Tag: M.W=100-150

Baehr, Susanne published the artcileSelective Enzymatic Oxidation of Silanes to Silanols, Quality Control of 597-52-4, the publication is Angewandte Chemie, International Edition (2020), 59(36), 15507-15511, database is CAplus and MEDLINE.

Compared to the biol. world’s rich chem. for functionalizing carbon, enzymic transformations of the heavier homolog silicon are rare. We report that a wild-type cytochrome P 450 monooxygenase (P 450_BM3 from Bacillus megaterium, CYP102A1) has promiscuous activity for oxidation of hydrosilanes to give silanols. Directed evolution was applied to enhance this non-native activity and create a highly efficient catalyst for selective silane oxidation under mild conditions with oxygen as the terminal oxidant. The evolved enzyme leaves C-H bonds present in the silane substrates untouched, and this biotransformation does not lead to disiloxane formation, a common problem in silanol syntheses. Computational studies reveal that catalysis proceeds through hydrogen atom abstraction followed by radical rebound, as observed in the native C-H hydroxylation mechanism of the P 450 enzyme. This enzymic silane oxidation extends nature’s impressive catalytic repertoire.

Angewandte Chemie, International Edition 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 C6H16OSi, Quality Control of 597-52-4.

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

De Gasparo, Raoul published the artcileBiological Evaluation and X-ray Co-crystal Structures of Cyclohexylpyrrolidine Ligands for Trypanothione Reductase, an Enzyme from the Redox Metabolism of Trypanosoma, Safety of 2-Morpholinoethanol, the publication is ChemMedChem (2018), 13(9), 957-967, database is CAplus and MEDLINE.

The tropical diseases human African trypanosomiasis, Chagas disease, and the various forms of leishmaniasis are caused by parasites of the family of trypanosomatids. These protozoa possess a unique redox metabolism based on trypanothione and trypanothione reductase (TR), making TR a promising drug target. We report the optimization of properties and potency of cyclohexylpyrrolidine inhibitors of TR by structure-based design. The best inhibitors were freely soluble and showed competitive inhibition constants (K_i) against Trypanosoma (T.) brucei TR and T. cruzi TR and in vitro activities (half-maximal inhibitory concentration, IC₅₀) against these parasites in the low micromolar range, with high selectivity against human glutathione reductase. X-ray co-crystal structures confirmed the binding of the ligands to the hydrophobic wall of the “mepacrine binding site” with the new, solubility-providing vectors oriented toward the surface of the large active site.

ChemMedChem 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, Safety of 2-Morpholinoethanol.

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

Newman, Melvin S. published the artcilegem-Dialkyl effect in medicinal agents, Quality Control of 39943-41-4, the publication is Journal of Medicinal Chemistry (1972), 15(10), 1003-6, database is CAplus and MEDLINE.

Modification of various drugs (cholinergic agonists and antagonists, ganglionic blockers, antihistamines, local anesthetics) containing a dialkylaminoethoxy group R2N(CH2)2O by insertion of a gem-dialkylmethylene group, forming R2NCH2CR12CH2O, did not produce progressive changes in activity related to the nature of the gem-dialkyl substituents. The gem-dialkyl substituents used were Me, Et, and cycloalkyl (cyclopropyl to cyclohexyl). Varying these substituents altered the distance between N and O atoms in the alkanolamine group, which was evidently not an important parameter for activity.

Journal of Medicinal Chemistry published new progress about 39943-41-4. 39943-41-4 belongs to alcohols-buliding-blocks, auxiliary class Cyclopropanes, name is (1-((Dimethylamino)methyl)cyclopropyl)methanol, and the molecular formula is C7H15NO, Quality Control of 39943-41-4.

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

Vysotsky, Yu. B. published the artcileQuantum Chemical Semiempirical Approach to the Structural and Thermodynamic Characteristics of Fluoroalkanols at the Air/Water Interface, Recommanded Product: 3,3,3-Trifluoropropan-1-ol, the publication is Journal of Physical Chemistry B (2005), 109(1), 454-462, database is CAplus and MEDLINE.

In the framework of quantum chem. PM3 approximation, the geometrical structure and thermodn. functions characteristics of the formation of monomers (n = 1-14, 34), dimers (n = 1-14, 34), and trimers and tetramers (n = 1-8) of fluoroalkanols with the composition C_nF_2n+1CH₂CH₂OH are calculated It is shown that, in contrast to the fatty alcs., which have a flat zigzag structure, the fluoroalkanol monomers are helical with an average backbone torsion angle equal to 162°. For the min.-energy structure of dimers, the self-organization of the mols. in a dimer was observed; that leads to an opposite alternation of the torsion angles corresponding to the matching atoms in the two mols. that form the dimer. This results in the fact that the most stable conformation of the dimer is the double helix. The lead (39.5 Å) and diameter (7.3 Å) of the double helix are determined from the calculations of C₃₄F₆₉CH₂CH₂OH dimers. Enthalpy, entropy, and Gibbs energy of the clusterization are shown to be linearly dependent on the length of the fluorinated chain. From the anal. of these thermodn. quantities, it is concluded that dimerization of fluoroalkanols at the air/water interface takes place if the hydrocarbon link number exceeds 6, whereas for ordinary alcs. this characteristic number is 11. These calculated values agree with exptl. data. The additive scheme for the evaluation of the clusterization free energies for arbitrary clusters is developed and applied to obtain the estimate of the Gibbs clusterization energy for infinitely large clusters.

Journal of Physical Chemistry B 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 C11H8O3, Recommanded Product: 3,3,3-Trifluoropropan-1-ol.

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

Smolinski, Michael P. published the artcileDiscovery of Novel Dual Mechanism of Action Src Signaling and Tubulin Polymerization Inhibitors (KX2-391 and KX2-361), Formula: C6H13NO2, the publication is Journal of Medicinal Chemistry (2018), 61(11), 4704-4719, database is CAplus and MEDLINE.

The discovery of potent, peptide site directed, tyrosine kinase inhibitors has remained an elusive goal. Herein we describe the discovery of two such clin. candidates that inhibit the tyrosine kinase Src. Compound 1 is a phase 3 clin. trial candidate that is likely to provide a first in class topical treatment for actinic keratosis (AK) with good efficacy and dramatically less toxicity compared to existing standard therapy. Compound 2 is a phase 1 clin. trial candidate that is likely to provide a first in class treatment of malignant glioblastoma and induces 30% long-term complete tumor remission in animal models. The discovery strategy for these compounds iteratively utilized mol. modeling, along with the synthesis and testing of increasingly elaborated proof of concept compounds, until the final clin. candidates were arrived at. This was followed with mechanism of action (MOA) studies that revealed tubulin polymerization inhibition as the second MOA.

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 C22H12F6O6S2, Formula: C6H13NO2.

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

Spinaci, Andrea published the artcileA3 Adenosine Receptor Antagonists with Nucleoside Structures and Their Anticancer Activity, Category: alcohols-buliding-blocks, the publication is Pharmaceuticals (2022), 15(2), 164, database is CAplus and MEDLINE.

The overexpression of the A3 adenosine receptor (AR) in a number of cancer cell types makes it an attractive target for tumor diagnosis and therapy. Hence, in the search for new A3AR ligands, a series of novel 2,N⁶-disubstituted adenosines (Ados) I (R¹ = (CH₂)₂C₆H₅, (CH₂)₂CH(C₆H₅)₂; R² = (CH₂)₃CH₃, C₆H₅) was synthesized and tested in radioligand binding and functional assays at ARs. Derivatives bearing a 2-phenethylamino group in the N⁶-position were found to exert higher A3AR affinity and selectivity than the corresponding N⁶-(2,2-diphenylethyl) analogs. 2-Chloro-N⁶-phenylethylAdo was found to be a potent full A3AR agonist with a Ki of 0.024 nM and an EC₅₀ of 14 nM, in a cAMP accumulation assay. Unlike 2-chloro-N⁶-phenylethylAdo, the other ligands behaved as A3AR antagonists, which concentration-dependently reduced cell growth and exerted cytostatic activity on the prostate cancer cell line PC3, showing comparable and even more pronounced effects with respect to the ones elicited by the reference full agonist Cl-IB-MECA. In particular, the N⁶-(2,2-diphenylethyl)-2-phenylethynylAdo (GI₅₀ = 14μM, TGI = 29μM, and LC₅₀ = 59μM) showed the highest activity proving to be a potential antitumor agent. The cytostatic effect of both A3AR agonist (Cl-IB-MECA) and antagonists (other newly synthesized compounds) confirm previous observations according to which, in addition to the involvement of A3ARs, other cellular mechanisms are responsible for the anticancer effects of these ligands.

Pharmaceuticals 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 C8H15ClN2, Category: alcohols-buliding-blocks.

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

Masferrer-Rius, Eduard published the artcileAromatic C-H Hydroxylation Reactions with Hydrogen Peroxide Catalyzed by Bulky Manganese Complexes, Product Details of C9H12O, the publication is Advanced Synthesis & Catalysis (2021), 363(15), 3783-3795, database is CAplus.

The oxidation of aromatic substrates to phenols with H₂O₂ as a benign oxidant remains an ongoing challenge in synthetic chem. Herein, the authors successfully achieved to catalyze aromatic C-H bond oxidations using a series of biol. inspired manganese catalysts in fluorinated alc. solvents. While introduction of bulky substituents into the ligand structure of the catalyst favors aromatic C-H oxidations in alkylbenzenes, oxidation occurs at the benzylic position with ligands bearing electron-rich substituents. Therefore, the nature of the ligand is key in controlling the chemoselectivity of these Mn-catalyzed C-H oxidations Introduction of bulky groups into the ligand prevents catalyst inhibition through phenolate-binding, consequently providing higher catalytic turnover numbers for phenol formation. Furthermore, employing halogenated carboxylic acids in the presence of bulky catalysts provides enhanced catalytic activities, which can be attributed to their low pK_a values that reduces catalyst inhibition by phenolate protonation as well as to their electron-withdrawing character that makes the manganese oxo species a more electrophilic oxidant. Moreover, to the best of the authors’ knowledge, the new system can accomplish the oxidation of alkylbenzenes with the highest yields so far reported for homogeneous arene hydroxylation catalysts. Overall the authors’ data provide a proof-of-concept of how Mn(II)/H₂O₂/RCO₂H oxidation systems are easily tunable by the solvent, carboxylic acid additive, and steric demand of the ligand. The chemo- and site-selectivity patterns of the current system, a negligible KIE, the observation of an NIH-shift, and the effectiveness of using ^tBuOOH as oxidant overall suggest that hydroxylation of aromatic C-H bonds proceeds through a metal-based mechanism, with no significant involvement of hydroxyl radicals, and via an arene oxide intermediate.

Advanced Synthesis & Catalysis 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, Product Details of C9H12O.

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

Kelly, Tanya published the artcileA Kinetic and Mechanistic Study of the Reactions of OH Radicals and Cl Atoms with 3,3,3-Trifluoropropanol under Atmospheric Conditions, Synthetic Route of 2240-88-2, the publication is Journal of Physical Chemistry A (2005), 109(2), 347-355, database is CAplus and MEDLINE.

Product distribution studies of the OH radical and Cl atom initiated oxidation of CF₃CH₂CH₂OH in air at 1 atm and 298 ± 5 K have been carried out in laboratory and outdoor atm. simulation chambers in the presence and absence of NO_x. The results show that CF₃CH₂CHO is the only primary product and that the aldehyde is fairly rapidly removed from the system. In the absence of NO_x the major degradation product of CF₃CH₂CHO is CF₃CHO, and the combined yields of the two aldehydes formed from CF₃CH₂CH₂OH are close to unity (0.95 ± 0.05). In the presence of NO_x small amounts of CF₃CH₂C(O)O₂NO₂ were also observed (<15%). At longer reaction times CF₃CHO is removed from the system to give mainly CF₂O. The laser photolysis-laser induced fluorescence technique was used to determine values of k(OH + CF₃CH₂CH₂OH) = (0.89 ± 0.03) × 10^-12 and k(OH + CF₃CH₂CHO) = (2.96 ± 0.04) × 10^-12 cm³ mol.^-1 s^-1. A relative rate method has been employed to measure the rate coefficients k(OH + CF₃CH₂CH₂OH) = (1.08 ± 0.05) × 10^-12, k(OH + C₆F₁₃CH₂CH₂OH) = (0.79 ± 0.08) × 10^-12, k(Cl + CF₃CH₂CH₂OH) = (22.4 ± 0.4) × 10^-12, and k(Cl + CF₃CH₂CHO) = (25.7 ± 0.4) × 10^-12 cm³ mol.^-1 s^-1. The results from this investigation are discussed in terms of the possible importance of emissions of fluorinated alcs. as a source of fluorinated carboxylic acids in the environment.

Journal of Physical Chemistry A 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, Synthetic Route of 2240-88-2.

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

Rahal, Mahmoud published the artcileRapid estimation of vibrational zero-point energies of silicon compounds, Recommanded Product: Triethylsilanol, the publication is Computational & Theoretical Chemistry (2013), 182-187, database is CAplus.

In this paper, we extended the application of our empirical formula for the calculation of vibrational zero-point energies (ZPEs) to silicon compounds The bond contribution of Si-C, Si-H, Si-O, Si-Cl and Si-Si were determined The results obtained for more than 90 chem. systems containing these bonds are in good agreement with the exptl. available values. The estimated zero-point energies were compared with the results obtained by application of the extended empirical formula of Schulmann and Disch and with the scaled values obtained using the semi-empirical method (AM1) and the DFT method (B3LYP/6-31G^*), in all cases with satisfactory results.

Computational & Theoretical Chemistry 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 C6H16OSi, Recommanded Product: Triethylsilanol.

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

Pettus, Liping H. published the artcileDiscovery of AM-6494: A Potent and Orally Efficacious β-Site Amyloid Precursor Protein Cleaving Enzyme 1 (BACE1) Inhibitor with in Vivo Selectivity over BACE2, Formula: C3H5F3O, the publication is Journal of Medicinal Chemistry (2020), 63(5), 2263-2281, database is CAplus and MEDLINE.

β-Site amyloid precursor protein cleaving enzyme 1 (BACE1) is an aspartyl protease that plays a key role in the production of amyloid β (Aβ) in the brain and has been extensively pursued as a target for the treatment of Alzheimer’s disease (AD). BACE2, an aspartyl protease that is structurally related to BACE1, has been recently reported to be involved in melanosome maturation and pigmentation. Herein, we describe the development of a series of cyclopropylthiazines as potent and orally efficacious BACE1 inhibitors. Lead optimization led to the identification of 20, a mol. with biochem. IC₅₀ BACE2/BACE1 ratio of 47. Administration of 20 resulted in no skin/fur color change in a 13-day mouse hypopigmentation study and demonstrated robust and sustained reduction of CSF and brain Aβ₄₀ levels in rat and monkey pharmacodynamic models. On the basis of a compelling data package, 20 (AM-6494) was advanced to preclin. development.

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, Formula: C3H5F3O.

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