Category: alcohols-buliding-blocks

Fischer, F. published the artcilePreparation and properties of mono- and dipinaconeboric acid, Category: alcohols-buliding-blocks, the publication is Zeitschrift fuer Chemie (1964), 4(8), 301-2, database is CAplus.

By repeating the preparation of monopinaconeboric acid (I) by Hermans (CA 19, 1386), I, m. 68-72°, was obtained only occasionally; most of the time a mixture, m. 60-180°, was formed which, recrystallized several times from petr. ether, gave dipinaconeboric acid (II), m. 218-25°. Some of the tautomeric forms are shown. Pinacone-6H₂O (III) and 1.6-2 equivalents B(OH)₃ (IV) as concentrated aqueous solutions mixed and evaporated in vacuo over concentrated H₂SO₄, and the residue extracted 8 hrs. with petr. ether gave I, readily soluble in H₂O and most organic solvents. Similar runs with IV and 2.5 equivalents III yielded II, b. 280°, m. 219-21° (Bu₂O), sparingly soluble in H₂O and most organic solvents. II becomes moist and deliquesces on proplonged standing in air. II dissolved in H₂O at room temperature within a few days (in 0.5 hr. at 100°) with decomposition to I, III, and IV. The infrared spectrum of I in CHCl₃ indicates that it is in equilibrium with a dimer; the equilibrium is shifted towards the dimer with increasing concentration The infrared spectrum of II indicates the formation of an acid complex at concentrations above 0.0125M.

Zeitschrift fuer Chemie 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, Category: alcohols-buliding-blocks.

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

Xu, Katherine J. published the artcileBisphenol S induces Agrp expression through GPER1 activation and alters transcription factor expression in immortalized hypothalamic neurons: A mechanism distinct from BPA-induced upregulation, HPLC of Formula: 80-09-1, the publication is Molecular and Cellular Endocrinology (2022), 111630, database is CAplus and MEDLINE.

The increasing prevalence of obesity around the world has brought concern upon ubiquitously present obesogenic environmental compounds, such as bisphenol A (BPA). Increasingly tightened regulations on the industrial use of BPA have prompted a transition to a structurally similar alternative, bisphenol S (BPS). BPS displays endocrine-disrupting behaviors similar to those of BPA and increases body weight, food intake and the hypothalamic expression of Agrp in vivo. However, the mechanisms behind this deleterious effect are unclear. Here, we report an increase in the mRNA level of Agrp at 4 h following BPS treatment in immortalized murine hypothalamic cell lines of embryonic and adult origin (mHypoE-41, mHypoA-59). BPS-induced changes in the expression of transcription factors and estrogen receptors that occurred concurrently with Agrp upregulation demonstrated similarities to BPA-induced changes, however, there were also changes that were unique to BPS. Specifically, while Chop, Atf3, Atf4, Atf6, Klf4, and Creb1 were upregulated and Gper1 was downregulated by both BPA and BPS, Esr1 mRNA levels were upregulated and Foxo1 and Stat3 levels remained unchanged by BPS. Finally, inhibition of GPER1 by G15 prevented BPS-mediated Agrp upregulation, independent of Atf3 and Klf4 upregulation. Overall, our results demonstrate the ability of BPS to increase Agrp mRNA expression through GPER1 signaling and to alter transcription factor expression in hypothalamic neurons, further elucidating the endocrine-disrupting potential of this alternative industrial chem.

Molecular and Cellular Endocrinology published new progress about 80-09-1. 80-09-1 belongs to alcohols-buliding-blocks, auxiliary class Ploymers, name is 4,4′-Sulfonyldiphenol, and the molecular formula is C8H6ClF3, HPLC of Formula: 80-09-1.

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

Xu, Chunfa published the artcileA Multistage Halogen Bond Catalyzed Strain-Release Glycosylation Unravels New Hedgehog Signaling Inhibitors, COA of Formula: C12H20O6, the publication is Journal of the American Chemical Society (2019), 141(13), 5381-5391, database is CAplus and MEDLINE.

Halogen bonding (XB) has recently emerged as a promising noncovalent activation mode that can be employed in catalysis. However, methodologies utilizing XB remain rare, and the hydrogen-bonding (HB) catalysis congeners are more widespread in comparison. Herein, we demonstrate a remarkable case whereby employment of XB catalysis in strain-release glycosylation generates O,N-glycosides in excellent anomeric selectivity exceeding HB activation. Deeper investigation unraveled XB catalyst dependencies on multiple stages of the mechanism and a hitherto unknown XB-glycosyl acceptor activation. We present a proof of concept to interrogate sp³-rich glycosidic chem. space for novel biol. activity, by integrating XB-catalyzed construction of a glycosidic compound collection, and evaluating these analogs via cell-based phenotypic screens. We show that XB-catalyzed strain-release glycosylation defines a new class of glycosides that inhibit the hedgehog signaling pathway through a nonsmoothened mode of action, opening new opportunities to combat acquired cancer resistance.

Journal of the American Chemical Society 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 C4H5NS2, COA of Formula: C12H20O6.

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

Nikolic, Vladimir published the artcileBiodegradation of copolymer obtained by grafting reaction between methacrylic acid and starch, Synthetic Route of 622-40-2, the publication is Polymer Bulletin (Heidelberg, Germany) (2019), 76(5), 2197-2213, database is CAplus.

Biodegradation of methacrylic acid and starch graft copolymers was investigated for the first time in this manuscript. Synthesized copolymer was characterized by ¹H NMR spectroscopy (NMR), Fourier transformed IR spectroscopy (FTIR), SEM (SEM) and elemental anal. Copolymers with different percentage of grafting, G (%), were buried in three different types of soil. Biodegradation was monitored by measuring mass loss of the samples and using FTIR and SEM. The highest weight loss was in soil for the orchid growth (all samples had biodegradation higher than 89%), followed by soil for the cactus growth (mass loss higher than 70%) and soil rich in humus where some of the samples had biodegradation rate near or less than 50%. The correlation between G (%) and percent of weight loss after biodegradation was not significant in any types of soil. FTIR and SEM showed that after biodegradation, samples still contained both building components. Respiration test showed higher O₂ consumption and CO₂ production comparing to polystyrene which confirmed biodegradability of the accessible starch in copolymer. Based on the obtained results, degradation mechanism is proposed. First step is biodegradation of easily accessible starch followed by dissolution of the poly(methacrylic acid). This mechanism confirmed that biodegradation depends not only on the percentage of grafting, but also on mol. packaging, chains arrangement and the number and types of microorganisms present in the specific types of soils.

Polymer Bulletin (Heidelberg, Germany) 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, Synthetic Route of 622-40-2.

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

Liu, Lulu published the artcileDesign, synthesis and biological evaluation of tyrosine derivatives as Mcl-1 inhibitors, Computed Properties of 518303-20-3, the publication is European Journal of Medicinal Chemistry (2020), 112142, database is CAplus and MEDLINE.

The upregulation of the protein myeloid cell leukemia-1 (Mcl-1) is closely associated with various human cancers, which can result in the evasion of apoptosis and a low survival rate. Therefore, developing Mcl-1 inhibitors has become a promising paradigm for cancer therapy. Herein, we designed and synthesized a novel series of tyrosine derivatives, among which compounds (I) (R¹ = 3,5-di-Me-4-Cl-Ph, X = H, R² = OBut, n = 2; R¹ = 3,5-di-Me-4-Cl-Ph, X = H, R² = Ph, n = 1; R¹ = naphthyl, X = Br, R² = 4-Me-benzyl, n = 1) exhibited very high binding affinity to Mcl-1 with K_i values of 0.18, 0.27 and 0.23μM, resp. Interestingly, compound I (R¹ = 3,5-di-Me-4-Cl-Ph, X = H, R² = Ph, n = 1) showed not only potent activity against Mcl-1 but also considerable selectivity over Bcl-2 and Bcl-xL, which was rationalized by mol. docking and fragment-centric topog. mapping (FCTM). It is worth noting that compounds I (R¹ = 3,5-di-Me-4-Cl-Ph, X = H, R² = OBut, n = 2; R¹ = 3,5-di-Me-4-Cl-Ph, X = H, R² = Ph, n = 1; R¹ = naphthyl, X = Br, R² = 4-Me-benzyl, n = 1) displayed potent antiproliferative activity against several cancer cell lines and could induce apoptosis of KM3 and HepG2 cells in a dose-dependent manner.

European Journal of Medicinal Chemistry published new progress about 518303-20-3. 518303-20-3 belongs to alcohols-buliding-blocks, auxiliary class Apoptosis,Bcl-2, name is 2-((4-(4-Bromophenylsulfonamido)-1-hydroxynaphthalen-2-yl)thio)acetic acid, and the molecular formula is C18H14BrNO5S2, Computed Properties of 518303-20-3.

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

Yan, Si-Shun published the artcileVisible-light photoredox-catalyzed selective carboxylation of C(sp³)-F bonds with CO₂, COA of Formula: C6H16OSi, the publication is Chem (2021), 7(11), 3099-3113, database is CAplus.

A novel selective carboxylation of C(sp³)-F bonds with CO₂ via visible-light photoredox catalysis. A variety of mono-, di-, and trifluoroalkylarenes as well as α,α-difluorocarboxylic esters and amides undergo such reactions to give important aryl acetic acids and α-fluorocarboxylic acids, including several drugs and analogs, under mild conditions. Notably, mechanistic studies and DFT calculations demonstrate the dual role of CO₂ as an electron carrier and electrophile during this transformation. The fluorinated substrates would undergo single-electron reduction by electron-rich CO₂ radical anions, which were generated in situ from CO₂ via sequential hydride-transfer reduction and hydrogen-atom-transfer processes.

Chem published new progress about 597-52-4. 597-52-4 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is Triethylsilanol, and the molecular formula is C18H12ClNO, COA of Formula: C6H16OSi.

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

Zong, Xinlong published the artcileFluoride Anion-Catalyzed Mukaiyama-aldol Reaction: Rapid Access to α-Fluoro-β-Hydroxy Esters, Synthetic Route of 106-25-2, the publication is Journal of Organic Chemistry (2022), 87(10), 6918-6926, database is CAplus and MEDLINE.

A protocol of fluoride anion-mediated Mukaiyama aldol reaction with low catalytic loading in short reaction time to incorporate fluorine at α position into β-hydroxy esters was reported. The method shown good functional-group tolerance and scale-up potential, moreover, was applicable to the late-stage modification of natural products and small mol. drugs.

Journal of Organic Chemistry published new progress about 106-25-2. 106-25-2 belongs to alcohols-buliding-blocks, auxiliary class Natural product, name is cis-3,7-Dimethyl-2,6-Octadien-1-Ol, and the molecular formula is C37H30ClIrOP2, Synthetic Route of 106-25-2.

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

Gao, Zhangshan published the artcileTesticular toxicity of bisphenol compounds: Homeostasis disruption of cholesterol/testosterone via PPARα activation, Recommanded Product: 4,4′-Sulfonyldiphenol, the publication is Science of the Total Environment (2022), 155628, database is CAplus and MEDLINE.

The widespread application of bisphenols (BPs) has made them ubiquitous in the environment. Although the side effects of bisphenol A (BPA) substitutes have received increasing attention, studies on their reproductive toxicity remain lacking. In this research, the effects of BPA and its substitutes, including bisphenol S (BPS), bisphenol F (BPF), and bisphenol AF (BPAF), on the male reproductive system were evaluated. Results proved that these BPs disturbed germ cell proliferation, induced germ cell apoptosis, and perturbed sperm physiologies and spermatogenesis, which resulted from the disruption of testosterone (T) biosynthesis in Leydig cells (LCs). Importantly, in vitro and in vivo studies indicated that the exhausted cholesterol in LCs accounted for the reduced T production Furthermore, the knockdown of peroxisome proliferator-activated receptor alpha (PPARα) remarkably ameliorated the downregulation of cholesterogenesis-related genes (i.e., Hmgcs1, Hmgcr, and Srebf2), indicating that PPARα played a critical role in BPs-induced testicular dysfunction. Overall, our studies indicated that BPS, BPF, and BPAF could induce testicular toxic effects similar to that of BPA, which were associated with the PPARα pathway.

Science of the Total Environment published new progress about 80-09-1. 80-09-1 belongs to alcohols-buliding-blocks, auxiliary class Ploymers, name is 4,4′-Sulfonyldiphenol, and the molecular formula is C12H10O4S, Recommanded Product: 4,4′-Sulfonyldiphenol.

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

Wu, Huaimo published the artcileAn efficient approach for the synthesis of 1,2-dihydroxanthones enabled by one-pot Claisen condensation/cyclization reactions, Name: 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is Organic & Biomolecular Chemistry (2021), 19(18), 4126-4131, database is CAplus and MEDLINE.

In this report, a mild, efficient and green method for the synthesis of 1,2-dihydroxanthones (DHXs) I (R = H, Me, 3-methylbut-2-en-1-yl; R¹ = H, Me; R² = Me, Ph, 2,2,2-trifluoroethyl, but-3-en-1-yl, etc.; R³ = H, Me; R⁴ = H, F, OMe, Cl, Br, I; R⁵ = H, Me, OMe, Cl, CF₃, F; R⁴R⁵ = -CH:CHCH:CH-; R⁶ = H, Cl, Me, prop-2-en-1-yl) and II (R⁷ = H, OMe) has been developed in one pot through Claisen condensation and O-cyclization under waste-induced relay catalysis with min. organic solvents. The byproduct (HMDS or NH₃·H₂O) of the first step turned out to be the promoter for the second step, which could efficiently proceed in aqueous media without the addition of other catalysts. The reactions using trifluoroethyl salicylates 2-OH-3-R⁶-4-R⁵-5-R⁴-6-R³C₆HC(O)OCH₂CF₃ could be performed under mild conditions to ensure the generation of vulnerable DHXs I and II in high yields. The substrate scope is very broad regardless of the substituent type and its position on the structure. Specifically, the versatility of DHXs I (R = R¹ = R³ = R⁴ = R⁵ = R⁶ = H; R² = Me) was demonstrated by their conversion to xanthones I (R = 3-methylbut-2-en-1-yl; R¹ = R³ = R⁴ = R⁵ = R⁶ = H; R² = Me)/II (R⁷ = H) and other complex structures III/IV.

Organic & Biomolecular Chemistry published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C18H28BNO2, Name: 2-Hydroxy-4-(trifluoromethyl)benzoic acid.

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

Hu, Dejin published the artcileSynthesis and herbicidal activities of N^ε-[(anilino)carbonyl]-N^α-[(3-phenyl-5-isoxazolyl)carbonyl]lysine, HPLC of Formula: 438565-33-4, the publication is Youji Huaxue (2010), 30(9), 1366-1371, database is CAplus.

Recently the D1 protease located in the thylakoid membranes of higher plants was found to be a potential herbicide target and based on a lead compound [N^α-[(5-isoxazolyl)carbonyl]lysine, D1 protease inhibitor] a series of novel N⁵-[(phenylamino)carbonyl]-N₂-[(3-phenyl-5-isoxazolyl)carbonyl]lysine derivatives were designed. The synthesis of the target compounds was achieved using as reactants 3-phenyl-5-isoxazolecarbonyl chlorides and N⁵-[(phenylamino)carbonyl]lysine and the products thus obtained were confirmed by IR, ¹H-NMR and elemental anal. The biol. activity was examined in vivo and it was discovered that most compounds possessed moderate herbicidal activity. Meanwhile, the e activity of one compound was evaluated against spinach D1 protease (i.e., thylakoid protein precursor processing peptidase, chloroplast protein precursor-processing proteinase, photosystem D1 protein precursor carboxyl-terminal processing proteinase, proteinase CtpA) and the result showed its inhibiting effect against this enzyme.

Youji Huaxue published new progress about 438565-33-4. 438565-33-4 belongs to alcohols-buliding-blocks, auxiliary class Isoxazole,Chloride,Benzene,Alcohol, name is 3-(2-Chlorophenyl)-5-isoxazolemethanol, and the molecular formula is C10H8ClNO2, HPLC of Formula: 438565-33-4.

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