Month: February 2023

Synthesis and Biological Evaluation of Novel 2,4-Diaminoquinazoline Derivatives as SMN2 Promoter Activators for the Potential Treatment of Spinal Muscular Atrophy was written by Thurmond, John;Butchbach, Matthew E. R.;Palomo, Marty;Pease, Brian;Rao, Munagala;Bedell, Louis;Keyvan, Monica;Pai, Grace;Mishra, Rama;Haraldsson, Magnus;Andresson, Thorkell;Bragason, Gisli;Thosteinsdottir, Margret;Bjornsson, Jon Mar;Coovert, Daniel D.;Burghes, Arthur H. M.;Gurney, Mark E.;Singh, Jasbir. And the article was included in Journal of Medicinal Chemistry in 2008.SDS of cas: 120121-01-9 This article mentions the following:

Proximal spinal muscular atrophy (SMA) is an autosomal recessive disorder characterized by death of motor neurons in the spinal cord that is caused by deletion and/or mutation of the survival motor neuron gene (SMN1). Adjacent to SMN1 are a variable number of copies of the SMN2 gene. The two genes essentially differ by a single nucleotide, which causes the majority of the RNA transcripts from SMN2 to lack exon 7. Although both SMN1 and SMN2 encode the same Smn protein amino acid sequence, the loss of SMN1 and incorrect splicing of SMN2 have the consequence that Smn protein levels are insufficient for the survival of motor neurons. The therapeutic goal of our medicinal chem. effort was to identify small-mol. activators of the SMN2 promoter that, by up-regulating gene transcription, would produce greater quantities of full-length Smn protein. Our initial medicinal chem. effort explored a series of C5 substituted benzyl ether based 2,4-diaminoquinazolines that were found to be potent activators of the SMN2 promoter; however, inhibition of DHFR was shown to be an off-target activity that was linked to ATP depletion. A structure-guided approach was used to overcome DHFR inhibition while retaining SMN2 promoter activation. A lead compound, the [(fluorobenzyl)piperidinylmethoxy]quinazolinediamine I, was identified as having high potency and 2.3-fold induction of the SMN2 promoter. I possessed desirable pharmaceutical properties, including excellent brain exposure and long brain half-life following oral dosing to mice. I up-regulated expression of the mouse SMN gene in NSC-34 cells, a mouse motor neuron hybrid cell line. In type 1 SMA patient fibroblasts, I induced Smn in a dose-dependent manner when analyzed by immunoblotting and increased the number of intranuclear particles called gems. The compound restored gems numbers in type I SMA patient fibroblasts to levels near unaffected genetic carriers of SMA. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9SDS of cas: 120121-01-9).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) 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.SDS of cas: 120121-01-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

General Method for the Amination of Aryl Halides with Primary and Secondary Alkyl Amines via Nickel Photocatalysis was written by Song, Geyang;Nong, Ding-Zhan;Li, Jing-Sheng;Li, Gang;Zhang, Wei;Cao, Rui;Wang, Chao;Xiao, Jianliang;Xue, Dong. And the article was included in Journal of Organic Chemistry in 2022.Category: alcohols-buliding-blocks This article mentions the following:

It was reported that Ni(II)-bipyridine complex catalyzed efficient C-N coupling of aryl chlorides and bromides with various primary and secondary alkyl amines under direct excitation with light. Intramol. C-N coupling was also demonstrated. The feasibility and applicability of the protocol in organic synthesis was attested by more than 200 examples. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Category: alcohols-buliding-blocks).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) 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. 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.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Nano-silica melamine trisulfonic acid as an efficient and reusable heterogeneous catalyst in esterification reactions was written by Javaherian, Mohammad;Latifi, Saeideh;Heidarizadeh, Fariba. And the article was included in Journal of the Iranian Chemical Society in 2022.Product Details of 873-76-7 This article mentions the following:

The use of nano-silica melamine trisulfonic acid as a reusable heterogeneous solid acid catalyst in the esterification reaction of carboxylic acids and alcs. is reported. The reaction conditions were optimized by testing temperature, each component of catalyst, feedstock ratios as well as load of catalyst. The synthesized catalyst was characterized by X-ray diffraction, SEM, Fourier transform IR spectroscopy, and thermogravimetric anal. techniques. The results showed that nano-silica melamine trisulfonic acid was an efficient dehydrating agent in the condensing reactions between different kinds of aliphatic and aromatic carboxylic acids and alcs. The method was simple, rapid, straightforward, catalyst reusability, and holds potential for further application in acid-catalyzed organic synthesis and industrial requirements. In the experiment, the researchers used many compounds, for example, (4-Chlorophenyl)methanol (cas: 873-76-7Product Details of 873-76-7).

(4-Chlorophenyl)methanol (cas: 873-76-7) 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.Product Details of 873-76-7

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Nickel-Catalyzed Thermal Redox Functionalization of C(sp³)-H Bonds with Carbon Electrophiles was written by Gong, Yuxin;Su, Lei;Zhu, Zhaodong;Ye, Yang;Gong, Hegui. And the article was included in Angewandte Chemie, International Edition in 2022.Category: alcohols-buliding-blocks This article mentions the following:

A Ni-catalyzed arylation and alkylation of C(sp₃)-H bonds with organohalides to forge C(sp₃)-C bonds by merging economical Zn and tBuOOtBu (DTBP) as the external reductant and oxidant was reported. The mild and easy-to-operate protocol enabled facile carbofunctionalization of N-/O-α- and cyclohexane C-H bonds, and preparation of a few intermediates of bioactive compounds and drug derivatives Preliminary mechanistic studies implied addition of an alkyl radical to a NiII salt. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Category: alcohols-buliding-blocks).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) 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. 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.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Passion fruit seed extract enriched in piceatannol obtained by microwave-assisted extraction was written by Silva, Gislaine C.;Rodrigues, Rodney A. F.;Bottoli, Carla B. G.. And the article was included in Sustainable Chemistry and Pharmacy in 2021.Electric Literature of C14H12O4 This article mentions the following:

Apart from being food, passion fruit (Passiflora edulis Sims) offers seeds to be used as an oil source, and the residual seed cake from oil extraction contains piceatannol, a mol. that can prevent skin damages. In this work, microwave-assisted extraction (MAE) was evaluated as a technique for the preparation of piceatannol-rich seed cake extracts, and its performance was compared to the conventional Soxhlet extraction MAE and Soxhlet exhibited different selectivities for the seed cake compounds A sequential MAE at 87°C, with 70% EtOH, for 30 min each cycle, provided a fine brown powder with 27.17 ± 0.9μg of piceatannol per mg of the extract, while Soxhlet extraction for 120 min resulted in a dark lumpy extract containing 13.03 ± 0.4μg mg-1. Thus, MAE was shown to be a promising alternative to produce a passion fruit seed extract for cosmetic purposes, adding value to a residue from the passion fruit chain by providing a faster extraction and a more color friendly and easier-to-handle product with higher levels of piceatannol in comparison to the conventional method. In the experiment, the researchers used many compounds, for example, (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6Electric Literature of C14H12O4).

(E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. 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.Electric Literature of C14H12O4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Diverse synthetic approaches towards C1′-branched acyclic nucleoside phosphonates was written by Kalcic, Filip;Dracinsky, Martin;Janeba, Zlatko. And the article was included in Organic & Biomolecular Chemistry in 2021.Reference of 5856-63-3 This article mentions the following:

Herein we describe and compare five convenient approaches leading to key synthetic 6-chloropurine acyclic nucleoside phosphonates (ANPs), e.g. I, bearing the 9-phosphonomethoxyethyl (PME) moiety branched at the C₁‘ position. These intermediates can be further vastly diversified into target C1′-branched ANPs bearing either natural or unnatural nucleobases. The importance of C1′-branched ANPs is emphasized by their analogy with C1’-substituted cyclic nucleotides (such as remdesivir, a broad-spectrum antiviral agent) and evaluation of their biol. activity (e.g. antiviral, antineoplastic, and antiprotozoal) will be a tempting subject of further research. In the experiment, the researchers used many compounds, for example, (R)-2-Aminobutan-1-ol (cas: 5856-63-3Reference of 5856-63-3).

(R)-2-Aminobutan-1-ol (cas: 5856-63-3) 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.Reference of 5856-63-3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes was written by Zhong, Mingbing;Gagne, Yohann;Hope, Taylor O.;Pannecoucke, Xavier;Frenette, Mathieu;Jubault, Philippe;Poisson, Thomas. And the article was included in Angewandte Chemie, International Edition in 2021.COA of Formula: C16H20B2N2O2 This article mentions the following:

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B₂Pin₂ permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and alkynes. The hydroborated products were isolated in high yields, with excellent diastereoselectivities and a high functional group tolerance under mild conditions. The hydroboration reactions were developed under continuous flow conditions to demonstrate their synthetic utility. The reaction mechanism was studied and suggested an oxidation reaction between an in situ formed borate and the Cu-photocatalyst in its excited state for the boryl radical 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: 1214264-88-6COA 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. 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.COA of Formula: C16H20B2N2O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Acrylate and methacrylate contact allergy and allergic contact disease: a 13-year review was written by Spencer, Ashley;Gazzani, Paul;Thompson, Donna A.. And the article was included in Contact Dermatitis in 2016.Application of 4074-88-8 This article mentions the following:

Summary : Background : (Meth)acrylates are important causes of contact allergy and allergic contact disease, such as dermatitis and stomatitis, with new and emerging sources resulting in changing clin. presentations. Objectives : To identify the (meth)acrylates that most commonly cause allergic contact disease, highlight their usefulness for screening, and examine their relationship with occupational and clin. data. Methods : A retrospective review of results from patch tests performed between July 2002 and Sept. 2015, in one tertiary Cutaneous Allergy Unit, was performed Results : A series of 28 (meth)acrylates was applied to 475 patients. Results were pos. in 52 cases, with occupational sources being identified in 24. Industrial exposures and acrylic nails were responsible for 13 and 10 cases, resp., with wound dressings being implicated in 7. We found that four individual (meth)acrylates (2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, bisphenol A glycerolate dimethacrylate, and Et acrylate), if used as a screening tool, could have identified 47 (90.4%) of our pos. cases. Conclusions : Our 13-yr experience indicates a changing landscape of (meth)acrylate contact allergy and allergic contact disease, with an observed shift in exposures away from manufacturing and towards acrylic nail sources. Wound dressings are highlighted as emerging sources of sensitization. Larger studies are required to establish the sensitivity and specificity of the four (meth)acrylates proposed for potential screening. In the experiment, the researchers used many compounds, for example, Diethyleneglycoldiacrylate (cas: 4074-88-8Application of 4074-88-8).

Diethyleneglycoldiacrylate (cas: 4074-88-8) 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. 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 of 4074-88-8

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Gum ghatti (Indian gum). III. Neutral oligosaccharides formed on partial acid hydrolysis of the gum was written by Aspinall, G. O.;Auret, Barbara J.;Hirst, E. L.. And the article was included in Journal of the Chemical Society in 1958.Related Products of 10030-85-0 This article mentions the following:

Gum ghatti (100 g.) in 1.95 l. H₂O was heated to 100°, 50 ml. 4N H₂SO₄ added, and the solution boiled 1.5 hrs. The cooled solution was neutralized with Ba(OH)₂ and BaCO₃, filtered, concentrated to 400 ml., and poured into 2 l. EtOH. The precipitated degraded polysaccharide A (I) (50 g.) was separated and the liquor concentrated to 200 ml., passed through Amberlite IR-120 (H) and IR-4B (OH), and conced. to 35 g. sirup B (II). I was hydrolyzed again to give a further 15 g. II. II (50 g.) in 200 ml. H₂O was chromatographed on 800 g. 1:1 C-Celite. Elution with H₂O gave 36 g. monosaccharides [arabinose (III), galactose (IV), xylose, and rhamnose (trace)] and a small fraction (0.8 g.) which gave L-rhamnose hydrate, m. 90-1° [α]_D -2°. Oligosaccharides were eluted with EtOHH₂O. Chromatography of fraction 1 (0.23 g.) showed 6-(O-β-galactopyranosyl)galactose (V), 3-(O-β-arabopyranosyl)arabinose (VI) and a pentose-containing disaccharide. Hydrolysis of the mixture gave III and IV. Fraction 2 (1.1 g.) was chromatographed on cellulose with 10:4:3 EtOAc-C₅H₅N-H₂O to give 0.15 g. of mixture III, IV and arabinose-containing disaccharides and 0.56 g. sirup B, [α]_D 31°. Methylation of 200 mg. II followed by hydrolysis and chromatography on cellulose with 7:3 pert. ether-BuOH gave 40 mg. 2,3,4,6-tetra-O-methyl-D-galactose (VII) (aniline derivative, m. 198°), 35 mg. mixture of VII and 2,3,4-tri-O-methylgalactose (VIII), and 39 mg. VIII (aniline derivative, m. 159-60°). Fraction 3 (205 mg.) chromatographed on cellulose gave 65 mg. mixture III, IV and three III-containing disaccharides, 10 mg. VI, 30 mg. disaccharide, [α]_D 125°, which hydrolyzed to IV and glucose, and 50 mg. V. Fraction 4 gave 155 mg. sugar (IX), m. 202-3° [α]_D 80°. Methylation of 100 mg. IX followed by hydrolysis and chromatography on cellulose gave 28 mg. VII with a trace of 2,5-di-O-methylarabinose (X), 5 mg. X, 10 mg. tri-O-methylgalactose, 2,4-di-O-methylarabinose (XI), and 20 mg. XI, [α]_D 120°. Fraction 5 (80 mg.) separated on cellulose gave 25 mg. mixture of III-containing disaccharides, 5 mg. 3-(O-β-galactopyranosyl)arabinose (XII), 25 mg. 3-(O-β-D-galactopyranosyl)-D-galactose, m. 151-2°, [α]_D 69°, and 3 mg. V. Chromatography of 0.58 g. fraction 6 (0.83 g.) on cellulose gave 0.45 g. trisaccharide (XIII), [α]_D 20°, and traces of V and monosaccharides. Partial and complete hydrolysis of XIII gave V and IV, resp. Methylation of 200 mg. XIII followed by hydrolysis gave 36 mg. VII and 80 mg. VIII. Fraction 7 gave 265 mg. trisaccharide (XIV), m. 191°, [α]_D 39°. Partial hydrolysis of XIV gave III, IV, XII, and V. Methylation of 200 mg. XIV followed by hydrolysis gave 47 mg. VII, 5 mg. X (2,5-di-O-methyl-L-arabonamide, m. 122°), 40 mg. VIII, and 32 mg. XI. Fraction 8 contained 0.47 g. sugar, [α]_D 14°, which on partial hydrolysis gave V. Fraction 9 gave 100 mg. tetrasaccharide, m. 171°, [α]_D 26°, which on partial hydrolysis gave III, IV, XII, and V. Fraction 10 gave a sugar, m. 177-9° (decomposition), [α]_D 19°, which on partial hydrolysis gave III, IV, XII, and V. Thus, the first 3 members of the series O-(β-D-galactopyranosyl)-[(1 → 6)-O-(β-D-galactopyranosyl)]_n-(1 → 6)-D-galactose (n = 0, 1, 2) and the first 4 members of the series O-(β-D-galactopyranosyl)-[(1 → 6)-O-(β-D-galactopyranosyl)]_n-(1 → 3)-L-arabinose (n = 0, 1, 2, 3) have been characterized. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal hydrate (cas: 10030-85-0Related Products of 10030-85-0).

(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal hydrate (cas: 10030-85-0) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. 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 10030-85-0

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Boracene-based alkylborate enabled Ni/Ir hybrid catalysis was written by Sato, Yukiya;Miyamoto, Yusuke;Sumida, Yuto;Hosoya, Takamitsu;Ohmiya, Hirohisa. And the article was included in Organic & Biomolecular Chemistry in 2020.COA of Formula: C12H16BBrO2 This article mentions the following:

Boracene-based alkylborate enabled visible light-mediated metallaphotoredox catalysis. The directly excited borate was easily oxidatively quenched by an excited Ir photoredox catalyst. Ni/Ir hybrid catalysis afforded the products under significantly low irradiance. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4COA of Formula: C12H16BBrO2).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) 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. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.COA of Formula: C12H16BBrO2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts