Category: alcohols-buliding-blocks

Kanakubo, Masashi published the artcileRoom-Temperature Phosphorescence of Thiophene Boronate Ester-Cross Linked Polyvinyl Alcohol; A Triplet-to-Singlet FRET-Induced Multi-Color Afterglow Luminescence with Sulforhodamine B, Computed Properties of 239075-02-6, the publication is Bulletin of the Chemical Society of Japan (2021), 94(4), 1204-1209, database is CAplus.

A thiophene-derived boronate ester-crosslinked polyvinyl alc., 1-PVA, has been prepared, which was found to exhibit room-temperature phosphorescence (RTP) at 475 nm upon UV irradiation (λem = 254 nm). The quantum yield (Fp) was determined to be 6.3% with a phosphorescence lifetime of 256 ms, the cyanish afterglow being visually detected after switching the UV lamp off. The emission properties were rationalized by El-Sayed’s rule, where introduction of a sulfur atom brings about n → π* transition in the T2 state to promote an ISC channel. Given that the phosphorescence spectrum at 77 K was consistent with that in the PVA film, the rigid environment of PVA-based matrix may stabilize the triplet state. In addition, the delayed emissive color was tuned by doping various amounts of sulforhodamine B (SRhoB) in the film; a triplet-to-singlet Forster-type resonance energy transfer process occurred from crosslinked thiophene boronate to SRhoB acceptor which modified the emission to a white-light afterglow. Given water-sensitivity of the resultant film, high-contrast water writing on the film was achieved, which would be profitable for a low-cost security film.

Bulletin of the Chemical Society of Japan published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Computed Properties of 239075-02-6.

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

Itoga, Moeko published the artcileIridium-catalyzed α-selective deuteration of alcohols, Computed Properties of 111-29-5, the publication is Chemical Science (2022), 13(30), 8744-8751, database is CAplus and MEDLINE.

The α-selective, iridium(III)-bipyridonate-catalyzed hydrogen(H)/deuterium(D) isotope exchange of alcs. using deuterium oxide (D₂O) as the primary deuterium source to afford deuterated alcs. RCD₂OH [R = Ph, 2-MeC₆H₄, 4-FC₆H₄, etc.], R¹DCOHR² [R¹ = Ph, 4-ClC₆H₄, 4-BrC₆H₄, etc.; R² = Me, cyclopropyl, Ph] was reported. This method enabled the direct, chemoselective deuteration of primary and secondary alcs. under basic or neutral conditions without being affected by coordinative functional groups such as imidazole and tetrazole. Successful substrates for deuterium labeling include the pharmaceuticals losartan potassium, rapidosept, guaifenesin and diprophylline. The deuterated losartan potassium showedhigher stability toward the metabolism by CYP2C9 than the protiated analog. Kinetic and DFT studies indicated that the direct deuteration proceeded through dehydrogenation of alc. to the carbonyl intermediate, conversion of [IrIII-H] to [IrIII-D] with D2O, and deuteration of the carbonyl intermediate to give the α-deuterated products.

Chemical Science published new progress about 111-29-5. 111-29-5 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ploymers, name is Pentane-1,5-diol, and the molecular formula is C5H12O2, Computed Properties of 111-29-5.

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

Wakioka, Masayuki published the artcileSynthesis of a 1,2-dithienylethene-containing donor-acceptor polymer via palladium-catalyzed direct arylation polymerization (DArP), Product Details of C20H28B2O4S2, the publication is Molecules (2018), 23(4), 981/1-981/10, database is CAplus and MEDLINE.

This paper reports the synthesis of D-A polymers containing 1,2-dithienylethene (DTE) units via palladium-catalyzed direct arylation polymerization (DArP). The reaction of dibromoisoindigo (1-Br) and DTE (2-H), in the presence of Pd₂(dba)₃·CHCl₃ (0.5 mol%), P(2-MeOC₆H₄)₃ (L1) (2 mol%), pivalic acid (1 equiv) as catalyst precursors, and Cs₂CO₃ (3 equiv) as a base affords poly(1-alt-2) with a high mol. weight (M_n up to 44,900). Although, it has been known that monomers, with plural C-H bonds, tend to form insoluble materials via direct arylation at undesirable C-H positions; the reaction of 1-Br and 2-H cleanly proceeds without insolubilization. The resulting polymer has a well-controlled structure and exhibits good charge transfer characteristics in an organic field-effect transistor (OFET), compared to the polymer produced by Migita-Kosugi-Stille cross-coupling polymerization The DArP product displays an ideal linear relationship in the current-voltage curve, whereas the Migita-Kosugi-Stille product shows a V_G-dependent change in the charge mobility.

Molecules published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C8H6ClF3, Product Details of C20H28B2O4S2.

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

Wang, Yinli published the artcileEnhanced Molecular Recognition through Substrate-Additive Complex Formation in N-Heterocyclic-Carbene-Catalyzed Kinetic Resolution of α-Hydroxythioamides, COA of Formula: C8H8O3, the publication is ACS Catalysis (2022), 12(10), 6100-6107, database is CAplus.

A new way of understanding enhanced mol. recognition through substrate-additive complex formation and the development of the first catalytic kinetic resolution of α-hydroxythioamides RCH(OH)C(S)NH(R¹) (R = Me, cyclopropyl, Ph, etc.; R¹ = Et, t-Bu, 3,5-bis(trifluoromethyl)phenyl, etc.), which are versatile synthetic building blocks, using chiral N-heterocyclic carbene I-catalyzed enantioselective acylation assisted by a carboxylate additive viz., 9-Julolidinecarboxylic acid was described. Mass spectrometry provided evidence for the role of the additive, which forms a hydrogen-bonded complex with α-hydroxythioamide, resulting in both rate and selectivity enhancements. The synthetic applications of the resolved α-hydroxythioamides highlight the usefulness of the developed method.

ACS Catalysis published new progress about 90-64-2. 90-64-2 belongs to alcohols-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Alcohol,Natural product, name is 2-Hydroxy-2-phenylacetic acid, and the molecular formula is C7H9NO, COA of Formula: C8H8O3.

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

Liu, Yong published the artcileConstruction of diverse C-S/C-Se bonds via nickel catalyzed reductive coupling employing thiosulfonates and a selenosulfonate under mild conditions, HPLC of Formula: 20880-92-6, the publication is Organic Chemistry Frontiers (2022), 9(5), 1375-1382, database is CAplus.

A nickel-catalyzed reductive cross coupling between organic iodides and thiosulfonates and a selenosulfonate under mild conditions was disclosed. This practical method provides a facile access to a series of unsym. thioethers with low catalyst loading, good functional group tolerance, and excellent chemo-selectivity. Notably, the synthetic applications of the approach feature scaling-up of reactions, late-stage modification of pharmaceuticals, and preparation of various useful targeted compounds, including sulfoximine, bipyridine, and vortioxetine. Primary mechanistic studies showed that a radical pathway was involved. Moreover, diverse C-S/C-Se bond formations were achieved under mild reaction conditions.

Organic Chemistry Frontiers 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

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

Hou, Wei published the artcileCloning, expression and activity analysis of sndh-sdh gene cluster of Gluconobacter oxydans, Category: alcohols-buliding-blocks, the publication is Shengwu Jishu Tongxun (2012), 23(3), 389-392, database is CAplus.

Objective: To clone the sndh-sdh gene cluster from Gluconobacter oxydans H763 and investigate the expression and biol. activity of sorbosone dehydrogenase-sorbose dehydrogenase (SNDH-SDH) in Escherichia coli DH5α and G. oxydans 621H. Methods & Results: The sndh-sdh gene cluster, including promoter, structural gene and terminator sequence, was directly amplified using PCR method from G. oxydans H763 genome DNA. Then the 3533 bp amplification product was retrieved and ligated into the vector pMD18T and transformed into E. coli DH5α. Its expression and biol. activity were examined by DCIP assay when sorbose or xylose was used as substrate. After the cell lysis was added to the DCIP detection solution, its color changed from bluish green to yellow, which suggested that the expression product had dehydrogenase activity. The vector pBBR1MCS2-sndh-sdh was constructed and conjugated into G. oxydans 621H. After the recombinant strain was cultivated in the medium containing sorbitol or sorbose as substrate, the metabolic products in the supernatant were assayed by thin-layer chromatog., and chromatoplate showed the 2-keto-L-gulonic acid (2-KLG) spots. Conclusion: The above results indicated that the SNDH-SDH was expressed in E. coli DH5α and G. oxydans 621H.

Shengwu Jishu Tongxun published new progress about 526-98-7. 526-98-7 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Other Sugar Units, name is (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, and the molecular formula is C6H10O7, Category: alcohols-buliding-blocks.

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

Hu, Ying published the artcileA mannosylated cell-penetrating peptide-graft-polyethylenimine as a gene delivery vector, Safety of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is Biomaterials (2014), 35(13), 4236-4246, database is CAplus and MEDLINE.

Polyethylenimine (PEI) is widely applied in non-viral gene delivery vectors. PEI with high mol. weight is highly effective in gene transfection but is high cytotoxic. Conversely, PEI with low mol. weight displays lower cytotoxicity but less delivering efficiency. To overcome this issue, a novel copolymer with mannosylated, a cell-penetrating peptide (CPP), grafting into PEI with mol. weight of 1800 (Man-PEI₁₈₀₀-CPP) were prepared in this study to target antigen-presenting cells (APCs) with mannose receptors and enhance transfection efficiency with grafting CPP. The copolymer was characterized by ¹H NMR and FTIR. Spherical nanoparticles were formed with diameters of about 80-250 nm by mixing the copolymer and DNA at various charge ratios of copolymer/DNA(N/P). Gel retardation assays indicated that Man-PEI₁₈₀₀-CPP polymers efficiently condensed DNA at low N/P ratios. Cytotoxicity studies showed that Man-PEI₁₈₀₀-CPP/DNA complexes maintained in a high percentage of cell viability compared to the PEI with mol. weight of 25 k (PEI_25k). Laser scan confocal microscopy and flow cytometry confirmed that Man-PEI₁₈₀₀-CPP/DNA complexes resulted in higher cell uptake efficiency on DC2.4 cells than on Hela cells line. The transfection efficiency of Man-PEI₁₈₀₀-CPP was significantly higher than that of PEI_25k on DC2.4 cells. More importantly, the complexes were mainly distributed in the epidermis and dermis of skin and targeted on splenocytes after percutaneous coating based on microneedles in vivo. These results indicated that Man-PEI₁₈₀₀-CPP was a potential APCs targeted of non-virus vector for gene therapy.

Biomaterials 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, Safety of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol.

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

Xu, Jiaojiao published the artcileMicroneedle-Assisted, DC-Targeted Codelivery of pTRP-2 and Adjuvant of Paclitaxel for Transcutaneous Immunotherapy, Related Products of alcohols-buliding-blocks, the publication is Small (2017), 13(28), n/a, database is CAplus and MEDLINE.

This work aims at developing an immunotherapeutic strategy to deliver a cancer DNA vaccine targeting dendritic cells (DCs), to trigger their maturation and antitumor function, and reduce immune escape using a polymeric nanocomplex of paclitaxel (PTX)-encapsulated sulfobutylether-β-cyclodextrin (SBE)/mannosylated N,N,N-trimethylchitosan (mTMC)/DNA. To enhance DC-targeting and revoke immunosuppression is the major challenge for eliciting effective antitumor immunity. This codelivery system is characterized by using low-dose PTX as an adjuvant that is included inside SBE, and the PTX/SBE further serves as an anionic crosslinker to self-assemble with the cationic mTMC/DNA polyplexes. This system is used in combination with a microneedle for transcutaneous vaccination. Once penetrating into the epidermis, the mannosylated nanocomplexes would preferentially deliver the pTRP-2 DNA vaccine inside the DCs. Phenotypic maturation is demonstrated by the increased expression of costimulatory mols. of CD80 and CD86, and the elevated secretion of IL-12p70. The mixed leukocyte reactions reveal that the PTX/SBE-mTMC/DNA nanocomplexes enhance the proliferation of CD4+ and CD8+ T cells, and inhibit the generation of immune-suppressive FoxP3+ T cells. The system shows high antitumor efficacy in vivo. The PTX/SBE-mTMC/DNA nanocomplexes for DC-targeted codelivery of DNA vaccine and adjuvant PTX yield synergistic effects on the DC maturation and its presenting functions, thus increasing immune stimulation and reducing immune escape.

Small 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 C18H17NO8, Related Products of alcohols-buliding-blocks.

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

Hu, Ying published the artcileSynthesis of mannosylated polyethylenimine and its potential application as cell-targeting non-viral vector for gene therapy, Related Products of alcohols-buliding-blocks, the publication is Polymers (Basel, Switzerland) (2014), 6(10), 2573-2587, 15 pp., database is CAplus.

Mannose polyethylenimine with a mol. weight of 25 k (Man-PEI25k) was synthesized via a phenylisothiocyanate bridge using mannopyranosylphenyl isothiocyanate as a coupling reagent, and characterized by 1H NMR (NMR) and FT-IR (Fourier transform IR spectroscopy) anal. Spherical nanoparticles were formed with diameters of 80-250 nm when the copolymer was mixed with DNA at various charge ratios of copolymer/DNA (N/P). Gel electrophoresis demonstrated that the DNA had been condensed and retained by the PEI derivates at low N/P ratios. The Man-PEI25k/DNA complexes were less cytotoxic than the PEI complexes with a mol. weight of 25 k (PEI25k) at the same N/P ratio. Laser scan confocal microscopy and flow cytometry confirmed that the Man-PEI25k/DNA complexes gave higher cell uptake efficiency in (Dendritic cells) DC2.4 cells than HeLa cells. The transfection efficiency of Man-PEI25k was higher than that of PEI25k towards DC2.4 cells. These results indicated that Man-PEI25k could be used as a potential DC-targeting non-viral vector for gene therapy.

Polymers (Basel, Switzerland) 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