5234-06-0

Basic information

• Product Name: 2-((2-naphthyloxy)methyl)-oxiran
• Synonyms: ((2-naphthalenyloxy)methyl)-oxiran;2-((2-naphthyloxy)methyl)-oxiran;2-(2,3-expoxypropoxy)-naphthalen;2-glycidyloxynaphthalene;2-naphthylglycidylether;beta-naphthylglycidylether;ether,2,3-epoxypropyl2-naphthyl;glycidylbeta-naphthylether
• CAS NO: 5234-06-0
• Molecular Formula: C₁₃H₁₂O₂
• Molecular Weight: 200.23318
• EINECS: 226-030-6
• Mol File: 5234-06-0.mol

Chemical Properties

• Melting Point: 60-64 °C
• Boiling Point: 348.7°Cat760mmHg
• Flash Point: 152°C
• Appearance: /
• Density: 1.192g/cm³
• Vapor Pressure: 9.96E-05mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: 2-((2-naphthyloxy)methyl)-oxiran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((2-naphthyloxy)methyl)-oxiran(5234-06-0)
• EPA Substance Registry System: 2-((2-naphthyloxy)methyl)-oxiran(5234-06-0)

Safety Data

• Hazardous Substances Data: 5234-06-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-((2-naphthyloxy)methyl)-oxiran is used as a prodrug for ibuprofen, a widely used nonsteroidal anti-inflammatory drug (NSAID) with analgesic, antipyretic, and anti-inflammatory properties. As a prodrug, it is designed to be converted into the active drug within the body, potentially offering improved pharmacokinetics, reduced side effects, or enhanced targeting.
In the pharmaceutical industry, 2-((2-naphthyloxy)methyl)-oxiran serves as a monoester of ibuprofen, which is utilized for its analgesic activity. This application takes advantage of the compound's ability to be metabolized into the active drug, providing pain relief and potentially reducing the risk of gastrointestinal side effects associated with direct NSAID use.

InChI:InChI=1/C13H12O2/c1-2-4-11-7-12(6-5-10(11)3-1)14-8-13-9-15-13/h1-7,13H,8-9H2/t13-/m1/s1

Upstream product

• 122432-36-4 3-(1-Bromonaphth-2-yloxy)-1,2-epoxypropane 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 135-19-3 β-naphthol 
• 124-38-9 carbon dioxide 
• 20133-94-2 1-chloro-3-(naphthalen-2-yloxy)propan-2-ol 
• 70987-78-9 (S)-Glycidyl tosylate 
• 20133-94-2 (R)-1-Chloro-3-(naphthalen-2-yloxy)-propan-2-ol 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 573-97-7 1-bromo-2-naphthol 
• 106-89-8 epichlorohydrin 
• 96-23-1 1,3-Dichloro-2-propanol 

Downstream Products

• 391901-97-6 (2 S)-1-[(4-aminophenethyl)amino]-3-(2-naphthyloxy)-2-propanol 
• 912284-00-5 (S)-3-(naphthalen-2-yloxy)propane-1,2-diol 
• 205306-84-9 (R)-3-(naphthalen-2-yloxy)propane-1,2-diol 
• 5234-06-0 (S)-(-)-3-(2'-naphthyloxy)-1,2-epoxypropane 
• 129098-62-0 3-(2-naphthyloxy)-1,2-epoxypropane 
• 34798-63-5 3-(4-methoxy-phenyl)-5-naphthalen-2-yloxymethyl-2-phenyl-oxazolidine 
• 34798-58-8 5-naphthalen-2-yloxymethyl-2,3-diphenyl-oxazolidine 
• 5255-99-2 5-naphthalen-2-yloxymethyl-3-phenyl-oxazolidin-2-one 
• 63434-27-5 1-{[2-(3,4-Dimethoxy-phenyl)-ethyl]-methyl-amino}-3-(naphthalen-2-yloxy)-propan-2-ol 

Relevant articles and documents

Facile microwave-assisted synthesis and antitubercular evaluation of novel aziridine derivatives

Novel 2-(aryloxymethyl)aziridines and 2-((3-aryl-1-phenylallyloxy)methyl)aziridine derivatives were prepared via ring-opening reaction of epoxides. The synthesized derivatives were characterized by using elemental analysis (EA), FT-IR, 13C NMR, and 1H NMR. The in vitro antitubercular activities of the synthesized compounds were evaluated against Mycobacterium tuberculosis H37Rv (MTB H37Rv) strain using MTT-MABA assay. All the aziridine derivatives exhibited improved persuasive antitubercular activity against MTB H37Rv in comparison with standard drugs. Among the tested compounds, 2-(naphthalene-1-yloxy) methyl aziridine (5b), 2-(naphthalene-2-yloxy)methylaziridine (5c), 2-(m-tolyloxymethyl)aziridine (5e), 2-(3-(4-methoxyphenyl)-1-phenylalloxy)methylaziridine (12b) and 2-(3-(2-chlorophenyl)-1-phenylallyloxy)methylaziridine (12c) revealed promising activity against MTB H37Rv. Specifically, compound 5b and 12 b showed three-times more active (MIC = 0.5 μg/mL) than the standard drugs ethambutol (MIC = 1.56 μg/mL) and ciprofloxacin (MIC = 1.56 μg/mL).

Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents

Malignant melanoma (MM) presents as the highest morbidity and mortality type in skin cancer. Herein, inspired by the previously reported anti-melanoma effect of propranolol, a widely applied β adrenergic receptor antagonist as cardiovascular drug, we set out to exploit its potential as anti-melanoma therapy based on the drug repurposing strategy. Structural optimization of propranolol yielded 5m, which exhibits dramatically improved potency on human melanoma cell growth (1.98–3.70 μM), compared to propranolol (59.5–75.8 μM). Further investigation demonstrated that 5m could inhibit colony formation of melanoma cell line (completely abolished at 2 μM for 5m, partially inhibited at 50 μM for propranolol), induce cell apoptosis and cell cycle arrest in the G2/M phase (both observed at 1 μM). Preliminary mechanism study indicated that 5m could disrupt the cellular microtubule network, which suggested tubulin as a potential target. Docking study provided a structural insight into the interaction between 5m and tubulin. In summary, our study presents a drug repurposing case that redirects a cardiovascular agent to an anti-melanoma agent.

Engineering a homochiral metal-organic framework based on an amino acid for enantioselective separation

A chiral metal-organic framework possessing an open amphiphilic channel is constructed from a dicarboxylate ligand derived from an amino acid and is shown to be an efficient and recyclable chiral solid adsorbent, which is capable of separating racemic secondary alcohols, epoxides, and ibuprofen with very high enantioselectivity.

A facile and efficient method for synthesis of β-iodocarboxylates from terminal epoxides

A facile and efficient method has been developed for synthesis of β-iodocarboxylates in the presences of Ph3P/I2. Starting from epoxides, a series of β-iodocarboxylate compounds can be directly obtained in toluene media with excellent yields. Moreover, the method was successfully applied for the late-stage modification of natural products, such as isosteviol and vincamine derivatives, achieving the corresponding β-iodocarboxylates in good yields.

Enantioselective Resolution Copolymerization of Racemic Epoxides and Anhydrides: Efficient Approach for Stereoregular Polyesters and Chiral Epoxides

Herein we report an efficient strategy for preparing isotactic polyesters and chiral epoxides via enantioselective resolution copolymerization of racemic terminal epoxides with anhydrides, mediated by enantiopure bimetallic complexes in conjunction with a nucleophilic cocatalyst. The chirality of both the axial linker and the diamine backbones of the ligand are responsible for the chiral induction of this kinetic resolution copolymerization process. The catalyst systems exhibit exceptional levels of enantioselectivity with a kinetic resolution coefficient exceeding 300 for various racemic epoxides, affording highly isotactic copolymers (selectivity factors of more than 300) with a completely alternating structure and low polydispersity index. Most of the produced isotactic polyesters are typical semicrystalline materials with melting temperatures in the range from 77 to 160 °C.

Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide

Chiral binaphthyl-strapped Zn(II) porphyrins with triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO2. Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides.

NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b] [1,4]oxathiin-3-yl)methanols from aryloxymethylthiiranes

(2,3-Dihydrobenzo[b][1,4]oxathiin-3-yl)methanols were synthesized via reactions of aryloxymethylthiiranes and N-bromosuccinimide (NBS) in DMSO under microwave irradiation. The reaction mechanism was proposed as an intramolecular aromatic electrophilic substitution of 1-bromo-2-(aryloxymethyl)thiiran-1-iums, generated from aryloxymethylthiiranes and NBS, and the subsequent DMSO nucleophilic ring opening reaction of thiiran-1-iums followed by the water displacement. The current method provides a direct and simple strategy in the efficient preparation of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from readily available aryloxymethylthiiranes.

Synthesis and evaluation of 4-(2-hydroxypropyl)piperazin-1-yl) derivatives as Hsp90 inhibitors

We previously reported 4-(3-((6-bromonaphthalen-2-yl)oxy)-2-hydroxypropyl)-N,N-dimethylpiperazine-1-sulfonamide (1) as a novel heat shock protein 90 inhibitor with moderate activity. In our ongoing efforts for the discovery of Hsp90 modulators we undertake structural investigations on 1. Series of the titled compound were designed, synthesized and evaluated. We have found that compounds with a hydroxyl group at C-4 of the aryl ring on the piperazine moiety possess Hsp90 inhibition properties. Compound 6f with improved activity could be further developed and optimized as Hsp90 inhibitor.

Dinuclear salen cobalt complex incorporating Y(OTf)3: enhanced enantioselectivity in the hydrolytic kinetic resolution of epoxides

The activation of inactive Jacobsen's chiral salen Co(ii) (salen = N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine) compound is attained by dinuclear chiral salen Co(iii)-OTf complex formation with yttrium triflate. The yttrium metal not only displays a promoting effect on electron transfer, but also assists in forming two stereocentres of a Lewis acid complex with Co(iii)-OTf. We found that the binuclear Co-complex significantly enhanced reactivity and enantioselectivity in the hydrolytic kinetic resolution of terminal epoxides compared to its analogous monomer and kinetic data are also consistent with these results.

THERAPEUTIC COMPOUNDS

The present invention relates to therapeutic compounds useful for the treatment of neurodegenerative and neuromuscular diseases and/or triplet repeat diseases (e.g. Friedreich's ataxia). The compounds have the structural formula I shown below: wherein Q, X, p, R1, q, R3 and R4 are as defined herein. The present invention also relates to pharmaceutical compositions comprising the compounds defined herein, the use of these compositions for the treatment of neurodegenerative and neuromuscular diseases and/or triplet repeat diseases (e.g. Friedreich's ataxia), and to processes for the preparation of the pharmaceutical compositions defined herein.