Category: esters-buliding-blocks

Ochiai, Shiho published the artcileSynthesis of Benzylidenesuccinates through Rhodium(III)-Catalyzed C-H Alkenylation with Itaconate, Quality Control of 617-52-7, the publication is Asian Journal of Organic Chemistry (2022), 11(2), e202100774, database is CAplus.

The dehydrogenative coupling of aromatic amides, e.g., (1-methyl-1H-indol-2-yl)-1-pyrrolidinylmethanone with di-Me itaconate proceeds smoothly under rhodium catalysis through ortho C-H bond cleavage directed by their amide group to produce benzylidenesuccinates, e.g., I. Aromatic carboxylic acids, e.g., 2-thiophenecarboxylic acid including benzoic and phthalic acids also couple with the itaconate to give 1 : 2 coupling products, e.g., II predominantly. Benzylidenesuccinic acid derivatives have been known to show various biol. activities. These reactions provide easy access to the important structures.

Asian Journal of Organic Chemistry published new progress about 617-52-7. 617-52-7 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Aliphatic hydrocarbon chain,Ester, name is Dimethyl itaconate, and the molecular formula is C7H10O4, Quality Control of 617-52-7.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Rochais, Christophe published the artcileOne-pot synthesis of new aza- and diaza-aminophenanthrenes, Safety of Methyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate, the publication is Tetrahedron (2011), 67(32), 5806-5810, database is CAplus.

The synthesis of a series of benzo(iso)quinoline and phenanthroline derivatives has been achieved using an efficient one-pot procedure. It proceeds through a Suzuki-Miyaura cross-coupling followed by a Dieckmann-Thorpe ring closure under microwave irradiation and provides easy access to building blocks not readily available through other methods.

Tetrahedron published new progress about 956229-86-0. 956229-86-0 belongs to esters-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ester,Boronate Esters,Boronic acid and ester, name is Methyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate, and the molecular formula is C15H21BO4, Safety of Methyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Beevor, Peter S. published the artcileIdentification and field evaluation of components of female sex pheromone of millet stem borer, Coniesta ignefusalis, Name: (Z)-Dodec-9-en-1-yl acetate, the publication is Journal of Chemical Ecology (1999), 25(12), 2643-2663, database is CAplus.

Five active compounds were detected during analyses of ovipositor washings and effluvia from virgin female Coniesta ignefusalis moths by gas chromatog. (GC) linked to electroantennog. (EAG) recording from a male moth. These were identified as (Z)-7-dodecen-1-ol (Z7-12:OH), (Z)-5-decen-1-ol (Z5-10:OH), (Z)-7-dodecenal (Z7-12:Ald), (Z)-7-dodecenyl acetate (Z7-12:Ac), and (Z)-9-tetradecen-1-ol (Z9-14:OH) by comparison of their GC retention times, mass spectra, and EAG activities with those of synthetic standards Laboratory tests of dispensers for these compounds showed that release rates from polyethylene vials increased to relatively uniform values after three to four days, but release from septa was very rapid and nonuniform and decreased to low levels after two to three days. Trapping tests in Niger showed that the major component, Z7-12:OH, and two of the minor components, Z5-10:OH and Z7-12:Ald, were essential for attraction of male C. ignefusalis moths. The most attractive blend contained these three components in a 100:5:3.3 ratio in a polyethylene vial, which emitted the components in similar proportions to those produced by the female C. ignefusalis moth. Water traps baited with this blend containing 1 mg of Z7-12:OH caught more male C. ignefusalis moths than traps baited with newly emerged female moths. Addition of up to 10% of the corresponding E isomers of the pheromone components had no effect on catches, but addition of the other two minor components detected, Z7-12:Ac and/or Z9-14:OH, to the attractive blend at naturally occurring levels caused significant reductions in trap catch.

Journal of Chemical Ecology published new progress about 16974-11-1. 16974-11-1 belongs to esters-buliding-blocks, auxiliary class Aliphatic Chain, name is (Z)-Dodec-9-en-1-yl acetate, and the molecular formula is C14H26O2, Name: (Z)-Dodec-9-en-1-yl acetate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Bairagi, Keshab M. published the artcileAntidiabetic Activity of Dihydropyrimidine Scaffolds and Structural Insight by Single Crystal X-ray Studies, HPLC of Formula: 30414-53-0, the publication is Medicinal Chemistry (Sharjah, United Arab Emirates) (2020), 16(7), 996-1003, database is CAplus and MEDLINE.

This research project is designed to identify the anti-diabetic effects of the newly synthesized compounds to conclude the perspective of consuming one or more of these new synthetic compounds for diabetes management. A series of dihydropyrimidine (DHPM) derivative bearing electron releasing and electron-withdrawing substituent′s on Ph ring (a-j) were synthesized and screened for antihyperglycemic(anti-diabetic) activity on streptozotocin (STZ) induced diabetic rat model. The newly synthesized compounds were characterized by using FT-IR, m.p., ¹H and ¹³C NMR anal. The crystal structure and supramol. features were analyzed through single-crystal X-ray study. Anti-diabetic activity testing of newly prepared DHPM scaffolds was mainly based on their relative substituent on the Ph ring along with urea and thiourea. Among the synthesized DHPM scaffold, the test compound c having chlorine group on Ph ring at the ortho position to the hydropyrimidine ring with urea and Me acetoacetate derivative shows moderate lowering of glucose level. However, the title compounds Me 4-(4-hydroxy-3-methoxyphenyl)- 6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate(g) and Et 4-(3-ethoxy-4- hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate(h) having methoxy and ethoxy substituents on Ph ring show significant hypoglycemic activity compared to the remaining compounds from the Scheme 1. The exptl. rat models for the study were divided into 13 groups (n = 10); group 1 animals were treated with 0.5% CMC (0.5mL) (vehicle); group 2 were considered the streptozotocin (STZ)/nicotinamide diabetic control group (DC) and untreated, group 3 diabetic animals were administered with gliclazide 50 mg/kg and act as a reference drug group. The remaining groups of the diabetic animals were administered with the newly synthesized dihydropyrimidine compounds in a single dose of 50 mg/kg orally using the oral gavage, daily for 7 days continuously. The blood glucose level was measured before and 72 h after nicotinamide-STZ injection, for confirmation of hyperglycemia and type 2 diabetes development. Blood glucose levels were significantly (p<0.05) reduced after treatment with these derivatives The mean percentage reduction for gliclazide was 50%, while that of synthesized compounds were approx. 36%. Our result suggests that the synthesized new DHPM derivative containing alkoxy group on the Ph ring shows a significant lowering of glucose level compared to other derivatives

Medicinal Chemistry (Sharjah, United Arab Emirates) published new progress about 30414-53-0. 30414-53-0 belongs to esters-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Ketone,Ester, name is Methyl 3-oxovalerate, and the molecular formula is C6H10O3, HPLC of Formula: 30414-53-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Chan, Justin W. published the artcileThe nucleophilic, phosphine-catalyzed thiol-ene click reaction and convergent star synthesis with RAFT-prepared homopolymers, COA of Formula: C5H10O2S, the publication is Polymer (2009), 50(14), 3158-3168, database is CAplus.

The synthesis of 3-arm star polymers from reversible addition-fragmentation chain transfer (RAFT)-prepared precursor homopolymers in combination with thiol-ene click chem. is described. Homopolymers of Bu acrylate and N,N-diethylacrylamide were prepared with 1-cyano-1-methylethyl dithiobenzoate and 2,2′-azobis(2-methylpropionitrile) yielding materials with polydispersity indexes (M_w/M_n) ≤ 1.18 and controlled mol. weights as determined by a combination of NMR spectroscopy, size exclusion chromatog. (SEC), and matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS). Subsequent one-pot reaction of homopolymer, hexylamine (HexAM), dimethylphenylphosphine (DMPP), and trimethylolpropane triacrylate (TMPTA) results in cleavage of the thiocarbonylthiol end-group (by HexAM) of the homopolymer yielding a macromol. thiol that undergoes DMPP-initiated thiol-Michael addition to TMPTA yielding 3-arm star polymers. The presence of DMPP is demonstrated to serve an important second role in effectively suppressing the presence of any polymeric disulfide as determined by SEC. Such phosphine-mediated thiol-ene reactions are shown to be extremely rapid, as verified by a combination of FTIR and NMR spectroscopies, with complete consumption of the C=C bonds occurring in a matter of min. MALDI-TOF MS and SEC were used to verify the formation of 3-arm stars. A broadening in the mol. weight distribution (M_w/M_n ∼ 1.35) was observed by SEC that was attributed to the presence of residual homopolymer and possibly 2-arm stars formed from trimethylolpropane diacrylate impurity. Interestingly, the MALDI anal. also indicated the presence of 1- and 2-arm species most likely formed from the fragmentation of the parent 3-arm star during anal. Finally, a control experiment verified that the consumption of C=C bonds does not occur via a radical pathway.

Polymer published new progress about 19788-49-9. 19788-49-9 belongs to esters-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Ester, name is Ethyl 2-mercaptopropanoate, and the molecular formula is C5H10O2S, COA of Formula: C5H10O2S.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Dai, Huimin published the artcileSolvent-Controlled, Tunable β-OAc and β-H Elimination in Rh(III)-Catalyzed Allyl Acetate and Aryl Amide Coupling via C-H Activation, Name: 3-(Methoxycarbonyl)benzoic acid, the publication is Organic Letters (2016), 18(14), 3410-3413, database is CAplus and MEDLINE.

The Heck reaction between arenes and allyl acetate led to cinnamyl derivatives and allyl products depending on the regioselectivity of β-elimination. The regioselectivity can be controlled by the solvent in the Rh(III)-catalyzed arene-allyl acetate coupling via C-H activation: (1) in THF, cinnamyl derivatives via β-H elimination were generated; (2) in MeOH, allyl products via β-OAc elimination were produced. Both routes have advantages such as excellent γ-selectivity toward allyl acetate, good to excellent yields, and broad substrate scope.

Organic Letters published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C9H8O4, Name: 3-(Methoxycarbonyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Sharma, Apekshya published the artcileDesigning Safer Solvents to Replace Methylene Chloride for Liquid Chromatography Applications Using Thin-Layer Chromatography as a Screening Tool, Quality Control of 627-93-0, the publication is Separations (2021), 8(10), 172, database is CAplus.

Methylene chloride, commonly known as dichloromethane (DCM), is a widely used chem. for chromatog. separation within the polymer, chem., and pharmaceutical industries. With the ability to effectively solvate heterocyclic compounds, and properties including a low b.p., high d., and low cost, DCM has become the solvent of choice for many different applications. However, DCM has high neurotoxicity and is carcinogenic, with exposure linked to damage to the brain and the central nervous system, even at low exposure levels. This research focuses on sustainability and works towards finding safer alternative solvents to replace DCM in pharmaceutical manufacturing The research was conducted with three active pharmaceutical ingredients (API) widely used in the pharmaceutical industry: acetaminophen, aspirin, and ibuprofen. Thin-layer chromatog. (TLC) was used to investigate if an alternative solvent or solvent blend could show comparable separation performance to DCM. The use of the Hansen Solubility Parameter (HSP) theory and solubility testing allowed for the identification of potential alternative solvents or solvent blends to replace DCM. HSP values for the three APIs were exptl. determined and used to identify safer solvents and blends that could potentially replace DCM. Safer solvents or binary solvent blends were down-selected based on their dissolution power, safety, and price. The down-selected solvents (e.g., Et acetate) and solvent blends were further evaluated using three chem. hazard classification approaches to find the best fitting nonhazardous replacement to DCM. Several safer solvent blends (e.g., mixtures composed of Me acetate and Et acetate) with adequate TLC performance were identified. Results from this study are expected to provide guidance for identifying and evaluating safer solvents to sep. APIs using chromatog.

Separations published new progress about 627-93-0. 627-93-0 belongs to esters-buliding-blocks, auxiliary class Ploymers, name is Dimethyl adipate, and the molecular formula is C10H12O5, Quality Control of 627-93-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Zhang, Li published the artcileSynthesis of yolk-shell magnetic porous organic nanospheres supported Pd catalyst for oxidation of alcohols and Heck reactions, Synthetic Route of 103-26-4, the publication is Chemical Engineering Journal (Amsterdam, Netherlands) (2021), 130237, database is CAplus.

Yolk-shell magnetic porous organic nanospheres (MPONs) supported Pd nanoparticles (Pd@MPONs) were synthesized by encapsulating Fe₃O₄ and Pd nanoparticles in one cavity of hollow porous organic nanospheres (HPONs) using a continuous “ship-in-bottle” strategy. The obtained Pd@MPONs possessed a hierarchically micro/mesoporous structure, high surface area (354 m²/g) and displayed excellent magnetic response (9 emu/g). They showed high catalytic performance in the oxidation of alcs. under mild conditions and the Heck-Mizoroki reaction, and brilliant magnetic recyclability, they can be removed rapidly from a reaction system using external magnetic fields without any catalytic activity decrease. Hence, the Pd@MPONs are easily recoverable nanocatalysts which have practical significance in the future sustainable industry.

Chemical Engineering Journal (Amsterdam, Netherlands) published new progress about 103-26-4. 103-26-4 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester,Protease,Tyrosinase,Natural product, name is Methyl 3-phenyl-2-propenoate, and the molecular formula is C3H5BN2O2, Synthetic Route of 103-26-4.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Prakash, Thazha P. published the artcileComprehensive Structure-Activity Relationship of Triantennary N-Acetylgalactosamine Conjugated Antisense Oligonucleotides for Targeted Delivery to Hepatocytes, Quality Control of 10378-06-0, the publication is Journal of Medicinal Chemistry (2016), 59(6), 2718-2733, database is CAplus and MEDLINE.

The comprehensive structure-activity relationships of triantennary GalNAc conjugated ASOs for enhancing potency via ASGR mediated delivery to hepatocytes is reported. Seventeen GalNAc clusters were assembled from six distinct scaffolds and attached to ASOs. The resulting ASO conjugates were evaluated in ASGR binding assays, in primary hepatocytes, and in mice. Five structurally distinct GalNAc clusters were chosen for more extensive evaluation using ASOs targeting SRB-1, A1AT, FXI, TTR, and ApoC III mRNAs. GalNAc-ASO conjugates exhibited excellent potencies (ED₅₀ 0.5-2 mg/kg) for reducing the targeted mRNAs and proteins. This work culminated in the identification of a simplified tris-based GalNAc cluster (THA-GN3), which can be efficiently assembled using readily available starting materials and conjugated to ASOs using a solution phase conjugation strategy. GalNAc-ASO conjugates thus represent a viable approach for enhancing potency of ASO drugs in the clinic without adding significant complexity or cost to existing protocols for manufacturing oligonucleotide drugs.

Journal of Medicinal Chemistry published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Quality Control of 10378-06-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Ren, Jinxuan published the artcileDimethyl itaconate inhibits neuroinflammation to alleviate chronic pain in mice, Product Details of C7H10O4, the publication is Neurochemistry International (2022), 105296, database is CAplus and MEDLINE.

The metabolite itaconate has both anti-inflammatory and immunomodulatory effects. However, its influence on chronic pain is unclear. Here, we demonstrated that i.p. injection of the itaconate derivative di-Me itaconate (DI) alleviated chronic pain symptoms, such as allodynia and hyperalgesia, in spinal nerve ligation (SNL) and inflammatory pain models. Moreover, i.p. DI reduced the secretion of inflammatory cytokines (i.e., interleukin-1β, tumor necrosis factor-alpha) in dorsal root ganglion (DRG), spinal cord and hind paw tissues, suppressed the activation of macrophages in the DRG and glial cells in the spinal dorsal horn and decreased the phosphorylation of extracellular signal-regulated kinase 1/2 (ERK1/2) in the DRG and spinal cord. DI boosted nuclear factor-erythroid 2 p45-related factor 2 (Nrf2) levels in the DRG and spinal cord of SNL mice. I.p. administration of the Nrf2 inhibitor ML385 abolished the analgesic effect of DI and decreased the expression of Nrf2 in the DRG and spinal cord. Similarly, administration of DI potently reversed the lipopolysaccharide (LPS)-induced inflammatory effect in microglia. Reduction of endogenous itaconate levels by pretreatment with immune-responsive gene 1 (IRG1) siRNA blocked Nrf2 expression, which impaired the analgesic and anti-inflammatory effects of DI in vitro. Therefore, our findings revealed for the first time that i.p. DI elicited anti-inflammatory effect and sustained chronic pain relief, which may be regarded as a promising therapeutic agent for chronic pain treatment.

Neurochemistry International published new progress about 617-52-7. 617-52-7 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Aliphatic hydrocarbon chain,Ester, name is Dimethyl itaconate, and the molecular formula is C7H10O4, Product Details of C7H10O4.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics