Category: 52244-70-9

Das, Arup Jyoti; Das, Sajal Kumar published the artcile< One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds>, Electric Literature of 52244-70-9, the main research area is tetrahydronaphthothiochromene hexahydrobenzophenanthrene preparation diastereoselective; arylthiomethylbutanal Friedel Crafts hydroxyalkylation alkylation cascade.

Presented herein is a BF3·OEt2-mediated, diastereoselective one-pot double cyclization of 4-aryl-2-[(arylthio)methyl]butanals leading to the formation of cis-tetrahydro-6H-naphtho[2,1-c]thiochromenes for the first time. Mechanistically, the formation of the title products involves the one-pot intramol. Friedel-Crafts hydroxyalkylation/intramol. Friedel-Crafts alkylation cascade. This synthetic methodol. is featured by its high atom economy, broad substrate scope, mild transition-metal-free reaction conditions, capability to assemble two new rings in one pot, and moderate to high yields (up to 94% yield). It was then applied in the synthesis of a thia analog of brazilane and a chromeno[3,4-c]chromene derivative Moreover, the methodol. was successfully extended to the synthesis of cis-hexahydrobenzo[c]phenanthrenes. Specifically, 1,5-diarylpentan-3-ones were first subjected to the Corey-Chaykovsky reaction, and the resulting epoxides, without being chromatog. isolated, were treated with BF3·OEt2 to afford the cyclized products in high yields (up to 84% yield over two steps).

Journal of Organic Chemistry published new progress about Chromans Role: SPN (Synthetic Preparation), PREP (Preparation) (thio-). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Electric Literature of 52244-70-9.

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

Wang, Gary T.; Lane, Ben; Fesik, Stephen W.; Petros, Andrew; Luly, Jay; Krafft, Grant A. published the artcile< Synthesis and FKBP binding of small molecule mimics of the tricarbonyl region of FK506>, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol, the main research area is FK506 glyoxylpipecolate moiety protein binding.

Small acyclic model compounds were synthesized to examine the importance of the C(9) carbonyl group of FK506 for FKBP binding. 4-(4′-Methoxyphenyl)-1-Bu (3”,4”,5”-trimethoxyphenylglyoxyl)pipecolate, containing the N-(glyoxyl)pipecolate motif of FK506, was found to bind to FKBP with IC50 of 16 μM. Replacement of the carbonyl group at the position corresponding to C(9) of FK506 with small nonpolar groups (hydrogen, methylene or Me group) significantly reduced the binding affinity.

Bioorganic & Medicinal Chemistry Letters published new progress about FK506-binding proteins Role: BIOL (Biological Study). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol.

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

Poon, Kevin W. C.; Dudley, Gregory B. published the artcile< Mix-and-Heat Benzylation of Alcohols Using a Bench-Stable Pyridinium Salt>, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol, the main research area is alc benzylation pyridinium triflate; ether benzyl preparation.

2-Benzyloxy-1-methylpyridinium triflate (I) is a stable, neutral organic salt that converts alcs. into benzyl ethers upon warming. The synthesis and reactivity of I are described herein. Benzylation of a wide range of alcs. occurs in good to excellent yields.

Journal of Organic Chemistry published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol.

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

Li, Yangyang; Li, Yuqiang; Peng, Long; Wu, Dong; Zhu, Lei; Yin, Guoyin published the artcile< Nickel-catalyzed migratory alkyl-alkyl cross-coupling reaction>, Related Products of 52244-70-9, the main research area is alkyl halide migratory cross coupling bond formation nickel catalyst.

A migratory cross-coupling strategy, which can overcome this obstacle to access the desired cross-coupling products ArCH(R)(CH2)nCR1R2R3 (Ar = Ph, 4-fluorophenyl, indol-3-yl, etc.; R = cyclopentyl, cyclohexyl, cycloheptyl, N-benzyl-piperidin-4-yl, 2-methyl-propan-1-yl; R1 = H, D; R2 = H, D; R3 = H; n = 0-3, 5), 1-cyclopentyl-indan, 1-cycloheptyl-indan, (1-cyclopentyl-3-methyl-pentyl)benzene was described. Accordingly, a selective migratory cross-coupling of two alkyl electrophiles (RBr, ArCH(R)(CH2)nCR1R2R3 (R3 = Br or Cl), 2-bromoindan, (5-bromo-1-cyclopentyl-3-methyl-pentyl)benzene) has been accomplished by nickel catalysis. Remarkably, this alkyl-alkyl cross-coupling reaction provides a platform to prepare 2°-2° carbon-carbon bonds from 1° and 2° carbon coupling partners. Preliminary mechanistic studies suggest that chain-walking occurs at both alkyl halides in this reaction, thus a catalytic cycle with the key step involving two alkylnickel(II) species is proposed for this transformation.

Chemical Science published new progress about Aromatic hydrocarbons Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Related Products of 52244-70-9.

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

Hirsh, Andrew J.; Molino, Bruce F.; Zhang, Jianzhong; Astakhova, Nadezhda; Geiss, William B.; Sargent, Bruce J.; Swenson, Brian D.; Usyatinsky, Alexander; Wyle, Michael J.; Boucher, Richard C.; Smith, Rick T.; Zamurs, Andra; Johnson, M. Ross published the artcile< Design, Synthesis, and Structure-Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers: Drugs for Cystic Fibrosis and Chronic Bronchitis>, Application In Synthesis of 52244-70-9, the main research area is pyrazinoylguanidine epithelial sodium channel blocker preparation.

Amiloride, the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogs of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent short-circuit current than amiloride. Compounds I [R = NH(CH2)4C6H4O(CH2)2OH-4, NH(CH2)4C6H4O(CH2)3OH-4, NH(CH2)4C6H4OCH2CH(OH)CH2OH-4 (both R and S isomers)] showed the greatest potency on ENaC with IC50 values below 10 nM. A regioselective difference in potency was found, whereas no stereospecific difference in potency on ENaC was displayed. Lead compound I [R = NH(CH2)4C6H4OCH2CH(OH)CH2OH-4 (racemic)] was 102-fold more potent and 5-fold less reversible than amiloride and displayed the lowest IC50 value ever reported for an ENaC blocker.

Journal of Medicinal Chemistry published new progress about Chronic bronchitis. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Application In Synthesis of 52244-70-9.

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

Liu, Yu; Cornella, Josep; Martin, Ruben published the artcile< Ni-Catalyzed Carboxylation of Unactivated Primary Alkyl Bromides and Sulfonates with CO2>, Application of C11H16O2, the main research area is nickel catalyzed carboxylation primary alkyl bromide sulfonate carbon dioxide; carboxylic acid synthesis.

A Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2 at atm. pressure is described. The method is characterized by its mild conditions and remarkably wide scope without the need for air- or moisture-sensitive reagents, which make it a user-friendly and operationally simple protocol en route to carboxylic acids. Thus, e.g., reductive carboxylation 1-bromo-6-(4-methoxyphenyl)hexane using NiCl2.glyme, 2,9-diethyl-1,10-phenanthroline ligand, Mn as reducing agent and CO2 afforded 7-(4-methoxyphenyl)heptanoic acid in 76% isolated yield.

Journal of the American Chemical Society published new progress about Bromoalkanes Role: RCT (Reactant), RACT (Reactant or Reagent) (primary). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Application of C11H16O2.

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

Nagasawa, Shota; Sasano, Yusuke; Iwabuchi, Yoshiharu published the artcile< Catalytic Oxygenative Allylic Transposition of Alkenes into Enones with an Azaadamantane-Type Oxoammonium Salt Catalyst>, Category: ethers-buliding-blocks, the main research area is allylic transposition oxygenative alkene azaadamantane type oxoammonium salt catalyst; enone preparation catalytic oxygenative allylic transposition alkene; alkenes; enones; organocatalysis; oxygenation; synthetic methods.

The first catalytic oxygenative allylic transposition of unactivated alkenes, e.g., Me2C:CH2(CH2)3OCOPh, into enones, e.g., H2C:C(Me)CO(CH2)3OCOPh, has been developed using an oxoammonium salt, azaadamantane I, as the catalyst. This reaction converts various tri- and trans-disubstituted alkenes into their corresponding enones with transposition of their double bonds at ambient temperature in good yields. The use of a less-hindered azaadamantane-type oxoammonium salt as the catalyst and a combination of two distinct stoichiometric oxidants, namely, iodobenzene diacetate and magnesium monoperoxyphthalate hexahydrate (MMPP·6H2O) are essential to facilitate the enone formation efficiently.

Chemistry – A European Journal published new progress about Alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Category: ethers-buliding-blocks.

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

McCalmont, William F.; Patterson, Jaclyn R.; Lindenmuth, Michael A.; Heady, Tiffany N.; Haverstick, Doris M.; Gray, Lloyd S.; Macdonald, Timothy L. published the artcile< Investigation into the structure-activity relationship of novel concentration dependent, dual action T-type calcium channel agonists/antagonists>, Synthetic Route of 52244-70-9, the main research area is structure activity calcium channel antagonist antitumor.

This paper describes the synthesis and biol. evaluation of a series of straight chain analogs of a compound (1) that was previously synthesized in our research program. These compounds, which are T-type calcium channel antagonists, exhibits potent anti-proliferative activity against a variety of cancer cells. A structure-activity relationship of these analogs against a variety of cancer cells has provided insight into a logical pharmacophore for this series of compounds Furthermore, this series of compounds has presented itself as a set of novel, concentration dependent, dual action agonists/antagonists for the T-type calcium channel.

Bioorganic & Medicinal Chemistry published new progress about Antitumor agents. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Synthetic Route of 52244-70-9.

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

Li, Zijian; Sun, Wenxuan; Wang, Xianxu; Li, Luyang; Zhang, Yong; Li, Chao published the artcile< Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides>, Computed Properties of 52244-70-9, the main research area is alkyl benzene aryl preparation electrochem; alc aryl bromide dehydroxylative cross coupling nickel catalyst.

As alcs. are ubiquitous throughout chem. science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, it is demonstrated that the combination of anodic preparation of alkoxy triphenylphosphonium ion and nickel catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp2)-C(sp3) bonds, in which free alcs. and aryl bromides e.g., bromobenzene-both readily available chems. can be directly used as coupling partners yielding arene derivative e.g., I. This nickel catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.

Journal of the American Chemical Society published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Computed Properties of 52244-70-9.

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

Sooriyaarachchi, Sanjeewani; Chofor, Rene; Risseeuw, Martijn D. P.; Bergfors, Terese; Pouyez, Jenny; Dowd, Cynthia S.; Maes, Louis; Wouters, Johan; Jones, T. Alwyn; Van Calenbergh, Serge; Mowbray, Sherry L. published the artcile< Targeting an aromatic hotspot in Plasmodium falciparum 1-deoxy-D-xylulose-5-phosphate reductoisomerase with β-arylpropyl analogues of fosmidomycin>, Computed Properties of 52244-70-9, the main research area is fosmidomycin arylpropyl analog preparation deoxyxylulose phosphate reductoisomerase Plasmodium targeting; antibiotics; antiprotozoal agents; oxidoreductases; structural biology; structure-activity relationships.

Blocking the 2-C-methyl-D-erythritol-4-phosphate pathway for isoprenoid biosynthesis offers new ways to inhibit the growth of Plasmodium spp. Fosmidomycin [(3-(N-hydroxyformamido)propyl)phosphonic acid] and its acetyl homolog, FR-900098 [(3-(N-hydroxyacetamido)propyl)phosphonic acid], potently inhibit 1-deoxy-D-xylulose-5-phosphate reductoisomerase, a key enzyme in this biosynthetic pathway. Here, arylpropyl substituents were introduced at the β-position of the hydroxamate analog of FR-900098 to study changes in lipophilicity, as well as electronic and steric properties. The potency of several new compounds on the P. falciparum enzyme approached that of fosmidomycin and FR-900098. Activities against the enzyme and parasite correlated well, supporting the mode of action. Seven x-ray structures showed that all of the new arylpropyl substituents displaced a key Trp residue of the active site flap, which had made favorable interactions with fosmidomycin and FR-900098. The plasticity of the flap allowed substituents to be accommodated in many ways; in most cases, the flap was largely disordered. The prepared compounds could be separated into 2 classes based on whether the substituent on the aromatic ring was at the meta or para position. Generally, meta-substituted compounds were better inhibitors, and in both classes, smaller size was linked to better potency.

ChemMedChem published new progress about Crystal growth. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Computed Properties of 52244-70-9.

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