Tag: M.W=100-150

Macsari, Istvan published the artcile3-Oxoisoindoline-1-carboxamides: Potent, State-Dependent Blockers of Voltage-Gated Sodium Channel Na_V1.7 with Efficacy in Rat Pain Models, Related Products of alcohols-buliding-blocks, the publication is Journal of Medicinal Chemistry (2012), 55(15), 6866-6880, database is CAplus and MEDLINE.

The voltage-gated sodium channel Na_V1.7 is believed to be a critical mediator of pain sensation based on clin. genetic studies and pharmacol. results. Clin. utility of nonselective sodium channel blockers is limited due to serious adverse drug effects. Here, we present the optimization, structure-activity relationships, and in vitro and in vivo characterization of a novel series of Na_V1.7 inhibitors based on the oxoisoindoline core. Extensive studies with focus on optimization of Na_V1.7 potency, selectivity over Na_V1.5, and metabolic stability properties produced several interesting oxoisoindoline carboxamides (16A, 26B, 28, 51, 60, and 62) that were further characterized. The oxoisoindoline carboxamides interacted with the local anesthetics binding site. In spite of this, several compounds showed functional selectivity vs. Na_V1.5 of more than 100-fold. This appeared to be a combination of subtype and state-dependent selectivity. Compound 28 showed concentration-dependent inhibition of nerve injury-induced ectopic in an ex vivo DRG preparation from SNL rats. Compounds 16A and 26B demonstrated concentration-dependent efficacy in preclin. behavioral pain models. The oxoisoindoline carboxamides series described here may be valuable for further investigations for pain therapeutics.

Journal of Medicinal Chemistry 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, Related Products of alcohols-buliding-blocks.

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

Toutov, Anton A. published the artcileSodium Hydroxide Catalyzed Dehydrocoupling of Alcohols with Hydrosilanes, Computed Properties of 2240-88-2, the publication is Organic Letters (2016), 18(22), 5776-5779, database is CAplus and MEDLINE.

An O-Si bond construction protocol employing abundantly available and inexpensive NaOH as the catalyst is described. The method enables the cross-dehydrogenative coupling of an alc. and hydrosilane to directly generate the corresponding silyl ether under mild conditions and without the production of stoichiometric salt byproducts. The scope of both coupling partners is excellent, positioning the method for use in complex mol. and materials science applications. A novel Si-based cross-coupling reagent is also reported.

Organic Letters 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 C13H18N2, Computed Properties of 2240-88-2.

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

Meshram, Anju published the artcileCharacterization of Pyrrolidine Alkaloids of Epipremnum aureum for Their Antitermite Activity Against Subterranean Termites with SEM Studies, Recommanded Product: 2-Morpholinoethanol, the publication is Proceedings of the National Academy of Sciences, India, Section B: Biological Sciences (2019), 89(1), 53-62, database is CAplus.

Epipremnum aureum (Linden and Andre) G. S. Bunting (E. aureum) is an ornamental foliage rich in phytoconstituents and serves as a potential source of bioactive compounds possessing beneficial biol. activities. The present study was carried out to isolate the pyrrolidine alkaloids of leaves with in vitro antitermite and antirepellant efficacy on paper and soil by direct-choice and no-choice assay. Spectrometric anal. of alkaloid fractions via UV-visible spectroscopy (UV-VIS), Fourier transform IR spectroscopy (FTIR) and gas chromatog. mass spectrometry (GC-MS) helped in the characterization of pyrrolidine alkaloids. Superior antitermite activities were observed, associated with high levels of 5-Oxoproline as compare to Me 5-oxo-2-pyrrolidinecarboxylate. Presence of higher contents of 4-Morpholineethanol showed effective antitermite activity and even low levels of 3-Amino-4-Hydroxybutanoic acid and 1H-1,2,4-Triazol-3-amine, N-methyl- also exposed significant activities for repellence and mortality of termites. Repellence and percentage mortality of termites by these alkaloid fractions were similar in results when compared with the standard alkaloid Nicotine and chem. termiticide Monocrotophos. These findings were also supported by SEM studies. Pyrrolidine alkaloids present in E. aureum have exposed strong in vitro antitermite and antirepellant activities against subterranean termites Odontotermes obesus. These findings strongly support the use of E. aureum to bear potential termiticidal properties, however further details need to be carried out.

Proceedings of the National Academy of Sciences, India, Section B: Biological Sciences 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, Recommanded Product: 2-Morpholinoethanol.

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

Brahmachari, Goutam published the artcileVisible Light-Driven and Singlet Oxygen-Mediated Photochemical Cross-Dehydrogenative C₃-H Sulfenylation of 4-Hydroxycoumarins with Thiols Using Rose Bengal as a Photosensitizer, Synthetic Route of 4410-99-5, the publication is Journal of Organic Chemistry (2021), 86(14), 9658-9669, database is CAplus and MEDLINE.

A visible light (white light-emitting diode/direct sunlight)-driven photochem. synthesis of a new series of biol. interesting 3-(alkyl/benzylthio)-4-hydroxy-2H-chromen-2-ones has been achieved through a cross-dehydrogenative C₃-H sulfenylation of 4-hydroxycoumarins with thiols at ambient temperature in the presence of rose bengal in acetonitrile under an oxygen atm. The notable features of this newly developed method are mild reaction conditions, energy efficiency, metal-free synthesis, good to excellent yields, use of low-cost materials, and eco-friendliness.

Journal of Organic Chemistry published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C8H10S, Synthetic Route of 4410-99-5.

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

Chen, Shuqiang published the artcileWater-soluble derivatives of evodiamine: Discovery of evodiamine-10-phosphate as an orally active antitumor lead compound, Category: alcohols-buliding-blocks, the publication is European Journal of Medicinal Chemistry (2021), 113544, database is CAplus and MEDLINE.

10-Hydroxyevodiamine is a multitargeting antitumor lead compound with excellent in vitro activity. However, its in vivo antitumor potency is rather limited, which has hampered its further clin. development. To overcome this obstacle, a series of novel water-soluble derivatives of 10-hydroxyevodiamine were designed and synthesized. Most of them exhibited good to excellent antitumor activities against several cancer cell lines. In particular, phosphate derivative I was orally active and showed improved in vivo antitumor efficacy in HCT116 xenograft models. Further antitumor mechanism studies indicated that compound I acted by triple Top1/Top2/tubulin inhibition and induced apoptosis with G₂/M cell cycle arrest. Taken together, this study extended the structure-activity relationship of evodiamine and identified phosphate derivative I as a promising antitumor lead compound

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, Category: alcohols-buliding-blocks.

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

Huang, Huan-Ming published the artcileRadical Carbonyl Umpolung Arylation via Dual Catalysis, SDS of cas: 111-29-5, the publication is Journal of the American Chemical Society (2022), 144(4), 1899-1909, database is CAplus and MEDLINE.

A series of aryl benzoates I [R = iPr, tBu, cyclohexyl, etc.; R¹ = 4-NCC₆H₄, 2-NCC₆H₄, 2-pyridyl, etc.] via dual nickel and photoredox catalyzed radical carbonyl umpolung arylation of aldehydes and aryl bromides was reported. This redox-neutral approach provided a complementary method to construct Grignard-type products from (hetero)aryl bromides and aliphatic aldehydes, without the need for prefunctionalization. Sequential activation, hydrogen atom transfer and halogen atom transfer process could directly converted aldehydes to the corresponding ketyl radicals, which further react with aryl-nickel intermediates in an overall polarity-reversal process. This radical strategy tolerated-among others-acidic functional groups, heteroaryl motifs and sterically hindered substrates and was applied in the late-stage modification of drugs and natural products.

Journal of the American Chemical Society 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, SDS of cas: 111-29-5.

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

Ben Khemis, Ismahene published the artcileAdsorption of 2-phenylethanethiol on two broadly tuned human olfactory receptors OR1A1 and OR2W1: Interpretation of the effect of copper ions via statistical physics monolayer adsorption model, Safety of 2-Phenylethanethiol, the publication is Journal of Molecular Liquids (2021), 116926, database is CAplus.

This paper aims to investigate the effect of metal especially copper ions on the adsorption of a key food odorant (2-phenylethanethiol) on two human olfactory receptors OR1A1 and OR2W1 that was interpreted via a statistical physics monolayer model. To this purpose, four exptl. dose-olfactory response curves were used without and with the presence of Cu2+ for each human receptor. In order to reach a theor. interpretation of the exptl. data and understand the effect of the used metal on adsorption process introduced on the olfaction mechanism, a statistical physics monolayer adsorption model with identical and independent sites was applied. The used model showed that the presence of copper ions decreased the efficacy (olfactory response at saturation) of 2-phenylethanethiol key food odorant activating OR1A1, suggesting a neg. allosteric action. However, the presence of Cu2+ reduced the potency (concentration at half saturation) of the studied thiol key food odorant in activating OR2W1, suggesting an orthosteric competitive action. Furthermore, the molar adsorption energies retrieved from data anal. varied from 5.568 to 9.886 kJ/mol in studied systems, whose values showed that the process based on a phys. adsorption. Lastly, the dose-olfactory response curves of 2-phenylethanethiol on two broadly tuned human olfactory receptors OR1A1 and OR2W1 provided access to the olfactory receptor site size distribution (RSD) and also the adsorption energy distribution (AED).

Journal of Molecular Liquids published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C8H10S, Safety of 2-Phenylethanethiol.

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

Soukup, Ondrej published the artcileThe wide-spectrum antimicrobial effect of novel N-alkyl monoquaternary ammonium salts and their mixtures; the QSAR study against bacteria, Name: 2-Morpholinoethanol, the publication is European Journal of Medicinal Chemistry (2020), 112584, database is CAplus and MEDLINE.

In this study we have prepared 43 novel N-alkyl monoquaternary ammonium salts including 7 N,N-dialkyl monoquaternary ammonium salts differing bearing alkyl chain either of 12, 14 or 16 carbons. Together with 15 already published QASs we have studied the antimicrobial efficacy of all water-soluble compounds together with standard benzalkonium salts against Gram-pos. (G+) and Gram-neg. (G-) bacteria, anaerobic spore-forming Cl. difficile, yeasts, filamentous fungi and enveloped Varicella zoster virus (VZV). To address the mechanism of action, lipophilicity seems to be a key parameter which determines antimicrobial efficacy, however, exceptions are likely to occur and therefore QSAR anal. on the efficacy against G+ and G- bacteria was applied. We showed that antibacterial activity is higher when the mol. is larger, more lipophilic, less polar, and contains fewer oxygen atoms, fewer Me groups bound to heteroatoms or fewer hydrogen atoms bound to polarized carbon atoms. In addition, from an application point of view, we have formulated mixtures, on the basis of obtained efficiency of individual compounds, in order to receive wide-spectrum agent. All formulated mixtures completely eradicated tested G+ and G- strains, including the multidrug-resistant P. aeruginosa as well as in case of yeasts. Finally, 3 out of 4 formulated mixtures were safer than reference com. agent based on benzalkonium salts only in the skin irritation test using reconstructed human epidermidis.

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 C8H7N3, Name: 2-Morpholinoethanol.

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

Lazarus, Robert A. published the artcileMechanism of hydrolysis of phosphorylethanolamine diesters. Intramolecular nucleophilic amine participation, Computed Properties of 371-99-3, the publication is Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) (1980), 373-9, database is CAplus.

Intramol. displacement reactions at P in 7 RNHCH₂CH₂OP(O)(O^–)OAr (R = Et, Ar = substituted Ph) and 4 analogs (R = MeOCH₂CH₂, CF₃CH₂) were examined by pH-rate profiles and ³¹P NMR of the products of hydrolysis in H₂O at 35° and ionic strength 1.0 (KCl). The amine has a nucleophilic role. A rate enhancement of 10^6-7 is observed Structure-reactivity correlations derived using different pK_a values for amines and leaving groups give Broensted β_nucleophile and β_1g values of â‰?.7 and and â‰?1.25, resp. An uncoupled concerted mechanism is involved. The role of amine and oxyanion groups in the nucleophilic reactions of di- and triesters is discussed. Changing the catalyst from carboxy to an amino group increases the reactivity of a diester 1000-fold compared with a triester.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) 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

Lazarus, Robert A. published the artcileMechanism of hydrolysis of phosphorylethanolamine triesters. Multiple catalytic effects of an intramolecular amino group, Safety of 2-((2,2,2-Trifluoroethyl)amino)ethanol, the publication is Journal of the American Chemical Society (1979), 101(15), 4300-12, database is CAplus.

Intramol. displacement reactions at P are examined in N-alkyl-O-(arylphenylphosphoryl)ethanolamines in 45% dioxane-water (volume) at 35°. The examination of the pH-rate profiles, the detection of external buffer catalysis, and the observation of D solvent effects reveal the concurrent operation of 3 types of P-O bond cleavage mechanisms: electrostatic catalysis by the protonated ammonium moiety of external nucleophilic attack by buffer bases at D, general base-catalyzed intramol. nucleophilic attack by the amino function to form the cyclic phosphoramidate, and intramol. amine-assisted water displacement of the substituted phenol. A Broensted plot for the general base-catalyzed cyclization reaction supports either a concerted mechanism for the cyclization process bypassing the formation of a pentacovalent intermediate with a discrete lifetime or a mechanism involving H bonding stabilization of the rate-determining decomposition of the intermediate providing that this is faster than the diffusion away of the catalyst. In either case the lifetime of the pentacovalent intermediate is <10^-12s.

Journal of the American Chemical Society 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, Safety of 2-((2,2,2-Trifluoroethyl)amino)ethanol.

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