Tag: 100-200

Pyran series, its analogs, and related compounds. XXXV. Reaction of 4-chlorocoumarin and sodium alcoholates was written by Zagorevskii, V. A.;Savel’ev, V. L.;Dudykina, N. V.. And the article was included in Khim. Geterotsikl. Soedin. in 1970.HPLC of Formula: 1646-27-1 This article mentions the following:

Reaction of 4-chlorocoumarin (I) with NaOH in aqueous dioxane at 20° gave 92.5% (o-hydroxyphenyl)-propiolic acid (II); under reflux the reaction gave 80% benzofuran-2-carboxylic acid (III). II was hydrogenated over Pd/BaSO4 to give 81% (o-hydroxyphenyl)propionic acid. II, heated with aqueous NaOH, gave 83% III. I, treated with NaOMe in MeOH at 20°, gave 95.6% 4-methoxycoumarin (IV); at 70° the reaction gave 91.1% IV and 7.5% III. I with MeONa in MeOH-dioxane gave 64% IV, 17% III, and 12% III Me ester. Reaction of I with EtONa in EtOH at 70° gave 38% 4-ethoxycoumarin (V), 11% III, and 31.6% III Et ester (VI). In EtOH-dioxane the reaction gave 17.4% V, 7.5% III, and 48% VI. I with PhONa in dioxane gave 85% 4-phenoxycoumarin and 13% II. I with Me2NCH2CH2ONa in PhMe gave 15% (as HCl salt) 2-(dimethylamino)ethoxy]coumarin, ester (VII) of III, 15% III, and 18% 4-[2-(dimethylamino)ethoxy]coumarin, which with concentrated HCl gave 4-hydroxycoumarin; VII.HCl similarly gave III. V treated with EtONa in EtOH-dioxane gave 24% 4-hydroxycoumarin and traces of VI; analogous results were obtained in EtOH alone. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1HPLC of Formula: 1646-27-1).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. Benzofurans are stable towards alkali and readily polymerize on treatment with sulfuric acid, due to which they are useful for the preparation of low cost chemically relatively inert resins.HPLC of Formula: 1646-27-1

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Inhibition of aromatase (P450_Arom) by some 1-(benzofuran-2-ylmethyl)imidazoles was written by Owen, Caroline P.;Nicholls, Paul J.;Smith, H. John;Whomsley, Rhys. And the article was included in Journal of Pharmacy and Pharmacology in 1999.Related Products of 1646-27-1 This article mentions the following:

Studies of a series of 1-(benzofuran-2-ylmethyl)imidazoles, 1-5, previously proposed as potential agents for prostatic cancer by their inhibition of 17β-hydroxylase: 17,20-lyase (P 450 17), have been extended to their selectivity against placental microsomal aromatase (P 450_Arom) in man. The compounds were 3-7-fold more potent than aminoglutethimide and had some selectivity for P 450 17 as expressed by the ratio (IC50 P 450_Arom)/(IC50 P 450) 17/17.0 (2), 10.3 (3), 34.6 (4) and 42.0 (5), where IC50 is the concentration resulting in 50% inhibition. The lower potency of 1-5 towards P 450_Arom compared with the racemic α-phenyl-substituted compounds (6, 80-1000 × aminoglutethimide) and some racemic α-Me (8.5 and 12.2 × aminoglutethimide) and α-Et (12.1 and 32.9 × aminoglutethimide) analogs has been rationalized. This work selectively extends studies of the P 450 17 inhibitor 5, a potential prostatic cancer agent, towards other cytochrome P 450 enzymes in the steroidogenic pathway and provides a general method for determining the relative influence of chem. manipulation of a parent inhibitor towards two enzymes in the pathway using addnl. literature data. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Related Products of 1646-27-1).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.Related Products of 1646-27-1

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Synthesis and evaluation of 2-pyridylbenzothiazole, 2-pyridylbenzoxazole and 2-pyridylbenzofuran derivatives as ¹¹C-PET imaging agents for β-amyloid plaques was written by Swahn, Britt-Marie;Wensbo, David;Sandell, Johan;Sohn, Daniel;Slivo, Can;Pyring, David;Malmstroem, Jonas;Arzel, Erwan;Vallin, Michaela;Bergh, Margareta;Jeppsson, Fredrik;Johnson, Allan E.;Jureus, Anders;Neelissen, Jan;Svensson, Samuel. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C9H9BO4 This article mentions the following:

The syntheses and SAR of new series of β-amyloid binding agents are reported. The effort to optimize signal-to-background ratios for these ligands are described. Compounds I (X = S, O) and II displayed desirable lipophilicity and pharmacokinetic properties. Compounds I (X = S, O) were evaluated with in vitro autoradiog. studies and in vivo in APP/PS1 transgenic mice. It is shown that it was possible to increase the signal-to-background ratios compared to PIB 1, as demonstrated by compounds I (X = S, O). In the experiment, the researchers used many compounds, for example, (5-Methoxybenzofuran-2-yl)boronic acid (cas: 551001-79-7Formula: C9H9BO4).

(5-Methoxybenzofuran-2-yl)boronic acid (cas: 551001-79-7) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. In nature, benzofurans have occupied an important role among the plant phenols & several pharmacologically active compounds.Formula: C9H9BO4

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

SeO₂-Mediated One-Pot Synthesis of 3-Cyanofurans from 3-Oxo-3-arylpropanenitriles and Substituted Acetaldehydes was written by Zhou, Jie;Zhu, Xinhai;Huang, Manna;Wan, Yiqian. And the article was included in European Journal of Organic Chemistry in 2017.Application In Synthesis of Methyl benzofuran-2-carboxylate This article mentions the following:

An SeO₂-mediated one-pot method was established for the synthesis of 3-cyanofurans I (R¹ = 2-Cl, 4-OMe, 2-F, 4-Cl, etc.; R² = i-Pr, t-Bu, Et, etc.) from 3-oxo-3-arylpropanenitriles and substituted acetaldehydes. The generality of the reaction was explored, and a plausible mechanism is proposed. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Application In Synthesis of Methyl benzofuran-2-carboxylate).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives.Benzofuran is one of the most significant oxygen-containing heterocycles consisting of fused benzene and furan ring, which are widely presented in various naturally occurring and synthetically active compounds. Introduction of benzofurans in organic synthesis, particularly drug synthesis, involves generally the use of their metalated species as nucleophiles in addition reactions or in metal-catalysed cross-coupling reactions.Application In Synthesis of Methyl benzofuran-2-carboxylate

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Highly efficient direct visible-light-mediated oxidative esterification of aldehydes was written by Lindroth, Rickard;Bryce-Rogers, Hogan P.;Merke, Thomas P. M.;Wallentin, Carl-Johan. And the article was included in Photochemical & Photobiological Sciences in 2022.Formula: C10H8O3 This article mentions the following:

A very efficient one-pot procedure for the direct oxidation of aldehydes to esters RC(O)OR¹ [R = Ph, cyclohexyl, 4-MeOC₆H₄, etc.; R¹ = Me, Et, t-Bu, etc.] mediated by visible-light was presented. Utilizing a combination of indium triflate and N-bromosuccinimide, NBS, with either ortho-esters or alcs. provided rapid access to a variety of esters RC(O)OR¹. Certain substrates convert fully within a few seconds, other more challenging tert-Bu esters RC(O)OR¹ [R = 4-PhC₆H₄; R¹ = t-Bu] were formed in good yield after no more than 4 h. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Formula: C10H8O3).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Formula: C10H8O3

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Conjugation phenomena in α- and β-substituted pyrroles studied by infrared and ultraviolet spectrophotometry was written by Scrocco, Marisa;Caglioti, Luciano;Caglioti, V.. And the article was included in Atti accad. nazl. Lincei Rend., Classe sci. fis., mat. e nat. in 1958.Quality Control of Methyl benzofuran-2-carboxylate This article mentions the following:

Effects of ring substituents on the NH stretching frequency v(NH) of pyrroles (I) are further investigated. 2-Me, 3-Me, 2,4-Me₂, and 2,5-Me₂ substitutions cause only a very slight increase in v(NH) of I, an effect opposite to hyperconjugation. The v(CO) of the 3-CO₂Me compound previously given as 1700 cm.^-1 was resolved into 2 peaks, 1712 (strong) and 1698; similarly the 2-CO₂Me compound had maximum at 1715 and 1697 (strong), the lower ν presumably vibrations of internal chelates. The following data were similarly interpreted: (I substituents, strong v(NH), weak v(NH), strong v(CO), weak v(CO), ultraviolet maximum (log ε) and ultraviolet maximum (log ε) given): 3-CO₂Me, 3490, 3320, 1712, 1698 cm.^-1, 240 mμ (3.82), and – (-); 2-CO₂Me, 3326, 3472, 1697, 1715 cm.^-1, 261 (4.22) and 234.5 mμ (3.82); 2-CHO, 3284, 3468, 1650, 1666 cm.^-1, 279 (4.27), and 246 mμ (3.73); 2-Ac, 3294, 3466, 1640, 1662 cm.^-1, 276.5 (4.21) and 247 mμ (3.61); 2-COCH₂Cl, -, -, 1639, 1663 cm.^-1, 288.5 (4.3) and 246 mμ (3.6); 2-CO₂Me, 4-NO₂, -, -, -, -, 229 (4.26) and 285 mμ (3.75); 2-Ac, 5-CN, -, -, -, -, 248 (3.85) and 265 mμ (3.80). In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Quality Control of Methyl benzofuran-2-carboxylate).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.Quality Control of Methyl benzofuran-2-carboxylate

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

The design, synthesis, and biological evaluation of PIM kinase inhibitors was written by Tsuhako, Amy Lew;Brown, David S.;Koltun, Elena S.;Aay, Naing;Arcalas, Arlyn;Chan, Vicky;Du, Hongwang;Engst, Stefan;Franzini, Maurizio;Galan, Adam;Huang, Ping;Johnston, Stuart;Kane, Brian;Kim, Moon H.;Douglas Laird, A.;Lin, Rui;Mock, Lillian;Ngan, Iris;Pack, Michael;Stott, Gordon;Stout, Thomas J.;Yu, Peiwen;Zaharia, Cristiana;Zhang, Wentao;Zhou, Peiwen;Nuss, John M.;Kearney, Patrick C.;Xu, Wei. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Product Details of 54802-10-7 This article mentions the following:

A series of substituted benzofuropyrimidinones with pan-PIM activities and excellent selectivity against a panel of diverse kinases is described. Initial exploration identified aryl benzofuropyrimidinones that were potent, but had cell permeability limitations. Using X-ray crystal structures of the bound PIM-1 complexes with I, II, and III, the authors were able to guide the SAR and identify alkyl benzofuropyrimidinone IV with good PIM potencies, permeability, and oral exposure. In the experiment, the researchers used many compounds, for example, 3-Aminobenzofuran-2-carboxamide (cas: 54802-10-7Product Details of 54802-10-7).

3-Aminobenzofuran-2-carboxamide (cas: 54802-10-7) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. Benzofurans are stable towards alkali and readily polymerize on treatment with sulfuric acid, due to which they are useful for the preparation of low cost chemically relatively inert resins.Product Details of 54802-10-7

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Highly selective and sensitive ‘on-off’ fluorescent chemosensor for Fe³⁺ ions crafted by benzofuran moiety in both experimental and theoretical methods was written by Madhu, P.;Sivakumar, P.;Sribalan, Rajendran;Arumugam, Senthil M.. And the article was included in Luminescence in 2022.Category: benzofurans This article mentions the following:

A benzofuran glycinamide-based chemosensor, 3-(2-([4-fluorobenzyl]amino)acetamido)benzofuran-2-carboxamide (BGA) was developed and synthesized for the selective and sensitive detection of Fe³⁺ ions. The photophys. properties of the probe BGA were studied using UV-visible light absorption and fluorescence spectrophotometers. The chemosensor BGA showed a marked ‘on-off’ fluorescence response toward Fe³⁺ ions in the presence of other metal ions in DMSO/H₂O solution (9/1, volume/volume). The very low limits of detection (LOD) were calculated to be 10 nM and 43 nM using UV-visible light absorption and fluorescence spectrophotometers, resp. Job’s plot anal. revealed the formation of a BGA-Fe³⁺ complex with a 1:1 binding stoichiometry ratio using UV-visible light spectroscopy. The sensing mechanism was also demonstrated using d. functional theory calculation In the experiment, the researchers used many compounds, for example, 3-Aminobenzofuran-2-carboxamide (cas: 54802-10-7Category: benzofurans).

3-Aminobenzofuran-2-carboxamide (cas: 54802-10-7) belongs to benzofurans derivatives. Benzofuran is the “”parent”” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Category: benzofurans

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Potential Diagnostic Imaging of Alzheimer’s Disease with Copper-64 Complexes That Bind to Amyloid-β Plaques was written by McInnes, Lachlan E.;Noor, Asif;Kysenius, Kai;Cullinane, Carleen;Roselt, Peter;McLean, Catriona A.;Chiu, Francis C. K.;Powell, Andrew K.;Crouch, Peter J.;White, Jonathan M.;Donnelly, Paul S.. And the article was included in Inorganic Chemistry in 2019.Electric Literature of C9H9BO4 This article mentions the following:

Amyloid-β plaques, consisting of aggregated amyloid-β peptides, are one of the pathol. hallmarks of Alzheimer’s disease. Copper complexes formed using positron-emitting copper radionuclides that cross the blood-brain barrier and bind to specific mol. targets offer the possibility of noninvasive diagnostic imaging using positron emission tomog. New thiosemicarbazone-pyridylhydrazone based ligands that incorporate pyridyl-benzofuran functional groups designed to bind amyloid-β plaques have been synthesized. The ligands form stable complexes with copper(II) (K_d = 10^-18 M) and can be radiolabeled with copper-64 at room temperature Subtle changes to the periphery of the ligand backbone alter the metabolic stability of the complexes in mouse and human liver microsomes, and influenced the ability of the complexes to cross the blood-brain barrier in mice. A lead complex was selected based on possessing the best metabolic stability and brain uptake in mice. Synthesis of this lead complex with isotopically enriched copper-65 allowed us to show that the complex bound to amyloid-β plaques present in post-mortem human brain tissue using laser ablation-inductively coupled plasma-mass spectrometry. This work provides insight into strategies to target metal complexes to amyloid-β plaques, and how small modifications to ligands can dramatically alter the metabolic stability of metal complexes as well as their ability to cross the blood-brain barrier. In the experiment, the researchers used many compounds, for example, (5-Methoxybenzofuran-2-yl)boronic acid (cas: 551001-79-7Electric Literature of C9H9BO4).

(5-Methoxybenzofuran-2-yl)boronic acid (cas: 551001-79-7) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.Electric Literature of C9H9BO4

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Lithiation in flavones, chromones, coumarins, and benzofuran derivatives was written by Costa, Ana M. B. S. R. C. S.;Dean, Francis M.;Jones, Michael A.;Varma, Rajender S.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1985.Reference of 1646-27-1 This article mentions the following:

Flavones were lithiated in the 3-position by LiN(CHMe₂)₂ in THF at -78° to give stable derivatives which were readily converted to the corresponding carboxy, ethoxycarbonyl, mercapto, methylthio, trimethylsilyl, hydroxy, or other derivatives E.g., treatment of flavone with LiN(CHMe₂)₂ in THF at -78° gave 3-lithioflavone which reacted with CO₂ to give 92% 3-flavonecarboxylic acid. Benzofurans were preferentially lithiated at the 2-position; where this was blocked lithiation occurred in the 3-position in the presence of an activating group. Ring-opening of benzofurans occurred in some cases giving acetylenic phenols directly. Chromenes were lithiated at positions 2 and 3, depending on substitution. Coumarins generally behaved as esters and gave the corresponding amides with LiN(CHMe₂)₂, except for 4-methoxycoumarin which underwent lithiation in the 3-position. Deprotonation in the 32-position in ethers occurs easily only when there is an ether link antiperiplanar to the proton removed. The lithiated species are really unstable intermediates in trans eliminations leading to alkyne derivatives In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Reference of 1646-27-1).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.Reference of 1646-27-1

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem