Category: 56724-03-9

Awad, Tamer; De Ruiter, Jack; Clark, C. Randall published the artcile< Gas chromatography-mass spectrometry analysis of regioisomeric ring substituted methoxy methyl phenylacetones>, Reference of 56724-03-9, the main research area is regioisomeric ring substituted methoxy methyl phenylacetone GC mass spectrometry.

The methoxy Me phenylacetones share an isobaric relation (equivalent mass but different elemental composition) to the controlled precursor substance 3,4-methylenedioxyphenylacetone. The 10 methoxy Me phenylacetones as well as the methylenedioxyphenylacetones show essentially equivalent mass spectra with major fragment ions at m/z 135 and 43. Those methoxy Me phenylacetones with the methoxy group substituted ortho to the benzylic cation in the m/z 135 ion show a further fragmentation to lose formaldehyde (CH2O) and yield a significant ion at m/z 105. The loss of formaldehyde from the ortho methoxy benzyl cation was confirmed using com. available regioisomeric 2-, 3-, and 4-methoxyphenylacetones. The 10 regioisomeric methoxy Me phenylacetones were prepared from the appropriately substituted benzaldehydes. Complete gas chromatog. resolution of all ten regioisomeric ketones was obtained on a stationary phase containing modified β-cyclodextrin. Using the cyclodextrin containing phase, the ortho methoxy-substituted ketones (K1-K4) eluted before the meta-methoxy-substituted ketones (K5-K8) and the para-methoxy-substituted ketones (K9-K10) showed the greatest affinity for the stationary liquid phase and eluted last. Complete separation of the 10 ketones was not obtained on Rtx-1 and Rtx-200 columns. (c) 2007 Preston Publications.

Journal of Chromatographic Science published new progress about Fragmentation reaction. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Reference of 56724-03-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Resch, Verena; Lechner, Horst; Schrittwieser, Joerg H.; Wallner, Silvia; Gruber, Karl; Macheroux, Peter; Kroutil, Wolfgang published the artcile< Inverting the Regioselectivity of the Berberine Bridge Enzyme by Employing Customized Fluorine-Containing Substrates>, Name: 3-Methoxy-2-methylbenzaldehyde, the main research area is fluorine substrate preparation regiochem berberine bridge enzyme.

Fluorine is commonly applied in pharmaceuticals to block the degradation of bioactive compounds at a specific site of the mol. Blocking of the reaction center of the enzyme-catalyzed ring closure of 1,2,3,4-tetrahydrobenzylisoquinolines by a fluoro moiety allowed redirecting the berberine bridge enzyme (BBE)-catalyzed transformation of these compounds to give the formation of an alternative regioisomeric product, namely 11-hydroxy-functionalized tetrahydroprotoberberines instead of the commonly formed 9-hydroxy-functionalized products. Alternative strategies to change the regioselectivity of the enzyme, such as protein engineering, were not applicable in this special case due to missing substrate-enzyme interactions. Medium engineering, as another possible strategy, had clear influence on the regioselectivity of the reaction pathway, but did not lead to perfect selectivity. Thus, only substrate tuning by introducing a fluoro moiety at one potential reactive carbon center switched the reaction to the formation of exclusively one regioisomer with perfect enantioselectivity.

Chemistry – A European Journal published new progress about Enzyme functional sites, active. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Name: 3-Methoxy-2-methylbenzaldehyde.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Plaumann, H. P.; Keay, B. A.; Rodrigo, R. published the artcile< The regiospecific lithiation of aromatic acetals>, Name: 3-Methoxy-2-methylbenzaldehyde, the main research area is lithiation aromatic acetal regioselective; substituent effect lithiation aromatic acetal; deprotonation aromatic acetal substituent effect; benzaldehyde ortho substituted.

