80051-04-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(3-CHLOROPHENYL)-1,2-ETHANEDIOL is used as an antifungal agent for the treatment of various fungal infections such as athlete's foot, jock itch, and ringworm. It functions by inhibiting the synthesis of fungal cell membranes, thereby preventing the growth and reproduction of fungi.
Used in Topical Medications:
(R)-1-(3-CHLOROPHENYL)-1,2-ETHANEDIOL is used as an active ingredient in topical formulations like creams, lotions, and solutions. These formulations are applied directly to the affected area to treat the fungal infection, ensuring targeted delivery and localized action.
Used in Patient Care:
(R)-1-(3-CHLOROPHENYL)-1,2-ETHANEDIOL is used as a therapeutic agent to alleviate symptoms associated with fungal infections, such as itching, redness, and discomfort. It is generally well-tolerated, with common side effects including mild irritation, itching, or burning at the application site, which can be managed by following the healthcare professional's instructions.
It is essential to adhere to the prescribed treatment regimen and consult a healthcare professional for proper guidance to ensure the effectiveness of (R)-1-(3-CHLOROPHENYL)-1,2-ETHANEDIOL and to minimize the risk of adverse effects.

InChI:InChI=1/C8H9ClO2/c9-7-3-1-2-6(4-7)8(11)5-10/h1-4,8,10-11H,5H2/t8-/m1/s1

Upstream product

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Downstream Products

• 1453854-94-8 (R)-2-((tert-butyldimethylsilyl)oxy)-1-(3-chlorophenyl)ethyl methanesulfonate 
• 185035-36-3 (R)-(-)-1-(3-chlorophenyl)-1,2-ethanediol-2-methanesulfonate 

Relevant academic research and scientific papers

Reprogramming Epoxide Hydrolase to Improve Enantioconvergence in Hydrolysis of Styrene Oxide Scaffolds

Enantioconvergent hydrolysis by epoxide hydrolase is a promising method for the synthesis of important vicinal diols. However, the poor regioselectivity of the naturally occurring enzymes results in low enantioconvergence in the enzymatic hydrolysis of styrene oxides. Herein, modulated residue No. 263 was redesigned based on structural information and a smart variant library was constructed by site-directed modification using an “optimized amino acid alphabet” to improve the regioselectivity of epoxide hydrolase from Vigna radiata (VrEH2). The regioselectivity coefficient (r) of variant M263Q for the R-isomer of meta-substituted styrene oxides was improved 40–63-fold, and variant M263V also exhibited higher regioselectivity towards the R-isomer of para-substituted styrene oxides compared with the wild type, which resulted in improved enantioconvergence in hydrolysis of styrene oxide scaffolds. Structural insight showed the crucial role of residue No. 263 in modulating the substrate binding conformation by altering the binding surroundings. Furthermore, increased differences in the attacking distance between nucleophilic residue Asp101 and the two carbon atoms of the epoxide ring provided evidence for improved regioselectivity. Several high-value vicinal diols were readily synthesized (>88% yield, 90%–98% ee) by enantioconvergent hydrolysis using the reprogrammed variants. These findings provide a successful strategy for enhancing the enantioconvergence of native epoxide hydrolases through key single-site mutation and more powerful enzyme tools for the enantioconvergent hydrolysis of styrene oxide scaffolds into single (R)-enantiomers of chiral vicinal diols. (Figure presented.).

Highly regio- and enantio-selective hydrolysis of two racemic epoxides by GmEH3, a novel epoxide hydrolase from Glycine max

A novel epoxide hydrolase from Glycine max, designated GmEH3, was excavated based on the computer-aided analysis. Then, gmeh3, a GmEH3-encoding gene, was cloned and successfully expressed in E. coli Rosetta(DE3). Among the ten investigated rac-epoxides, GmEH3 possessed the highest and best complementary regioselectivities (regioselectivity coefficients, αS = 93.7% and βR = 97.2%) in the asymmetric hydrolysis of rac-m-chlorostyrene oxide (5a), and the highest enantioselectivity (enantiomeric ratio, E = 55.6) towards rac-phenyl glycidyl ether (7a). The catalytic efficiency (kcatS/KmS = 2.50 mM?1 s?1) of purified GmEH3 for (S)-5a was slightly higher than that (kcatR/KmR = 1.52 mM?1 s?1) for (R)-5a, whereas the kcat/Km (5.16 mM?1 s?1) for (S)-7a was much higher than that (0.09 mM?1 s?1) for (R)-7a. Using 200 mg/mL wet cells of E. coli/gmeh3 as the biocatalyst, the scale-up enantioconvergent hydrolysis of 150 mM rac-5a at 25 °C for 1.5 h afforded (R)-5b with 90.2% eep and 95.4% yieldp, while the kinetic resolution of 500 mM rac-7a for 2.5 h retained (R)-7a with over 99% ees and 43.2% yields. Furthermore, the sources of high regiocomplementarity of GmEH3 for (S)- and (R)-5a as well as high enantioselectivity towards rac-7a were analyzed via molecular docking (MD) simulation.

Manipulating regioselectivity of an epoxide hydrolase for single enzymatic synthesis of (: R)-1,2-diols from racemic epoxides

Both the activity and regioselectivity of Phaseolus vulgaris epoxide hydrolase were remarkably improved via reshaping two substrate tunnels based on rational design. The elegant one-step enantioconvergent hydrolysis of seven rac-epoxides was achieved by single mutants, allowing green and efficient access to valuable (R)-1,2 diols with high eep (90.1-98.3%) and yields.

Exploiting Designed Oxidase-Peroxygenase Mutual Benefit System for Asymmetric Cascade Reactions

A unique P450 monooxygenase-peroxygenase mutual benefit system was designed as the core element in the construction of a biocatalytic cascade reaction sequence leading from 3-phenyl propionic acid to (R)-phenyl glycol. In this system, P450 monooxygenase (P450-BM3) and P450 peroxygenase (OleTJE) not only function as catalysts for the crucial initial reactions, they also ensure an internal in situ H2O2 recycle mechanism that avoids its accumulation and thus prevents possible toxic effects. By directed evolution of P450-BM3 as the catalyst in the enantioselective epoxidation of the styrene-intermediate, formed from 3-phenyl propionic acid, and the epoxide hydrolase ANEH for final hydrolytic ring opening, (R)-phenyl glycol and 9 derivatives thereof were synthesized from the respective carboxylic acids in one-pot processes with high enantioselectivity.

Exploiting Designed Oxidase-Peroxygenase Mutual Benefit System for Asymmetric Cascade Reactions

A unique P450 monooxygenase-peroxygenase mutual benefit system was designed as the core element in the construction of a biocatalytic cascade reaction sequence leading from 3-phenyl propionic acid to (R)-phenyl glycol. In this system, P450 monooxygenase (P450-BM3) and P450 peroxygenase (OleTJE) not only function as catalysts for the crucial initial reactions, they also ensure an internal in situ H2O2 recycle mechanism that avoids its accumulation and thus prevents possible toxic effects. By directed evolution of P450-BM3 as the catalyst in the enantioselective epoxidation of the styrene-intermediate, formed from 3-phenyl propionic acid, and the epoxide hydrolase ANEH for final hydrolytic ring opening, (R)-phenyl glycol and 9 derivatives thereof were synthesized from the respective carboxylic acids in one-pot processes with high enantioselectivity.

HETEROCYCLIC COMPOUNDS AS KINASE INHIBITORS, COMPOSITIONS COMPRISING THE HETEROCYCLIC COMPOUND, AND METHODS OF USE THEREOF

(I) Disclosed herein are compounds of formula I, and/or a stereoisomer, a stable isotope, or a pharmaceutically acceptable salt thereof; and therapeutic uses of these compounds, which are kinase inhibitors potentially useful in the treatment of diseases treatable, such as cancers, as well aspharmaceutical compositions, comprising a compound of formula I, and/or a stereoisomer, a stable isotope, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

HETEROCYCLIC COMPOUNDS AS KINASE INHIBITORS, COMPOSITIONS COMPRISING THE HETEROCYCLIC COMPOUND, AND METHODS OF USE THEREOF

The present disclosure provides a compound of Formula (I) and/or a stereoisomer, a tautomer, a stable isotope, or a pharmaceutically acceptable salt thereof; and therapeutic uses of these compounds. They are kinase inhibitors potentially useful in the tre

Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles

A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and high reaction efficiency and enantioselectivity were maintained.

Stereoselective Hydrolysis of Epoxides by reVrEH3, a Novel Vigna radiata Epoxide Hydrolase with High Enantioselectivity or High and Complementary Regioselectivity

To provide more options for the stereoselective hydrolysis of epoxides, an epoxide hydrolase (VrEH3) gene from Vigna radiata was cloned and expressed in Escherichia coli. Recombinant VrEH3 displayed the maximum activity at pH 7.0 and 45 °C and high stability at pH 4.5-7.5 and 55 °C. Notably, reVrEH3 exhibited high and complementary regioselectivity toward styrene oxides 1a-3a and high enantioselectivity (E = 48.7) toward o-cresyl glycidyl ether 9a. To elucidate these interesting phenomena, the interactions of the three-dimensional structure between VrEH3 and enantiomers of 1a and 9a were analyzed by molecular docking simulation. Using E. coli/vreh3 whole cells, gram-scale preparations of (R)-1b and (R)-9a were performed by enantioconvergent hydrolysis of 100 mM rac-1a and kinetic resolution of 200 mM rac-9a in the buffer-free water system at 25 °C. These afforded (R)-1b with >99% eep and 78.7% overall yield after recrystallization and (R)-9a with >99% ees, 38.7% overall yield, and 12.7 g/L/h space-time yield.

Highly Enantioselective Iron-Catalyzed cis-Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-OOH Reactive Intermediate

The development of environmentally benign catalysts for highly enantioselective asymmetric cis-dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L=N,N′-dimethyl-N,N′-bis(2-methyl-8-quinolyl)-cyclohexane-1,2-diamine) as a catalyst, cis-diols in up to 99.8 % ee with 85 % isolated yield have been achieved in AD of alkenes with H2O2as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2]+H2O2” method is applicable to both (E)-alkenes and terminal alkenes (24 examples >80 % ee, up to 1 g scale). Mechanistic studies, including18O-labeling, UV/Vis, EPR, ESI-MS analyses, and DFT calculations lend evidence for the involvement of chiral FeIII-OOH active species in enantioselective formation of the two C?O bonds.