cyclopropylcarbinols could be converted to the corresponding tetrahydropyrans stereoselectively in the presence of Br酶nsted acids under mild conditions. A plausible Prins-type reaction mechanism has been proposed.Safety of 2-(But-3-yn-1-yloxy)tetrahydro-2H-pyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In vitro evaluation of viability, integrity, and inflammation in genital epithelia upon exposure to pharmaceutical excipients and candidate microbicides was written by Gali, Youssef;Delezay, Olivier;Brouwers, Joachim;Addad, Noura;Augustijns, Patrick;Bourlet, Thomas;Hamzeh-Cognasse, Hind;Arien, Kevin K.;Pozzetto, Bruno;Vanham, Guido. And the article was included in Antimicrobial Agents and Chemotherapy in 2010.Safety of 纬-Cyclodextrin xhydrate This article mentions the following:

The use of microbicides is a promising approach for the prevention of HIV-1 transmission. Unfortunately, various candidates failed in clin. trials. In some cases, the candidate microbicide even resulted in enhanced virus transmission. Therefore, there is an urgent need to develop more predictive preclin. strategies to anticipate the in vivo efficiency/toxicity rate, including in vitro assays that evaluate effects on epithelial integrity and inflammation. The present study aims to identify potential safety issues concerning the use of microbicides and excipients commonly used in vaginal microbicide preparations The toxicities of various active pharmaceutical ingredients (APIs; TMC-120, UC-781, tenofovir [PMPA], PRO-2000, and glycerol monolaurate [GML]) and excipients (preservatives, cosolvents, surfactants, and cyclodextrins) were evaluated using an in vitro dual-chamber model and uterine cervical explants. Epithelial viability and permeation of fluorescent virus-sized beads, as well as induction of interleukin-8 (IL-8; as a sensitive marker of an inflammatory response), were assessed. Surprisingly, cell viability and epithelial layer integrity were compromised by most excipients at concentrations near the typical concentration used in vaginal gels, and a significant increase in the production of IL-8 was observed at subtoxic concentrations Within the APIs, TMC-120, UC-781, and PMPA showed higher selectivity indexes than PRO-2000 and GML. In conclusion, identification of safety issues concerning the use of pharmaceutical excipients could help to formulate less toxic vaginal microbicide preparations In the experiment, the researchers used many compounds, for example, 纬-Cyclodextrin xhydrate (cas: 91464-90-3Safety of 纬-Cyclodextrin xhydrate).

纬-Cyclodextrin xhydrate (cas: 91464-90-3) belongs to tetrahydropyran derivatives. Tetrahydropyrans are useful synthons for biologically important compounds. There is large number of marine macrolide natural products that contain tetrahydropyran and tetrahydrofuran ring together. For instance, goniodomin A (actin targeting polyether), prorocentrolide (toxin halistatins), and percentotoxineSafety of 纬-Cyclodextrin xhydrate

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Aster-B coordinates with Arf1 to regulate mitochondrial cholesterol transport was written by Andersen, John-Paul;Zhang, Jun;Sun, Haoran;Liu, Xuyun;Liu, Jiankang;Nie, Jia;Shi, Yuguang. And the article was included in Molecular Metabolism in 2020.SDS of cas: 11024-24-1 This article mentions the following:

Cholesterol plays a pivotal role in mitochondrial steroidogenesis, membrane structure, and respiration. Mitochondrial membranes are intrinsically low in cholesterol content and therefore must be replenished with cholesterol from other subcellular membranes. However, the mol. mechanisms underlying mitochondrial cholesterol transport remains poorly understood. The Aster-B gene encodes a cholesterol binding protein recently implicated in cholesterol trafficking from the plasma membrane to the endoplasmic reticulum (ER). In this study, we investigated the function and underlying mechanism of Aster-B in mediating mitochondrial cholesterol transport.CRISPR/Cas9 gene editing was carried out to generate cell lines deficient in Aster-B expression. The effect of Aster-B deficiency on mitochondrial cholesterol transport was examined by both confocal imaging anal. and biochem. assays. Deletion mutational anal. was also carried out to identify the function of a putative mitochondrial targeting sequence (MTS) at the N-terminus of Aster-B for its role in targeting Aster-B to mitochondria and in mediating mitochondrial cholesterol trafficking.Ablation of Aster-B impaired cholesterol transport from the ER to mitochondria, leading to a significant decrease in mitochondrial cholesterol content. Aster-B is also required for mitochondrial transport of fatty acids derived from hydrolysis of cholesterol esters. A putative MTS at the N-terminus of Aster-B mediates the mitochondrial cholesterol uptake. Deletion of the MTS or ablation of Arf1 GTPase which is required for mitochondrial translocation of ER proteins prevented mitochondrial cholesterol transport, leading to mitochondrial dysfunction.We identified Aster-B as a key regulator of cholesterol transport from the ER to mitochondria. Aster-B also coordinates mitochondrial cholesterol trafficking with uptake of fatty acids derived from cholesterol esters, implicating the Aster-B protein as a novel regulator of steroidogenesis. In the experiment, the researchers used many compounds, for example, Digitonin (cas: 11024-24-1SDS of cas: 11024-24-1).

Digitonin (cas: 11024-24-1) belongs to tetrahydropyran derivatives. In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols. The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif. SDS of cas: 11024-24-1

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Allylation using allylborates was written by Hunter, Roger;Michael, Joseph P.;Tomlinson, Geoffrey D.. And the article was included in Tetrahedron in 1994.Computed Properties of C6H12O2 This article mentions the following:

The scope of allylations by organoborates was determined for a range of acetals activated by trimethylsilyl trifluoromethanesulfonate. Intermol. allylation of acyclic acetals proceeds smoothly and in high yield using lithium n-butyltriallylborate or lithium methyltriallylborate in THF at -78掳, while 1,3-dioxanes and dioxolanes give reduction products. Intramol. allylation may be carried out via anchoring the triallylborane using an alkoxide anion. Mechanistic studies indicate that allyl transfer is from boron and not silicon, while stereoselectivity studies on the crotylation of acyclic acetals as well as the allylation of chiral acetals derived from (2R,4R)-pentanediol indicate moderate levels fo diastereoselection. In the experiment, the researchers used many compounds, for example, 2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4Computed Properties of C6H12O2).

2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4) belongs to tetrahydropyran derivatives. Tetrahydropyran is a useful synthetic intermediate. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. Pyran derivatives such as pyran flavonoids are biologically important. Monosaccharides containing six-membered rings are called pyranose.Computed Properties of C6H12O2

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Palladium-catalyzed dearomative 1,4-difunctionalization of naphthalenes was written by Yang, Ping;Zheng, Chao;Nie, Yu-Han;You, Shu-Li. And the article was included in Chemical Science in 2020.Application of 856414-68-1 This article mentions the following:

A highly diastereoselective dearomatization of naphthalenes via a Pd-catalyzed 1,4-difunctionalization reaction is described. In the presence of a com. available palladium precursor and ligand, intramol. dearomative Heck-type insertion provides 蟺-allylpalladium intermediates which are readily captured by a series of nucleophiles in excellent yields (up to 99%). This reaction features mild conditions, broad substrate scope, and useful transformations of the products. In the experiment, the researchers used many compounds, for example, Ethyl 3-Oxo-3-(4-tetrahydropyranyl)propanoate (cas: 856414-68-1Application of 856414-68-1).

Ethyl 3-Oxo-3-(4-tetrahydropyranyl)propanoate (cas: 856414-68-1) belongs to tetrahydropyran derivatives. Numerous natural products have tetrahydropyran skeleton as the building block for designing new natural products and their derivatives e.g. aplysiatoxins, avermectins, oscillatoxins, talaromycins, latrunculins and acutiphycins. 2-(Arylmethylene)cyclopropylcarbinols could be converted to the corresponding tetrahydropyrans stereoselectively in the presence of Br酶nsted acids under mild conditions. A plausible Prins-type reaction mechanism has been proposed.Application of 856414-68-1

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Gentiopicrin and Swertiamarin contents in Gentiana macrophylla Pall. roots along elevation gradient in Donglingshan meadow, Beijing, China was written by Sadia, Sehrish;Aftab, Beenish;Tariq, Akash;Zhang, Jin-Tun;Razaq, Abdul. And the article was included in Pakistan Journal of Botany in 2020.HPLC of Formula: 17388-39-5 This article mentions the following:

Quality and quantity of chem. constituents in medicinal plants highly depends on environmental conditions. The contents of active constituents in Gentiana macrophylla Pall. may vary among different altitudes of mountain meadows and are affected by environmental factors. The aim of this study was to find the effect of environmental factors on Gentiopicrin and Swertiamarin contents in G. macrophylla roots along elevation gradient of Donglingshan meadow. Plant and environmental data were collected from 15 altitudes (50m distance away from each other) along 1600-2301 m elevation gradient by using Braun Blanquet approach. The contents of Gentiopicrin and Swertiamarin were estimated by using High Performance Liquid Chromatog. method. Relationship among Gentiopicrin and Swertiamarin contents, soil and other environmental variables was depicted by using Canoco 5 and SPSS software. Regression anal. showed that Gentiopicrin is strongly affected by Elevation, Slope aspect, Soil pH, Soil temperature, Total Nitrogen. Swertiamarin concentration is strongly affected by slope, soil pH and Magnesium. Gentiopicrin contents have statistical significant relation with elevation gradient as compared to Swertiamarin. Insight of important bioactive compounds provided by this study would be helpful for medicine quality control, conservation of G. macrophylla and discovery of new drugs. In the experiment, the researchers used many compounds, for example, (4aR,5R,6S)-4a-Hydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-4,4a,5,6-tetrahydropyrano[3,4-c]pyran-1(3H)-one (cas: 17388-39-5HPLC of Formula: 17388-39-5).

(4aR,5R,6S)-4a-Hydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-4,4a,5,6-tetrahydropyrano[3,4-c]pyran-1(3H)-one (cas: 17388-39-5) belongs to tetrahydropyran derivatives. Numerous natural products have tetrahydropyran skeleton as the building block for designing new natural products and their derivatives e.g. aplysiatoxins, avermectins, oscillatoxins, talaromycins, latrunculins and acutiphycins. The bismuth chloride-assisted cross-cyclization between homoallylic alcohols and epoxides provided various benzyl tetrahydropyran derivatives. The reaction afforded good yields of desired products and occurred under mild conditions.HPLC of Formula: 17388-39-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Cryo-EM structures of thermostabilized prestin provide mechanistic insights underlying outer hair cell electromotility was written by Futamata, Haon;Fukuda, Masahiro;Umeda, Rie;Yamashita, Keitaro;Tomita, Atsuhiro;Takahashi, Satoe;Shikakura, Takafumi;Hayashi, Shigehiko;Kusakizako, Tsukasa;Nishizawa, Tomohiro;Homma, Kazuaki;Nureki, Osamu. And the article was included in Nature Communications in 2022.Name: Digitonin This article mentions the following:

Outer hair cell elecromotility, driven by prestin, is essential for mammalian cochlear amplification. Here, we report the cryo-EM structures of thermostabilized prestin (PresTS), complexed with chloride, sulfate, or salicylate at 3.52-3.63 脜 resolutions The central pos.-charged cavity allows flexible binding of various anion species, which likely accounts for the known distinct modulations of nonlinear capacitance (NLC) by different anions. Comparisons of these PresTS structures with recent prestin structures suggest rigid-body movement between the core and gate domains, and provide mechanistic insights into prestin inhibition by salicylate. Mutations at the dimeric interface severely diminished NLC, suggesting that stabilization of the gate domain facilitates core domain movement, thereby contributing to the expression of NLC. These findings advance our understanding of the mol. mechanism underlying mammalian cochlear amplification. In the experiment, the researchers used many compounds, for example, Digitonin (cas: 11024-24-1Name: Digitonin).

Digitonin (cas: 11024-24-1) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. 2-(Arylmethylene)cyclopropylcarbinols could be converted to the corresponding tetrahydropyrans stereoselectively in the presence of Br酶nsted acids under mild conditions. A plausible Prins-type reaction mechanism has been proposed.Name: Digitonin

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Identification of Gentiana rigescens from different geographical origins based on HPLC and FTIR fingerprints was written by Zhao, Yanli;Yuan, Tianjun;Wu, Lihua;Zhang, Ji;Zuo, Zhitian;Wang, Yuanzhong. And the article was included in Analytical Methods in 2020.Related Products of 17388-39-5 This article mentions the following:

Gentiana rigescens is a traditional Chinese medicine with efficacy in liver protection, as a cholagogic, anti-hyperglycemic, and anti-hypertension agent, and in relieving spasms and pain. The geog. environments of different locations are very complicated, with different soils, climates, sun exposure, etc.; this has a remarkable effect on the quality of medicinal herbs. To identify different geog. origins of G. rigescens, we analyzed the high-performance liquid chromatog. (HPLC) and Fourier transform IR spectroscopy (FTIR) fingerprints of G. rigescens with the aid of chemometrics. Five variable selection methods, including competitive adaptive reweighted sampling (CARS), random frog (RF), subwindow permutation anal. (SPA), Monte Carlo uninformative variable elimination (MC-UVE) and genetic algorithms (GA), were used to screen the characteristic variables for both the HPLC and FTIR fingerprints. Then, the corresponding partial least squares discriminant anal. (PLS-DA) models were built. The results showed that for both HPLC and FTIR, the GA-PLS-DA models were the most robust models for identification of the geog. origins of G. rigescens, which indicated that the recognition results of HPLC and FTIR are consistent. Through HPLC-FTIR two-dimensional (2D) hetero-correlation anal., the results showed a substantial correlation between HPLC and FTIR, which suggests that spectral correlative chromatog. for multicomponent comparison can be conducted. In terms of G. rigescens, qual. identification using FTIR is more convenient, rapid, environment-friendly and inexpensive than that using HPLC. In the experiment, the researchers used many compounds, for example, (4aR,5R,6S)-4a-Hydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-4,4a,5,6-tetrahydropyrano[3,4-c]pyran-1(3H)-one (cas: 17388-39-5Related Products of 17388-39-5).

(4aR,5R,6S)-4a-Hydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-4,4a,5,6-tetrahydropyrano[3,4-c]pyran-1(3H)-one (cas: 17388-39-5) belongs to tetrahydropyran derivatives. Tetrahydropyrans and furans principally constitute as a central motif in diverse medicinally privileged molecules. The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif. Related Products of 17388-39-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Acetylation of the Catalytic Lysine Inhibits Kinase Activity in PI3K未 was written by Fournier, Julie C. L.;Evans, John P.;Zappacosta, Francesca;Thomas, Daniel A.;Patel, Vipulkumar K.;White, Gemma V.;Campos, Sebastien;Tomkinson, Nicholas C. O.. And the article was included in ACS Chemical Biology in 2021.Quality Control of Tetrahydropyran-4-yl-carboxylic acid This article mentions the following:

Covalent inhibition is a powerful strategy to develop potent and selective small mol. kinase inhibitors. Targeting the conserved catalytic lysine is an attractive method for selective kinase inactivation. The authors have developed novel, selective inhibitors of phosphoinositide 3-kinase 未 (PI3K未) which acylate the catalytic lysine, Lys779, using activated esters as the reactive electrophiles. The acylating agents were prepared by adding the activated ester motif to a known selective dihydroisobenzofuran PI3K未 inhibitor. Three esters were designed, including an acetate ester which was the smallest lysine modification evaluated. Covalent binding to the enzyme was characterized by intact protein mass spectrometry of the PI3K未-ester adducts. An enzymic digest coupled with tandem mass spectrometry identified Lys779 as the covalent binding site, and a biochem. activity assay confirmed that PI3K未 inhibition was a direct result of covalent lysine acylation. A simple chem. modification such as lysine acetylation is sufficient to inhibit kinase activity. The selectivity of the compounds was evaluated against lipid kinases in cell lysates using a chemoproteomic binding assay. Due to the conserved nature of the catalytic lysine across the kinome, the authors believe the covalent inhibition strategy presented here could be applicable to a broad range of clin. relevant targets. In the experiment, the researchers used many compounds, for example, Tetrahydropyran-4-yl-carboxylic acid (cas: 5337-03-1Quality Control of Tetrahydropyran-4-yl-carboxylic acid).

Tetrahydropyran-4-yl-carboxylic acid (cas: 5337-03-1) belongs to tetrahydropyran derivatives. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. The Prins reaction of homoallylic alcohols with aldehydes afforded an alternative method for the preparation of tetrahydropyrans.Quality Control of Tetrahydropyran-4-yl-carboxylic acid

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Pentacoordinate Organoaluminum Chemistry: Catalytic Efficiency of Me₃Al in the Epoxide Cleavage with Alkynyllithiums was written by Ooi, Takashi;Kagoshima, Naoko;Ichikawa, Hayato;Maruoka, Keiji. And the article was included in Journal of the American Chemical Society in 1999.Synthetic Route of C6H12O2 This article mentions the following:

A new and highly effective catalytic method for epoxide alkynylations was developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me₃Al via pentacoordinate organoaluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether, (1-benzyloxy)-3-butene oxide, in toluene with PhC顚咰Li under the influence of catalytic Me₃Al (1h mol%) proceeded smoothly at 0 掳C for 5 h to furnish the alkynylation product, 1-(benzyloxy)-6-phenyl-5-hexyn-3-ol, in 76% yield [3% without Me₃Al catalyst; 78% with stoichiometric Me₃Al under similar conditions]. This represents the first catalytic procedure for the amphiphilic alkylation of epoxides. The participation of pentacoordinate Me₃Al complexes of epoxy ethers is emphasized by comparing the reactivity with the corresponding simple epoxide, 5-phenyl-1-pentene oxide, which was not susceptible to nucleophile attack of PhC顚咰Li with catalytic Me₃Al under similar conditions. The pentacoordinate complex formation of Me₃Al with (1-benzyloxy)-3-butene oxide is characterized by low-temperature ¹³C and ²⁷Al NMR spectroscopy. This approach is also applicable to the selective alkynylation of tosyl aziridines with adjacent ether functionality, which provides a promising method for amino alc. synthesis. In the experiment, the researchers used many compounds, for example, 2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4Synthetic Route of C6H12O2).

2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. The bismuth chloride-assisted cross-cyclization between homoallylic alcohols and epoxides provided various benzyl tetrahydropyran derivatives. The reaction afforded good yields of desired products and occurred under mild conditions.Synthetic Route of C6H12O2

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics