Month: December 2022

Favalli, Nicholas published the artcileLarge screening of DNA-compatible reaction conditions for Suzuki and Sonogashira cross-coupling reactions and for reverse amide bond formation, Safety of (2-Methoxyphenyl)methanamine, the publication is Bioorganic & Medicinal Chemistry (2021), 116206, database is CAplus and MEDLINE.

Progress in DNA-encoded chem. library synthesis and screening crucially relies on the availability of DNA-compatible reactions, which proceed with high yields and excellent purity for a large number of possible building blocks. In the past, exptl. conditions have been presented for the execution of Suzuki and Sonogashira cross-coupling reactions on-DNA. In this article, our aim was to optimize Suzuki and Sonogashira reactions, comparing our results to previously published procedures. We have tested the performance of improved conditions using 606 building blocks (including boronic acids, pinacol boranes and terminal alkynes), achieving >70% conversion for 84% of the tested mols. Moreover, we describe efficient exptl. conditions for the on-DNA synthesis of amide bonds, starting from DNA derivatives carrying a carboxylic acid moiety and 300 primary, secondary and aromatic amines, as amide bonds are frequently found in DNA-encoded chem. libraries thanks to their excellent DNA compatibility.

Bioorganic & Medicinal Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Safety of (2-Methoxyphenyl)methanamine.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Zampella, Angela published the artcileStereochemistry of sphinxolides and reidispongiolides. Asymmetric synthesis of the C17-C22 fragment of reidispongiolide A, HPLC of Formula: 99438-28-5, the publication is European Journal of Organic Chemistry (2002), 785-790, database is CAplus.

Five fragments, [I (R = α, β-OH), II, III (R = α, β-OH)] embedding all the stereogenic centers of reidispongiolide A (IV), have been prepared by a controlled ozonolysis of the IV. The absolute stereochem. of the asym. centers of II, corresponding to the C17-C22 portion of IV, was determined by enantioselective synthesis and application of the advanced Mosher method.

European Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C4H7BrO2, HPLC of Formula: 99438-28-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Ahmed, Mahmood published the artcileA tripartite asymmetric allylboration – silicon tethered alkene ring closing metathesis – in situ ring opening protocol for the regiospecific generation of functionalized (E)-disubstituted homoallylic alcohols, Application of (+)-B-Methoxydiisopinocampheylborane, the publication is Tetrahedron (1999), 55(11), 3219-3232, database is CAplus.

Molybdenum carbene I catalyzed ring closing metathesis of (alkenyl)silyl ethers of homochiral allylic alcs., e.g. II, to afford 1,2-oxasilines, e.g. III, which were elaborated in situ to give (E)-4-alkyl-1,2- disubstituted 3-buten-1-ol and (Z)-4-alkyl-4-silyl-1,2-disubstituted 3-buten-1-ol derivatives as single geometric isomers.

Tetrahedron published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Application of (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Mastral, Ana Maria published the artcileFriedel-Crafts reaction. Comparative study of alkylation of anisole with diverse alkylation agents, Synthetic Route of 2944-47-0, the publication is Afinidad (1979), 36(363), 401-4, database is CAplus.

Alkylation of anisole was carried out with MeCH:CH₂, PrCl, PrOH, or ROCHMeCH₂HgBr (R = H, Me, Ac) in the presence AlCl₃, FeCl₃, or BF₃.Et₂O. Best results were achieved using the organomercury compounds, which gave mainly o– or p-MeOC₆H₄CH₂CHMeOR.

Afinidad published new progress about 2944-47-0. 2944-47-0 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 2-Isopropylanisole, and the molecular formula is C10H14O, Synthetic Route of 2944-47-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Zirwas, Matthew J. published the artcileAnti-pruritic efficacy of itch relief lotion and cream in patients with atopic history: comparison with hydrocortisone cream, Formula: C17H28ClNO3, the publication is Journal of Drugs in Dermatology (2017), 16(3), 243-247, database is CAplus and MEDLINE.

Objective: To evaluate the speed of onset and duration of relief of two ceramide-containing formulations with 1% pramoxine hydroxide (CeraVe Itch Relief Lotion and Cream,Valeant Pharmaceuticals North America LLC, Irvine, CA) in patients with atopic history, including those with active flare and the comparative efficacy of CeraVe Itch Relief Cream to hydrocortisone 1% cream and night-time itch relief with continued use. Methods: Two double-blind, split-body, randomized studies in 66 male and female subjects, ages 11+ years, with history of atopic dermatitis (AD). Itch severity was assessed on a 10-point scale (where 0=none and 7-9=severe). Study one: single applications of ceramide-containing lotion or cream incorporating 1% pramoxine hydrochloride applied to opposite sides of the body. Study two (part 1): single application of ceramide-containing cream or hydrocortisone 1% cream. Study two (part 2): ceramide-containing pramoxine cream applied up to 4 times in a 24-h period, over the course of 6 days. Itch relief assessed at baseline, 2, and 5 min, 1 (2 in study two), 4, and 8 h post-application. Efficacy and aesthetic attributes were assessed at the same timepoints. Clin. evaluation of performance and mildness of the ceramide-containing 1% pramoxine hydrochloride cream at day 6 (study two, part 2). Results: Study one: Relief of itching was rapid and long-lasting with significant reductions in severity after 2 min, and continued improvement over the 8 h test period (P <than.001 vs. baseline at all timepoints). Mean itch severity scores reduced progressively from 6 (moderate) at baseline to 1-2 (mild) after 8 h, with all patients experiencing relief from itching. Rapid and long-lasting relief to dry, itchy, irritated skin was confirmed through patient self-assessment. Both lotion and cream formulations were non-greasy, absorbed quickly and easily, and were non-irritating. Study two: Ceramide-containing cream incorporating 1% pramoxine hydrochloride provided comparable improvement in itch relief (24.6% reduction in mean itch severity 2 min post-application, and 58.0% reduction 8 h post-application) compared to hydrocortisone cream 1% (18.5% reduction and 59.7% reduction, resp.). Daily use of the ceramide-containing 1% pramoxine cream over 6-days provided all-night relief (87.5% agreement), and perception of skin looking and feeling healthier with each use (71.9% and 81.3% agreement, resp.). Limitations: Results of study one and subsequent comparative study with hydrocortisone 1% cream are based on a single application. There were no placebo controls. Conclusions: Ceramide-containing lotion or cream containing 1% pramoxine provides both rapid and long-lasting relief of itching following a single application in atopic patients with or without active flare. Both formulations were well tolerated with aesthetic appeal. Comparable itch relief to hydrocortisone 1% cream was seen with the ceramide-containing cream over an 8-h period following a single application. Further ceramide-containing 1% pramoxine hydrochloride cream was well tolerated with continued use over 6 days, delivering comfort and all-night relief for patients with atopic history suffering from reoccurrant itching.

Journal of Drugs in Dermatology published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C6H12F3NO5S, Formula: C17H28ClNO3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Yerien, Damian E. published the artcileRose Bengal-photocatalyzed perfluorohexylation reactions of organic substrates in water. Applications to late-stage syntheses, Application In Synthesis of 91-16-7, the publication is Photochemical & Photobiological Sciences (2022), 21(5), 803-812, database is CAplus and MEDLINE.

Rose Bengal-photocatalyzed perfluorohexylation of olefins, alkynes and electron-rich aromatic compounds in water was achieved employing perfluorohexyl iodide as fluoroalkyl source and TMEDA as sacrificial donor under green LED irradn to afford perfluoro compounds R¹CHICH₂C₆F₁₃ [R¹ = CH₂OPh, CHOH(CH₂)₅], R²HC=CHC₆F₁₃ [R² = Ph, n-pentyl, (D)-(-)Norgestreyl] and I [R³ = 4-Me, 4-NO₂, 2,6-(Me)₂, etc.; R⁴ = OMe, NH₂]. Alkenes and alkynes rendered products derived from the atom transfer radical addition (ATRA) pathway, and in the case of alkynes, exclusively as E-stereoisomers. These were the first examples of photocatalyzed ATRA reactions carried out excursively in water alone. The reactions of aromatic compounds under the current protocol in water present the advantage of employing a perfluoroalkyl iodide (C₆F₁₃-I) as source of perfluorohexyl radicals. Examples of photocatalytic late-stage incorporations of fluoroalkyl moieties into two com. drugs of widespread used were reported.

Photochemical & Photobiological Sciences published new progress about 91-16-7. 91-16-7 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether,Inhibitor,Inhibitor,Inhibitor, name is 1,2-Dimethoxybenzene, and the molecular formula is C2H10Cl2N2, Application In Synthesis of 91-16-7.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Singh, Bara published the artcilePd-Catalyzed Nazarov-Type Cyclization: Application in the Total Synthesis of β-Diasarone and Other Complex Cyclopentanoids, Synthetic Route of 91-16-7, the publication is Organic Letters (2022), 24(4), 1043-1048, database is CAplus and MEDLINE.

Author describe the palladium-catalyzed Nazarov-type cyclization of easily accessible (hetero)arylallyl acetates to pentannulated (hetero)arenes. This method provides ready access to various types of bi-, tri-, tetra-, and pentacyclic cyclopentanoids under neutral conditions. The synthetic utility is further demonstrated in the first total synthesis of β-diasarone (I) and several other complex cyclopentanoids relevant to medicinal chem. and materials science.

Organic Letters published new progress about 91-16-7. 91-16-7 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether,Inhibitor,Inhibitor,Inhibitor, name is 1,2-Dimethoxybenzene, and the molecular formula is C5H10N2OS, Synthetic Route of 91-16-7.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Dubois, Jacques Emile published the artcileElectrophilic aromatic substitution. Bromination of methoxybenzenes. Evaluation of steric effect of bulky alkyl substituents, Synthetic Route of 2944-47-0, the publication is Nouveau Journal de Chimie (1981), 5(1), 33-8, database is CAplus.

Bulky alkyl group steric effects on substituted methoxybenzenes are quant. determined as the difference between exptl. bromination rate constants and those calculated by taking into account electronic effects only. Two kinds of results are observed For di- or trisubstituted compounds, no steric inhibition to the transmission of Me or MeO group electronic effects is observed when these substituents are flanked in a vicinal position by an Me₂CH or Me₃C group. In contrast, important steric effects are observed for 4,5,2-Me₂(Me₂CH)C₆H₂OMe and for the ortho position (to the OMe group) in o-Me₃C C₆H₄OMe.

Nouveau Journal de Chimie published new progress about 2944-47-0. 2944-47-0 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 2-Isopropylanisole, and the molecular formula is C10H14O, Synthetic Route of 2944-47-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Bann, Samantha J. published the artcileA chemical-intervention strategy to circumvent peptide hydrolysis by D-stereoselective peptidases, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Journal of Medicinal Chemistry (2019), 62(22), 10466-10472, database is CAplus and MEDLINE.

D-Stereoselective peptidases that degrade nonribosomal peptides (NRPs) were recently discovered and could have serious implications for the future of NRPs as antibiotics. Herein, we report chem. modifications that can be used to impart resistance to the D-peptidases BogQ and TriF. New tridecaptin A analogs were synthesized that retain strong antimicrobial activity and have significantly enhanced D-peptidase stability. Invitro assays confirmed that synthetic analogs retain the ability to bind to their cellular receptor, peptidoglycan intermediate lipid II.

Journal of Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Bolt, Yaroslav V. published the artcileNovel Benzothiophene-Based Fluorescent Dye Exhibiting a Large Stokes Shift, Name: 1,2-Dimethoxybenzene, the publication is Synlett (2021), 32(20), 2059-2062, database is CAplus.

We report a simple two-step method for the synthesis of a novel highly fluorescent benzothiophene-based dye comprising five fused rings and exhibiting a large Stokes shift (Δλ = 152 nm or Δν = 5482 cm^-1 in ethanol). Structural features of the obtained compound allow easy functionalization of the carbon core and open new possibility for the development of a series of new classes of fluorescent dyes.

Synlett published new progress about 91-16-7. 91-16-7 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether,Inhibitor,Inhibitor,Inhibitor, name is 1,2-Dimethoxybenzene, and the molecular formula is C8H10O2, Name: 1,2-Dimethoxybenzene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem