Category: esters-buliding-blocks

An efficient one-pot construction of substituted pyrimidinones was written by Lu, Yuelie;Xiang, Tingjian;Bartberger, Michael D.;Bernard, Charles;Bostick, Tracy;Huang, Liang;Liu, Longbin;Siegmund, Aaron;Sukay, Gregory;Guo, Gary;Elipe, Maria Silva;Tormos, Wanda;Dominguez, Celia;Koch, Kevin;Burgess, Laurence E.;Basil, Thomas C.;Ibrahim, Prabha;Hummel, Conrad. And the article was included in Tetrahedron in 2006.SDS of cas: 587-88-2 This article mentions the following:

A concise, scalable synthesis of 5-aryl-3-methyl-2-methylthio-6-pyridin-4-yl-3H-pyrimidin-4-ones (aryl = 3-MeC₆H₄, 4-FC₆H₄, 3,4-Cl₂C₆H₃, 2-naphthyl, etc.), as building block for p38 kinase inhibitor B, from Et arylacetates, 4-cyanopyridine and Me isothiocyanate is described. Subsequent hydrolysis of the methylthio group to the hydroxy group and chlorination provided the key intermediates, 2-chloro-3-methyl-6-pyridin-4-yl-5-aryl-3H-pyrimidin-4-ones. This class of reactive building blocks enabled the rapid evaluation of a variety of side chains at the 2-position of the pyrimidinone in SAR studies of inhibitors of p38 MAP kinase. In the experiment, the researchers used many compounds, for example, Ethyl 2-(4-fluorophenyl)acetate (cas: 587-88-2SDS of cas: 587-88-2).

Ethyl 2-(4-fluorophenyl)acetate (cas: 587-88-2) 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.SDS of cas: 587-88-2

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

Binding Peptide-Guided Immobilization of Lipases with Significantly Improved Catalytic Performance Using Escherichia coli BL21(DE3) Biofilms as a Platform was written by Dong, Hao;Zhang, Wenxue;Xuan, Qize;Zhou, Yao;Zhou, Shengmin;Huang, Jiaofang;Wang, Ping. And the article was included in ACS Applied Materials & Interfaces in 2021.HPLC of Formula: 84-61-7 This article mentions the following:

Developing novel immobilization methods to maximize the catalytic performance of enzymes has been a permanent pursuit of scientific researchers. Engineered Escherichia coli biofilms have attracted great concern as surface display platforms for enzyme immobilization. However, current biol. conjugation methods, such as the SpyTag/SpyCatcher tagging pair, that immobilize enzymes onto E. coli biofilms seriously hamper enzymic performance. Through phage display screening of lipase-binding peptides (LBPs) and co-expression of CsgB (nucleation protein of curli nanofibers) and LBP2-modified CsgA (CsgALBP2, major structural subunit of curli nanofibers) proteins, we developed E. coli BL21::铻朇sgA-CsgB-CsgALBP2 (LBP2-functionalized) biofilms as surface display platforms to maximize the catalytic performance of lipase (Lip181). After immobilization onto LBP2-functionalized biofilm materials, Lip181 showed increased thermostability, pH, and storage stability. Surprisingly, the relative activity of immobilized Lip181 increased from 8.43 to 11.33 U/mg through this immobilization strategy. Furthermore, the highest loading of lipase on LBP2-functionalized biofilm materials reached up to 27.90 mg/g of wet biofilm materials, equivalent to 210.49 mg/g of dry biofilm materials, revealing their potential as a surface with high enzyme loading capacity. Addnl., immobilized Lip181 was used to hydrolyze phthalic acid esters, and the hydrolysis rate against di-Bu phthalate was up to 100%. Thus, LBP2-mediated immobilization of lipases was demonstrated to be far more advantageous than the traditional SpyTag/SpyCatcher strategy in maximizing enzymic performance, thereby providing a better alternative for enzyme immobilization onto E. coli biofilms. In the experiment, the researchers used many compounds, for example, Dicyclohexyl phthalate (cas: 84-61-7HPLC of Formula: 84-61-7).

Dicyclohexyl phthalate (cas: 84-61-7) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. 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.HPLC of Formula: 84-61-7

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

Stereospecific Synthesis of Peptidyl 浼?Keto Amides as Inhibitors of Calpain was written by Harbeson, Scott L.;Abelleira, Susan M.;Akiyama, Alan;Barrett, Robert III;Carroll, Renee M.;Straub, Julie Ann;Tkacz, Jaroslaw N.;Wu, Chichih;Musso, Gary F.. And the article was included in Journal of Medicinal Chemistry in 1994.Product Details of 87694-53-9 This article mentions the following:

Peptidyl 浼?keto amides have been synthesized and tested as inhibitors of the cysteine protease calpain. A stereospecific synthesis was devised in which protected dipeptidyl 浼?hydroxy amides were oxidized with TEMPO/hypochlorite to the corresponding 浼?keto amides. This oxidation was accomplished in good yields and without epimerization of the chiral center adjacent to the ketone. The potent inhibition of porcine calpain I by the L,L diastereomers, combined with the poor inhibition by the L,D diastereomers, established the requirement for the all-L stereochem. of the active inhibitor. The early lead inhibitors were very hydrophobic and, therefore, poorly soluble in aqueous solutions Using the stereospecific route, new compounds were prepared with polar groups at the C- and N-termini. These modifications resulted in more soluble inhibitors that were still potent inhibitors of calpain. Studies of the stability of these 浼?keto amides showed that absolute stereochem. can be maintained in acidic and unbuffered environments but general base-catalyzed epimerization of the chiral center adjacent to the ketone occurred rapidly. The 浼?hydroxy precursors were inactive as inhibitors of calpain, which supports the hypothesis that the 浼?keto compounds reversibly form an enzyme-bound tetrahedral species that results from the nucleophilic addition of the catalytic thiol of calpain to the electrophilic ketone of the inhibitor. 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: 87694-53-9Product Details of 87694-53-9).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) 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. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Product Details of 87694-53-9

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

Preparation of sulfonated galactose-based glycopolymers and interactions with lectins was written by Ye, Bao-tong;Cai, Zhi;Wu, Jing;Lin, Xin;Chen, Jing-xiao;Chen, Jing-hua. And the article was included in Gaofenzi Xuebao in 2018.Reference of 4163-60-4 This article mentions the following:

A series of sulfonated galactose-based glycopolymers with different chem. structures were synthesized through reversible addition-fragmentation chain transfer (RAFT) polymerization Galactose modified hydroxyethyl methacrylate and sodium p-styrene sulfonate were used as monomers to construct homo-, block-, and random-glycopolymers. The chem. structures and mol. weights of the synthesized polymers were characterized through ¹H-NMR spectroscopy and GPC-MALLS analyses. Results showed that each glycopolymer possessed an average mol. weight of 1.5 鑴?10⁴ with narrow mol. weight distribution (PDI 閳?1.1). The turbidimetry assay indicated that the interactions between the glycopolymers and peanut agglutinin (PNA), which were used as model lectin, were influenced by the structure of the glycopolymers. The introduction of the sulfonic group significantly improved the PNA-binding ability of the glycopolymers through the synergistic effect of specific recognition and electrostatic interactions. Importantly, this effect was adjustable by varying the amount and distribution of the sulfonic groups. Both block- and random-glycopolymers exhibited significantly enhanced PNA-binding behavior with increasing amount of sulfonic groups. Moreover, the binding ability peaked when the molar ratio of the sulfonic groups was 66.7%. By contrast, the random-type glycopolymer, namely, P(Gal₂₁-r-SS₄₁), exhibited the strongest PNA-binding ability, which increased by 2.7-fold compared with that of the homo-type glycopolymer PGal. The ELISA assay further revealed that the polymerization and random distribution of the sulfonic groups in the glycopolymer substantially enhanced the recognition between PNA and the galactose moiety. The inhibition rate of galactose (30 mmol/L) against the PNA binding of PGal, P(Gal₂₁-r-SS₄₃), and P(Gal₂₁-r-SS₄₁) were 80%, 57.3%, and 34.2%, resp. However, the contents of the galactose moiety in these samples were 3.8, 2.1 and 2.0 mmol/L, resp. Overall, the order of PNA-binding ability was: P(Gal-r-SS) > P(Gal-b-SS) > PGal > PSS. In addition, the viability of B16 cancer cells and COS7 normal cells was higher than 80% when the concentration of the glycopolymers was 256 mg/L, indicating a good biocompatibility of these polymers. Based on the anal. of glycopolymer-lectin interactions, P(>) effectively inhibited the migration of B16 tumor cells and thus can be applied in clin. therapy for tumor metastasis. 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: 4163-60-4Reference of 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. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. 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.Reference of 4163-60-4

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

Preparation of poly(pentafluorophenyl acrylate) functionalized SiO2 beads for protein purification was written by Kim, Sura;Ku, Jayoung;Park, Jaemin;Kharbash, Raisa;Li, Sheng. And the article was included in Journal of Visualized Experiments in 2018.Application In Synthesis of Benzyl benzodithioate This article mentions the following:

We demonstrate a simple method to prepare poly(pentafluorophenyl acrylate) (poly(PFPA)) grafted silica beads for antibody immobilization and subsequent immunoprecipitation (IP) application. The poly(PFPA) grafted surface is prepared via a simple two-step process. In the first step, 3-aminopropyltriethoxysilane (APTES) is deposited as a linker mol. onto the silica surface. In the second step, poly(PFPA) homopolymer, synthesized via the reversible addition and fragmentation chain transfer (RAFT) polymerization, is grafted to the linker mol. through the exchange reaction between the pentafluorophenyl (PFP) units on the polymer and the amine groups on APTES. The deposition of APTES and poly(PFPA) on the silica particles are confirmed by XPS, as well as monitored by the particle size change measured via dynamic light scattering (DLS). To improve the surface hydrophilicity of the beads, partial substitution of poly(PFPA) with aminefunctionalized poly(ethylene glycol) (amino-PEG) is also performed. The PEG-substituted poly(PFPA) grafted silica beads are then immobilized with antibodies for IP application. For demonstration, an antibody against protein kinase RNA-activated (PKR) is employed, and IP efficiency is determined by Western blotting. The anal. results show that the antibody immobilized beads can indeed be used to enrich PKR while nonspecific protein interactions are minimal. In the experiment, the researchers used many compounds, for example, Benzyl benzodithioate (cas: 27249-90-7Application In Synthesis of Benzyl benzodithioate).

Benzyl benzodithioate (cas: 27249-90-7) 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.Application In Synthesis of Benzyl benzodithioate

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

Synthesis of N-[4-hydroxy(alkoxy, acyloxy)-3-alkoxy-benzylidene]-1-(1-adamantyl)ethanamines from 1-(1-adamantyl)ethanamine hydrochloride (Rimantadine) was written by Dikusar, E. A.;Kozlov, N. G.. And the article was included in Russian Journal of Organic Chemistry in 2007.Application In Synthesis of 4-Formyl-2-methoxyphenyl isobutyrate This article mentions the following:

Reactions of 1-(1-adamantyl)ethanamine hydrochloride with substituted aromatic aldehydes gave previously unknown Schiff bases containing an adamantane fragment. In the experiment, the researchers used many compounds, for example, 4-Formyl-2-methoxyphenyl isobutyrate (cas: 20665-85-4Application In Synthesis of 4-Formyl-2-methoxyphenyl isobutyrate).

4-Formyl-2-methoxyphenyl isobutyrate (cas: 20665-85-4) 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. 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.Application In Synthesis of 4-Formyl-2-methoxyphenyl isobutyrate

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

Optimization of Potency and Pharmacokinetic Properties of Tetrahydroisoquinoline Transient Receptor Potential Melastatin 8 (TRPM8) Antagonists was written by Horne, Daniel B.;Tamayo, Nuria A.;Bartberger, Michael D.;Bo, Yunxin;Clarine, Jeffrey;Davis, Carl D.;Gore, Vijay K.;Kaller, Matthew R.;Lehto, Sonya G.;Ma, Vu V.;Nishimura, Nobuko;Nguyen, Thomas T.;Tang, Phi;Wang, Weiya;Youngblood, Beth D.;Zhang, Maosheng;Gavva, Narender R.;Monenschein, Holger;Norman, Mark H.. And the article was included in Journal of Medicinal Chemistry in 2014.Recommanded Product: 16413-26-6 This article mentions the following:

Trifluoromethylaryl-substituted tetrahydroisoquinolinecarboxamides, tetrahydronaphthyridinecarboxamides, a tetrahydropyridopyrimidinecarboxamide, and a tetrahydropyridopyrazinecarboxamide such as tetrahydronaphthyridinecarboxamide I were prepared as inhibitors of the transient receptor potential melastatin 8 (TRPM8) cation channel, the predominant mammalian thermosensor for both temperature- and cooling agent-induced sensations in a subpopulation of peripheral sensory neurons, for potential use in the treatment of pain and bladder disorders. The inhibition of human and rat TRPM8 cation channels by the compounds and their degradation by liver microsomes were determined; for I and three other compounds, the oral and i.v. pharmacokinetics were determined in rats. I demonstrated robust efficacy at inhibiting the response of TRPM8 to cooling agents (icilin) and cold temperatures in rats with ED₉₀ values <3 mg/kg. Trifluoromethylaryl Grignard reagents used for the preparation of some of the title compounds have been found to decompose very exothermically and should be prepared and used with caution. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Recommanded Product: 16413-26-6).

3-Cyanophenylisocyanate (cas: 16413-26-6) 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. 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.Recommanded Product: 16413-26-6

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

Novel complex N-heterocycles via intramolecular 1,5-electrocyclizations: octahydropyrido[4”,3”:2′,3′]cyclobuta[1′,2′:4,5]pyrrolo[2,3-b]pyridines was written by Walter, Harald;Sundermann, Carsten. And the article was included in Heterocycles in 1998.SDS of cas: 14667-47-1 This article mentions the following:

2-Amino-3-isoprenylpyridine (I) and 2-amino-5-chloro-3-isoprenylpyridine (II) are prepared The toluenesulfonic acid catalyzed reaction of I and II with 1-benzyl-, 1-benzoyl-, and 1-methylpiperidin-4-one lead to novel pyrrolo[2,3-b]pyridines (III; R¹ = H, Cl; R² = Me, benzyl, benzoyl) in good to excellent yields in diastereoisomerically pure form. An intramol. 1,5-electrocyclization of a dipolar reactive intermediate as a key step is proposed for the formation of III. In the experiment, the researchers used many compounds, for example, Methyl 2-aminonicotinate (cas: 14667-47-1SDS of cas: 14667-47-1).

Methyl 2-aminonicotinate (cas: 14667-47-1) 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. 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.SDS of cas: 14667-47-1

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

Silver-catalyzed three-component reaction of phenyldiazoacetate with arylamine and imine was written by Chen, Bai-Ling;Wang, Zhen;Zhang, You-Can;Zhao, Zhi-Gang;Chen, Zili. And the article was included in Chinese Journal of Catalysis in 2018.Related Products of 19432-68-9 This article mentions the following:

A new method was developed to diastereoselectively synthesize polysubstituted 1,2-diamine compounds from the reaction of diazoesters with arylamines and diaryl imines by using the dioxazoline ligand L₂-ligated silver catalyst. The Lewis acidity of the silver catalyst affected the different types of substrate diastereoselectivities; It also led to the formation of amine-exchange side products. In the experiment, the researchers used many compounds, for example, Methyl 2-thienylacetate (cas: 19432-68-9Related Products of 19432-68-9).

Methyl 2-thienylacetate (cas: 19432-68-9) 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. 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.Related Products of 19432-68-9

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

Amide isosteres in structure-activity studies of antibacterial minor groove binders was written by Khalaf, Abedawn I.;Anthony, Nahoum;Breen, David;Donoghue, Gavin;MacKay, Simon P.;Scott, Fraser J.;Suckling, Colin J.. And the article was included in European Journal of Medicinal Chemistry in 2011.Formula: C7H8N2O4 This article mentions the following:

Antibacterial minor groove binders related to the natural product, distamycin, are development candidates for novel antibiotics. Alkenes have been found to be effective substitutes for the isosteric amide links in some positions and alkyl groups larger than Me have been found to increase binding to DNA in both selectivity and affinity. However the impact of other isosteres such as diazenes and the position of an alkyl group with respect to DNA binding and antibacterial activity are not known. The effects of some systematic variations in the structure of polyamide minor groove binders are investigated. Isosteres of the amide link (alkenes and diazenes) are compared: it is shown that all three are competent for binding to DNA but that alkene links give the tightest binding and highest antibacterial activity; no significant antibacterial activity was found for compounds with a diazene link. Within a series of alkene linked compounds, the effect of branched N-alkyl substituents on binding to DNA and antibacterial activity is investigated: it was found that C3 and C4 branched chains are acceptable at the central pyrrole residue but that at the pyrrole ring adjacent to the basic tail group, a C4 branched chain was too large both for DNA binding and for antibacterial activity. The active branched alkyl chain compounds were found to be especially active against Mycobacterium aurum, a bacterium related to the causative agent of tuberculosis. In the experiment, the researchers used many compounds, for example, Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7Formula: C7H8N2O4).

Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7) 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. Esters contain a carbonyl center, which gives rise to 120鎺?C閳ユ弲閳ユ彊 and O閳ユ弲閳ユ彊 angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C閳ユ彊閳ユ弲 bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Formula: C7H8N2O4

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