Tag: 100-200

Dioxygenase-catalysed oxidation of disubstituted benzene substrates: benzylic monohydroxylation versus aryl cis-dihydroxylation and the meta effect was written by Boyd, Derek R.;Sharma, Narain D.;Bowers, Nigel I.;Dalton, Howard;Garrett, Mark D.;Harrison, John S.;Sheldrake, Gary N.. And the article was included in Organic & Biomolecular Chemistry in 2006.Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:

Biotransformations of a series of ortho-, meta- and para-substituted ethylbenzene and propylbenzene substrates have been carried out, using Pseudomonas putida UV4, a source of toluene dioxygenase (TDO). The ortho- and para-substituted alkylbenzene substrates yielded, exclusively, the corresponding enantiopure cis-dihydrodiols of the same absolute configuration. However, the meta isomers, generally, gave benzylic alc. bioproducts, in addition to the cis-dihydrodiols (the meta effect). The benzylic alcs. were of identical (R) absolute configuration but enantiomeric excess values were variable. The similar (2R) absolute configurations of the cis-dihydrodiols are consistent with both the Et and Pr groups having dominant stereodirecting effects over the other substituents. The model used earlier, to predict the regio- and stereo-chem. of cis-dihydrodiol bioproducts derived from substituted benzene substrates has been refined, to take account of non-sym. substituents like Et or Pr groups. The formation of benzylic hydroxylation products, from meta-substituted benzene substrates, without further cis-dihydroxylation to yield triols provides a further example of the meta effect during toluene dioxygenase-catalyzed oxidations In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Absolute proton affinities of some substituted toluenes: the additivity rule of thumb for ipso attack was written by Eckert-Maksic, Mirjana;Knezevic, Andrea;Maksic, Zvonimir B.. And the article was included in Journal of Physical Organic Chemistry in 1998.Reference of 15777-70-5 This article mentions the following:

The problem of the ipso protonation of toluene and its predominantly disubstituted derivatives was considered by the MP2(fc)/6-31G^**//HF/6-31G^*+ZPE(HF/6-31G^*) theor. model. The substituents involved covered a wide range of different donor-acceptor capabilities. It is shown that the calculated MP2 ipso proton affinities of substituted toluenes follow mutatis mutandis the same additivity rule which was found earlier to be operative in polysubstituted benzenes, naphthalenes and biphenylenes. The additivity equation is both intuitively appealing and useful, being able to offer quant. estimates of the proton affinity by very simple calculation It is based on the concept of the increment, which in turn describes the influence of a single substituent on the proton affinity. Any substituent behaves as a rule as if the other were non-existent, thus giving rise to the independent substituent approximation (ISA). The performance of the additivity rule of thumb is very good, as evidenced by the average absolute deviation of 1 kcal mol^-1. Larger deviations are possible, but they rarely occur, being indicative of a difference in interactions between substituents in the initial neutral base and in the final cationic conjugate acid. Finally, it follows as a corollary of the present anal. that protonation ipso to the CH₃ group is never thermodynamically the most favorable site of proton attack in the benzene ring, provided that there is a single unsubstituted carbon atom within the aromatic moiety. The relevance of ipso protonation in persubstituted benzenes is briefly discussed. In the experiment, the researchers used many compounds, for example, 4-Hydroxy-3-methylbenzonitrile (cas: 15777-70-5Reference of 15777-70-5).

4-Hydroxy-3-methylbenzonitrile (cas: 15777-70-5) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Reference of 15777-70-5

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Industrially viable process for reduction of esters to alcohols with sodium borohydride under buffer and aqueous alcoholic conditions was written by Chavakula, Ramadas;Rao, M. Narayana;Babu, B. Gopi;Kumar, K. Praveen;Rao, Ch. Srinivasa. And the article was included in Journal of the Indian Chemical Society in 2014.Application In Synthesis of (5-Methylpyridin-3-yl)methanol This article mentions the following:

A simple and convenient procedure for the synthesis of alcs. from esters by reduction method using sodium borohydride in the presence of dipotassium hydrogen orthophosphate under aqueous alc. conditions is described. This method uses inexpensive, safe and environmentally friendly reducing agent. In the experiment, the researchers used many compounds, for example, (5-Methylpyridin-3-yl)methanol (cas: 102074-19-1Application In Synthesis of (5-Methylpyridin-3-yl)methanol).

(5-Methylpyridin-3-yl)methanol (cas: 102074-19-1) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Application In Synthesis of (5-Methylpyridin-3-yl)methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Design and synthesis of cyanamides as potent and selective N-acylethanolamine acid amidase inhibitors was written by Malamas, Michael S.;Farah, Shrouq I.;Lamani, Manjunath;Pelekoudas, Dimitrios N.;Perry, Nicholas Thomas;Rajarshi, Girija;Miyabe, Christina Yume;Chandrashekhar, Honrao;West, Jay;Pavlopoulos, Spiro;Makriyannis, Alexandros. And the article was included in Bioorganic & Medicinal Chemistry in 2020.Synthetic Route of C9H17NO3 This article mentions the following:

N-acylethanolamine acid amidase (NAAA) inhibition represents an exciting novel approach to treat inflammation and pain. NAAA is a cysteine amidase which preferentially hydrolyzes the endogenous biolipids palmitoylethanolamide (PEA) and oleoylethanolamide (OEA). PEA is an endogenous agonist of the nuclear peroxisome proliferator-activated receptor-伪 (PPAR-伪), which is a key regulator of inflammation and pain. Thus, blocking the degradation of PEA with NAAA inhibitors results in augmentation of the PEA/PPAR-伪 signaling pathway and regulation of inflammatory and pain processes. We have prepared a new series of NAAA inhibitors exploring the azetidine-nitrile (cyanamide) pharmacophore that led to the discovery of highly potent and selective compounds Key analogs demonstrated single-digit nanomolar potency for hNAAA and showed >100-fold selectivity against serine hydrolases FAAH, MGL and ABHD6, and cysteine protease cathepsin K. Addnl., we have identified potent and selective dual NAAA-FAAH inhibitors to investigate a potential synergism between two distinct anti-inflammatory mol. pathways, the PEA/PPAR-伪 anti-inflammatory signaling pathway,^1-4 and the cannabinoid receptors CB1 and CB2 pathways which are known for their antiinflammatory and antinociceptive properties.^5-8 Our ligand design strategy followed a traditional structure-activity relationship (SAR) approach and was supported by mol. modeling studies of reported X-ray structures of hNAAA. Several inhibitors were evaluated in stability assays and demonstrated very good plasma stability (t_1/2 > 2 h; human and rodents). The disclosed cyanamides represent promising new pharmacol. tools to investigate the potential role of NAAA inhibitors and dual NAAA-FAAH inhibitors as therapeutic agents for the treatment of inflammation and pain. In the experiment, the researchers used many compounds, for example, 1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3Synthetic Route of C9H17NO3).

1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Synthetic Route of C9H17NO3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

A base promoted multigram synthesis of aminoisoxazoles: valuable building blocks for drug discovery and peptidomimetics was written by Chalyk, Bohdan A.;Kandaurova, Inna Y.;Hrebeniuk, Kateryna V.;Manoilenko, Olga V.;Kulik, Irene B.;Iminov, Rustam T.;Kubyshkin, Vladimir;Tverdokhlebov, Anton V.;Ablialimov, Osman K.;Mykhailiuk, Pavel K.. And the article was included in RSC Advances in 2016.Name: 1-Boc-Azetidine-3-yl-methanol This article mentions the following:

A practical multigram metal free synthesis of isoxazole-containing building blocks from com. available amino acids was elaborated. The key reaction was a regioselective [3+2]-cycloaddition of in-situ generated nitrile oxides with alkynes/enamines. The obtained building blocks were used in the preparation of bioactive compounds and peptidomimetics. In the experiment, the researchers used many compounds, for example, 1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3Name: 1-Boc-Azetidine-3-yl-methanol).

1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Name: 1-Boc-Azetidine-3-yl-methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase SmADH2 via an environmentally friendly TBCR system was written by Yang, Zeyu;Fu, Hengwei;Ye, Wenjie;Xie, Youyu;Liu, Qinghai;Wang, Hualei;Wei, Dongzhi. And the article was included in Catalysis Science & Technology in 2020.Quality Control of (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:

Alc. dehydrogenases (ADHs) together with the economical substrate-coupled cofactor regeneration system play a pivotal role in the asym. synthesis of chiral alcs.; however, severe challenges concerning the poor tolerance of enzymes to 2-propanol and the adverse effects of the byproduct, acetone, limit its applications, causing this strategy to lapse. Herein, a novel ADH gene smadh2 was identified from Stenotrophomonas maltophilia by traditional genome mining technol. The gene was cloned into Escherichia coli cells and then expressed to yield SmADH2. SmADH2 has a broad substrate spectrum and exhibits excellent tolerance and superb activity to 2-propanol even at 10.5 M (80%, volume/volume) concentration Moreover, a new thermostatic bubble column reactor (TBCR) system is successfully designed to alleviate the inhibition of the byproduct acetone by gas flow and continuously supplement 2-propanol. The organic waste can be simultaneously recovered for the purpose of green synthesis. In the sustainable system, structurally diverse chiral alcs. are synthesized at a high substrate loading (>150 g L^-1) without adding external coenzymes. Among these, about 780 g L^-1 (6 M) Et acetoacetate is completely converted into Et (R)-3-hydroxybutyrate in only 2.5 h with 99.9% ee and 7488 g L^-1 d^-1 space-time yield. Mol. dynamics simulation results shed light on the high catalytic activity toward the substrate. Therefore, the high 2-propanol tolerance SmADH2 with the TBCR system proves to be a potent biocatalytic strategy for the synthesis of chiral alcs. on an industrial scale. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Quality Control of (R)-1-(3-Chlorophenyl)ethanol).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Quality Control of (R)-1-(3-Chlorophenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Structure-Activity Relationship Explorations and Discovery of a Potent Antagonist for the Free Fatty Acid Receptor 2 was written by Hoejgaard Hansen, Anders;Christensen, Henriette B.;Pandey, Sunil K.;Sergeev, Eugenia;Valentini, Alice;Dunlop, Julia;Dedeo, Domonkos;Fratta, Simone;Hudson, Brian D.;Milligan, Graeme;Ulven, Trond;Rexen Ulven, Elisabeth. And the article was included in ChemMedChem in 2021.Recommanded Product: 2968-93-6 This article mentions the following:

Free fatty acid receptor 2 (FFA2) is a sensor for short-chain fatty acids that has been identified as an interesting potential drug target for treatment of metabolic and inflammatory diseases. Although several ligand series are known for the receptor, there is still a need for improved compounds One of the most potent and frequently used antagonists is the amide-substituted phenylbutanoic acid known as CATPB (1). We here report the structure-activity relationship exploration of this compound, leading to the identification of homologues with increased potency. The preferred compound 37 (TUG-1958) was found, besides improved potency, to have high solubility and favorable pharmacokinetic properties. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6Recommanded Product: 2968-93-6).

2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6) belongs to alcohols. The oxygen atom of the strongly polarized O鈥旽 bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Recommanded Product: 2968-93-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Indium(III)-Catalyzed Synthesis of Primary Carbamates and N-Substituted Ureas was written by Jain, Isha;Malik, Payal. And the article was included in Synlett in 2022.Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol This article mentions the following:

An indium triflate-catalyzed synthesis of primary carbamates RXC(O)NH₂ [R = i-Bu, Bn, Ph, etc.; X= O, N] from alcs. and urea as an ecofriendly carbonyl source was developed. Various linear, branched, and cyclic alcs. were converted into the corresponding carbamates in good to excellent yields. This method also provided access to N-substituted ureas by carbamoylation of amines. All the products were obtained by simple filtration or crystallization, without the need for chromatog. purification Mechanistic investigations suggested that the carbamoylation reaction proceeded through activation of urea by O-coordination with indium, followed by nucleophilic attack by the alc. or amine on the carbonyl center of urea. The inexpensive and easily available starting materials and catalyst, the short reaction times, and the ease of product isolation highlighted the inherent practicality of the developed method. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol).

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthesis of the first sulfur-35-labeled hERG radioligand was written by Raab, Conrad E.;Butcher, John W.;Connolly, Thomas M.;Karczewski, Jerzy;Yu, Nathan X.;Staskiewicz, Steven J.;Liverton, Nigel;Dean, Dennis C.;Melillo, David G.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2006.Related Products of 29364-29-2 This article mentions the following:

The synthesis of the first high specific activity S-35-labeled hERG radioligand, [³⁵S]MK-0499, for use in high-throughput-screening (HTS) assays of drug candidates for hERG interaction is described. The radioligand is prepared by [³⁵S]sulfonylation of a high diastereomeric excess (de) aniline precursor prepared from unlabeled MK-0499. In the experiment, the researchers used many compounds, for example, Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2Related Products of 29364-29-2).

Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Related Products of 29364-29-2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Metabolic, cellular and defense responses to single and co-exposure to carbamazepine and methylmercury in Dreissena polymorpha was written by Baratange, Clement;Paris-Palacios, Severine;Bonnard, Isabelle;Delahaut, Laurence;Grandjean, Dominique;Wortham, Laurence;Sayen, Stephanie;Gallorini, Andrea;Michel, Jean;Renault, David;Breider, Florian;Loizeau, Jean-Luc;Cosio, Claudia. And the article was included in Environmental Pollution (Oxford, United Kingdom) in 2022.Category: alcohols-buliding-blocks This article mentions the following:

Carbamazepine (CBZ) and Hg are widespread and persistent micropollutants in aquatic environments. Both pollutants are known to trigger similar toxicity mechanisms, e.g. reactive oxygen species (ROS) production Here, their effects were assessed in the zebra mussel Dreissena polymorpha, frequently used as a freshwater model in ecotoxicol. and biomonitoring. Single and co-exposures to CBZ (3.9 渭g L-1) and MeHg (280 ng L-1) were performed for 1 and 7 days. Metabolomics analyses evidenced that the co-exposure was the most disturbing after 7 days, reducing the amount of 25 metabolites involved in protein synthesis, energy metabolism, antioxidant response and osmoregulation, and significantly altering cells and organelles structure supporting a reduction of functions of gills and digestive glands. CBZ alone after 7 days decreased the amount of 伪-aminobutyric acid and had a moderate effect on the structure of mitochondria in digestive glands. MeHg alone had no effect on mussels metabolome, but caused a significant alteration of cells and organelles structure in gills and digestive glands. Single exposures and the co-exposure increased antioxidant responses vs control in gills and digestive glands, without resulting in lipid peroxidation, suggesting an increased ROS production caused by both pollutants. Data globally supported that a higher number of hyperactive cells compensated cellular alterations in the digestive gland of mussels exposed to CBZ or MeHg alone, while CBZ + MeHg co-exposure overwhelmed this compensation after 7 days. Those effects were unpredictable based on cellular responses to CBZ and MeHg alone, highlighting the need to consider mol. toxicity pathways for a better anticipation of effects of pollutants in biota in complex environmental conditions. In the experiment, the researchers used many compounds, for example, (2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6Category: alcohols-buliding-blocks).

(2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6) belongs to alcohols. The oxygen atom of the strongly polarized O鈥旽 bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts