Tag: 100-200

Sulfonamidopyrrolidinone Factor Xa Inhibitors: Potency and Selectivity Enhancements via P-1 and P-4 Optimization was written by Choi-Sledeski, Yong Mi;McGarry, Daniel G.;Green, Daniel M.;Mason, Helen J.;Becker, Michael R.;Davis, Roderick S.;Ewing, William R.;Dankulich, William P.;Manetta, Vincent E.;Morris, Robert L.;Spada, Alfred P.;Cheney, Daniel L.;Brown, Karen D.;Colussi, Dennis J.;Chu, Valeria;Heran, Christopher L.;Morgan, Suzanne R.;Bentley, Ross G.;Leadley, Robert J.;Maignan, Sebastien;Guilloteau, Jean-Pierre;Dunwiddie, Christopher T.;Pauls, Henry W.. And the article was included in Journal of Medicinal Chemistry in 1999.Recommanded Product: 15777-70-5 This article mentions the following:

Sulfonamidopyrrolidinones were previously disclosed as a selective class of factor Xa (fXa) inhibitors, culminating in the identification of RPR120844 as a potent member with efficacy in vivo. Recognizing the usefulness of the central pyrrolidinone template for the presentation of ligands to the S-1 and S-4 subsites of fXa, studies to optimize the P-1 and P-4 groups were initiated. Sulfonamidopyrrolidinones containing 4-hydroxy- and 4-aminobenzamidines were discovered to be effective inhibitors of fXa. X-ray crystallog. experiments in trypsin and mol. modeling studies suggest that our inhibitors bind by insertion of the 4-hydroxybenzamidine moiety into the S-1 subsite of the fXa active site. Of the P-4 groups examined, the pyridylthienyl sulfonamides were found to confer excellent potency and selectivity especially in combination with 4-hydroxybenzamidine. Compound I (RPR130737) was shown to be a potent fXa inhibitor (K_i = 2 nM) with selectivity against structurally related serine proteinases (>1000 times). Preliminary biol. evaluation demonstrates the effectiveness of this inhibitor in common assays of thrombosis in vitro (e.g. activated partial thromboplastin time) and in vivo (e.g. rat FeCl₂-induced carotid artery thrombosis model). In the experiment, the researchers used many compounds, for example, 4-Hydroxy-3-methylbenzonitrile (cas: 15777-70-5Recommanded Product: 15777-70-5).

4-Hydroxy-3-methylbenzonitrile (cas: 15777-70-5) 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.Recommanded Product: 15777-70-5

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The enantioselective reduction of 2′-fluoroacetophenone utilizing a simplified CBS-reduction procedure was written by Garrett, Christine E.;Prasad, Kapa;Repic, Oljan;Blacklock, Thomas J.. And the article was included in Tetrahedron: Asymmetry in 2002.HPLC of Formula: 171032-87-4 This article mentions the following:

A practical, non-enzymic, catalytic process was developed for the enantioselective reduction of 2′-fluoroacetophenone. A number of catalysts were screened for the oxazaborolidine-type reduction of this ketone to obtain an optimized system. It was shown that the simplest procedure uses the catalyst formed in situ from (S)-α,α-diphenyl-2-pyrrolidinemethanol and borane-diethylaniline. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4HPLC of Formula: 171032-87-4).

(S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.HPLC of Formula: 171032-87-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Fe(III) superoxide radicals in halloysite nanotubes for visible-light-assisted benzyl alcohol oxidation and oxidative C-C coupling of 2-naphthol was written by Baruah, Manash J.;Bora, Tonmoy J.;Dutta, Rupjyoti;Roy, Subhasish;Guha, Ankur Kanti;Bania, Kusum K.. And the article was included in Molecular Catalysis in 2021.Application of 1777-82-8 This article mentions the following:

Selective oxidation of benzyl alcs. to aldehydes and 2-naphthol to BINOL was achieved by activation of mol. oxygen (O₂) and hydrogen peroxide (H₂O₂) over an iron-oxide catalyst embedded in halloysite nanotube. ESR spectroscopy (ESR), Raman and in situ FTIR spectroscopic anal. provided direct evidence for the involvement of superoxide radical bound Fe^III species in the oxidation reaction. Both the anal. suggested the end-on binding of superoxide radical with Fe^III-center. The stability of such radical bound Fe^III-species in halloysite nanotube was analyzed through d. functional theory (DFT) calculations Results suggested that end-on (η¹) binding was favorable by 13.5 kcal/ mol than the side-on (η²) binding mode. The formation of such reactive species was believed to play the crucial role in bringing the high selectivity in the catalytic oxidation of benzyl alc. and oxidative C-C coupling of 2-naphthol. UV-Vis spectroscopic studies on the oxidation of benzyl alc. suggested for the initial adsorption of substrate mol. on the catalyst surface followed by its interaction with Fe^III -superoxide/hydroperoxide species generated upon photoirradiation with visible light in presence of O₂. The presence of a suitable band gap ∼2.14 eV enabled the catalyst to catalyze the reaction under visible light irradiation Both the reactions (benzyl alc. and 2-naphthol oxidation) were tested in presence of both O₂ and H₂O₂ as oxidants at ambient temperature The influence of different parameters like rate of oxygen flow, amount of peroxide, nature of solvent, and catalyst amount on the conversion and selectivity of the reactions were studied to understand their role in the catalytic reactions. Successful oxidation of 2-naphthol with H₂O₂ as oxidant was a real success to overcome the limitations associated with this reaction using H₂O₂ as oxidant. In the experiment, the researchers used many compounds, for example, (2,4-Dichlorophenyl)methanol (cas: 1777-82-8Application of 1777-82-8).

(2,4-Dichlorophenyl)methanol (cas: 1777-82-8) 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. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Application of 1777-82-8

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Nitrogen dioxide-catalyzed aerobic oxidation of benzyl alcohols under cocatalyst and acid-free conditions was written by Ren, Fangping;Tian, Xinzhe;Ren, Yun-Lai;Zhao, Shuang;Wang, Jianji;Zhao, Bo. And the article was included in Catalysis Communications in 2017.SDS of cas: 1777-82-8 This article mentions the following:

Nitrogen dioxide is usually considered as a mediator between dioxygen and the catalysts for the aerobic oxidation of alcs. Here, we report that nitrogen dioxide has an ability to catalyze this reaction, which not only avoids the use of the cocatalysts or the acids in traditional approaches, but also reveals a method for the present transformation with a single component catalyst. A series of primary and secondary benzyl alcs. underwent this transformation to give the targeted products in low to high yields. In the experiment, the researchers used many compounds, for example, (2,4-Dichlorophenyl)methanol (cas: 1777-82-8SDS of cas: 1777-82-8).

(2,4-Dichlorophenyl)methanol (cas: 1777-82-8) 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. 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.SDS of cas: 1777-82-8

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Localizable and Photoactivatable Fluorophore for Spatiotemporal Two-Photon Bioimaging was written by Zhou, Liyi;Zhang, Xiaobing;Lv, Yifan;Yang, Chao;Lu, Danqing;Wu, Yuan;Chen, Zhuo;Liu, Qiaoling;Tan, Weihong. And the article was included in Analytical Chemistry (Washington, DC, United States) in 2015.Related Products of 60463-12-9 This article mentions the following:

Photoactivatable probe-based fluorescent imaging has become an efficient and attractive technique for spatiotemporal microscopic studies of biol. events. However, almost all previously reported photoactivatable organic probes have been based on hydrosol. precursors, which produced water-soluble active fluorophores able to readily diffuse away from the photocleavage site, thereby dramatically reducing spatial resolution Hydroxyphenylquinazolinone (HPQ), a small organic dye known for its classic luminescence mechanism through excited-state intramol. proton transfer (ESIPT), shows strong light emission in the solid state, but no emission in solution HPQ was employed as a precursor to develop a localizable, photoactivatable two-photon probe (PHPQ) for spatiotemporal bioimaging applications. After photocleavage, PHPQ releases a precipitating HPQ fluorophore which shows both one-photon and two-photon excited yellow-green fluorescence, thereby producing a localizable fluorescence signal that affords high spatial resolution for bioimaging, with >200-fold one-photon and 150-fold two-photon fluorescence enhancement. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Related Products of 60463-12-9).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Related Products of 60463-12-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Effects of different amino acid levels and a carvacrol-thymol blend on growth performance and intestinal health of weaned pigs was written by Wang, Yanan;Yang, Zhipeng;Zhou, Yuanfei;Tan, Jiajian;Sun, Haiqing;Sun, Defa;Mu, Yuyun;Peng, Jian;Wei, Hongkui. And the article was included in Journal of Animal Science and Biotechnology in 2022.Name: 5-Isopropyl-2-methylphenol This article mentions the following:

Over the past years, antibiotic growth promoter had been restricted in animal husbandry production in many countries because of antimicrobial resistance and foodborne antibiotic residues. However, the problems of poor intestinal health and low growth efficiency of piglets have not been solved completely in an antibiotic-free diet, and it is urgent to explore alternatives to antimicrobial growth promoters. Here, a total of 532 weaned pigs were assigned to one of 4 treatments, the low amino acid (AA) level diet (d 1 to d 14 is 1.35%, d 15 to d 42 is 1.25%) (Low AA), the low AA level diet supplementation with a carvacrol-thymol blend (50 mg carvacrol and 50 mg thymol/kg of diet) (CB) (Low AA+CB), the high AA level diet (d 1 to d 14 is 1.50%, d 15 to d 42 is 1.40%) (High AA), and the high AA level diet supplementation with a CB (High AA+CB), resp. Then we measured growth performance and intestinal health indicators of weaned pigs. Results showed that high AA level significantly reduced plasma urea nitrogen, plasma Interleukin-6 (IL-6) and fecal lipocalin-2 contents (P < 0.05), significantly increased the relative abundance of fecal Lactobacillus and Enterococcus, and had a trend to increase the fecal secretory IgA (sIgA) and mucin 2 (MUC 2) contents (P < 0.05) in piglets, thereby alleviating the diarrhea of piglets and reducing the feed conversion ratio (FCR) of piglets during d 1~14 after weaning. Dietary supplementation with CB significantly increased the activity of plasma antioxidant enzymes T-SOD and GSH-px (P < 0.05), while significantly reduced plasma malondialdehyde (MDA), plasma interleukin-1β (IL-1β), plasma endotoxin and D-lactic acid contents (P < 0.05). Meanwhile, CB significantly decreased fecal lipocalin-2 contents and the abundance of fecal Escherichia coli (P < 0.05). Thus, we hypothesis that dietary supplementation with CB significantly increased the average daily gain (ADG) of piglets (P < 0.05) during d 1∼14 after weaning through promoting intestinal health. These results suggest that high AA level and dietary supplementation with CB improved the growth performance of weaned pigs in an antibiotic-free diet by improving AA metabolism and intestinal antioxidant capacity. In the experiment, the researchers used many compounds, for example, 5-Isopropyl-2-methylphenol (cas: 499-75-2Name: 5-Isopropyl-2-methylphenol).

5-Isopropyl-2-methylphenol (cas: 499-75-2) 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. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Name: 5-Isopropyl-2-methylphenol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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-α (PPAR-α), 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-α 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-α 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―O−). 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