Tag: 200-300

Investigation of mechanism-based thrombin inhibitors: Implications of a highly conserved water molecule for the binding of coumarins within the S pocket was written by Frederick, Raphael;Charlier, Caroline;Robert, Severine;Wouters, Johan;Masereel, Bernard;Pochet, Lionel. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2006.Product Details of 224309-64-2 This article mentions the following:

The synthesis of novel coumarins bearing on the lateral side chain in the 3-position an amine or a guanidine group is described. In vitro evaluation highlighted I which possesses a meta aniline side chain as a very potent THR inhibitor. Surprisingly, the introduction of a guanidine moiety always led to a decrease in THR inhibiting properties. We, thus, used docking experiments to rationalize the SAR in the series. This study showed the crucial role of a conserved water mol. in the specificity pocket of THR during docking simulation in order to explain the inactivity of guanidine derivatives In the experiment, the researchers used many compounds, for example, tert-Butyl (4-hydroxycyclohexyl)carbamate (cas: 224309-64-2Product Details of 224309-64-2).

tert-Butyl (4-hydroxycyclohexyl)carbamate (cas: 224309-64-2) 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. 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.Product Details of 224309-64-2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Ultrasound-promoted aminolysis of epoxides in aqueous media. A rapid procedure with no pH adjustment for additive-free synthesis of β-aminoalcohols was written by Abaee, M. Saeed;Hamidi, Vahid;Mojtahedi, Mohammad M.. And the article was included in Ultrasonics Sonochemistry in 2008.Formula: C13H19NO This article mentions the following:

An efficient and environmentally friendly procedure promoted by ultrasound irradiation was developed for stereoselective ring opening of various epoxides with aromatic and aliphatic amines under aqueous conditions in the presence of no catalyst or additive. Chemoselectivity of the protocol was shown by competition of piperidine and aniline to react with different epoxides resulting in exclusive formation of the resp. products of piperidine. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Formula: C13H19NO).

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. The oxygen atom of the strongly polarized O―H 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. 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.Formula: C13H19NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The novel ketoprofen amides – synthesis and biological evaluation as antioxidants, lipoxygenase inhibitors and cytostatic agents was written by Rajic, Zrinka;Hadjipavlou-Litina, Dimitra;Pontiki, Eleni;Kralj, Marijeta;Suman, Lidija;Zorc, Branka. And the article was included in Chemical Biology & Drug Design in 2010.Application of 59960-32-6 This article mentions the following:

The novel amides of ketoprofen and its reduced derivatives (5a-f, 4a-n, 6a-g) with aromatic and cycloalkyl amines or hydroxylamines were prepared and screened for their reducing and cytostatic activity as well as for their ability to inhibit soybean lipoxygenase and lipid peroxidation 1,1-Diphenyl-picrylhydrazyl test for reducing ability revealed that ketoprofen amides were more potent antioxidants than the amides of the reduced ketoprofen derivatives The most active compound was benzhydryl ketoprofen amide 5f. Lipoxygenase inhibition of the tested compounds varied from strong to very weak. The most potent compound was benzhydryl derivative 6f (IC₅₀ = 20.5 μM). Aromatic and cycloalkyl amides 4 and 5 were more potent lipoxygenase inhibitors than derivatives with carboxylic group. Aromatic amides of series 4 and 5 showed excellent lipid peroxidation inhibition (92.2-99.9%). On the other hand, the most pronounced cytostatic activity was exerted by O-benzyl derivative 4i, although in general all tested reduced and non-reduced lipophilic derivatives showed similar activity. In the experiment, the researchers used many compounds, for example, 2-(3-(Hydroxy(phenyl)methyl)phenyl)propanoic acid (cas: 59960-32-6Application of 59960-32-6).

2-(3-(Hydroxy(phenyl)methyl)phenyl)propanoic acid (cas: 59960-32-6) belongs to alcohols. The oxygen atom of the strongly polarized O―H 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. 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.Application of 59960-32-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Asymmetric amination of meso-epoxide with vegetable powder as a low-toxicity catalyst was written by Takeuchi, Yuki;Asano, Tatsuhiro;Tsuzaki, Kazuya;Wada, Koichi;Kurata, Hiroyuki. And the article was included in Molecules in 2020.Recommanded Product: 40571-86-6 This article mentions the following:

This paper describes the scope and limitation of substrates subjected to asym. amination with epoxides catalyzed by a soluble soybean polysaccharide (Soyafibe S-DN), which we recently discovered from the reaction of 1,2-epoxycyclohexane with cyclopropylamine. Various meso-epoxides reacted with various amines afforded the corresponding products with good enantiomeric selectivity. Since it was found that pectin was found to have a catalytic ability after screening com. available polysaccharides, we studied 33 different vegetable powders having pectic substances, and we found that many vegetable powders showed catalytic ability. These results should guide in using vegetable components as low-toxic catalysts for the production of pharmaceuticals. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Recommanded Product: 40571-86-6).

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. 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.Recommanded Product: 40571-86-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis was written by Guo, Peng;Wang, Ke;Jin, Wen-Jie;Xie, Hao;Qi, Liangliang;Liu, Xue-Yuan;Shu, Xing-Zhong. And the article was included in Journal of the American Chemical Society in 2021.Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:

Herein, a dynamic kinetic cross-coupling approach for the direct functionalization of alcs were reported. The feasibility of this strategy was demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcs. with (hetero)aryl electrophiles. The reaction proceeded with a broad substrate scope of both coupling partners. The electron-rich, electron-poor and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enabled the direct arylation of benzylic alc. in the presence of various nucleophilic groups, including non-activated primary/secondary/tertiary alcs., phenols, and free indoles. It thus offered a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biol. active mols. and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process was an initial step in the reaction with aryl electrophiles. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. 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.Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

S-(Methyl-d₃) Arylsulfonothioates: A Family of Robust, Shelf-stable, and Easily Scalable Reagents for Direct Trideuteromethylthiolation was written by Zhang, Yan;Liu, Wen;Xu, Yuenian;Liu, Yong;Peng, Jiajian;Wang, Minyan;Bai, Ying;Lu, Hua;Shi, Zhuangzhi;Shao, Xinxin. And the article was included in Organic Letters in 2022.Application In Synthesis of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:

A family of electrophilic deuterated methylthiolating reagents, S-(Methyl-d₃) arylsulfonothioates, was developed in two or three steps from cheap d₄-MeOH in high yields. S-(Methyl-d₃) arylsulfonothioates represent a kind of powerful deuterated methylthiolating reagent and allow modular (trideuteromethyl)thiolation with a variety of nucleophiles or electrophiles including aryl(hetero) iodides, boronic acids esters, terminal alkynes, β-ketoester, and oxindole under mild reaction conditions. A structure-reactivity research study was conducted and provided a new avenue for the development of deuterated methylthiolating reagents and efficient methodol. for (trideuteromethyl)thiolation. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Application In Synthesis of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) 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 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Copper-Catalyzed Asymmetric Borylative Ring Opening of Diazabicycles was written by Lee, Hyesu;Han, Jung Tae;Yun, Jaesook. And the article was included in ACS Catalysis in 2016.COA of Formula: C16H20B2N2O2 This article mentions the following:

Highly enantioselective, copper-catalyzed ring opening of bicyclic hydrazines using a diboron reagent was accomplished with (R,R)-taniaphos as a chiral ligand. Desymmetrization of various bicyclic hydrazines by boryl substitution afforded 3-Bpin-4-hydrazino-cyclopentene derivatives with enantioselectivity up to >99% under mild conditions. The resulting allylic boron products were utilized in further organic transformations. Kinetic resolution of a racemic bicyclic oxazine gave useful information about the relative rates of C-O and C-N bond cleavage. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6COA of Formula: C16H20B2N2O2).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) 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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.COA of Formula: C16H20B2N2O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Trans-Diborylation of Alkynes: Pseudo-Intramolecular Strategy Utilizing a Propargylic Alcohol Unit was written by Nagashima, Yuki;Hirano, Keiichi;Takita, Ryo;Uchiyama, Masanobu. And the article was included in Journal of the American Chemical Society in 2014.Quality Control of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine This article mentions the following:

Authors present the first trans-selective diborylation reaction of alkynes. By theor. calculation-assisted reaction anal., authors designed a pseudo-intramol. reaction of diboron, propargyl alc., and a base to facilitate B-B bond activation and C-B bond formation with high efficiency. This approach provides synthetically versatile and densely functionalized 4-borylated 1,2-oxaborol-2(5H)-oles (vinyldiboronates) in a straightforward manner. Detailed computational anal. showed that the directing alkoxide functionality markedly lowers the activation energy of B-C bond formation. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6Quality Control of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) belongs to alcohols. The oxygen atom of the strongly polarized O―H 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. 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.Quality Control of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Discovery and SAR Studies of Orally Active Somatostatin Receptor Subtype-2 (SSTR2) Agonists for the Treatment of Acromegaly was written by Ishida, Akiharu;Tajima, Yohei;Okabe, Yasuyuki;Matsushita, Takeshi;Sekiguchi, Tetsuya;Imaide, Satomi;Nomura, Yoshinori;Tanaka, Motoyuki;Nojima, Shoji;Yoshida, Atsushi;Iyoda, Yoko;Aoki, Shohei;Nishio, Takuya;Komagata, Tatsuya;Iwaki, Masanori;Shono, Tomoyuki;Naganawa, Atsushi;Imagawa, Akira. And the article was included in ACS Chemical Neuroscience in 2020.Safety of tert-Butyl (4-hydroxycyclohexyl)carbamate This article mentions the following:

Acromegaly is a disease caused by the oversecretion of growth hormone. It is currently treated by i.v. injection with cyclic peptide drugs that activate somatostatin receptor subtype 2 (SSTR2). Here, novel nonpeptidic, small-mol., and orally active SSTR2 agonists were identified from a hit compound (13). Pharmacophore studies enabled scaffold hopping to obtain a unique 3,4,5-trisubstituted pyridine motif. Further optimization conferred potent SSTR2 agonistic activity and metabolic stability. Several compounds were evaluated and these showed good oral pharmacokinetic profiles in rats, and one representative compound (25)(I) showed highly potent inhibition of growth hormone secretion induced by growth hormone-releasing hormone in rats. Based on these results, 25 was identified as a promising lead for further optimization. A structure-activity relationship (SAR) study and the metabolic stability data for this compound are also described. In the experiment, the researchers used many compounds, for example, tert-Butyl (4-hydroxycyclohexyl)carbamate (cas: 224309-64-2Safety of tert-Butyl (4-hydroxycyclohexyl)carbamate).

tert-Butyl (4-hydroxycyclohexyl)carbamate (cas: 224309-64-2) belongs to alcohols. The oxygen atom of the strongly polarized O―H 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.Safety of tert-Butyl (4-hydroxycyclohexyl)carbamate

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Copper-Catalyzed Aerobic Oxidative Cyclization Cascade to Construct Bridged Skeletons: Total Synthesis of (-)-Suaveoline was written by Tan, Qiuyuan;Yang, Zhao;Jiang, Dan;Cheng, Yuegang;Yang, Jiao;Xi, Song;Zhang, Min. And the article was included in Angewandte Chemie, International Edition in 2019.SDS of cas: 60666-70-8 This article mentions the following:

Based on the discovery of copper-catalyzed cyclopropanol ring-opening addition to iminium ions, an unprecedented catalytic aerobic C-H oxidation/cyclopropanol cyclization cascade using CuCl₂ as the multifunctional catalyst and air as the oxidant was developed to construct the azabicyclo[3.3.1]nonane skeleton, which is widespread in natural products and medicines. Using this method, concise asym. total synthesis of the indole alkaloid (-)-suaveoline was achieved. This study not only provides an efficient, low-cost, and environmentally benign method for constructing such bridged frameworks, but also enriches the realm of cyclopropanol chem. and C-H functionalization. In the experiment, the researchers used many compounds, for example, (2-Bromo-5-chlorophenyl)methanol (cas: 60666-70-8SDS of cas: 60666-70-8).

(2-Bromo-5-chlorophenyl)methanol (cas: 60666-70-8) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. 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.SDS of cas: 60666-70-8

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts