Month: December 2022

Gaiser, Birgit I. published the artcileProbing the Existence of a Metastable Binding Site at the β₂-Adrenergic Receptor with Homobivalent Bitopic Ligands, Application In Synthesis of 57044-25-4, the publication is Journal of Medicinal Chemistry (2019), 62(17), 7806-7839, database is CAplus and MEDLINE.

Herein, we report the development of bitopic ligands aimed at targeting the orthosteric binding site (OBS) and a metastable binding site (MBS) within the same receptor unit. Previous mol. dynamics studies on ligand binding to the β₂-adrenergic receptor (β₂AR) suggested that ligands pause at transient, less-conserved MBSs. We envisioned that MBSs can be regarded as allosteric binding sites and targeted by homobivalent bitopic ligands linking two identical pharmacophores. Such ligands were designed based on docking of the antagonist (S)-alprenolol into the OBS and an MBS and synthesized. Pharmacol. characterization revealed ligands with similar potency and affinity, slightly increased β₂/β₁AR-selectivity, and/or substantially slower β₂AR off-rates compared to (S)-alprenolol. Truncated bitopic ligands suggested the major contribution of the metastable pharmacophore to be a hydrophobic interaction with the β₂AR, while the linkers alone decreased the potency of the orthosteric fragment. Altogether, the study underlines the potential of targeting MBSs for improving the pharmacol. profiles of ligands.

Journal of Medicinal Chemistry 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

Chen, Xingmei published the artcileMachine learning-based prediction of toxicity of organic compounds towards fathead minnow, Quality Control of 622-40-2, the publication is RSC Advances (2020), 10(59), 36174-36180, database is CAplus and MEDLINE.

Predicting the acute toxicity of a large dataset of diverse chems. against fathead minnows (Pimephales promelas) is challenging. In this paper, 963 organic compounds with acute toxicity towards fathead minnows were split into a training set (482 compounds) and a test set (481 compounds) with an approx. ratio of 1 : 1. Only six mol. descriptors were used to establish the quant. structure-activity/toxicity relationship (QSAR/QSTR) model for 96 h pLC₅₀ through a support vector machine (SVM) along with genetic algorithm. The optimal SVM model (R² = 0.756) was verified using both internal (leave-one-out cross-validation) and external validations. The validation results (q_int² = 0.699 and q_ext² = 0.744) were satisfactory in predicting acute toxicity in fathead minnows compared with other models reported in the literature, although our SVM model has only six mol. descriptors and a large data set for the test set consisting of 481 compounds

RSC Advances 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, Quality Control of 622-40-2.

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

Berecz, Gabor published the artcileTowards Tianeptine Analogues: Synthesis of New Ring Systems Containing a Dibenzo[c,f[1,2]thiazepine S,S -Dioxide Core, Quality Control of 622-40-2, the publication is Synthesis (2022), 54(17), 3874-3882, database is CAplus.

In the course of the synthesis of fused-ring analogs of the antidepressant drug tianeptine, representatives of three new heterocyclic ring systems, indolo[1,7- bc][1,2]benzothiazepines (and their 4,5-dihydro analogs), 5,6-dihydroquino[1,8- bc][1,2]benzothiazepine, and [1,2]benzothiazepino[4,3,2- jk]carbazoles, as well as their intermediates, was prepared The tetracyclic and pentacyclic ring systems containing either an oxo or a hydroxy functional group are suitable for introducing various side chains, including potential pharmacophores. For this latter transformation, examples are demonstrated by conversion of the hydroxy group into a chloro moiety and subsequent reaction with amines or with primary alcs. bearing a tertiary amino side chain. Two fused-ring derivatives exhibiting the side-chain characteristics of tianeptine was also synthesized. Altogether 40 compounds were described in the present manuscript, eight of them are also characterized by single-crystal X-ray diffraction.

Synthesis 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, Quality Control of 622-40-2.

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

Powis, Ivan published the artcileA photoionization investigation of small, homochiral clusters of glycidol using circularly polarized radiation and velocity map electron-ion coincidence imaging, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is Physical Chemistry Chemical Physics (2014), 16(2), 467-476, database is CAplus and MEDLINE.

A detailed study of the valence photoionization of small homochiral glycidol (C₃O₂H₆) clusters is carried out with the help of circularly-polarized VUV synchrotron radiation by recording photoionization-based spectroscopic data detected by velocity map electron imaging with coincidence ion selection. We show that information on the stability of cationic as well as neutral chiral clusters can be obtained with enhanced sensitivity by examining the chiral fingerprint encapsulated in Photoelectron CD (PECD) spectra. In particular, by varying the clustering conditions we demonstrate that the PECD signal effectively carries the signature of the neutral precursor species, prior to any fragmentation of the ion, as may be inferred from the below-threshold monomer measurements (including ion imaging). Here the monomer’s direct ionization channel is closed and the monomer ion hence must result exclusively as a fragment from dissociative ionization of the dimer (or higher) clusters. At higher photon energies, the mass-selection on the electron spectroscopy data, achieved through filtering the electron images in coincidence with selected ion masses, evidently succeeds in providing a degree of size-selection on the neutral clusters being ionized with, in particular, a clear differentiation of monomer and dimer PECD, showing the strong sensitivity of this chiroptical effect to the non-local long-range mol. potential.

Physical Chemistry Chemical Physics 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, Recommanded Product: (R)-Oxiran-2-ylmethanol.

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

Cincinelli, Raffaella published the artcileIntramolecular N-acyliminium ion versus Friedel-Crafts cyclization onto 3-indoles: synthesis of the novel rings pyrrolizino[2,1-b]indole and homologues, Quality Control of 4543-95-7, the publication is Tetrahedron (2009), 65(17), 3465-3472, database is CAplus.

Acid treatment of indole-2-carboxylic acid secondary δ-,ε-, and ζ-oxoamides cyclize to the novel heterocyclic ring systems pyrrolizino[2,1-b]indole (I, n = 1), indolizino[2,1-b]indole (I, n = II), and 9a,11-diaza-indeno[1,2-a]azulene (I, n = 3) with varying substitution. Tertiary amides cyclize through a simple Friedel-Crafts ring closure, thus allowing the synthesis of tricyclic ring systems containing larger rings, e.g., II.

Tetrahedron published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, Quality Control of 4543-95-7.

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

Lo Leggio, Leila published the artcileThe Structure and Specificity of Escherichia coli Maltose Acetyltransferase Give New Insight into the LacA Family of Acyltransferases, Name: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, the publication is Biochemistry (2003), 42(18), 5225-5235, database is CAplus and MEDLINE.

The crystallog. three-dimensional structure of the Escherichia coli maa gene product, previously identified as a maltose O-acetyltransferase (MAT) [Brand, B., and Boos, W. (1991) J. Biol. Chem. 266, 14113-14118] has been determined to 2.15 Å resolution by the single anomalous dispersion method using data from a crystal cocrystd. with trimethyllead acetate. It is shown here that MAT acetylates glucose exclusively at the C6 position and maltose at the C6 position of the nonreducing end glucosyl moiety. Furthermore, MAT shows higher affinity toward artificial substrates containing an alkyl or hydrophobic chain as well as a glucosyl unit. The presence of a long hydrophobic patch near the acceptor site provides the structural explanation for this preference. The three-dimensional structure reveals the expected trimeric left-handed parallel β-helix structure found in all other known hexapeptide repeat enzymes. In particular, the structure shows similarities both overall and at the putative active site to the recently determined structure of galactoside acetyltransferase (GAT), the lacA gene product [Wang, X.-G., Olsen, L. R., and Roderick, S. L. (2002) Structure 10, 581-588]. The structure, together with the new biochem. data, suggests that GAT and MAT are more closely related than previously thought and might have similar cellular functions. However, while GAT is specific for acetylation of galactosyl units, MAT is specific for glucosyl units and is able to acetylate maltooligosaccharides, an important property for biotechnol. applications. Structural differences at the acceptor site reflect the differences in substrate specificity.

Biochemistry published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Name: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol.

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

Nomura, Sachiko published the artcileDifferential metabolism of 4-n- and 4-tert-octylphenols in perfused rat liver, Formula: C14H22O2, the publication is Life Sciences (2008), 83(5-6), 223-228, database is CAplus and MEDLINE.

Octylphenols, widely used in a variety of detergents and plastics, are known to exhibit estrogenicity in vivo. The details of their metabolism are needed to better understand the endocrine disruptions. We have previously shown that alkylphenols, having short alkyl chains, are glucuronidated and readily excreted into the bile from the liver, while 4-n-nonylphenol, having longer alkyl chains, remains as the alkylphenol’s glucuronide in the tissue. This study elucidated the dependence of the metabolism on the shape of the alkyl chains by comparing 4-n-octylphenol and 4-tert-octylphenols in a perfused rat liver. Both octylphenols were highly glucuronidated by the liver microsomal fractions. The Vmax value of 4-tert-octylphenol glucuronidation was twice as high as that of 4-n-octylphenol in the liver microsomes. On the other hand, the Km values, being measures of enzymic activity against these chems., were similar. 4-n-Octylphenol and 4-tert-octylphenol were both glucuronidated by a UDP-glucuronosyltransferase isoform, UGT2B1, expressed in the liver. In the liver perfusion, almost all of the 4-n-octylphenol perfused was metabolized directly to the glucuronide, whereas a portion of 4-tert-octylphenol was hydroxylated and then glucuronidated. The glucuronide of 4-n-octylphenol accumulated in the liver tissue in the same manner as 4-n-nonylphenol, but 4-tert-octylphenol and the hydroxylated metabolites were excreted readily into the bile. Only a small amount of 4-n-octylphenol-glucuronide and glucuronides of 4-tert-octylphenol and its hydroxylated metabolites could be excreted into the bile of Eisai hyperbilirubinemic rats (EHBR). These animals are deficient in xenobiotic conjugate transporter, multidrug resistance-associated protein (MRP-2), indicating that the glucuronides of both octylphenols are transported by MRP-2. These results indicate that the differences in metabolism of these octylphenols are due to the shape of their alkyl chains, suggesting that the estrogenic activities of not only the parent chems. but also these metabolites must be taken into consideration.

Life Sciences published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, Formula: C14H22O2.

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

Hao, Qian-Qian published the artcileModulation of Solid-State Optical Properties of o-Hydroxynaphthoic Acids through Formation of Charge Transfer Cocrystals with TCNB, Formula: C11H8O3, the publication is Crystal Growth & Design (2020), 20(11), 7492-7500, database is CAplus.

Charge transfer cocrystals offer an opportunity to alter the photophys. characteristics of organic chromophores in the solid state. A set of new charge transfer cocrystals of three positional isomers of o-hydroxynaphthoic acid with 1,2,4,5-tetracyanobenzene (TCNB) as the electron acceptor was prepared and subjected to single-crystal and powder X-ray diffraction, thermal anal., vibrational, and UV-vis absorption and fluorescence spectroscopic measurements. Crystal structure analyses reveal that the donor and acceptor mols. are combined in a 2:1 stoichiometric ratio and stacked alternately through a typical mixed face-to-face arrangement (DAD···DAD), forming a columnlike charge transfer structure involving π-stacking interactions. All of the cocrystals exhibit distinct tunable emission colors and photoluminescence characteristics due to the charge transfer transition states. This research indicates that the cocrystal strategy can be applied to effectively modulate the optical properties of o-hydroxynaphthoic acid compounds, which have a great research value in optoelectronic applications. A set of new charge transfer cocrystals of three positional isomers of o-hydroxynaphthoic acid with TCNB as the electron acceptor was successfully prepared and fully characterized, and they exhibit distinct tunable photoluminescence characteristics due to the mixed DAD···DAD columnlike charge transfer structures.

Crystal Growth & Design 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 C11H8O3, Formula: C11H8O3.

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

Ding, Shi published the artcileDesign, synthesis and structure-activity relationship evaluation of novel LpxC inhibitors as Gram-negative antibacterial agents, Related Products of alcohols-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry Letters (2018), 28(2), 94-102, database is CAplus and MEDLINE.

LpxC inhibitors are new-type antibacterial agents developed in the last twenty years, mainly against Gram-neg. bacteria infections. To develop novel LpxC inhibitors with good antibacterial activities and biol. metabolism, the authors summarized the basic skeleton of reported LpxC inhibitors, designed and synthesized several series of compounds and tested their antibacterial activities against Escherichia coli and Pseudomonas aeruginosa in vitro. Structure-activity relations are discussed. The metabolism stability of YDL-2, YDL-5, YDL-8, YDL-14, YDL-20-YDL-23 were evaluated in liver microsomes, which indicated that the 2-amino iso-Pr group may be a preferred structure than the 2-hydroxy Et group in the design of LpxC inhibitors.

Bioorganic & 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, Related Products of alcohols-buliding-blocks.

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

Gohon, Yann published the artcileBacteriorhodopsin/amphipol complexes: structural and functional properties, Safety of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, the publication is Biophysical Journal (2008), 94(9), 3523-3537, database is CAplus and MEDLINE.

The membrane protein bacteriorhodopsin (BR) can be kept soluble in its native state for months in the absence of detergent by amphipol (APol) A8-35, an amphiphilic polymer. After an actinic flash, A8-35-complexed BR undergoes a complete photocycle, with kinetics intermediate between that in detergent solution and that in its native membrane. BR/APol complexes form well defined, globular particles comprising a monomer of BR, a complete set of purple membrane lipids, and, in a peripheral distribution, ∼2 g APol/g BR, arranged in a compact layer. In the absence of free APol, BR/APol particles can autoassoc. into small or large ordered fibrils.

Biophysical Journal published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Safety of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol.

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