Category: alcohols-buliding-blocks

Sircar, Ila published the artcileCalcium channel blocking and positive inotropic activities of ethyl 5-cyano-1,4-dihydro-6-methyl-2-[(phenylsulfonyl)methyl]-4-aryl-3-pyridinecarboxylate and analogs. Synthesis and structure-activity relationships, Formula: C10H15NO, the publication is Journal of Medicinal Chemistry (1991), 34(7), 2248-60, database is CAplus and MEDLINE.

A series of 2-[(arylsulfonyl)methyl]-4-aryl-5-cyano-1,4-dihydropyridine-3-carboxylic acid esters and analogs, e.g., I, were prepared via a three component Hantzsch reaction using a substituted benzaldehyde, enamine, and the requisite β-keto ester. These compounds possess unique profile, namely calcium channel blocking and pos. inotropic activities in vitro. Compound I was selected as the best compound in the series and was studied in detail. The synthesis and biol. profiles of enantiomers of I are also reported. The data indicate that although the calcium channel blocking property of I is stereospecific the pos. inotropic activity is not. Examples of 3- and 6-cyano and other closely related 1,4-dihydropyridine derivatives are described and evaluated for comparison and were found to be devoid of dual activities mentioned above.

Journal of Medicinal Chemistry published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C8H6BrF3S, Formula: C10H15NO.

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

Wang, Yekai published the artcileMetabolic signature of the aging eye in mice, HPLC of Formula: 86-48-6, the publication is Neurobiology of Aging (2018), 223-233, database is CAplus and MEDLINE.

Aging is a major risk factor for age-related ocular diseases including age-related macular degeneration in the retina and retinal pigment epithelium (RPE), cataracts in the lens, glaucoma in the optic nerve, and dry eye syndrome in the cornea. We used targeted metabolomics to analyze metabolites from young (6 wk) and old (73 wk) eyes in C57 BL6/J mice. Old mice had diminished electroretinogram responses and decreased number of photoreceptors in their retinas. Among the 297 detected metabolites, 45-114 metabolites are significantly altered in aged eye tissues, mostly in the neuronal tissues (retina and optic nerve) and less in cornea, RPE/choroid, and lens. We noted that changes of metabolites in mitochondrial metabolism and glucose metabolism are common features in the aged retina, RPE/choroid, and optic nerve. The aging retina, cornea, and optic nerve also share similar changes in NAD (NAD), 1-methylnicotinamides, 3-methylhistidine, and other methylated metabolites. Metabolites in taurine metabolism are strikingly influenced by aging in the cornea and lens. In conclusion, the aging eye has both common and tissue-specific metabolic signatures. These changes may be attributed to dysregulated mitochondrial metabolism, reprogrammed glucose metabolism and impaired methylation in the aging eye. Our findings provide biochem. insights into the mechanisms of age-related ocular changes.

Neurobiology of Aging published new progress about 86-48-6. 86-48-6 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment,Natural product, name is 1-Hydroxy-2-naphthoic acid, and the molecular formula is C12H14O2, HPLC of Formula: 86-48-6.

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

Boontanonda, Pavares published the artcilePalladium(II)-catalyzed ring expansion of methylenecyclobutanes and related systems, Formula: C5H10O, the publication is Journal of the Chemical Society, Chemical Communications (1977), 583-4, database is CAplus.

Treatment of methylenecyclobutane (I; R = H) with PdCl₂-CuCl₂-O₂-H₂O in C₆H₆ at 0° gave 75% cyclopentanone (II; R = H). I (R = CH₂NHAc, CN) underwent analogous oxidative ring expansion at room temperature and 60° resp. on treatment with PdCl₂-CuCl₂-O₂-H₂O in EtOAc to give 65 and 82% II resp., whereas similar treatment of camphene (iso-PrOH, 65°), methylenecamphor (EtOAc, 45°) and methylenecyclopentane (EtOAc, 65°) gave only low yields of the corresponding ring expanded products. Methylenenorbornane (iso-PrOH, 45°), and β-pinene (Me₃COH, 45°) gave the corresponding bis-π-allyl palladium chloride dimers quant. on treatment with PdCl₂3-CuCl₂-O₂-H₂O whereas similar treatment of 4-RC₆H₄CPh:CH₂ (R = H, MeO) gave 28.5% Ph₂CO and 28.5% PhCH₂COPh, and 62.5% PhCOC₆H₄OMe-4, resp.

Journal of the Chemical Society, Chemical Communications 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, Formula: C5H10O.

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

Riva, Beatrice published the artcilePyrtriazoles, a Novel Class of Store-Operated Calcium Entry Modulators: Discovery, Biological Profiling, and in Vivo Proof-of-Concept Efficacy in Acute Pancreatitis, Formula: C6H13NO2, the publication is Journal of Medicinal Chemistry (2018), 61(21), 9756-9783, database is CAplus and MEDLINE.

In recent years, channels that mediate store-operated calcium entry (SOCE, i.e., the ability of cells to sense a decrease in endoplasmic reticulum luminal calcium and induce calcium entry across the plasma membrane) have been associated with a number of disorders, spanning from immune disorders to acute pancreatitis and have been suggested to be druggable targets. In the present contribution, we exploited the click chem. approach to synthesize a class of SOCE modulators where the arylamide substructure that characterizes most inhibitors so far described is substituted by a 1,4-disubstituted 1,2,3-triazole ring. Within this series, inhibitors of SOCE were identified and the best compound I proved effective in an animal model of acute pancreatitis, a disease characterized by a hyperactivation of SOCE. Strikingly, two enhancers of the process were discovered, affording invaluable research tools to further explore the (patho)physiol. role of capacitative calcium entry.

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, Formula: C6H13NO2.

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

Wahlang, Banrida published the artcileAssociations between residential exposure to volatile organic compounds and liver injury markers, HPLC of Formula: 90-64-2, the publication is Toxicological Sciences (2022), 185(1), 50-63, database is CAplus and MEDLINE.

Occupational exposures to volatile organic compounds (VOCs) have been associated with numerous health complications including steatohepatitis and liver cancer. To address this knowledge gap, the objective of this cross-sectional study is to investigate associations between VOCs and liver injury biomarkers in community residents. Subjects were recruited from six Louisville neighborhoods, and informed consent was obtained. Exposure biomarkers included 16 creatinine-adjusted urinary metabolites corresponding to 12 parent VOCs. Serol. disease biomarkers measured included cytokertain-18 (K18 M65 and M30), liver enzymes, and direct bilirubin. The population comprised of approx. 60% females and 40% males; White persons accounted 78% of the population; with more nonsmokers (n = 413) than smokers (n = 250). In the overall population, metabolites of acrolein, acrylonitrile, acrylamide, 1,3-butadiene, crotonaldehyde, styrene, and xylene were pos. associated with alk. phosphatase. These associations persisted in smokers, with the exception of crotonaldehyde, and addition of N,N-dimethylformamide and propylene oxide metabolites. Although no pos. associations were observed for K18 M30, the benzene metabolite was pos. associated with bilirubin, irresp. of smoking status. Taken together, the results demonstrated that selected VOCs were pos. associated with liver injury biomarkers. These findings will enable better risk assessment and identification of populations vulnerable to liver disease.

Toxicological Sciences 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 C5H5BrN2, HPLC of Formula: 90-64-2.

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

Luo, Min published the artcileInvading Escherichia coli genetics with a xenobiotic nucleic acid carrying an acyclic phosphonate backbone (ZNA), Application In Synthesis of 57044-25-4, the publication is Journal of the American Chemical Society (2019), 141(27), 10844-10851, database is CAplus and MEDLINE.

A synthetic orthogonal polymer embracing a chiral acyclic-phosphonate backbone [(S)-ZNA] is presented that uniquely adds to the emerging family of xenobiotic nucleic acids (XNAs). (S)-ZNA consists of reiterating six-atom structural units and can be accessed in few synthetic steps from readily available phophonomethylglycerol nucleoside (PMGN) precursors. Comparative thermal stability experiments conducted on homo- and heteroduplexes made of (S)-ZNA are described that evince its high self-hybridization efficiency in contrast to poor binding of natural complements. Although preliminary and not conclusive, CD data and dynamic modeling computations provide support to a left-handed geometry of double-stranded (S)-ZNA. Nonetheless, PMGN diphosphate monomers were recognized as substrates by Escherichia coli polymerase I as well as being imported into E. coli cells equipped with an algal nucleotide transporter. A further investigation into the in vivo propagation of (S)-ZNA culminated with the demonstration of the first synthetic nucleic acid with an acyclic backbone that can be transliterated to DNA by the E. coli cellular machinery.

Journal of the American Chemical Society 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 In Synthesis of 57044-25-4.

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

Luo, Min published the artcileAmidate Prodrugs of Cyclic 9-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]adenine with Potent Anti-Herpesvirus Activity, SDS of cas: 57044-25-4, the publication is ACS Medicinal Chemistry Letters (2018), 9(4), 381-385, database is CAplus and MEDLINE.

A series of amidate prodrugs I of cyclic 9-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine (cHPMPA) featuring different amino acid motifs were synthesized. All phosphonamidates derived from (S)-cHPMPA displayed a broad spectrum activity against herpesviruses with EC₅₀ values in the low nanomolar range. A phosphonobisamidate prodrug of (S)-HPMPA also exhibited a remarkably potent antiviral activity. In addition, the leucine ester prodrug of (S)-cHPMPA and phosphonobisamidate valine ester prodrug of (S)-HPMPA proved stable in human plasma. These data warrant further development of cHPMPA prodrugs, especially against human cytomegalovirus (HCMV), for which there is a high need for treatment in transplant recipients.

ACS Medicinal Chemistry 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, SDS of cas: 57044-25-4.

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

Andorfer, Mary C. published the artcileUnderstanding Flavin-Dependent Halogenase Reactivity via Substrate Activity Profiling, Safety of 4-(1H-Pyrrol-1-yl)phenol, the publication is ACS Catalysis (2017), 7(3), 1897-1904, database is CAplus and MEDLINE.

The activity of four native FDHs and four engineered FDH variants on 93 low mol. weight arenes was used to generate FDH substrate activity profiles. These profiles provided insights into how substrate class, functional group substitution, electronic activation, and binding impact FDH activity and selectivity. The enzymes studied could halogenate a far greater range of substrates than previously recognized, but significant differences in their substrate specificity and selectivity were observed Trends between the electronic activation of each site on a substrate and halogenation conversion at that site were established, and these data, combined with docking simulations, suggest that substrate binding can override electronic activation even on compounds differing appreciably from native substrates. These findings provide a useful framework for understanding and exploiting FDH reactivity for organic synthesis.

ACS Catalysis published new progress about 23351-09-9. 23351-09-9 belongs to alcohols-buliding-blocks, auxiliary class Pyrrole,Benzene,Alcohol, name is 4-(1H-Pyrrol-1-yl)phenol, and the molecular formula is C10H9NO, Safety of 4-(1H-Pyrrol-1-yl)phenol.

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

Anderl, Felix published the artcileTotal Synthesis of Belizentrin Methyl Ester: Report on a Likely Conquest, Safety of (R)-Oxiran-2-ylmethanol, the publication is Angewandte Chemie, International Edition (2018), 57(33), 10712-10717, database is CAplus and MEDLINE.

The assigned structure of the dinoflagellate-derived toxin belizentrin was prepared by total synthesis in form of the corresponding Me ester I for stability reasons. The successful route features an unusual solution for the preparation of a recalcitrant ylide on a C-glycosidic segment; moreover, it involves an asym. hetero-Diels-Alder reaction en route to the tertiary hemiacetal substructure, a Negishi cross-coupling of two elaborate building blocks, and a macrocyclization based on an intramol. aminolysis of a spirolactone. A modified Kocienski olefination ultimately allowed the polyol side chain to be attached to the macrocycle although this transformation faced the exceptional base sensitivity of this polyunsaturated target compound

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 C3H6O2, Safety of (R)-Oxiran-2-ylmethanol.

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

Drees, Becky L. published the artcileThe GCN4 leucine zipper can functionally substitute for the heat shock transcription factor’s trimerization domain, Related Products of alcohols-buliding-blocks, the publication is Journal of Molecular Biology (1997), 273(1), 61-74, database is CAplus and MEDLINE.

The heat shock transcription factor (HSF) is the only known sequence-specific, homotrimeric DNA-binding protein. HSF binds to a DNA recognition site called a heat shock element (HSE), which contains varying numbers of nGAAn units (“GAA boxes”) arranged in inverted repeats. To investigate the role of trimerization on HSF’s DNA-binding properties, the authors replaced the trimerization domain, which self-assembles to form a three-stranded α-helical coiled coil, with the GCN4 leucine zipper, which forms a two-stranded α-helical coiled coil. Surprisingly, this substitution did not effect the ability of HSF to function in vivo. Biochem. studies of an HSF-leucine zipper chimera in comparison to an HSF truncation show that the HSF-leucine zipper chimera, though dimeric in solution and dimeric when bound to a two-box HSE, forms a trimeric complex when bound to a three-box HSE. The ability to form trimers depends on the presence of three contiguous GAA boxes present in inverted repeats. The proximity of the leucine zippers due to the orientation of the binding sites suggests that the leucine zippers might be forming a three-stranded coiled coil and several experiments lend support to this model. The ability of the leucine zipper to change oligomeric states in context might explain why the leucine zipper can replace the trimerization domain of HSF in vivo.

Journal of Molecular Biology published new progress about 70539-42-3. 70539-42-3 belongs to alcohols-buliding-blocks, auxiliary class pyrrolidine,Ester,Amide,Inhibitor,Inhibitor, name is Bis(2,5-dioxopyrrolidin-1-yl) O,O’-ethane-1,2-diyl disuccinate, and the molecular formula is C18H20N2O12, Related Products of alcohols-buliding-blocks.

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