The reaction of 11 di-Me aromatic acetals with alkyllithiums are described. In compounds with substituents ortho to the acetal very little deprotonation occurred, whereas with no substituent present lithiation occurred readily. E.g., I (R = H, R1 = OMe) with Me3CLi (-23°), MeI, and acid gave 95% II, whereas no reaction occurred when I (R = OMe, R1 = H) was treated similarly. The reaction provides a facile entry to 2,3- and 2,3,4-substituted benzaldehydes.

Tetrahedron Letters published new progress about Aryl aldehydes Role: SPN (Synthetic Preparation), PREP (Preparation). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Name: 3-Methoxy-2-methylbenzaldehyde.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zarenezhad, Elham; Montazer, Mohammad Nazari; Tabatabaee, Masoumeh; Irajie, Cambyz; Iraji, Aida published the artcile< New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches>, Application In Synthesis of 56724-03-9, the main research area is biscoumarin derivative synthesis solid phase methodol silico approach; Biscoumarin; MM-GBSA; MoO3-nanoparticle; Molecular dynamics simulations.

The simple and greener one-pot approach for the synthesis of biscoumarin derivatives using catalytic amounts of nano-MoO3 catalyst under mortar-pestle grinding was described. The use of non-toxic and mild catalyst, cost-effectiveness, ordinary grinding, and good to the excellent yield of the final product makes this procedure a more attractive pathway for the synthesis of biol. remarkable pharmacophores. Accordingly, biscoumarin derivatives were successfully extended in the developed protocols. Next, a computational investigation was performed to identify the potential biol. targets of this set of compounds In this case, first, a similarity search on different virtual libraries was performed to find an ideal biol. target for these derivatives Results showed that the synthesized derivatives can be α-glucosidase inhibitors. In another step, mol. docking studies were carried out against human lysosomal acid-alpha-glucosidase (PDB ID: 5NN8) to determine the detailed binding modes and critical interactions with the proposed target. In silico assessments showed the gold score value in the range of 17.56 to 29.49. Addnl., mol. dynamic simulations and the MM-GBSA method of the most active derivative against α-glucosidase were conducted to study the behavior of selected compounds in the biol. system. Ligand 1 stabilized after around 30 ns and participated in various interactions with Trp481, Asp518, Asp616, His674, Phe649, and Leu677 residues.

BMC Chemistry published new progress about Bond angle. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Application In Synthesis of 56724-03-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Son, Eun Chae; Kim, Seung Yeon; Kim, Sung-Gon published the artcile< Squaramide-Catalyzed Asymmetric Intramolecular Oxa-Michael Reaction of α,β-Unsaturated Carbonyls Containing Benzyl Alcohol: Construction of Chiral 1-Substituted Phthalans>, Quality Control of 56724-03-9, the main research area is hydroxymethylphenylalkenyl carbonyl compound squaramide organocatalyst intramol oxa Michael reaction; dihydroisobenzofuranyl carbonyl compound enantioselective preparation.

Using cinchona squaramide-based organocatalyst, enones as well as α,β-unsaturated esters containing benzyl alc. provided their corresponding 1,3-dihydroisobenzofuranyl-1-methylene ketones and 1,3-dihydroisobenzofuranyl-1-methylene esters in excellent yields with high enantioselectivities. In addition, enantioenriched 1,3-dihydroisobenzofuranyl-1-methylene ketone obtained from the Wittig/oxa-Michael reaction cascade of 1,3-dihydro-2-benzofuran-1-ol.

Journal of Organic Chemistry published new progress about Aralkyl alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Quality Control of 56724-03-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Satish, Sohal; Chitral, Rohan; Kori, Amitkumar; Sharma, Basantkumar; Puttur, Jayashree; Khan, Afreen A.; Desle, Deepali; Raikuvar, Kavita; Korkegian, Aaron; Martis, Elvis A. F.; Iyer, Krishna R.; Coutinho, Evans C.; Parish, Tanya; Nandan, Santosh published the artcile< Design, synthesis and SAR of antitubercular benzylpiperazine ureas>, Name: 3-Methoxy-2-methylbenzaldehyde, the main research area is piperazine carboxamide preparation tuberculostatic SAR antibacterial antitumor docking; Antitubercular; Benzylpiperazine ureas; Lead compounds; QcrB inhibitors.

N-furfuryl piperazine ureas disclosed by scientists at GSK Tres Cantos were chosen as antimycobacterial hits from a phenotypic whole-cell screen. Bioisosteric replacement of the furan ring in the GSK Tres Cantos mols. with a Ph ring led to mol. I with an MIC of 1μM against Mtb H37Rv, low cellular toxicity (HepG2 IC50 ∼ 80μM), good DMPK properties and specificity for Mtb. With the aim of delineating the SAR associated with compound I, fifty-five analogs were synthesized and screened against Mtb. The SAR suggested that the piperazine ring, benzyl urea and piperonyl moieties were essential signatures of this series. Active compounds in this series were metabolically stable, have low cellular toxicity and were valuable leads for optimization. Mol. docking suggests these mols. occupy the Q0 site of QcrB like Q203.

Molecular Diversity published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Name: 3-Methoxy-2-methylbenzaldehyde.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Flippin, Lee A.; Berger, Jacob; Parnes, Jason S.; Gudiksen, Mark S. published the artcile< Effect of the Substitution Pattern on Reactions of Methoxylated Araldehyde 2,4-Dimethyl-3-pentylimines with Organolithium Reagents>, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde, the main research area is methoxyphenylmethylenepentanamine butylation phenylation; substitution effect lithiation araldehyde methylpentylimine; metalation regioselective araldimine; imine methoxybenzaldehyde lithiation substitution effect.

Araldehyde imines, e.g., N-[(methoxyphenyl)methylene]dimethyl-3-pentanamines I (R, R1, R2 = H, OMe) reacted with BuLi via facile nucleophilic aromatic substitution to give benzaldehydes II. Exceptions to this trend were observed when the araldimine substrate contained methoxy groups at both C-2 and C-5. Thus, the 2,5-dimethoxy analog of I reacted with BuLi – followed by MeI quench and acid hydrolysis – to give a complex aldehyde mixture derived from metalation and SNAr processes, e.g. 3,6-dimethoxy-2-methylbenzaldehyde and 2-butyl-5-methoxybenzaldehyde, whereas the 2,4,5-trimethoxy analog of I under identical conditions, gave exclusive metalation and electrophilic capture at C-6 to give 3,4,6-trimethoxy-2-methylbenzaldehyde in 83% yield. Araldehyde 2,4-dimethyl-3-pentylimines that cannot undergo an SNAr reaction are potential candidates for directed metalation reactions although this usage is limited by occasional unwanted side-reactions, lack of selectivity or reactivity, and unpredictability.

Journal of Organic Chemistry published new progress about Alkylation. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Sano, H.; Nishimura, J. published the artcile< Product class 11: dimethylenecyclobutenes and quinodimethanes>, Name: 3-Methoxy-2-methylbenzaldehyde, the main research area is review dimethylene cyclobutene preparation organic synthesis; quinodimethane preparation organic synthesis review.

A review of methods to prepare dimethylenecyclobutenes and quinodimethanes.

Science of Synthesis published new progress about Cycloalkenes Role: SPN (Synthetic Preparation), PREP (Preparation) (dimethylene-). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Name: 3-Methoxy-2-methylbenzaldehyde.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Herdman, Christine A.; Devkota, Laxman; Lin, Chen-Ming; Niu, Haichan; Strecker, Tracy E.; Lopez, Ramona; Liu, Li; George, Clinton S.; Tanpure, Rajendra P.; Hamel, Ernest; Chaplin, David J.; Mason, Ralph P.; Trawick, Mary Lynn; Pinney, Kevin G. published the artcile< Structural interrogation of benzosuberene-based inhibitors of tubulin polymerization>, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde, the main research area is preparation benzosuberene tubulin polymerization inhibitor.

The discovery of 3-methoxy-9-(3′,4′,5′-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulen-4-ol (a benzosuberene-based analog referred to as KGP18) was originally inspired by the natural products colchicine and combretastatin A-4 (CA4). The relative structural simplicity and ease of synthesis of KGP18, coupled with its potent biol. activity as an inhibitor of tubulin polymerization and its cytotoxicity (in vitro) against human cancer cell lines, has resulted in studies focused on new analog design and synthesis. The goal was to probe the relationship of structure to function in this class of anticancer agents. A series of twenty-two new benzosuberene-based analogs of KGP18 was designed and synthesized. These compounds vary in their methoxylation pattern and sep. incorporate trifluoromethyl groups around the pendant aryl ring for the evaluation of the effect of functional group modifications on the fused six-membered aromatic ring. In addition, the 8,9-saturated congener of KGP18 has been synthesized to assess the necessity of unsaturation at the carbon atom bearing the pendant aryl ring. Six of the mols. from this benzosuberene-series of compounds were active (IC50 < 5 μM) as inhibitors of tubulin polymerization while four analogs were comparable (IC50 approx. 1 μM) in their tubulin inhibitory activity to CA4 and KGP18. The potency of a bis-trifluoromethyl analog I and the unsaturated KGP18 derivative II as inhibitors of tubulin assembly along with their moderate cytotoxicity suggested the potential utility of these compounds as vascular disrupting agents (VDAs) to selectively target microvessels feeding tumors. Accordingly, water-soluble and DMSO-soluble phosphate prodrug salts of each were synthesized for preliminary in vivo studies to assess their potential efficacy as VDAs. Bioorganic & Medicinal Chemistry published new progress about Antitumor agents. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Boutin, Sophie; Maltais, Rene; Roy, Jenny; Poirier, Donald published the artcile< Synthesis of 17β-hydroxysteroid dehydrogenase type 10 steroidal inhibitors: Selectivity, metabolic stability and enhanced potency>, Application In Synthesis of 56724-03-9, the main research area is androstane D ring derivative preparation HSD10 inhibitor; 17β-HSD10; Alzheimer disease; Enzyme; Inhibitor; Solid-phase synthesis; Steroid.

17Beta-Hydroxysteroid dehydrogenase type 10 (17β-HSD10) is the only mitochondrial member of 17β-HSD family. This enzyme can oxidize estradiol (E2) into estrone (E1), thus reducing concentration of this neuroprotective steroid. Since 17β-HSD10 possesses properties that suggest a possible role in Alzheimer’s disease, its inhibition appears to be a therapeutic strategy. After we identified the androsterone (ADT) derivative I as a first steroidal inhibitor of 17β-HSD10, new analogs were synthesized to increase the metabolic stability, to improve the selectivity of inhibition over 17β-HSD3 and to optimize the inhibitory potency. From six D-ring derivatives of I (17-C=O), two compounds (17β-H/17α-OH and 17β-OH/17α-CCH) were more metabolically stable and did not inhibit the 17β-HSD3. Moreover, solid phase synthesis was used to extend the mol. diversity on the 3β-piperazinylmethyl group of the steroid base core. Eight over 120 new derivatives were more potent inhibitors than I for the transformation of E2 to E1, with the 4-(4-trifluoromethyl-3-methoxybenzyl)piperazin-1-ylmethyl-ADT (D-3,7) being 16 times more potent (IC50 = 0.14μM). Finally, D-ring modification of D-3,7 provided 17β-OH/17α-CCH derivative and 17β-H/17α-OH derivative, which were more potent inhibitor than I (1.8 and 2.4 times, resp.).

European Journal of Medicinal Chemistry published new progress about Alzheimer disease. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Application In Synthesis of 56724-03-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem