Month: February 2023

Synthesis and antiinflammatory activity of cis- and trans-6,6a,7,8,9,10,10a,11-octahydro-11-oxodibenzo[b,e]thiepinacetic and -oxepinacetic acids was written by Kurokawa, Mikio;Uno, Hitoshi;Nakamura, Hideo;Sato, Fuminori;Naruto, Shunsuke. And the article was included in Journal of Medicinal Chemistry in 1990.Synthetic Route of C11H14O3 This article mentions the following:

Eight cis– and trans-6,6a,7,8,9,10,10a,11-octahydro-11-oxodibenzo[b,e]thiepin- and -oxepinacetic acids I (X = S, O; R = 2- and 3-CH₂CO₂H and -CHMeCO₂H) were prepared, and their antiinflammatory activities were examined in the rat carrageenan hind-paw edema test. The antiinflammatory activity depended on the configurations at C-6a, C-10a, and C-2 of the acetic moiety. The 6a,10a-trans compounds exhibited considerable antiinflammatory activity, while the 6a,10a-cis compounds were inactive. Among the trans compounds, I (X = S, O; R = 3-CHMeCO₂H) showed antiinflammatory activity superior to that of indomethacin. Trans phenethyl ester I (X = S; R = 3-CHMeCO₂CH₂CH₂Ph) (II) showed potent antiinflammatory activity, and its safety index was >14 times as high as that of indomethacin. II is the most favorable compound with high antiinflammatory activity and little ulcerogenicity. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0Synthetic Route of C11H14O3).

Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Synthetic Route of C11H14O3

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

Exploring the lipids involved in the formation of characteristic lactones in Japanese Black cattle was written by Ueda, Shuji;Sasaki, Ryo;Nakabayashi, Rio;Yamanoue, Minoru;Sirai, Yasuhito;Iwamoto, Eiji. And the article was included in Metabolites in 2021.Related Products of 706-14-9 This article mentions the following:

The meat from Japanese Black cattle (Japanese Wagyu) is finely marbled and exhibits a rich and sweet aroma known as Wagyu beef aroma. To clarify the key metabolites involved in the aroma, we analyzed the correlation between lactone and lipid composition in Japanese Black cattle. Using gas chromatog.-olfactometry, we identified 39 characteristic odorants of the intermuscular fat. Seven characteristic lactones considered to be involved in Wagyu beef aroma were quantified and compared in the marbled area and intermuscular fat using a stable isotope dilution assay. Among them, γ-hexalactone was the only lactone whose level was significantly higher in the marbled area. To explore the lipid species involved in lactone formation, we analyzed samples with different aroma characteristics. Liquid chromatog.-mass spectrometry revealed eight lipid classes and showed significant differences in triacylglycerides (TAGs). To determine the mol. species of TAGs, we performed high-performance liquid chromatog. anal. and identified 14 TAG species. However, these analyses showed that seven lactones had a low correlation with the TAGs. However, γ-hexalactone showed a pos. correlation with linoleic acid. This study suggests that lipid composition affects the characteristic lactone profile involved in the Wagyu beef aroma. In the experiment, the researchers used many compounds, for example, 5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9Related Products of 706-14-9).

5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Related Products of 706-14-9

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

Directing Drugs to Bugs: Antibiotic-Carbohydrate Conjugates Targeting Biofilm-Associated Lectins of Pseudomonas aeruginosa was written by Meiers, Joscha;Zahorska, Eva;Roehrig, Teresa;Hauck, Dirk;Wagner, Stefanie;Titz, Alexander. And the article was included in Journal of Medicinal Chemistry in 2020.Synthetic Route of C16H22O11 This article mentions the following:

Chronic infections by Pseudomonas aeruginosa are characterized by biofilm formation, which effectively enhances resistance toward antibiotics. Biofilm-specific antibiotic delivery could locally increase drug concentration to break antimicrobial resistance and reduce the drug’s peripheral side effects. Two extracellular P. aeruginosa lectins, LecA and LecB, are essential structural components for biofilm formation and thus render a possible anchor for biofilm-targeted drug delivery. The standard-of-care drug ciprofloxacin suffers from severe systemic side effects and was therefore chosen for this approach. We synthesized several ciprofloxacin-carbohydrate conjugates and established a structure-activity relationship. Conjugation of ciprofloxacin to lectin probes enabled biofilm accumulation in vitro, reduced the antibiotic’s cytotoxicity, but also reduced its antibiotic activity against planktonic cells due to a reduced cell permeability and on target activity. This work defines the starting point for new biofilm/lectin-targeted drugs to modulate antibiotic properties and ultimately break antimicrobial resistance. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Synthetic Route of C16H22O11).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Synthetic Route of C16H22O11

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

Substrate Specificity Profiling and Identification of a New Class of Inhibitor for the Major Protease of the SARS Coronavirus was written by Goetz, D. H.;Choe, Y.;Hansell, E.;Chen, Y. T.;McDowell, M.;Jonsson, C. B.;Roush, B. C.;McKerrow, J.;Craik, C. S.. And the article was included in Biochemistry in 2007.Synthetic Route of C16H24N2O4 This article mentions the following:

Severe acute respiratory syndrome (SARS) is an emerging infectious disease associated with a high rate of mortality. The SARS-associated coronavirus (SARS-CoV) has been identified as the etiol. agent of the disease. Although public health procedures have been effective in combating the spread of SARS, concern remains about the possibility of a recurrence. Various approaches are being pursued for the development of efficacious therapeutics. One promising approach is to develop small mol. inhibitors of the essential major polyprotein processing protease 3Clpro. Here we report a complete description of the tetrapeptide substrate specificity of 3Clpro using fully degenerate peptide libraries consisting of all 160 000 possible naturally occurring tetrapeptides. The substrate specificity data show the expected P1-Gln P2-Leu specificity and elucidate a novel preference for P1-His containing substrates equal to the expected preference for P1-Gln. These data were then used to develop optimal substrates for a high-throughput screen of a 2000 compound small-mol. inhibitor library consisting of known cysteine protease inhibitor scaffolds. We also report the 1.8 Å X-ray crystal structure of 3Clpro bound to an irreversible inhibitor. This inhibitor, an α,β-epoxyketone, inhibits 3Clpro with a k₃/K_i of 0.002 μM^-1 s^-1 in a mode consistent with the substrate specificity data. Finally, we report the successful rational improvement of this scaffold with second generation inhibitors. These data provide the foundation for a rational small-mol. inhibitor design effort based upon the inhibitor scaffold identified, the crystal structure of the complex, and a more complete understanding of P1-P4 substrate specificity. In the experiment, the researchers used many compounds, for example, (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9Synthetic Route of C16H24N2O4).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Synthetic Route of C16H24N2O4

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

Volatile composition of bilberry wines fermented with non-Saccharomyces and Saccharomyces yeasts in pure, sequential and simultaneous inoculations was written by Liu, Shuxun;Laaksonen, Oskar;Yang, Baoru. And the article was included in Food Microbiology in 2019.Application In Synthesis of Isopentyl 3-methylbutanoate This article mentions the following:

Bilberry (Vaccinium myrtillus L.) juice was fermented with Torulaspora delbrueckii (TD291 and TD70526) and Schizosaccharomyces pombe (SP3796 and SP70572) in pure fermentation as well as in sequential and simultaneous inoculations with Saccharomyces cerevisiae 1116 (SC1116). Altogether, 56 volatile compounds were identified and semi-quantified with HS-SPME-GC/MS in bilberry products. Yeast fermentation prominently enhanced the aroma complexity of bilberry with a sharp increase in alcs., esters, aldehydes, and acetals. Compared to S. cerevisiae, T. delbrueckii produced less ethanol but more fusel alcs. that potentially enhance “alc.” and “nail polish” odors in TD70526 and less “fruity” esters in TD291. SP70572 resulted in high productions of undesirable compounds of acetoin and acetaldehyde but a low content of higher alcs. and esters, SP3796 produced a high content of fatty acid Et esters and acetoin. In comparison with monoculture of non-Saccharomyces yeast, sequential and simultaneous cultures of S. pombe and S. cerevisiae significantly decreased the content of acetoin while increased the relative level of esters; sequential cultures of T. delbrueckii and S. cerevisiae remarkably increased the concentration of acetaldehyde; simultaneous inoculations of S. cerevisiae with TD70526 and TD291 significantly decreased the content of fusel alcs. and increased the content of esters, resp. The findings suggested that non-Saccharomyces yeasts possess the potential to affect and modulate the aromatic profile of fermented bilberry products. Sequential and simultaneous inoculations with S. pombe strains and S. cerevisiae as well as simultaneous fermentation using T. delbrueckii strains and S. cerevisiae are optimal strategies to pos. influence the aroma profile of bilberry wines. In the experiment, the researchers used many compounds, for example, Isopentyl 3-methylbutanoate (cas: 659-70-1Application In Synthesis of Isopentyl 3-methylbutanoate).

Isopentyl 3-methylbutanoate (cas: 659-70-1) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Application In Synthesis of Isopentyl 3-methylbutanoate

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

Pillar[5]arene-Containing Metallacycles and Host-Guest Interaction Caused Aggregation-Induced Emission Enhancement Platforms was written by Tuo, Wei;Sun, Yan;Lu, Shuai;Li, Xiaopeng;Sun, Yao;Stang, Peter J.. And the article was included in Journal of the American Chemical Society in 2020.Recommanded Product: 4163-60-4 This article mentions the following:

Coordination-driven Pt metallacycles have shown potential in controllable modular self-assembly, which has made a vital contribution to biomedicine, catalysis, and multiresponsive materials. Herein, pillar[5]arene units were integrated into one skeleton through coordination-driven self-assembly, resulting in the formation of a hexagonal Pt(II) metallacycle decorated with six pillar[5]arenes. The host-guest interactions of the as-prepared metallacycle (pillar[5]arenes as hosts) and 1-butyl-4-[4-(diphenylamino)styryl]pyridinium (guest) were investigated. The metallacycle was found to facilitate the coaggregation between the guests and pillar[5]arenes through a synergistic effect, thus engendering a sharp increase in fluorescence intensity. The resultant aggregate was investigated by DLS and TEM. Our studies imply that the pillar[5]arene-containing metallacycle can serve as a potential platform for realizing emission enhancement effects. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Recommanded Product: 4163-60-4).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Recommanded Product: 4163-60-4

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

In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles was written by Chen, Rongxiang;Ogunlana, Abosede Adejoke;Fang, Shangwen;Long, Wenhao;Sun, Hongmei;Bao, Xiaoguang;Wan, Xiaobing. And the article was included in Organic & Biomolecular Chemistry in 2018.Synthetic Route of C9H10O3S This article mentions the following:

A [3 + 2] cycloaddition reaction of β-keto esters with nitrile oxides, which were generated in situ from copper carbene and tert-Bu nitrite, is reported. This three-component reaction provides methodol. for the direct synthesis of fully substituted isoxazole derivatives, featuring mild reaction conditions, readily accessible starting materials and simple operation. The exptl. studies and DFT calculations suggest that the reaction starts with the generation of the key intermediate nitrile oxides, followed by a [3 + 2] cycloaddition reaction of β-keto esters to give the final isoxazole products. In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8Synthetic Route of C9H10O3S).

Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Synthetic Route of C9H10O3S

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

Dependence of Thermal Stability on Molecular Structure of RAFT/MADIX Agents: A Kinetic and Mechanistic Study was written by Zhou, Yanwu;He, Junpo;Li, Changxi;Hong, Linxiang;Yang, Yuliang. And the article was included in Macromolecules (Washington, DC, United States) in 2011.Recommanded Product: Benzyl benzodithioate This article mentions the following:

The thermal decomposition of different classes of RAFT/MADIX agents, namely dithioesters, trithiocarbonates, xanthates, and dithiocarbamates, were studied through heating in solution The decomposition behavior is complicated interplay of the effects of stabilizing Z-group and leaving R-group. The mechanism of the decomposition is mainly through three pathways, i.e., β-elimination, α-elimination, and homolysis of dithiocarbamate (particularly for universal RAFT agent). The most important pathway is the β-elimination of thiocarbonylthio compounds possessing β-hydrogen, leading to the formation unsaturated species. For the leaving group containing solely α-hydrogen, such as benzyl, α-elimination takes place, resulting in the formation of (E)-stilbene through a carbene intermediate. Homolysis occurs specifically in the case of a universal RAFT agent, in which a thiocarbonyl radical and an alkylthio radical are generated, finally forming thiolactone through a radical process. The stabilities of the RAFT/MADIX agents are studied by measuring the apparent kinetics and activation energy of the thermal decomposition reactions. Both Z-group and R-group influence the stability of the agents through electronic and steric effects. Lone pair electron donating heteroatoms of Z-group show a remarkable stabilizing effect while electron withdrawing substituents, either in Z- or R-group, tends to destabilize the agent. In addition, bulkier or more β-hydrogens result in faster decomposition rate or lower decomposition temperature Thus, the stability of the RAFT/MAIDX agents decreases in the order where R is (with identical Z = phenyl) -CH₂Ph (5) >-PS (PS-RAFT 15) > -C(Me)HPh (2) >-C(Me)₂C(=O)OC₂H₅ (7) >-C(Me)₂Ph(1) > -PMMA (PMMA-RAFT 16) > -C(Me)₂CN (6). For those possessing identical leaving group such as 1-phenylethyl, the stability decreases in the order of O-Et (11) > -N(CH₂CH₃)₂ (13) > -SCH(CH₃)Ph (8) > -Ph (2) > -CH₂Ph (4) > -PhNO₂ (3). These results consort with the chain transfer activities measured by the CSIRO group and agree well with the ab initio theor. results by Coote. In addition, the difference between thermal stabilities of the universal RAFT agents at neutral and protonated states was demonstrated. In the experiment, the researchers used many compounds, for example, Benzyl benzodithioate (cas: 27249-90-7Recommanded Product: Benzyl benzodithioate).

Benzyl benzodithioate (cas: 27249-90-7) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Recommanded Product: Benzyl benzodithioate

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

Complexation of hexosammonium ions: evidence for contributions from OH···OH hydrogen bonds in a hydroxylic medium was written by Savage, Paul B.;Gellman, Samuel H.. And the article was included in Journal of the American Chemical Society in 1993.Application In Synthesis of (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate This article mentions the following:

The synthesis and complexation properties of macrocycle 3 (I) are described. Simpler macrocycle 1 (II) was previously shown to bind primary ammonium ions in CDCl₃/CD₃OD mixtures; the authors now report that 3 binds hexosammonium ions in 10 volume% CD₃OD in CDCl₃. The following K_a values were measured for 3 and several hexosamine-HCl as their (p-tert-butylbenzyl)thioglycoside derivatives: β-glucosammonium (3,000 M^-1), α-glucosammonium (2,800 M^-1), β-galactosammonium (1,400 M^-1), β-mannosammonium (1,000 M^-1), α-mannosammonium (2,200 M^-1). Macrocycle 3 binds cyclohexylammonium chloride with a K_a of only 570 M^-1, i.e., significantly less strongly than the hexosammonium ions. In contrast, macrocycle 1 binds cyclohexylammonium chloride more tightly than the hexosammonium ions (e.g., 1,700 M^-1 for 1 + cyclohexylammonium chloride vs. 870 M^-1 for 1 + β-glucosammonium derivative). Thus, interactions between the peripheral hydroxyl groups of macrocycle 3 and the monosaccharide hydroxyls contribute to the stability of the bound state. This observation is particularly interesting in light of the fact that the solvent (2.5 M CD₃OD) contains ample hydroxyl groups for competitive H-bonding interaction. In the experiment, the researchers used many compounds, for example, (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (cas: 6730-10-5Application In Synthesis of (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate).

(2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (cas: 6730-10-5) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Application In Synthesis of (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate

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

Synthesis and Evaluation of Metabotropic Glutamate Receptor Subtype 5 Antagonists Based on Fenobam was written by Gichinga, MosesG.;Olson, Jeremy P.;Butala, Elizabeth;Navarro, Hernan A.;Gilmour, Brian P.;Mascarella, S. Wayne;Carroll, F. Ivy. And the article was included in ACS Medicinal Chemistry Letters in 2011.Safety of 3-Cyanophenylisocyanate This article mentions the following:

In an effort to discover potent and selective metabotropic glutamate receptor subtype 5 (mGluR5) antagonists, 15 tetrahydropyrimidinone analogs of 1-(3-chlorophenyl)-3-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)-urea (fenobam) were synthesized. These compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro efficacy assay. The IC₅₀ value for 1-(3-chlorophenyl)-3-(1-methyl-4-oxo-1,4,5,6-tetrahydropyrimidine)urea was essentially identical to that of fenobam. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Safety of 3-Cyanophenylisocyanate).

3-Cyanophenylisocyanate (cas: 16413-26-6) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Safety of 3-Cyanophenylisocyanate

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