Tag: 100-200

《Serendipitous discovery of aryl boronic acids as β-lactamase inhibitors》 was published in Bioorganic & Medicinal Chemistry Letters in 2020. These research results belong to Yang, Shu-Wei; Pan, Jianping; Root, Yuriko; Scapin, Giovanna; Xiao, Li; Su, Jing. Quality Control of 3-Methoxyphenylboronic acid The article mentions the following:

High throughput screening for β-lactamase inhibitors afforded biphenyl hits such as 1. Hit confirmation and X-ray soaking experiments with Pseudomonas Aeruginosa AmpC enzyme led to the identification of an aryl boronic acid-serine complex 4, which was formed from Ph boronic acid 8 (an impurity in compound 1) and ethylene glycol (the cryoprotectant in the soaking experiment). In the experiment, the researchers used many compounds, for example, 3-Methoxyphenylboronic acid(cas: 10365-98-7Quality Control of 3-Methoxyphenylboronic acid)

3-Methoxyphenylboronic acid(cas: 10365-98-7) belongs to boronic acids. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis.Quality Control of 3-Methoxyphenylboronic acid

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The author of 《2,7-naphthyridinone-based MET kinase inhibitors: A promising novel scaffold for antitumor drug development》 were Zhuo, Lin-Sheng; Xu, Hong-Chuang; Wang, Ming-Shu; Zhao, Xing-E.; Ming, Zhi-Hui; Zhu, Xiao-Lei; Huang, Wei; Yang, Guang-Fu. And the article was published in European Journal of Medicinal Chemistry in 2019. Application of 4637-24-5 The author mentioned the following in the article:

As part of our effort to develop new mol. targeted antitumor drug, a novel 2,7-naphthyridone-based MET kinase inhibitor, I, was identified. Knowledge of the binding mode of BMS-777607 in MET led to the design of new inhibitors that utilize novel 2,7-naphthyridone scaffold to conformationally restrain the key pharmacophoric groups (block C). Detailed SAR studies resulted in the discovery of a new MET inhibitor I, displaying favorable in vitro potency and oral bioavailability. More importantly, I exhibited excellent in vivo efficacy (tumor growth inhibition/TGI of 114% and 95% in 50 mg/kg, resp.) both in the U-87 MG and HT-29 xenograft models. The favorable drug-likeness of I indicated that 2,7-naphthyridinone may be used a promising novel scaffold for antitumor drug development. The preclin. studies of I are under way. The experimental process involved the reaction of N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5Application of 4637-24-5)

N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Application of 4637-24-5

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Ether – Wikipedia,
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The author of 《Radiosynthesis of a carbon-11-labeled AMPAR allosteric modulator as a new PET radioligand candidate for imaging of Alzheimer’s disease》 were Miao, Caihong; Dong, Fugui; Jia, Limeng; Li, Wei; Wang, Min; Zheng, Qi-Huang; Xu, Zhidong. And the article was published in Bioorganic & Medicinal Chemistry Letters in 2019. SDS of cas: 10365-98-7 The author mentioned the following in the article:

Methoxyphenoxybenzothiadiazinedione I (R = 11CH3) was prepared as an allosteric PET ligand for the α-amino-3-hydroxy-5-methyl-4-isoxazolepropanoic acid receptor (AMPAR) for potential use as an imaging agent for Alzheimer’s disease. I (R = Me) and I (R = H) were prepared in eight and nine steps and 3% and 1% yields, resp. Methylation of I (R = H) with 11CH3OTf yielded I as the minor product in 10-15% radiochem. yield (based on [11C]CO2), with N4-methylation as the major reaction. The radiochem. purity was >99%, and the molar activity at end of bombardment (EOB) was 370-740 GBq/μmol with a total synthesis time of 35-40 min from EOB. The lipophilicity of I (R = 11CH3) and its N4-methylated isomer were determined and compared to the calculated lipophilicities for I (R = 11CH3) and its N4- and N2-methylated isomers. In the experiment, the researchers used 3-Methoxyphenylboronic acid(cas: 10365-98-7SDS of cas: 10365-98-7)

3-Methoxyphenylboronic acid(cas: 10365-98-7) belongs to boronic acids. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis.SDS of cas: 10365-98-7

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Ether – Wikipedia,
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The author of 《SO3H-functionalized nano-MGO-D-NH2: Synthesis, characterization and application for one-pot synthesis of pyrano[2,3-d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives in aqueous media》 were Alinezhad, Heshmatollah; Tarahomi, Mehrasa; Maleki, Behrooz; Amiri, Amirhassan. And the article was published in Applied Organometallic Chemistry in 2019. HPLC of Formula: 135-02-4 The author mentioned the following in the article:

An SO3H-functionalized nano-MGO-D-NH2 catalyst has been prepared by multi-functionalization of a magnetic graphene oxide (GO) nanohybrid and evaluated in the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives The GO/Fe3O4 (MGO) hybrid was prepared via an improved Hummers method followed by the covalent attachment of 1,4-butanesultone with the amino group of the as-prepared polyamidoamine-functionalized MGO (MGO-D-NH2) to give double-functionalized magnetic nanoparticles as the catalyst. The prepared nanoparticles were characterized to confirm their synthesis and to precisely determine their physicochem. properties. In summary, the prepared catalyst showed marked recyclability and catalytic performance in terms of reaction time and yield of products. The results of this study are hoped to aid the development of a new class of heterogeneous catalysts to show high performance and as excellent candidates for industrial applications. The experimental process involved the reaction of 2-Methoxybenzaldehyde(cas: 135-02-4HPLC of Formula: 135-02-4)

2-Methoxybenzaldehyde(cas: 135-02-4) is used as a flavor agent in foods including nonalcoholic/alcoholic beverages, baked goods, chewing gum, confections, frozen dairy, fruit ices, hard/soft candy, instant coffee, tea, Jams, jellies, and milk products. It also has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.HPLC of Formula: 135-02-4

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Ether – Wikipedia,
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The author of 《Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII-Catalyzed Three-Component C-H Bond Addition to Internally Substituted Dienes and Carbonyls》 were Sun, Dongbang; Shen, Zican; Ellman, Jonathan A.. And the article was published in Angewandte Chemie, International Edition in 2019. Safety of 2-(Benzyloxy)acetaldehyde The author mentioned the following in the article:

An efficient CoIII-catalyzed three-component strategy to prepare homoallylic alcs. containing acyclic quaternary centers is disclosed. This transformation enables the introduction of two C-C σ bonds through C-H bond activation and sequential addition to internally substituted dienes and a wide range of aldehydes and activated ketones. Isoprene and other internally monosubstituted dienes are effective inputs, with the reaction proceeding with high diastereoselectivity for those substrate combinations that result in more than one stereogenic center. Moreover, the opposite relative stereochem. can be achieved by employing 1,2-disubstituted dienes. A mechanism for the transformation is proposed based upon the relative stereochem. of the products and studies with isotopically labeled starting materials. The results came from multiple reactions, including the reaction of 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Safety of 2-(Benzyloxy)acetaldehyde)

2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).Safety of 2-(Benzyloxy)acetaldehyde

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In 2019,Angewandte Chemie, International Edition included an article by Anthony, David; Lin, Qiao; Baudet, Judith; Diao, Tianning. Category: ethers-buliding-blocks. The article was titled 《Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes》. The information in the text is summarized as follows:

A nickel-catalyzed asym. diarylation reaction of vinylarenes enabled the preparation of chiral α,α,β-triarylated ethane scaffolds, which existed in a number of biol. active mols. The use of reducing conditions with aryl bromides as coupling partners obviated the need for stoichiometric organometallic reagents and tolerated a broad range of functional groups. The application of an N-oxyl radical as a ligand to a nickel catalyst represented a novel approach to facilitate nickel-catalyzed cross-coupling reactions.1-Bromo-3-methoxybenzene(cas: 2398-37-0Category: ethers-buliding-blocks) was used in this study.

1-Bromo-3-methoxybenzene(cas: 2398-37-0) is a compound useful in organic synthesis and other chemical processes. It is an intermediate used for pharmaceuticals, perfumes and agrochemicals.Category: ethers-buliding-blocks

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Ether – Wikipedia,
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《Adventitious root cultures of Decalepis salicifolia for the production of 2-hydroxy-4-methoxybenzaldehyde, a vanillin isomer flavor metabolite》 was written by Rodrigues, Vereena; Kumar, Amit; Prabhu, Kamasamudra N.; Pragadheesh, V. S.; Shukla, Ashutosh K.; Sundaresan, Velusamy. Computed Properties of C8H8O3This research focused onvanillin 2H4MB flavor production adventitious root culture Decalepis; 2-Hydroxy-4-methoxybenzaldehyde; Critically endangered; Endemic; Utleria salicifolia; Vanillin. The article conveys some information:

Decalepis salicifolia (Bedd. ex. Hook.f.) Venter is a potential natural source of the vanillin isomer, 2-hydroxy-4-methoxybenzaldehyde (2H4MB), an aromatic compound However, the utilization of the plant is hindered especially due to its critically endangered status and the root-specific accumulation of the compound The use of in vitro culture techniques offers a sustainable means for the production of valuable metabolites. In this study, an efficient system was established for the production of 2H4MB in the adventitious root cultures of D. salicifolia. Leaf explants of in vitro grown plants produced on an average 4.33 ± 2.07 number of roots with root initiation frequency of 95.69 ± 3.74% in woody plant medium supplemented with 0.5 mg/L α-naphthalene acetic acid (NAA) and 1.0 mg/L kinetin (Kn). The adventitious root biomass accumulation of 10.61 ± 0.89 g fresh weight (FW) was obtained in woody plant liquid media containing 0.5 mg/L NAA and 0.3 mg/L indole-3-butyric acid (IBA) in 60 days of inoculation. Field-grown plants of the same age produced 0.30 ± 0.02 g FW, which was 35-fold lower than the adventitious root culture. The total production of 2H4MB in the same growth period was 4.9-fold higher in adventitious root culture (139.54μg) as compared to field-grown plants (28.62μg). Furthermore, sucrose concentration of 2% was favorable for biomass accumulation, whereas 5% was favorable for 2H4MB production On the other hand, media pH 5.0 was suitable for biomass production and pH 7.0 was best suited for accumulation of 2H4MB. The adventitious roots also showed stable production of biomass and 2H4MB over 2 years. The established adventitious root culture system is suitable for further large-scale production of 2H4MB for flavor and fragrance industrial applications. Key points: • Biomass accumulation was higher in adventitious root cultures than in field-grown plants. • Manipulation of sucrose concentration and media pH led to increased 2H4MB production • Adventitious roots showed stable biomass and 2H4MB production over 2 years. In the experimental materials used by the author, we found 2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3Computed Properties of C8H8O3)

2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3) is the main component of root bark essential oil of Periploca sepium Bunge. It is a potential tyrosinase inhibitor present in African medicinal plants. 2-Hydroxy-4-methoxybenzaldehyde was used in the synthesis of Schiff base ligand.Computed Properties of C8H8O3

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Ether – Wikipedia,
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Related Products of 60656-87-3In 2021 ,《Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation》 appeared in Angewandte Chemie, International Edition. The author of the article were Shi, Chang-Yun; Eun, Jungmin; Newhouse, Timothy R.; Yin, Liang. The article conveys some information:

Catalytic asym. remote conjugate borylation is challenging as the control of regioselectivity is not trivial, the electrophilicity of remote sites is extenuated, and the remote asym. induction away from the carbonyl group is difficult. Herein, catalytic asym. conjugate 1,6-, 1,8- and 1,10-borylation was developed with excellent regioselectivity, which delivered α-chiral boronates in moderate to high yields with high enantioselectivity. The produced chiral boronate smoothly underwent oxidation, cross-coupling, and one-carbon homologation to give synthetically versatile chiral compounds in moderate yields with excellent stereoretention. Furthermore, a stereomechanistic anal. was conducted using DFT calculations, which provides insights into the origins of the regioselectivity. Finally, the present 1,6-borylation was successfully applied in an efficient one-pot asym. synthesis of (-)-7,8-dihydrokavain. In the experiment, the researchers used 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Related Products of 60656-87-3)

2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).Related Products of 60656-87-3

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In 2022,Mohammed, Ehtesham U. R.; Porter, Zoe J.; Jennings, Ian G.; Al-Rawi, Jasim M. A.; Thompson, Philip E.; Angove, Michael J. published an article in Bioorganic & Medicinal Chemistry. The title of the article was 《Synthesis and biological evaluation of 4H-benzo[e][1,3]oxazin-4-ones analogues of TGX-221 as inhibitors of PI3Kβ》.Quality Control of m-Methoxyphenol The author mentioned the following in the article:

A novel series of TGX-221 analogs was prepared that include isosteric replacement of the 4H-pyrido[1,2-a]pyrimidin-4-one with a 4H-benzo[e][1,3]oxazin-4-one I (R = Ph, 3,5-F2C6H3, 3-ClC6H4, etc.; X = O, NH) scaffold. The compounds that included an -CH(CH3)NH- type linker showed comparable activity to TGX-221 analogs with the isosterism supported by the comparative SAR anal. The analogs containing an -CH(CH3)O- linker were less active but still showed useful SAR including a favored o-Me substitution. The experimental part of the paper was very detailed, including the reaction process of m-Methoxyphenol(cas: 150-19-6Quality Control of m-Methoxyphenol)

m-Methoxyphenol(cas: 150-19-6) may be used in synthesis of:C(4) symmetric calix[4]resorcinarene, 2-nitroso-5-methoxyphenol, 6-methoxy-2(3H)-benzoxazoloneQuality Control of m-Methoxyphenol

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《Structural investigation of perfluorocarboxylic acid derivatives formed in the reaction with N,N-dimethylformamide dialkylacetals》 was written by Strozynska, Monika; Gross, Juergen H.; Schuhen, Katrin. Safety of N,N-Dimethylformamide Dimethyl Acetal And the article was included in European Journal of Mass Spectrometry in 2020. The article conveys some information:

A structural investigation of perfluorocarboxylic acid derivatives formed in the reaction with N,N-dimethylformamide dialkylacetals employing several techniques of mass spectrometry (MS) is described. Two derivatizing reagents, DMF di-Me acetal (DMF-DMA) and DMF diethylacetal (DMF-DEA) were used. In contrast to carboxylic acids, perfluorocarboxylic acids are not able to form alkyl esters as the main product in this reaction. We found that perfluorooctanoic acid (PFOA) forms a salt with N,N-dimethylformamide dialkylacetals. This salt undergoes a further reaction inside the injection block of a gas chromatograph (GC) by loss of CO2 and then forms 1,1-perfluorooctane-(N,N,N,N-tetramethyl)-diamine. The GC-MS experiments using both electron ionization (EI) and pos.-ion chem. ionization (PCI) revealed that the same reaction products are formed with either derivatizing reagent. Subjecting the perfluorocarboxylic acid derivative to electrospray ionization (ESI) and direct anal. in real time (DART), both pos.- and neg.-ion modes indicated that cluster ions are formed. In the pos.-ion mode, this cluster ion consists of two iminium cations and one PFOA anion, while in the neg.-ion mode, it comprises two PFOA anions and one cation. The salt structure was further confirmed by liquid injection field desorption/ionization (LIFDI) as well as IR spectroscopy. We propose a simple mechanism of N,N,N’,N’-tetramethylformamidinium cation formation. The structure elucidation is supported by specific fragment ions as obtained by GC-EI-MS and GC-PCI-MS anal.N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5Safety of N,N-Dimethylformamide Dimethyl Acetal) was used in this study.

N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Safety of N,N-Dimethylformamide Dimethyl Acetal

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem