Month: December 2022

Roecker, Anthony J. published the artcileDiscovery of selective, orally bioavailable, N-linked arylsulfonamide Na_v1.7 inhibitors with pain efficacy in mice, Synthetic Route of 942603-91-0, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(10), 2087-2093, database is CAplus and MEDLINE.

The voltage-gated sodium channel Na_v1.7 is a genetically validated target for the treatment of pain with gain-of-function mutations in man eliciting a variety of painful disorders and loss-of-function mutations affording insensitivity to pain. Unfortunately, drugs thought to garner efficacy via Na_v1 inhibition have undesirable side effect profiles due to their lack of selectivity over channel isoforms. Herein we report the discovery of a novel series of orally bioavailable arylsulfonamide Na_v1.7 inhibitors with high levels of selectivity over Na_v1.5, the Na_v isoform responsible for cardiovascular side effects, through judicious use of parallel medicinal chem. and physicochem. property optimization. This effort produced inhibitors such as compound 5 with excellent potency, selectivity, behavioral efficacy in a rodent pain model, and efficacy in a mouse itch model suggestive of target modulation.

Bioorganic & Medicinal Chemistry Letters published new progress about 942603-91-0. 942603-91-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Fused-Heterocycles, name is Ethyl 2-methylene-5-oxohexahydro-1H-pyrrolizine-7a-carboxylate, and the molecular formula is C11H15NO3, Synthetic Route of 942603-91-0.

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

Valenca, Helber da Maia published the artcileBeneficial effects of Ilex paraguariensis in the prevention of obesity-associated metabolic disorders in mice, Formula: C6H8O4, the publication is Phytotherapy Research (2022), 36(2), 1032-1042, database is CAplus and MEDLINE.

Obesity is a chronic condition involving inflammation and oxidative stress that commonly predisposes affected individuals to develop metabolic disorders. We hypothesize that Ilex paraguariensis (IP) can modulate oxidative stress and inflammation underpinning metabolic disorders caused by obesity. C57BL/6 mice were fed a high-fat diet (HFD group) for 12 wk. Concomitantly, some mice were treated with roasted IP (15 mg/mL – HFD + IP) or di-Me fumarate (DMF) as a pos. control (2 mg/mL – HFD + DMF). The control group received standard chow and water ad libitum. Histol. analyses of fat tissue and liver, and quantification of mediators related to oxidative stress (Kelch-like ECH-associated protein 1/NF-E2-related factor 2, NADP(H) quinone oxidoreductase-1 [NQO1], heme oxygenase 1 [HO1], and superoxide dismutase) as well as metabolic profile blood biomarkers (glucose, leptin, resistin, high-d. lipoproteins [HDLs], and triglycerides) were performed. Metabolic disorders were prevented in mice treated with IP, as evidenced by the observation that glucose, HDL, and resistin levels were similar to those assessed in the control group. Morphol. analyses showed that both IP and DMF treatments prevented hepatic steatosis and adipocyte hypertrophy in visceral adipose tissue. Finally, although the antioxidant response stimulated by IP was quite limited, significant effects were found on NQO1 and HO1 expression. In conclusion, IP has promising preventative effects on the development of metabolic disorders caused by obesity.

Phytotherapy Research published new progress about 624-49-7. 624-49-7 belongs to esters-buliding-blocks, auxiliary class Inhibitor,Natural product, name is Dimethyl fumarate, and the molecular formula is C3H6O2, Formula: C6H8O4.

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

Ranger, Christopher M. published the artcileElectrophysiological and Behavioral Responses of an Ambrosia Beetle to Volatiles of its Nutritional Fungal Symbiont, Name: Methyl 3-phenyl-2-propenoate, the publication is Journal of Chemical Ecology (2021), 47(4-5), 463-475, database is CAplus and MEDLINE.

Ambrosia beetles (Coleoptera: Scolytinae) cultivate their fungal symbiont within host substrates as the sole source of nutrition on which the larvae and adults must feed. To investigate a possible role for semiochems. in this interaction, we characterized electrophysiol. and behavioral responses of Xylosandrus germanus to volatiles associated with its fungal symbiont Ambrosiella grosmanniae. During still-air walking bioassays, X. germanus exhibited an arrestment response to volatiles of A. grosmanniae, but not antagonistic fungi Beauveria bassiana, Metarhizium brunneum, Trichoderma harzianum, the plant pathogen Fusarium proliferatum, or malt extract agar. Solid phase microextraction-gas chromatog.-mass spectrometry identified 2-ethyl-1-hexanol, 2-phenylethanol, Me benzoate and 3-methyl-1-butanol in emissions from A. grosmanniae; the latter two compounds were also detected in emissions from B. bassiana. Concentration-responses using electroantennog. documented weak depolarizations to A. grosmanniae fungal volatiles, unlike the comparatively strong response to ethanol. When tested singly in walking bioassays, volatiles identified from A. grosmanniae elicited relatively weak arrestment responses, unlike the responses to ethanol. Xylosandrus germanus also exhibited weak or no long-range attraction to the fungal volatiles when tested singly during field trials in 2016-2018. None of the fungal volatiles enhanced attraction of X. germanus to ethanol when tested singly; in contrast, 2-phenylethanol and 3-methyl-1-butanol consistently reduced attraction to ethanol. Volatiles emitted by A. grosmanniae may represent short-range olfactory cues that could aid in distinguishing their nutritional fungal symbiont from other fungi, but these compounds are not likely to be useful as long-range attractants for improving detection or mass trapping tactics.

Journal of Chemical Ecology 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 C10H10O2, Name: Methyl 3-phenyl-2-propenoate.

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

Studzian, Maciej published the artcileSynthesis, Internalization and Visualization of N-(4-Carbomethoxy) Pyrrolidone Terminated PAMAM [G5:G3-TREN] Tecto(dendrimers) in Mammalian Cells, Category: esters-buliding-blocks, the publication is Molecules (2020), 25(19), 4406, database is CAplus and MEDLINE.

Tecto(dendrimers) are well-defined, dendrimer cluster type covalent structures. In this article, we present the synthesis of such a PAMAM [G5:G3-(TREN)]-N-(4-carbomethoxy) pyrrolidone terminated tecto(dendrimer). This tecto(dendrimer) exhibits nontraditional intrinsic luminescence (NTIL; excitation 376 nm; emission 455 nm) that has been attributed to three fluorescent components characterized by different fluorescence lifetimes. Furthermore, it has been shown that this PAMAM [G5:G3-(TREN)]-N-(4-carbomethoxy) pyrrolidone terminated tecto(dendrimer) is able to form a polyplex with double stranded DNA, and is nontoxic for HeLa and HMEC-1 cells up to a concentration of 10 mg/mL, even though it accumulates in endosomal compartments as demonstrated by its unique NTIL emission properties. Many of the above features would portend the proposed use of this tecto(dendrimer) as an efficient transfection agent. Quite surprisingly, transfection activity could not be demonstrated in HeLa cells, and the possible reasons are discussed in the article.

Molecules 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 C15H20O6, Category: esters-buliding-blocks.

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

Zurowska, Magdalena published the artcileEffect of lateral fluorine substitution far from the chiral center on mesomorphic behaviour of highly titled antiferroelectric (S) and (R) enantiomers, Category: esters-buliding-blocks, the publication is Journal of Molecular Liquids (2018), 504-510, database is CAplus.

Several new liquid crystalline chiral ester enantiomers in the (S) and (R) configuration were designed and characterised. In order to tune their mesomorphic properties, the mol. core was laterally substituted by fluorine atoms in different positions on the benzene ring placed in the mol. core far from the chiral center. All the materials possess the self-assembling behavior, specifically the paraelec. orthogonal smectic A*, the ferroelec. tilted smectic C* and antiferroelec. tilted smectic C_A* phases over a broad temperature range down to room temperature Properties of the materials were characterised by the polarising optical microscopy, differential scanning calorimetry, electro-optics and dielec. spectroscopy. Due to high chem. stability, reasonably broad temperature ranges of polar smectic mesophases (up to 110 °C) and very high values of the optical tilt angle (40-45°) at saturation, these materials can be used as chiral dopants for the multicomponent orthoconic mixture design aimed for development of advanced electro-optic and photonic devices.

Journal of Molecular Liquids published new progress about 50670-76-3. 50670-76-3 belongs to esters-buliding-blocks, auxiliary class Benzene,Phenol,Ester, name is Ethyl 4′-hydroxy-[1,1′-biphenyl]-4-carboxylate, and the molecular formula is C8H6ClNO, Category: esters-buliding-blocks.

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

Serushkina, O. V. published the artcileRegioselective replacement of nitro groups in 2,4,6-trinitrotoluene under the action of alkanethiols. Synthesis of ortho-(alkylthio)-substituted nitrotoluenes and their oxidation to sulfoxides and sulfones, Formula: C5H10O2S, the publication is Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (2001), 50(2), 261-264, database is CAplus.

The reactions of 2,4,6-trinitrotoluene with alkanethiols in the presence of K₂CO₃ (the molar ratio of the reactants is 1: 1: 1) in dipolar aprotic solvents result in selective replacement of the ortho-nitro group to form 2-alkylthio-4,6-dinitrotoluenes, which can be oxidized to the corresponding sulfoxides of sulfones. The 2nd ortho-nitro group can be replaced under the action of one more equivalent of alkanethiol on sulfides as exemplified in PhCH₂SH.

Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) 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 C10H18O, Formula: C5H10O2S.

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

Kerrigan, Nessan J. published the artcileStudies in the preparation of novel P-chirogenic binaphthyl monophosphanes (MOPs), Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Tetrahedron Letters (2003), 44(46), 8461-8465, database is CAplus.

Several routes to P-chirogenic binaphthyl monophosphines (MOPs) and their derivatives were investigated. Palladium catalyzed coupling of (R)-1,1′-binaphthyl-2,2′-ditriflate with R¹R²P(O)H in the presence of base gave 2′-(R¹R²-phosphinyl)-1,1-binaphthyl-2-triflate diastereomers (8a,b; R¹ = ^tBu, R² = Ph; 9a,b; R¹ = Ph, R² = 2-MeOC₆H₄). Phosphine oxides 8a and 8b were hydrolyzed, methylated and reduced by Si₂Cl₆ to give corresponding diastereomeric 2-methoxy-2′-methylphenylphosphino-1,1′-binaphthyls (12a,b). The absolute configuration of obtained chiral MOPs was established by x-ray crystallog. Substituents on phosphorus strongly influence the efficiency of the P-C coupling reaction, which is only slightly stereoselective.

Tetrahedron Letters published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

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

Wood, Murray R. published the artcileNovel one-pot synthesis of chain transfer agents for RAFT/MADIX polymerizations; trithiocarbonates, xanthates and dithiocarbamates, COA of Formula: C5H10O2S, the publication is Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) (2005), 46(2), 320-321, database is CAplus.

Starting from 1,1′-thiocarbonyldiimidazole and primary, secondary, or tertiary thiols, benzyl alc., or benzylamine, the title di- and trithiocarbonate and dithiocarbamate chain-transfer agents were prepared without the need for CS₂.

Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) 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 C18H21BO4, COA of Formula: C5H10O2S.

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

Wood, Murray R. published the artcileSelective one-pot synthesis of trithiocarbonates, xanthates, and dithiocarbamates for use in RAFT/MADIX living radical polymerizations, Application of Ethyl 2-mercaptopropanoate, the publication is Organic Letters (2006), 8(4), 553-556, database is CAplus and MEDLINE.

A facile route is developed for the production of chain transfer agents for reversible addition fragmentation chain transfer (RAFT) and macromol. design via the interchange of xanthates (MADIX) polymerizations, via a one-pot reaction. 1,1′-Thiocarbonyl diimidazole (TCDI) undergoes controlled monosubstitution when reacted with secondary thiols or alcs. The intermediate S/O-esters of imidazole-N-thionocarboxylic acid react efficiently with a range of primary thiols, alcs., and amines to form asym. dithiocarbonates, trithiocarbonates, and dithiocarbamates, resp. The synthesis provides a facile approach to the controlled radical polymerization of vinyl monomers through the reversible addition-fragmentation chain transfer (RAFT) mechanism.

Organic Letters 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 C18H21BO4, Application of Ethyl 2-mercaptopropanoate.

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

Wood, Murray R. published the artcileInvestigation of the Experimental Factors Affecting the Trithiocarbonate-Mediated RAFT Polymerization of Methyl Acrylate, Safety of Ethyl 2-mercaptopropanoate, the publication is Australian Journal of Chemistry (2007), 60(10), 772-778, database is CAplus.

The reversible addition-fragmentation chain transfer polymerization of acrylates, using Me acrylate (MA) as a monomer model, mediated by a trithiocarbonate was tested under several conditions where the exptl. parameters were systematically altered. The most significant parameter in controlling the rate and control of the polymerization was found to be the ratio of chain transfer agent (CTA) to initiator. Decreasing this ratio increased the rate of polymerization and had little noticeable effect on the control over mol. weight distribution. A ratio of CTA to initiator of unity was shown to give the best compromise between rate and control of the polymerization Targeted d.p. (equivalent to ratios of monomer to CTA) had negligible effect on the rate of polymerization and polydispersity index (PDI). Performing the polymerization in the presence of solvent (up to 41.2% (weight/weight) in toluene) had no neg. effect on the rate of polymerization Indeed, marginally higher conversions and lower PDIs than for bulk polymerization were achieved for similar reaction times. A higher amount of toluene (66.6% (weight/weight)) induced a lower rate of polymerization, but the evolution of mol. weight and PDI were unaffected. Polymerizations performed in the presence of toluene, N,N-dimethylformamide, and Me Et ketone showed that solvent polarity and aromaticity had no observable effect on the rate of polymerization and over the control of mol. weight distribution. The optimum conditions for the polymerization of MA, mediated by 2-ethylthiocarbonylsulfanyl-propionic acid Et ester at 50°C were found to be [CTA]/[AIBN] = 1/1 and ∼ 40% solvent (weight/weight).

Australian Journal of Chemistry 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 C12H25Br, Safety of Ethyl 2-mercaptopropanoate.

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