Category: alcohols-buliding-blocks

Cavallaro, Gennara published the artcileGlycosilated macromolecular conjugates of antiviral drugs with a polyaspartamide, Related Products of alcohols-buliding-blocks, the publication is Journal of Drug Targeting (2004), 12(9-10), 593-605, database is CAplus and MEDLINE.

Two new polymeric conjugates for specific liver targeting were prepared by conjugation of sugar moieties and antiviral drugs to α, β-poly[N-2-(hydroxyethyl)-dl-aspartamide] (PHEA). PHEA-galactopyranosylphenylthiocarbamide-mono-O-succinylganciclovir (conjugate 7) and PHEA-mannopyranosylphenylthiocarbamide-O-succinylacyclovir (conjugate 8) were synthesized according to a multi-step procedure which allowed for obtaining high product yield and process standardization. Conjugate 7 contained 7.5 and 8.5% of galactose and ganciclovir (substituent/repeating unit, mol/mol), resp., and conjugate 8 contained 14.2 and 10.8% of mannose and acyclovir, resp. In vitro studies demonstrated that both acyclovir and ganciclovir were released from the polymeric adducts at a release rate depending on the incubation medium. Though a detailed study evidenced that the two bioconjugates undergo different hydrolysis pathways, in both cases high drug release rate was found in plasma, while the glycosidic moiety was not released. Pharmacokinetic studies carried out by i.v. administration of the bioconjugates to Balb/c mice demonstrated that the conjugation of glycosidic moieties promoted the disappearance of the polymer from the blood stream. The two derivatives displayed a different pharmacokinetic profile. In particular, the mannosyl conjugation promoted the rapid disposition of the macromol. in the kidneys and in the liver, while prevented the accumulation in the spleen. On the contrary, the galactosyl derivative was found to dispose in the liver at the same extent of the naked polymer. Few considerations on the different behavior of the conjugates were reported.

Journal of Drug Targeting published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Related Products of alcohols-buliding-blocks.

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

Itagimatha, N. published the artcileRP-HPLC-UV method development and validation for simultaneous determination of terbutaline sulphate, ambroxol HCl and guaifenesin in pure and dosage forms, COA of Formula: C13H19Br2ClN2O, the publication is Annales Pharmaceutiques Francaises (2019), 77(4), 295-301, database is CAplus and MEDLINE.

The objective of the present work was to develop and validate a simple, sensitive, rapid and stable reverse-phase high performance liquid chromatog. (RP-HPLC) method for a combination of Terbutaline sulfate (TSL), Ambroxol hydrochloride (AML) and Guaifenesin (GFN).The combination of these drugs was analyzed by using Shimadzu LC 2010 CHT high performance liquid chromatog. (HPLC). Successful separation was achieved by isocratic elution on a reverse-phase C₁₈ column (sun fire) (250 mm, 4.6 mm, 5μg), using a mobile phase consisting of buffer: acetonitrile in the ratio 80: 20 (buffer – 0.1% volume/volume triethyleamine pH-3.0) followed by 1.0 mL/min flow rate. The wavelength of detection was at 220 nm.The chromatog. retention times were consistent at 3.0, 10.5 and 13.8 min for TSL, AML and GFN resp. For these three compounds, the lower limit of detection was 1.0, 1.25, and 1.5μg/mL and lower limit of quantification was 3.3, 4.1 and 5.0μg/mL resp. The linearity concentrations established for TSL, AML and GFN were 1.0-7.0, 1.5-7.5 and 4.0-14.0μg/mL resp. The correlation coefficients for all the drugs were found to be greater than 0.999. The relative standard deviation of inter- and intra-day were less than 2.0%.This method provides a necessary tool for quantification of the selected drugs for their assay. The proposed method is simple, accurate, reproducible and applied successfully to analyze three compounds in pure as well dosage form. This method provides a necessary tool for quantification of the selected drugs for their assay.

Annales Pharmaceutiques Francaises published new progress about 23828-92-4. 23828-92-4 belongs to alcohols-buliding-blocks, auxiliary class Membrane Transporter/Ion Channel,Sodium Channel, name is trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride, and the molecular formula is C13H19Br2ClN2O, COA of Formula: C13H19Br2ClN2O.

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

Bagherzadeh, Sharareh published the artcileCatalyst Control of Selectivity in CO₂ Reduction Using a Tunable Heterobimetallic Effect, COA of Formula: C6H13BO3, the publication is Journal of the American Chemical Society (2015), 137(34), 10898-10901, database is CAplus and MEDLINE.

A tunable bimetallic effect on product selectivity in catalytic CO₂ reduction was identified using N-heterocyclic carbene-ligated Cu complexes. While the monometallic Cu-only system catalyzes hydroboration of CO₂ with pinacolborane to produce formate exclusively, introducing a bimetallic effect with analogous Cu-Fe, Cu-W, and Cu-Mo catalysts produces mixtures of formate and CO. Within a series of isosteric catalysts, the selectivity of CO vs. formate was controlled by tuning the electronic nature of the Cu/M pairing, with high selectivity for CO being achieved using a Cu-Mo catalyst.

Journal of the American Chemical Society published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, COA of Formula: C6H13BO3.

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

Stones, Duane published the artcileModular solid-phase synthetic approach to optimize structural and electronic properties of oligo-boronic acid receptors and sensors for the aqueous recognition of oligosaccharides, HPLC of Formula: 673456-16-1, the publication is Chemistry – A European Journal (2004), 10(1), 92-100, database is CAplus and MEDLINE.

This article describes the design and optimization of the first entirely modular, parallel solid-phase synthetic approach for the generation of well-defined polyamine oligo-boronic acid receptors and fluorescence sensors for complex oligosaccharides. The synthetic approach allows an effective building of the receptor polyamine backbone, followed by the controlled diversification of the amine benzylic side chains. This approach enabled the testing, in a modular fashion, of the effect of different aryl-boronic acid units substituted with un-encumbering para electron-withdrawing or electron-donating groups. The feasibility of this approach toward automated synthesis was also investigated with the assembly of a sub-library of receptors by means of the Irori MiniKan technol. Several sub-libraries of anthracene-capped sensors containing two or three aryl-boronic acids were synthesized, and their binding to a series of model disaccharides was examined in neutral aqueous media. The calculation of association constants by fluorescence titrations confirmed that subtle changes in the structures of the inter-amine spacers in the polyamine backbone can have a significant effect on the stability of the resulting complexes. Most importantly, this study led to the determination of the preferred electronic characteristics for the aryl-boronate units, and suggests that a new generation of receptors containing very electron-poor aryl-boronic acids could lead to a significant improvement of binding affinities.

Chemistry – A European Journal published new progress about 673456-16-1. 673456-16-1 belongs to alcohols-buliding-blocks, auxiliary class Fluoride,Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester,, name is 2-(2-(Bromomethyl)-4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C14H14N2O2, HPLC of Formula: 673456-16-1.

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

Cooper, Anna G. published the artcileAlkyl indole-based cannabinoid type 2 receptor tools: Exploration of linker and fluorophore attachment, COA of Formula: C6H13NO2, the publication is European Journal of Medicinal Chemistry (2018), 770-789, database is CAplus and MEDLINE.

Cannabinoid type 2 (CB₂) receptor continues to emerge as a promising drug target for many diseases and conditions. New tools for studying CB₂ receptor are required to further inform how this receptor functions in healthy and diseased states. The alkyl indole scaffold is a well-recognized ligand for cannabinoid receptors, and in this study the indole C5-7 positions were explored for linker and fluorophore attachment. A new high affinity, CB₂ receptor selective inverse agonist was identified (16b, 3-(4-methoxybenzoyl)-1-[(oxan-4-yl)methyl]-7-propoxy-1H-indole) along with a general trend of C5-substituted indoles acting as agonists vs. C7-substituted indoles acting as inverse agonists. The indole C7 position was found to be the most tolerant to linker extension and resulted in a high affinity inverse agonist with a medium length linker (19, Me 5-[[3-(4-methoxybenzoyl)-1-[(oxan-4-yl)methyl]-1H-indol-7-yl]oxy]pentanoate). Although a high affinity fluorescent ligand for CB₂ receptor was not identified in this study, the indole C7 position shows great promise for fluorophore or probe attachment.

European Journal of Medicinal Chemistry published new progress about 622-40-2. 622-40-2 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Alcohol, name is 2-Morpholinoethanol, and the molecular formula is C6H13NO2, COA of Formula: C6H13NO2.

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

Ford, M. C. published the artcile3-Hydroxythiophene, Computed Properties of 17236-59-8, the publication is Journal of the Chemical Society (1956), 4985-7, database is CAplus.

The Grignard reagent from 3-bromothiophene (I) was treated with O with the production of a crude phenolic material, and two distillations gave the pure 3-hydroxythiophene (II), which was unstable, developing a reddish tinge and a disagreeable odor within a day, and finally resinifying. EtBr (18.5 g.) and 37 g. I (b₇₅₉ 157-8.5°) in 150 ml. Et₂O added to a briskly reacting mixture of 18.5 g. EtBr, 13.7 g. Mg, and 200 ml. Et₂O, the whole refluxed 18 hrs. under N and a solution of iso-PrMgBr (from 35 g. iso-PrBr) added, the mixture cooled to -10° and dry O passed in, the temperature maintained below 5°, after absorption had ceased the product set aside 20 hrs. at 5°, and then poured onto solid CO₂, after addition of chilled 2N H₂SO₄, the Et₂O layer separated, and the product purified gave 2.12 g. black product, which was stored over P₂O₅ and then distilled from glass wool giving II, yellow liquid, b_0.01 38-9°, redistilled at 0.02 mm. to a colorless oil with a phenolic odor. With aqueous FeCl₃ II gave an intense red color, and with diazotized PhNH₂ in the presence of alkali, a dark red precipitate; benzoate (prepared by the Schotten-Baumann method), irregular prisms, m. 40° (from ligroine); 3,5-dinitrobenzoate, yellow prisms, m. 150° (from MeOH); phenylcarbamate, felted needles, m. 120° (from ligroine). These derivatives were stable. I (20 g.) was recovered from the Et₂O solution of alkali-insoluble material. The infrared absorption curves were given for II in liquid film, 15% by volume CCl₄, and 8% by volume CCl₄. The absorption characteristic of an unsat. CO group definitely established the presence of the tautomeric 2,3-dihydro-3-oxothiophene (III). With increasing dilution the equilibrium was in favor of III; however, the strength of the OH band and the odor suggested that the pure substance must contain much II.

Journal of the Chemical Society published new progress about 17236-59-8. 17236-59-8 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Alcohol, name is Thiophen-3-ol, and the molecular formula is C4H4OS, Computed Properties of 17236-59-8.

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

Dickman, John published the artcileMass spectrometry in structural and stereochemical problems. CLXIX. Determination of the structures of the ions produced in the single and double McLafferty rearrangements by ion cyclotron resonance spectroscopy, Category: alcohols-buliding-blocks, the publication is Journal of the American Chemical Society (1969), 91(8), 2069-84, database is CAplus.

Two possible structural isomers of the C3H6O•+ ion produced by electron impact induced fragmentations are the keto ion Me2CO+• and the enol ion MeC(:CH2)O+H•. The electron impact induced double Mc-Lafferty rearrangement can also produce a C3H6O•+ ion which could conceivably exist in either the enol or sym. oxonium ion structure. Ion cyclotron resonance and pulsed double resonance spectroscopy are used to study the ion-mol. reactions of the keto species, generated from acetone; the enol species, generated from 2-hexanone (via a McLafferty rearrangement) and from 1-methylcyclobutanol; and the double McLafferty species, generated from 5-nonanone. Seven ion-mol. reactions are found which distinguish between the keto and enol ions, thus substantiating the proposed differences in structure. In all cases studied, the enol ion, from 2-hexanone and the enol ion from 1-methylcyclobutanol behave identically indicating their structures to be equivalent The same ion-mol. reactions which distinguish between the keto and enol isomers can be utilized to distinguish between the keto and double McLafferty species. The enol and double McLafferty species react identically in all systems studied thus suggesting identical structures and raising serious doubts about the earlier proposed existence of a sym. double McLafferty oxonium ion. Deuterium labeling is employed to distinguish between isomeric ions of identical mass.

Journal of the American Chemical Society published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Category: alcohols-buliding-blocks.

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

Dong, Zhe published the artcileMetallaphotoredox-enabled deoxygenative arylation of alcohols, HPLC of Formula: 20880-92-6, the publication is Nature (London, United Kingdom) (2021), 598(7881), 451-456, database is CAplus and MEDLINE.

Metal-catalyzed cross-couplings are a mainstay of organic synthesis and are widely used for the formation of C-C bonds, particularly in the production of unsaturated scaffolds1. However, alkyl cross-couplings using native sp3-hybridized functional groups such as alcs. remain relatively underdeveloped2. In particular, a robust and general method for the direct deoxygenative coupling of alcs. would have major implications for the field of organic synthesis. A general method for the direct deoxygenative cross-coupling of free alcs. must overcome several challenges, most notably the in situ cleavage of strong C-O bonds3, but would allow access to the vast collection of com. available, structurally diverse alcs. as coupling partners4. Authors report herein a metallaphotoredox-based cross-coupling platform in which free alcs. are activated in situ by N-heterocyclic carbene salts for carbon-carbon bond formation with aryl halide coupling partners. This method is mild, robust, selective and most importantly, capable of accommodating a wide range of primary, secondary and tertiary alcs. as well as pharmaceutically relevant aryl and heteroaryl bromides and chlorides. The power of the transformation has been demonstrated in a number of complex settings, including the late-stage functionalization of Taxol and a modular synthesis of Januvia, an antidiabetic medication. This technol. represents a general strategy for the merger of in situ alc. activation with transition metal catalysis.

Nature (London, United Kingdom) published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H20O6, HPLC of Formula: 20880-92-6.

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

Jin, Jian published the artcileAlcohols as alkylating agents in heteroarene C-H functionalization, Computed Properties of 2240-88-2, the publication is Nature (London, United Kingdom) (2015), 525(7567), 87-90, database is CAplus and MEDLINE.

Primary alcs., diols containing at least one primary alc. moiety, and tetrahydrofurans acted as alkylating agents for six-membered nitrogen heterocycles such as isoquinolines, quinolines, and pyridines in the presence of an iridium photocatalyst Ir(ppy)₂(dtbbp)PF₆ (ppy = 1,2′-phenylpyridinediyl; dtbpy = 4,4′-di-tert-butyl-2,2-bipyridine), a thiol such as α-mercaptopropanoic acid, and p-toluenesulfonic acid in DMSO under blue LED light to yield alkylated heterocycles such as 1-methylisoquinoline in 43-98% yields. The medicinal agents fasudil dihydrochloride and milrinone were methylated and 3-phenylpropylated, resp., using this method in 82% and 43% yields. The method avoids the use of thermal conditions or stoichiometric oxidants. The mechanism was studied using fluorescence quenching experiments; the key step in the process is proposed to be the spin-center shift of a hydroxyalkylheteroaryl radical to yield an alkylheteroaryl radical with loss of water, precedented in biol. and synthetic settings. In the absence of a thiol, the radical generated from 1-isoquinolinemethanol coupled with two alkenes and two 1-pyrrolecarboxylates to yield dihydrobenzoisoquinolines and pyrrolylmethylisoquinolines, resp., in 25-65% yields.

Nature (London, United Kingdom) published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Computed Properties of 2240-88-2.

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

Shu, Chao published the artcilePhotoinduced Fragmentation Borylation of Cyclic Alcohols and Hemiacetals, Quality Control of 20117-47-9, the publication is Organic Letters (2020), 22(18), 7213-7218, database is CAplus and MEDLINE.

A visible-light photoinduced fragmentation borylation of O-phthalimido cycloalkanols with bis(catecholato)diboron is described. Structurally diverse keto and formyloxy alkyl boronic esters are conveniently prepared by radical-mediated ring-opening of cyclic alcs. and hemiacetals, resp. The reactions proceed under mild conditions in the absence of additives or photocatalysts, display excellent functional group tolerance, and allow cleavage of 4-, 5-, 6-, and 7-membered ring substrates. The mechanism proceeds via sequential homolytic N-O and C-C bond cleavages, the latter of which involves β-scission of an alkoxy radical, generating a carbonyl and an alkyl radical that is trapped by the diboron reagent. Spectroscopic studies suggest direct photoexcitation of either the phthalimide or diboron substrates with blue-light can initiate a radical chain mechanism.

Organic Letters published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C8H6ClNO, Quality Control of 20117-47-9.

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