2461-35-0

Upstream product

• 93-59-4 Perbenzoic acid 
• 612-17-9 1,4-dihydronaphthalene 
• 91-20-3 naphthalene 
• 103039-11-8 1,2,3,4-tetrahydronaphthalene-2,3-chlorohydrin 
• 178151-72-9 (2R,3R)-2,3-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 426262-28-4 (2R,3R)-2-p-toluenesulphonyloxy-3-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 426262-33-1 (2R,3R)-2-methanesulphonyloxy-3-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 144-55-8 sodium hydrogencarbonate 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 101751-92-2 (2α,3β)-2-Hydroxy-3-bromo-1,2,3,4-tetrahydronaphthalene 
• 103038-41-1 3-bromo-1,2,3,4-tetrahydro-[2]naphthol 
• 2311-91-3 monoperoxyphthalic acid 

Downstream Products

• 109404-82-2 (+/-)-trans-3-(toluene-4-sulfonyloxy)-1,2,3,4-tetrahydro-[2]naphthol 
• 78720-79-3 trans-3-aminotetralin-2-ol 
• 37414-44-1 indan-2-carbaldehyde 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 89357-92-6 trans-2-methoxy-3-phenylseleno-1,2,3,4-tetrahydronaphthalene 
• 102749-32-6 (+/-)-trans-2,3-bis-(toluene-4-sulfonyloxy)-1,2,3,4-tetrahydro-naphthalene 
• 1116119-83-5 (2S,3S)-3-phenylthio-1,2,3,4-tetrahydro-2-naphthalenol 
• 41597-55-1 trans-(2RS,3RS)-1,2,3,4-tetrahydronaphthalene-2,3-diol 
• 91-20-3 naphthalene 
• 7732-18-5 water 
• 84587-64-4 1-n-propyl-1,4-dihydronaphthalene 
• 530-91-6 1,2,3,4-tetrahydronaphthalen-2 ol 

Relevant academic research and scientific papers

Cytochrome p450 can epoxidize an oxepin to a reactive 2,3-epoxyoxepin intermediate: Potential insights into metabolic ring-opening of benzene

Dimethyldioxirane epoxidizes 4,5-benzoxepin to form the reactive 2,3-epoxyoxepin intermediate followed by very rapid ring-opening to an o-xylylene that immediately isomerizes to the stable product 1H-2-benzopyran-1-carboxaldehyde. The present study demonstrates that separate incubations of 4,5-benzoxepin with three cytochrome P450 isoforms (2E1, 1A2, and 3A4) as well as pooled human liver microsomes (pHLM) also produce 1H-2-benzopyran-1-carboxaldehyde as the major product, likely via the 2,3-epoxyoxepin. The reaction of 4,5-benzoxepin with cerium (IV) ammonium nitrate (CAN) yields a dimeric oxidized molecule that is also a lesser product of the P450 oxidation of 4,5-benzoxepin. The observation that P450 enzymes epoxidize 4,5-benzoxepin suggests that the 2,3-epoxidation of oxepin is a major pathway for the ring-opening metabolism of benzene to muconaldehyde.

Asymmetric synthesis of azolium-based 1,2,3,4-tetrahydronaphthalen-2-ols through lipase-catalyzed resolutions

Abstract A series of racemic trans-1,2,3,4-tetrahydronaphthalen-2-ols bearing an azole nucleus at the C-1 or C-3 position has been synthesized by ring opening reactions of the corresponding epoxides using imidazole or 1,2,4-triazole. The kinetic resolutions of these racemates were undertaken through transesterification processes, finding good levels of activities and high to excellent enantiodiscrimination values for the Pseudomonas cepacia lipase immobilized on a ceramic carrier. Investigations into the optimum reaction conditions were carried out by consideration of different organic solvents, temperatures, enzyme loadings, and reaction times. With the best conditions in hand, the experiments were later carried out toward the resolution of the related racemic cis-alcohols, which were previously obtained through a Mitsunobu and deprotection chemical sequence from the trans-stereoisomers.

Synthesis and labeling of a piperazine-based library of 11C-labeled ligands for imaging of the vesicular acetylcholine transporter

The cholinergic system is involved in neurodegenerative diseases, and visualization of cholinergic innervations with positron emission tomography (PET) would be a useful tool in understanding these diseases. A ligand for the vesicular acetylcholine transporter (VAChT), acknowledged as a marker for cholinergic neurons, could serve as such a PET tracer. The aim was to find a VAChT PET tracer using a library concept to create a small but diverse library of labeled compounds. From the same precursor and commercially available aryl iodides 6a-f, six potential VAChT PET tracers, [11C]-(±)5a-f, were 11C-labeled by a palladium (0)-mediated aminocarbonylation, utilizing a standard protocol. The labeled compounds [11C]-(±) 5a-f were obtained in radiochemical purities >95% with decay-corrected radiochemical yields and specific radioactivities between 4-25% and 124-597 GBq/μmol, respectively. Autoradiography studies were then conducted to assess the compounds binding selectivity for VAChT. Labeled compounds [ 11C]-(±)5d and [11C]-(±)5e showed specific binding but not enough to permit further preclinical studies. To conclude, a general method for a facile synthesis and labeling of a small piperazine-based library of potential PET tracers for imaging of VAChT was shown, and in upcoming work, another scaffold will be explored using this approach A library of six piperazine-based ligands for the vesicular acetylcholine transporter were synthesized and labeled from a common precursor, commercially available aryl iodides and [11C]carbon monoxide. Labeled compounds were isolated with radiochemical yields ranging from 4% to 25% and with specific radioactivities between 124 and 597 GBq/μmol. As a simple preclinical evaluation of the labeled compounds, their binding potential to VAChT was assessed by autoradiography. Copyright

Crystalline Hetero-Stereocomplexed Polycarbonates Produced from Amorphous Opposite Enantiomers Having Different Chemical Structures

Abstract Stereocomplexation is the stereoselective interaction between two opposite enantiomeric polymers through an interlocked orderly assembly. Most studies focus on the stereocomplex formation from the crystalline opposite enantiomers having the identical structure; nevertheless, rare examples were reported regarding the crystalline stereocomplexes from enantiomeric polymers having different chemical structures. Herein we show a strategy for polymer orderly assembly through the formation of crystalline hetero-stereocomplexed polymeric materials by the cocrystallization of amorphous isotactic polycarbonates with different chemical structures and opposite configurations. The behaviors in the crystalline state are significantly different from that of the component enantiomeric polymers or their homo-stereocomplexes. This study is expected to open up a new way to prepare various semicrystalline materials having a wide variety of physical properties and degradability. Mixed enantiomers: A unique strategy for polymer assembly was demonstrated through the formation of crystalline hetero-stereocomplexed polymeric materials by the cocrystallization of amorphous isotactic polycarbonates with opposite configurations and different chemical structures. This study is expected to open up a new way to prepare various semicrystalline materials with a wide variety of physical properties and degradability.

Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols

Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectivel

Self-Masked Aldehyde Inhibitors: A Novel Strategy for Inhibiting Cysteine Proteases

Cysteine proteases comprise an important class of drug targets, especially for infectious diseases such as Chagas disease (cruzain) and COVID-19 (3CL protease, cathepsin L). Peptide aldehydes have proven to be potent inhibitors for all of these proteases. However, the intrinsic, high electrophilicity of the aldehyde group is associated with safety concerns and metabolic instability, limiting the use of aldehyde inhibitors as drugs. We have developed a novel class of self-masked aldehyde inhibitors (SMAIs) for cruzain, the major cysteine protease of the causative agent of Chagas disease - Trypanosoma cruzi. These SMAIs exerted potent, reversible inhibition of cruzain (Ki? = 18-350 nM) while apparently protecting the free aldehyde in cell-based assays. We synthesized prodrugs of the SMAIs that could potentially improve their pharmacokinetic properties. We also elucidated the kinetic and chemical mechanism of SMAIs and applied this strategy to the design of anti-SARS-CoV-2 inhibitors.

PEPTIDE CONJUGATES OF CYTOTOXINS AS THERAPEUTICS

The present invention relates to peptide conjugates of cytotoxins such as topoisomerase I inhibitors which are useful for the treatment of diseases such as cancer.

INHINITORS OF GLI1 AS THERAPEUTIC AGENTS

This disclosure relates to compounds, pharmaceutical compositions comprising them, and methods of using the compounds and compositions for treating diseases related to glioma- associated oncogene (Gli) expression. More particularly, this disclosure relate

Carbon Dioxide Copolymerization Study with a Sterically Encumbering Naphthalene-Derived Oxide

Poly(1,4-dihydronaphthalene carbonate) has been prepared via the catalytic coupling of carbon dioxide and 1,4-dihydronaphthalene oxide using chromium(III) catalysts. The copolymer formation is found to be greatly dependent on the steric environment around the metal center. Traditional (salen)CrIIIX/cocatalyst systems bearing bulky t-butyl groups hinder the approach of the large monomer, significantly diminishing polymer chain growth and providing the entropically favored cyclic byproduct in excess. In contrast, employing the sterically unencumbered azaannulene-derived catalyst, (tmtaa)CrIIIX/cocatalyst system (tmtaa = tetramethyltetraazaannulene) shows polymer selectivity close to 90% with three times the activity (TOF = 20-30 h-1). With the use of a bifunctional (salen)CrIII catalyst, even higher polymer selectivity (>90%) can be observed. The complete synthesis of a new bifunctional tetraazaannulene ligand for a more effective catalyst is also described herein.

Organocatalytic asymmetric hydrolysis of epoxides

The hydrolytic ring opening of epoxides is an important biosynthetic transformation and is also applied industrially. We report the first organocatalytic variant of this reaction, exploiting our recently discovered activation of carboxylic acids with chiral phosphoric acids via heterodimerization. The methodology mimics the enzymatic mechanism, which involves an enzyme-bound carboxylate nucleophile. A newly designed phosphoric acid catalyst displays high stereocontrol in the desymmetrization of meso-epoxides. The methodology shows wide generality with cyclic, acylic, aromatic, and aliphatic substrates. We also apply our method in the first highly enantioselective anti-dihydroxylation of simple olefins.