Heterocyclic Building Blocks-Tetrahydropyran

Stereoselective Total Synthesis of Rugulactone was written by Das, Biswanath;Srinivas, Yallamalla;Sudhakar, Chithaluri;Reddy, Parigi Raghavendar. And the article was included in Helvetica Chimica Acta in 2011.Recommanded Product: 2-(But-3-yn-1-yloxy)tetrahydro-2H-pyran This article mentions the following:

The stereoselective synthesis of the naturally occurring dihydropyranone rugulactone (I) has been accomplished starting from 3-phenylpropan-1-ol employing Maruoka allylation and ring-closing metathesis as the key steps. In the experiment, the researchers used many compounds, for example, 2-(But-3-yn-1-yloxy)tetrahydro-2H-pyran (cas: 40365-61-5Recommanded Product: 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. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. 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 percentotoxineRecommanded Product: 2-(But-3-yn-1-yloxy)tetrahydro-2H-pyran

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

Synthesis and hypotensive activity of a series of 2-substituted 5,6-dimethoxyindazoles was written by Schwan, Thomas J.;Honkomp, LeRoy J.;Davis, Charles S.;Lougheed, Guy S.. And the article was included in Journal of Pharmaceutical Sciences in 1978.Recommanded Product: 2-(Aminomethyl)tetrahydropyran This article mentions the following:

The synthesis and hypotensive activity in the dog of a series of 2-substituted 5,6-dimethoxyindazoles (e.g. I) are reported. Structure-activity relationships for this class of compounds are discussed. Indazoles containing the diethylaminoethyl, 3-pyridyl, and hydroxyethyl functions in the 2-position were the most effective in lowering blood pressure for the longest times (>270 min). In the experiment, the researchers used many compounds, for example, 2-(Aminomethyl)tetrahydropyran (cas: 6628-83-7Recommanded Product: 2-(Aminomethyl)tetrahydropyran).

2-(Aminomethyl)tetrahydropyran (cas: 6628-83-7) belongs to tetrahydropyran derivatives. Tetrahydropyran is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.Recommanded Product: 2-(Aminomethyl)tetrahydropyran

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

New Matrix Compounds for the Detection of Carboxyl-Containing Nonsteroidal Anti-Inflammatory Drugs by MALDI Mass Spectrometry was written by Khrushcheva, M. L.;Krivosheina, M. S.;Matveeva, M. D.;Zhilyaev, D. I.;Borisov, R. S.. And the article was included in Russian Journal of Applied Chemistry in 2020.Related Products of 41340-25-4 This article mentions the following:

Abstract: The possibility of employing the method of mass spectrometry with matrix-assisted laser desorption/ionization (MALDI) for the rapid detection of carboxyl-containing nonsteroidal anti-inflammatory drugs has been studied. Comparison of the results obtained using the previously described and newly proposed as matrix compounds 4-(dimethylamino)benzaldehyde and N,N-dimethyl-p-phenylenediamine, showed that the latter provide the registration of mass spectra containing intense peaks of deprotonated mols. of all drugs used in the work. Comparison of the time required for their detection by various mass spectrometric methods has shown that MALDI mass spectrometry provides the highest performance in streaming anal. In the experiment, the researchers used many compounds, for example, 2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid (cas: 41340-25-4Related Products of 41340-25-4).

2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid (cas: 41340-25-4) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.Related Products of 41340-25-4

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

Swertiamarin suppresses proliferation, migration, and invasion of hepatocellular carcinoma cells via negative regulation of FRAT1 was written by Xiao, Shufeng;Tang, Haoran;Bai, Yao;Zou, Renchao;Ren, Zongfang;Wu, Xuesong;Shi, Zhitian;Lan, Song;Liu, Wei;Wu, Tiangen;Zhang, Cheng;Wang, Lin. And the article was included in European Journal of Histochemistry in 2020.Safety of (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 This article mentions the following:

Studies have shown that swertiamarin (STM) has multiple biol. activities, but its antitumor effects and mol. mechanisms are still unclear. The present research aimed to validate the STM’s impacts on the proliferation, migration, and invasion of hepatocellular carcinoma (HCC) cells, and to study its potential mechanism. Two HCC cell lines were treated with STM. Tumor growth was observed by the mouse tumor xenografts model. HCC cell lines stably expressing frequently rearranged in advanced T-cell lymphomas 1 (FRAT1) were generated by lentivirus-mediated overexpression. Cell viability, proliferation, migration, and invasion were observed using Cell Counting Kit-8 (CCK8), the xCELLigence Real-Time Cell Analyzer system (RTCA), and transwell anal., resp. Quant. real-time polymerase chain reaction (qRT-PCR) and Western blotting were used to observe the expression of FRAT1 and proteins related to the Wnt/β-catenin signalling pathway. Tumor growth was inhibited by STM in vivo. STM suppressed the proliferation, migration, and invasion of HCC cells. STM neg. regulated FRAT1 expression, whereas overexpressed FRAT1 blocked the antitumor function of STM. The results revealed that STM suppressed the FRAT1/Wnt/β-catenin signalling pathway. The findings of this study provide new insights into investigation of therapeutic strategies against HCC. 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: 17388-39-5Safety of (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).

(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 are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif. Safety of (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

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

Silver (Ι)-assisted enantiomeric analysis of ginsenosides using electrospray ionization tandem mass spectrometry was written by Yu, Qing;Yu, Binbin;Yang, Hongmei;Li, Xue;Liu, Shuying. And the article was included in Journal of Mass Spectrometry in 2012.Category: tetrahydropyran This article mentions the following:

For identification of ginsenoside enantiomers, electrospray ionization mass spectrometry (ESI-MS) was used to generate silver complexes of the type [ginsenoside + Ag]⁺. Collision induced dissociation of the silver-ginsenoside complexes produced fragment ions by dehydration, allowing differentiation of ginsenoside enantiomers by the intensity of [M + Ag – H₂O]⁺ ion. In the meanwhile, an approach based on the distinct profiles of enantiomer-selective fragment ion intensity varied with collision energy was introduced to refine the identification and quantitation of ginsenoside enantiomers. Five pairs of enantiomeric ginsenosides were distinguished and quantified on the basis of the distribution of fragment ion [M + Ag – H₂O]⁺. This method was also extended to the identification of other type of ginsenoside isomers such as ginsenoside Rb2 and Rb3. For demonstrating the practicability of this novel approach, it was utilized to analyze the molar ratio of 20-(S) and 20-(R) type enantiomeric ginsenosides in enantiomer mixture in red ginseng extract The generation of characteristic fragment ion [M + Ag – H₂O]⁺ likely results from the reduction of potential energy barrier of dehydration because of the catalysis of silver ion. The mechanism of enantiomer identification of ginsenosides was discussed from the aspects of computational modeling and internal energy. Copyright © 2012 John Wiley & Sons, Ltd. In the experiment, the researchers used many compounds, for example, 20(R)-Ginsenoside Rh2 (cas: 112246-15-8Category: tetrahydropyran).

20(R)-Ginsenoside Rh2 (cas: 112246-15-8) 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. 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 percentotoxineCategory: tetrahydropyran

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

2-Aminopyrimidin-4(1H)-one as the novel bioisostere of urea: Discovery of novel and potent CXCR2 antagonists was written by Lu, Hongfu;Yang, Ting;Xu, Zhongmiao;Wren, Paul B.;Zhang, Yueting;Cai, Xin;Patel, Metul;Dong, Kelly;Zhang, Qing;Zhang, Wei;Guan, Xiaoming;Xiang, Jianing;Elliott, John D.;Lin, Xichen;Ren, Feng. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2014.Category: tetrahydropyran This article mentions the following:

2-Aminopyrimidin-4(1H)-one was proposed as the novel bioisostere of urea. Bioisosteric replacement of the reported urea series of the CXCR2 antagonists with 2-aminopyrimidin-4(1H)-ones led to the discovery of the novel and potent CXCR2 antagonist I. 2-Aminopyrimidin-4(1H)-one I demonstrated a good potential (reasonable solubility and high permeability) and superior chem. stability especially in simulated gastric fluid compared with ureas. In the experiment, the researchers used many compounds, for example, Ethyl 3-Oxo-3-(4-tetrahydropyranyl)propanoate (cas: 856414-68-1Category: tetrahydropyran).

Ethyl 3-Oxo-3-(4-tetrahydropyranyl)propanoate (cas: 856414-68-1) belongs to tetrahydropyran derivatives. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif. Category: tetrahydropyran

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

Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids was written by Wang, Jiang;Hoerrner, Megan E.;Watson, Mary P.;Weix, Daniel J.. And the article was included in Angewandte Chemie, International Edition in 2020.Recommanded Product: Tetrahydropyran-4-yl-carboxylic acid This article mentions the following:

While ketones are among the most versatile functional groups, their synthesis remains reliant upon reactive and low-abundance starting materials. In contrast, amide formation is the most-used bond-construction method in medicinal chem. because the chem. is reliable and draws upon large and diverse substrate pools. A new method for the synthesis of ketones is presented here that draws from the same substrates used for amide bond synthesis: amines and carboxylic acids. A nickel terpyridine catalyst couples N-alkyl pyridinium salts with in situ formed carboxylic acid fluorides or 2-pyridyl esters under reducing conditions (Mn metal). The reaction has a broad scope, as demonstrated by the synthesis of 35 different ketones bearing a wide variety of functional groups with an average yield of 60±16%. This approach is capable of coupling diverse substrates, including pharmaceutical intermediates, to rapidly form complex ketones. In the experiment, the researchers used many compounds, for example, Tetrahydropyran-4-yl-carboxylic acid (cas: 5337-03-1Recommanded Product: 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. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.Recommanded Product: Tetrahydropyran-4-yl-carboxylic acid

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

Exploration of scientific connotation of processing of Shanzhuyu (Corni Fructus) with wine based on network pharmacology was written by Wu, Xinhua;Qu, Hui;Cao, Yuan;Fang, Zhuyuan. And the article was included in Zhonghua Zhongyiyao Xuekan in 2021.HPLC of Formula: 17388-39-5 This article mentions the following:

Objective: Processing with wine is one of the important processing methods of Shanzhuyu (Corni Fructus), which may significantly enhance its effects of nourishing liver and kidney, as well as preventing decrepitude and strengthening immunity. This study aimed to clarify the mol. mechanism of how the ingredient variation affected the efficacy of processed Shanzhuyu (Corni Fructus), and elucidate the scientific connotation of this processing methodol. based on network pharmacol. Methods: The major different ingredients between crude and processed Shanzhuyu (Corni Fructus) were screened out based on literature. The potential targets of these ingredients were predicted according to SIB, SEA, STITCH, TCMSP database, and the core targets were selected out by STRING database and Metascape. Cytoscape software were used to construct protein-protein interactions network and ingredient-target network. GO function and KEGG pathways involved in the targets were analyzed by DAVID database. BioGps database was used to locate the target organs. Results: Nine differential components and 43 core targets were screened out. The network anal. results showed that 85 GO terms and 14 KEGG pathways were involved. The results of organ localization showed that the core disease site was liver. Conclusion: The changes in the efficacy between crude and processed Shanzhuyu (Corni Fructus) resulted from chem. composition alteration and their interactions. The enhancement of pharmaceutical efficacy of processed Shanzhuyu (Corni Fructus) may be accomplished by regulation of neuroactive ligand-receptor interaction, cAMP signaling pathway, PI3K-Akt signaling pathway and so on. 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. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.HPLC of Formula: 17388-39-5

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

Liquid chromatographic methods for separation, determination, and bioassay of enantiomers of etodolac: A review was written by Singh, Manisha;Sethi, Sonika;Bhushan, Ravi. And the article was included in Journal of Separation Science in 2020.Quality Control of 2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid This article mentions the following:

The control of enantiomeric purity and determination of individual enantiomeric drug mols. remains the subject of importance for clin., anal., and regulatory purposes and to facilitate an accurate evaluation of the risks posed by them to human health. A large number of pharmaceuticals are marketed and administered as racemates. Etodolac is among such nonsteroidal anti-inflammatory drugs. Overall literature reports on its enantioseparation are scanty. Liquid chromatog. (LC) methods of enantioseparation of (±)-etodolac, including certain unconventional ones, are well covered and discussed in this paper. Methods of direct approach without using chiral columns or chiral thin-layer chromatog. plate and of indirect approach using certain chiral derivatizing agents such as (S)-naproxen and (S)-levofloxacin are described. Most interesting aspects include establishment of structure and mol. asymmetry of chem. different types of diastereomeric derivatives using liquid chromatog. with mass spectrometry (LC-MS), ¹H NMR spectroscopy and by drawing conformations in three dimensional views by using certain software. The methods provide chirality recognition even in the absence of pure enantiomers. Besides, recovery of pure enantiomers by detagging or via solubility difference of chiral inducing reagent and the analyte, without racemization at any stage, has been achieved. The limits of detection and quantification are much lower than the industry benchmarks. In the experiment, the researchers used many compounds, for example, 2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid (cas: 41340-25-4Quality Control of 2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid).

2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid (cas: 41340-25-4) belongs to tetrahydropyran derivatives. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.Quality Control of 2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid

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