Tag: M.W=50-100

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

Yang, Tao published the artcilePhotoinduced Nickel-Catalyzed Deaminative Cross-Electrophile Coupling for C(sp²)-C(sp³) and C(sp³)-C(sp³) Bond Formation, Synthetic Route of 96-20-8, the publication is ACS Catalysis (2021), 11(11), 6519-6525, database is CAplus.

The N-alkylpyridinium salts, e.g., pyridinium, 1-cycloheptyl-2,4,6-triphenyl-, tetrafluoroborate can be efficiently merged with aryl or alkyl halides RX (R = 4-NCC₆H₄, 2-cyanopyridin-4-yl, 1-oxo-2,3-dihydro-1H-inden-5-yl, etc.; X = Br, I) in an intermol. fashion, affording products, e.g., 2-(4-cycloheptylbutyl)isoindoline-1,3-dione in up to 92% yield at ambient temperature These reactions harness the ability of N-alkylpyridinium salts to form electron donor-acceptor complexes with Hantzsch esters, enabling photoinduced single-electron transfer and fragmentation to afford alkyl radicals that are subsequently trapped by a Ni-based catalytic species to promote C(sp₂)-C(sp₃) and C(sp₃)-C(sp₃) bond formation. The operationally simple protocol is applicable to site-selective cross-coupling and tolerates diverse functional groups, including those that are sensitive toward metal reductants.

ACS Catalysis published new progress about 96-20-8. 96-20-8 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 2-Aminobutan-1-ol, and the molecular formula is C6H13I, Synthetic Route of 96-20-8.

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

Li, Xingyu published the artcilePhase Splitting Rules of the Primary/Secondary Amine-Tertiary Amine Systems: Experimental Rapid Screening and Corrected Quasi-Activity Coefficient Model, Category: alcohols-buliding-blocks, the publication is Industrial & Engineering Chemistry Research (2022), 61(23), 7709-7717, database is CAplus.

Several phase splitting systems have shown potential in reducing regeneration energy consumption for large-scale CO₂ capture in the last decade. The development of new phase splitting systems currently depends on exptl. screening. In this work, 90 sets of primary/secondary amine-tertiary amine anhydrous systems and 160 sets of primary/secondary amine-tertiary amine-water systems were used to investigate the phase splitting rules at the mol. level. The results show that the phase splitting behavior of the anhydrous system is directly affected by the carbamate solubility in the tertiary amine. The potential phase splitting system has a tertiary amine with proper lipophilicity. Among the aqueous systems, two different phase splitting zones were recognized: the salting-out effect zone with a lower amine log P and the cosolvent effect zone with a higher amine log P. Several thermotropic phase splitting systems are located at the edge of these two zones. The tertiary amine with more tert-amine groups and less hydroxyl groups would facilitate phase splitting. The primary/secondary amine with hydroxyl groups on the straight chain would facilitate phase splitting. A new parameter describing the primary amine/secondary amine as a nonelectrolyte is introduced to develop a new quasi-activity coefficient of the chem.-chem. aqueous system. This quasi-activity coefficient is applicable to the mono- or polyamine systems with different material ratios.

Industrial & Engineering Chemistry Research published new progress about 96-20-8. 96-20-8 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 2-Aminobutan-1-ol, and the molecular formula is C4H11NO, Category: alcohols-buliding-blocks.

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

Pan, Mingshi published the artcileRuthenium-catalyzed acceptorless dehydrogenative coupling of amino alcohols and ynones to access 3-acylpyrroles, Application In Synthesis of 96-20-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(14), 2379-2382, database is CAplus and MEDLINE.

Herein, a new strategy for the direct synthesis of functionalized pyrroles from β-amino alcs. and ynones via ruthenium-catalyzed acceptorless dehydrogenative coupling was demonstrated. This developed methodol. proceeded in an atom- and step-economic fashion together with the merits of broad substrate scope, operational simplicity, with water and hydrogen gas as the sole byproducts, which provided an alternative and sustainable way to access functionalized pyrroles. Further, this method was applied to the rapid synthesis of the COX-1/COX-2 inhibitor and boron dipyrromethene derivative successfully.

Chemical Communications (Cambridge, United Kingdom) published new progress about 96-20-8. 96-20-8 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 2-Aminobutan-1-ol, and the molecular formula is C4H11NO, Application In Synthesis of 96-20-8.

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