Tag: M.W=100-150

Tuokko, Sakari published the artcilePalladium on Charcoal Catalyzed 3,4-Hydroperoxidation of α-Substituted Enals with Triethylsilane and Water, Computed Properties of 597-52-4, the publication is Synlett (2016), 27(11), 1649-1652, database is CAplus.

Aldehyde α-hydroperoxides can be accessed from α-substituted acroleins with triethylsilane and water under Pd/C catalysis and aerobic conditions. The reaction is composed of a Pd/C-catalyzed conjugate reduction step and a hydroperoxidn. step. The hydroperoxidn. takes place via autoxidation of sufficiently stable enols formed in situ by transfer hydrogenation. Upon reduction, 2,2-disubstituted 1,2-diols are obtained directly from aldehydes.

Synlett 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 C7H8O3, Computed Properties of 597-52-4.

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

Rossi, Kyllikki published the artcileCarbon-13 NMR chemical shifts and ring conformations of 2-hydroxy-1,3,2-dioxaborolane and 2-hydroxy-1,3,2-dioxaborinane and their methyl derivatives, Computed Properties of 25240-59-9, the publication is Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1985), B39(8), 671-83, database is CAplus.

The ¹³C NMR chem. shifts of 2-hydroxy-1,3,2-dioxaborolane (half-chair) and -borinane (chair) and their Me derivatives are reported. Substituent effects on the chem. shifts have been derived, and their type and magnitude are closely related to the ring size, geometry, and other conformational aspects. ¹H NMR data for some 2-hydroxy-1,3,2-dioxaborinanes have been used to confirm the populations of their interconverting chair forms as deduced from the ¹³C NMR chem. shift correlations.

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry 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, Computed Properties of 25240-59-9.

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

Sadowsky, Jack D. published the artcileDevelopment of Efficient Chemistry to Generate Site-Specific Disulfide-Linked Protein- and Peptide-Payload Conjugates: Application to THIOMAB Antibody-Drug Conjugates, Quality Control of 73303-88-5, the publication is Bioconjugate Chemistry (2017), 28(8), 2086-2098, database is CAplus and MEDLINE.

Conjugation of small mol. payloads to specific cysteine residues on proteins via a disulfide bond represents an attractive strategy to generate redox-sensitive bioconjugates, which have value as potential diagnostic reagents or therapeutics. Advancement of such “direct-disulfide” bioconjugates to the clinic necessitates chem. methods to form disulfide connections efficiently, without byproducts. The disulfide connection must also be resistant to premature cleavage by thiols prior to arrival at the targeted tissue. We show here that commonly-employed methods to generate direct disulfide-linked bioconjugates are inadequate for addressing these challenges. We describe our efforts to optimize direct-disulfide conjugation chem., focusing on the generation of conjugates between cytotoxic payloads and cysteine-engineered antibodies (i.e., THIOMAB antibody-drug conjugates, or TDCs). This work culminates in the development of novel, high-yielding conjugation chem. for creating direct payload disulfide connections to any of several Cys mutation sites in THIOMAB antibodies or to Cys sites in other biomols. (e.g., human serum albumin and cell-penetrating peptides). We conclude by demonstrating that hindered direct disulfide TDCs with two Me groups adjacent to the disulfide, which have heretofore not been described for any bioconjugate, are more stable and more efficacious in mouse tumor xenograft studies than less hindered analogs.

Bioconjugate Chemistry published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C4H10OS, Quality Control of 73303-88-5.

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

Timko, Lukas published the artcileSynthesis, physicochemical properties and biological activities of novel alkylphosphocholines with foscarnet moiety, Name: 2-Morpholinoethanol, the publication is Bioorganic Chemistry (2020), 104224, database is CAplus and MEDLINE.

A series of alkylphosphocholines with foscarnet moiety was synthesized. The structure of these zwitterionic amphiphiles was modified in both polar and non-polar parts of surfactant mol. Investigations of physicochem. properties are represented by the determination of critical micelle concentration, the surface tension value at the cmc and the surface area per surfactant head group utilizing surface tension measurements. Hydrodynamic diameter of surfactant micelles was determined using the dynamic light scattering technique. Alkylphosphocholines exhibit significant cytotoxic, anticandidal (Candida albicans) and antiamoebal (Acanthamoeba spp. T4 genotype) activity. The relationship between the structure, physicochem. properties and biol. activity of the tested compounds revealed that lipophilicity has a significant influence on biol. activity of the investigated surfactants. More lipophilic alkylphosphocholines with octadecyl chains show cytotoxic activity against cancer cells which is higher than that of the compounds with shorter alkyl chains. The opposite situation was observed in case of anticandidal and antiamoebal activity of these surfactants. The most active compounds were found to have pentadecyl chains. The foscarnet analog of miltefosine C15-PFA-C showed the highest anticandidal activity. The min. value of anticandidal activity of this compound is 1,4μM thus representing the highest anticandidal activity found within the group of alkylphosphocholines.

Bioorganic 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 C22H38O2, Name: 2-Morpholinoethanol.

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

Linclau, Bruno published the artcileIntramolecular OH…Fluorine Hydrogen Bonding in Saturated, Acyclic Fluorohydrins: The γ-Fluoropropanol Motif, Formula: C3H5F3O, the publication is Chemistry – A European Journal (2015), 21(49), 17808-17816, database is CAplus and MEDLINE.

Fluorination is commonly exercised in compound property optimization. However, the influence of fluorination on hydrogen-bond (HB) properties of adjacent functional groups, as well as the HB-accepting capacity of fluorine itself, is still not completely understood. Although the formation of OH…F intramol. HBs (IMHBs) was established for conformationally restricted fluorohydrins, such interaction in flexible compounds remained questionable. Herein is demonstrated for the first time-and in contrast to earlier reports-the occurrence of OH…F IMHBs in acyclic saturated γ-fluorohydrins, even for the parent 3-fluoropropan-1-ol. The relative stereochem. has a crucial influence on the corresponding ^h1J(OH…F) values, as illustrated by syn- and anti-4-fluoropentan-2-ol (6.6 and 1.9 Hz). The magnitude of OH…F IMHBs and their strong dependence on the overall mol. conformational profile, fluorination motif, and alkyl substitution level, is rationalized by quantum chem. calculations For a given alkyl chain, the rule of shielding applies to OH…F IMHB energies. Surprisingly, the predicted OH…F IMHB energies are only moderately weaker than these of the corresponding OH…OMe. These results provide new insights of the impact of fluorination of aliphatic alcs., with attractive perspectives for rational drug design.

Chemistry – A European Journal 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, Formula: C3H5F3O.

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

Ramurthy, Savithri published the artcileDiscovery and optimization of novel pyridines as highly potent and selective glycogen synthase kinase 3 inhibitors, Computed Properties of 371-99-3, the publication is Bioorganic & Medicinal Chemistry Letters (2020), 30(4), 126930, database is CAplus and MEDLINE.

Glycogen synthase kinase-3 plays an essential role in multiple biochem. pathways in the cell, particularly in regards to energy regulation. As such, Glycogen synthase kinase-3 is an attractive target for pharmacol. intervention in a variety of disease states, particularly non-insulin dependent diabetes mellitus. However, due to homol. with other crucial kinases, such as the cyclin-dependent protein kinase CDC2, developing compounds that are both potent and selective is challenging. A novel series of derivatives of 5-nitro-N2-(2-(pyridine-2-ylamino)ethyl)pyridine-2,6-diamine were synthesized and potently inhibit glycogen synthase kinase-3 (GSK3). Potency in the low nanomolar range was obtained along with remarkable selectivity. The compounds activate glycogen synthase in insulin receptor-expressing CHO-IR cells and in primary rat hepatocytes, and have acceptable pharmacokinetics and pharmacodynamics to allow for oral dosing. The x-ray co-crystal structure of human GSK3-β in complex with compound 1-(6-((2-((6-amino-5-nitropyridin-2-yl)amino)ethyl)amino)-2-(2,4-dichlorophenyl)pyridin-3-yl)-4-methylpiperazin-2-one is reported and provides insights into the structural determinants of the series responsible for its potency and selectivity.

Bioorganic & Medicinal Chemistry Letters published new progress about 371-99-3. 371-99-3 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is 2-((2,2,2-Trifluoroethyl)amino)ethanol, and the molecular formula is C4H8F3NO, Computed Properties of 371-99-3.

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

Gollapelli, Krishna Kumar published the artcileRh(I)-catalyzed stereoselective desymmetrization of prochiral cyclohexadienones via highly exo-selective Huisgen-type [3 + 2] cycloaddition, COA of Formula: C9H12O, the publication is Chemical Science (2021), 12(4), 1544-1550, database is CAplus and MEDLINE.

A Rh(I)-catalyzed highly stereoselective desymmetrization of 2-alkynylbenzaldehyde-tethered cyclohexadienones triggered by intramol. Huisgen-type [3 + 2] cycloaddition was developed. This method enables convergent construction of complex epoxy-bridged polycyclic ring systems with five contiguous stereocenters with excellent exo-selectivity and broad substrate scope. The highly atom-economical process involves 6-endo-dig cyclization of carbonyl oxygen onto an activated alkyne resulting in a highly reactive metal-benzopyrylium intermediate, which readily undergoes intramol. [3 + 2] annulation/hydration. Asym. induction was also achieved for the first time in Rh(I)-catalyzed 1,3-dipolar cycloaddition using an easily accessible chiral diene as the ligand.

Chemical Science published new progress about 645-56-7. 645-56-7 belongs to alcohols-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 4-Propylphenol, and the molecular formula is C9H12O, COA of Formula: C9H12O.

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

Empel, Claire published the artcileProton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols, HPLC of Formula: 2240-88-2, the publication is Chemistry – A European Journal (2022), 28(15), e202104397, database is CAplus and MEDLINE.

A fundamental understanding of the reaction of diazoalkanes with alcs. to made this transformation amenable to a generalized approach towards formal alkylation reactions of alcs. with diazoalkanes was aimed. Exptl. and theor. studies suggested a direct proton transfer only in exceptional cases. In a more general setting, such O-H functionalization proceeded both under dark and photochem. conditions via a key hydrogen-bonded singlet carbene intermediate that underwent a protonation-addition mechanism. Applications of this approach in O-H functionalization reactions of alcs., including simple fluorinated, halogenated and aliphatic alcs. and showcase functional-group tolerance of this method in the reaction of biol. active and pharmaceutically relevant alcs. was concluded.

Chemistry – A European Journal 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, HPLC of Formula: 2240-88-2.

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

Heravi, Majid M. published the artcileNickel-Catalyzed Deoxycyanation of Activated Phenols via Cyanurate Intermediates with Zn(CN)₂: A Route to Aryl Nitriles, Quality Control of 17236-59-8, the publication is Organic Letters (2018), 20(9), 2753-2756, database is CAplus and MEDLINE.

A novel, and efficient nickel-catalyzed deoxycyanation of phenolic compounds using relatively nontoxic Zn(CN)₂ as the cyanide source was developed. The reaction of C-O bond activated phenolic compounds by 2,4,6-trichloro-1,3,5-triazine with Zn(CN)₂ in the presence of a nickel precatalyst afforded the aromatic nitriles in good to excellent yields.

Organic Letters 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, Quality Control of 17236-59-8.

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

Iranpoor, Nasser published the artcileNickel-Catalyzed One-Pot Deoxygenation and Reductive Homocoupling of Phenols via C-O Activation Using TCT Reagent, Safety of Thiophen-3-ol, the publication is Organic Letters (2015), 17(2), 214-217, database is CAplus and MEDLINE.

A new method for C-O bond activation of phenolic compounds has been achieved using 2,4,6-trichloro-1,3,5-triazine (TCT) to utilize in one-pot Ni-catalyzed deoxygenation and reductive homocoupling reactions. With this simple method, phenolic compounds were converted to their corresponding arenes or biaryl compounds under mild conditions [e.g., treatment of 2-naphthol with TCT followed by NiCl₂(PCy₃)₂ and MeOH/Zn/KI afforded naphthalene (85%), and treatment of p-cresol with TCT followed by NiCl₂(PCy₃)₂ and Zn/Et₄NI afforded 4,4′-dimethylbiphenyl (84%)]. The introduced methodol. has a broad scope and demonstrates good functional group compatibility.

Organic Letters 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, Safety of Thiophen-3-ol.

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