Category: 57044-25-4

Chen, Weiqi published the artcileSubstrate stereocontrol in bromine-induced intermolecular cyclization: asymmetric synthesis of pitavastatin calcium, Name: (R)-Oxiran-2-ylmethanol, the publication is Tetrahedron (2015), 71(29), 4730-4737, database is CAplus.

A novel approach to synthesize pitavastatin calcium, an effective HMG-CoA reductase inhibitor, based on readily available and attractively functionalized (R)-3-chloro-1,2-propanediol is reported. This work highlights an intermol. diastereoselective bromine-induced cyclization of homoallylic carbonate to meet stereochem. challenges in the synthesis of statins. An efficient route to a new triphenylphosphonium tetrafluoroborate salt of a quinoline core is also presented.

Tetrahedron published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Name: (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Qu, Chun-Ping published the artcileA new heterocycles compound combined with focused ultrasound inhibits breast cancer cell proliferation and invasion, Quality Control of 57044-25-4, the publication is Latin American Journal of Pharmacy (2021), 40(11), 2817-2820, database is CAplus.

The new (S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1), designed using (R)-3-chloropropane-1,2-diol and nitrobenzene as start material, was successfully obtained via multiple synthesis routes and finally characterized by IR, ¹H NMR, and single crystal X-ray crystallog. Its application values on the breast cancer treatment were evaluated and the related mechanism was explored as well. The CCK-8 assay was firstly conducted and the inhibitory effect of the new compound on the breast cancer cells was measured. Then, the reduction effect of the new compound on the breast cancer migration and invasion activity was measured with trans-well assay.

Latin American Journal of Pharmacy published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Quality Control of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Liang, Dongjun published the artcileA real-time, click chemistry imaging approach reveals stimulus-specific subcellular locations of phospholipase D activity, Application of (R)-Oxiran-2-ylmethanol, the publication is Proceedings of the National Academy of Sciences of the United States of America (2019), 116(31), 15453-15462, database is CAplus and MEDLINE.

The fidelity of signal transduction requires spatiotemporal control of the production of signaling agents. Phosphatidic acid (PA) is a pleiotropic lipid second messenger whose modes of action differ based on upstream stimulus, biosynthetic source, and site of production How cells regulate the local production of PA to effect diverse signaling outcomes remains elusive. Unlike other second messengers, sites of PA biosynthesis cannot be accurately visualized with subcellular precision. Here, we describe a rapid, chemoenzymic approach for imaging physiol. PA production by phospholipase D (PLD) enzymes. Our method capitalizes on the remarkable discovery that bulky, hydrophilic trans-cyclooctene-containing primary alcs. can supplant water as the nucleophile in the PLD active site in a transphosphatidylation reaction of PLD’s lipid substrate, phosphatidylcholine. The resultant trans-cyclooctene-containing lipids are tagged with a fluorogenic tetrazine reagent via a no-rinse, inverse electron-demand Diels-Alder (IEDDA) reaction, enabling their immediate visualization by confocal microscopy in real time. Strikingly, the fluorescent reporter lipids initially produced at the plasma membrane (PM) induced by phorbol ester stimulation of PLD were rapidly internalized via apparent nonvesicular pathways rather than endocytosis, suggesting applications of this activity-based imaging toolset for probing mechanisms of intracellular phospholipid transport. By instead focusing on the initial 10 s of the IEDDA reaction, we precisely pinpointed the subcellular locations of endogenous PLD activity as elicited by physiol. agonists of G protein-coupled receptor and receptor tyrosine kinase signaling. These tools hold promise to shed light on both lipid trafficking pathways and physiol. and pathol. effects of localized PLD signaling.

Proceedings of the National Academy of Sciences of the United States of America published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Application of (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Sherwood, Alexander M. published the artcileModular Approach to pseudo-Neoclerodanes as Designer κ-Opioid Ligands, SDS of cas: 57044-25-4, the publication is Organic Letters (2017), 19(19), 5414-5417, database is CAplus and MEDLINE.

Informed by previous semisynthetic work on salvinorin A, a modular total synthesis has been developed capable of producing novel compounds targeting the κ-opioid receptor. The strategy has permitted the deliberate simplification and introduction of functionality about the target mol. to provide access to mol. features on salvinorin A otherwise unattainable by semisynthesis. Using this approach, a potent pseudo-neoclerodane κ-opioid receptor ligand (I) has been realized.

Organic Letters published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C8H5F3N4, SDS of cas: 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Cheviet, Thomas published the artcileβ-Hydroxy- and β-Aminophosphonate Acyclonucleosides as Potent Inhibitors of Plasmodium falciparum Growth, Synthetic Route of 57044-25-4, the publication is Journal of Medicinal Chemistry (2020), 63(15), 8069-8087, database is CAplus and MEDLINE.

Malaria is an infectious disease caused by a parasite of the genus Plasmodium, and the emergence of parasites resistant to all current antimalarial drugs highlights the urgency of having new classes of mols. We developed an effective method for the synthesis of a series of β-modified acyclonucleoside phosphonate (ANP) derivatives, using com. available and inexpensive materials (i.e., aspartic acid and purine heterocycles). Their biol. evaluation in cell culture experiments and SAR revealed that the compounds’ effectiveness depends on the presence of a hydroxyl group, the chain length (four carbons), and the nature of the nucleobase (guanine). The most active derivative I inhibits the growth of Plasmodium falciparum in vitro in the nanomolar range (IC₅₀ = 74 nM) with high selectivity index (SI > 1350). This compound also showed remarkable in vivo activity in P. berghei-infected mice (ED₅₀ ~0.5 mg/kg) when administered by the i.p. route and is, although less efficient, still active via the oral route. It is the first ANP derivative with such potent antimalarial activity and therefore has considerable potential for development as a new antimalarial drug.

Journal of Medicinal Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Synthetic Route of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Qureshi, Zafar published the artcileApplication of the Palladium-Catalyzed Norbornene-Assisted Catellani Reaction Towards the Total Synthesis of (+)-Linoxepin and Isolinoxepin, Safety of (R)-Oxiran-2-ylmethanol, the publication is European Journal of Organic Chemistry (2014), 2014(19), 4053-4069, database is CAplus.

The authors’ ongoing effort towards the development of highly selective transition-metal-catalyzed carbon hydrogeb bond (C-H bond) activation processes has led to the expansion of a Catellani reaction. In a Pd⁰/Pd^II/Pd^IV-catalyzed tandem reaction (domino reaction), an aryl iodide, alkyl iodide and tert-Bu acrylate were combined to synthesize a carbon framework of the novel lignan (+)-linoxepin. The enantioselective synthesis highlights the work accomplished in the authors’ group and provides an excellent procedure for a reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biol. active mols. After a key Catellanireaction/Heck reaction, the synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not only the natural product (+)-linoxepin but also its isoform, which we have named isolinoxepin. The synthesis of the target compounds was achieved using 8-[(5-bromo-1,3-benzodioxol-4-yl)methoxy]-3a,4-dihydro-7-(methoxy)naphtho[2,3-c]furan-1(3H)-one as a key intermediate. The title compounds thus formed included (9aR)-9a,10-dihydro-6-methoxy-4H-1,3-benzodioxolo[4,5-c]isobenzofuro[4,5,6-ef][1]benzoxepin-12(9H)-one [(+)-linoxepin] and 10,12b-dihydro-6-methoxy-4H-1,3-benzodioxolo[4,5-c]isobenzofuro[4,5,6-ef][1]benzoxepin-12(9H)-one [racemic isolinoxepin].

European Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Safety of (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Toelle, Nina published the artcileLight-mediated total synthesis of 17-deoxyprovidencin, COA of Formula: C3H6O2, the publication is Angewandte Chemie, International Edition (2014), 53(15), 3859-3862, database is CAplus and MEDLINE.

An asym. synthesis of the diterpenoid 17-deoxyprovidencin I is described. Key steps include an aldol addition, a base-catalyzed Wipf-type furan formation, a Z-selective ring-closing metathesis for macrocyclization, a photochem. E/Z isomerization to a highly strained and conformationally restricted ring system, and the stereoselective formation of two epoxides on the ring.

Angewandte Chemie, International Edition published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C8H7ClO3, COA of Formula: C3H6O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Liu, Yan published the artcileBiocatalytic synthesis of C3 chiral building blocks by chloroperoxidase-catalyzed enantioselective halo-hydroxylation and epoxidation in the presence of ionic liquids, Application of (R)-Oxiran-2-ylmethanol, the publication is Biotechnology Progress (2015), 31(3), 724-729, database is CAplus and MEDLINE.

The optically active C3 synthetic blocks are remarkably versatile intermediates for the synthesis of numerous pharmaceuticals and agrochems. This work provides a simple and efficient enzymic synthetic route for the environment-friendly synthesis of C3 chiral building blocks. Chloroperoxidase (CPO)-catalyzed enantioselective halo-hydroxylation and epoxidation of chloropropene and allyl alc. was employed to prepare C3 chiral building blocks in this work, including (R)-2,3-dichloro-1-propanol (DCP*), (R)-2,3-epoxy-1-propanol (GLD*), and (R)-3-chloro-1-2-propanediol (CPD*). The ee values of the formed C3 chiral building blocks DCP*, CPD*, and glycidol were 98.1, 97.5, and 96.7%, resp. Moreover, the use of small amount of imidazolium ionic liquid enhanced the yield efficiently due to the increase of solubility of hydrophobic organic substrates in aqueous reaction media, as well as the improvement of affinity and selectivity of CPO to substrate. © 2015 American Institute of Chem. Engineers Biotechnol. Prog., 2015.

Biotechnology Progress published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Application of (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Obst, Jon K. published the artcileRevealing Metabolic Liabilities of Ralaniten To Enhance Novel Androgen Receptor Targeted Therapies, Safety of (R)-Oxiran-2-ylmethanol, the publication is ACS Pharmacology & Translational Science (2019), 2(6), 453-467, database is CAplus and MEDLINE.

Inhibition of the androgen receptor (AR) is the mainstay treatment for advanced prostate cancer. Ralaniten (formally EPI-002) prevents AR transcriptional activity by binding to its N-terminal domain (NTD) which is essential for transcriptional activity. Ralaniten acetate (EPI-506) the triacetate pro-drug of ralaniten, remains the only AR-NTD inhibitor to have entered clin. trials (NCT02606123). While well tolerated, the trial was ultimately terminated due to poor pharmacokinetic properties and resulting pill burden. Here we discovered that ralaniten was glucuronidated which resulted in decreased potency. Long-term treatment of prostate cancer cells with ralaniten results in upregulation of UGT2B enzymes with concomitant loss of potency. This has proven to be a useful model with which to facilitate the development of more potent second-generation AR-NTD inhibitors. Glucuronidated metabolites of ralaniten were also detected in the serum of patients in Phase 1 clin. trials. Therefore, we tested an analog of ralaniten (EPI-045) which was resistant to glucuronidation and demonstrated superiority to ralaniten in our resistant model. These data support that analogs of ralaniten designed to mitigate glucuronidation may optimize clin. responses to AR-NTD inhibitors.

ACS Pharmacology & Translational Science published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Safety of (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Borrel, Julien published the artcileCopper-Catalyzed Oxyalkynylation of C-S Bonds in Thiiranes and Thietanes with Hypervalent Iodine Reagents, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is Organic Letters (2020), 22(2), 422-427, database is CAplus and MEDLINE.

We report the oxyalkynylation of thiiranes and thietanes using ethynylbenziodoxolone reagents (EBXs) to readily access functionalized building blocks bearing an alkynyl, a benzoate, and an iodide group. The reaction proceeds with high atom efficiency most likely through an alkynyl-episulfonium intermediate. The transformation is copper-catalyzed and compatible with a large array of thiiranes and thietanes.

Organic Letters published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Recommanded Product: (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts