Tag: 100-200

Name: N,N-Dimethylformamide Dimethyl AcetalIn 2020 ,《Novel bis(pyrazole-benzofuran) hybrids possessing piperazine linker: Synthesis of potent bacterial biofilm and MurB inhibitors》 appeared in Bioorganic Chemistry. The author of the article were Mekky, Ahmed E. M.; Sanad, Sherif M. H.. The article conveys some information:

Novel 1,4-bis[(2-(3-(dimethylamino)-1-oxoprop-2-en-1-yl)benzofuran-5-yl)methyl]piperazine I [X = Me2NCH:CHC(O)] was prepared and used as a key synthon for the this protocol. 1,3-Dipolar cycloaddition of this synthon with the appropriate hydrazonyl chlorides R1C(O)CCl:NNHR2 (R1 = Me, EtO; R2 = Ph, 4-ClC6H4, 4-MeC6H4, 4-MeOC6H4, 4-O2NC6H4) afforded a new series of bis-pyrazoles I (X = 1-R2-3-(R1CO)-pyrazol-4-ylcarbonyl). Furthermore, the latter reacted with hydrazine hydrate to afford bis(pyrazolo[3,4-d]pyridazine)s I (X = 7-methyl-2-R2-2H-pyrazolo[3,4-d]pyridazin-4-yl, 7-oxo-2-R2-6,7-dihydro-2H-pyrazolo[3,4-d]pyridazin-4-yl). Reaction of the synthon I [X = Me2NCH:CHC(O)] with hydrazine hydrate or phenylhydrazine afforded the corresponding bis(pyrazole)s I (X = 1H-pyrazol-3-yl, 1-phenyl-1H-pyrazol-5-yl), resp. The reaction of I (X = MeCO) with Ph hydrazine followed by treatment with DMF-DMA resulted in I (X = 1-phenyl-1H-pyrazol-4-yl). Various bacterial strains and cell lines were selected to study the in-vitro antibacterial and cytotoxic activities for the synthesized compounds The compound I [X = 1-(4-nitrophenyl)-3-acetyl-1H-pyrazol-4-ylcarbonyl; (II)] showed the best antibacterial efficacies with MIC/MBC values of 1.2/1.2, 1.2/2.4 and 1.2/2.4μM against each of E. coli, S. aureus and S. mutans strains, resp. In addition, the inhibitory activity of some compounds as MRSA and VRE inhibitors were studied. The compound II gave the best inhibitory activity with MIC/MBC values of 18.1/36.2, 9.0/18.1 and 18.1/18.1μM, resp., against MRSA (ATCC:33591 and ATCC:43300) and VRE (ATCC:51575) bacterial strains, resp. This compound also showed more effective biofilm inhibition activities than the reference Ciprofloxacin. The compound II showed IC50 values of 3.0 ±0.05, 3.2 ±0.08 and 3.3 ± 0.07μM against S. aureus, S. mutans and E. coli strains, resp. Furthermore, exptl. study showed excellent inhibitory activities of compounds I [X = 1-R2-3-(R1CO)-pyrazol-4-ylcarbonyl; R2 = 4-ClC6H4, 4-O2NC6H4] against MurB enzyme. The compound II gave the best MurB inhibitory activity with IC50 value of 3.1μM. The in-silico study was performed to predict the capability of compounds I [X = 1-R2-3-(R1CO)-pyrazol-4-ylcarbonyl; R2 = 4-ClC6H4, 4-O2NC6H4] as potential inhibitors of MurB enzyme. In the experiment, the researchers used N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5Name: N,N-Dimethylformamide Dimethyl Acetal)

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.Name: N,N-Dimethylformamide Dimethyl Acetal

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Application of 10365-98-7In 2020 ,《Novel formyl peptide receptors (FPRs) agonists with pyridinone and pyrimidindione scaffolds that are potentially useful for the treatment of rheumatoid arthritis》 appeared in Bioorganic Chemistry. The author of the article were Crocetti, Letizia; Vergelli, Claudia; Guerrini, Gabriella; Cantini, Niccolo; Kirpotina, Liliya N.; Schepetkin, Igor A.; Quinn, Mark T.; Parisio, Carmen; Di Cesare Mannelli, Lorenzo; Ghelardini, Carla; Giovannoni, Maria Paola. The article conveys some information:

The resolution of inflammation is an active response involving the interaction of pro-resolving mediators with specific receptors, such as N-formyl peptide receptor 2 (FPR2). FPRs represent potentially important therapeutic targets for the treatment of some pathologies, including asthma and rheumatoid arthritis. Previously, we identified selective or mixed FPR agonists with a pyridazin-3(2H)-one scaffold, all containing a 4-bromophenylacetamide fragment at N-2. The most effective compounds in this series were EC3, a potent mixed FPR1/FPR2/FPR3 agonist, and EC10, which had a preference for FPR1. We report here a new series of pyridinone and pyrimidindione derivatives containing the 4-(bromophenyl)acetamide substituent that was essential for activity in the pyridazinone series. All new compounds were evaluated for FPR agonist activity in HL60 cells transfected with FPR1 or FPR2 and in human neutrophils. While most of the pyridinone derivatives had reasonable FPR agonist activity in the submicromolar/micromolar range, the pyrimidindione derivatives were less active. Compound 2a (N-(4-bromophenyl)-2-[3-cyano-5-(3-methoxyphenyl)-6-methyl-2-oxopyridin-1(2H)-yl]acetamide) was the most active pyridinone derivative and had a 10-fold preference for FPR2 (EC50 = 120 nM) vs. FPR1 (EC50 = 1.6 μM). To assess their therapeutic activity, compounds 2a, EC3, and EC10 were evaluated in vivo using a rat model of rheumatoid arthritis. All three compounds increased the pain threshold and reduced pain hypersensitivity in the treated rats vs. control rats, although 2a and EC10 were much more effective than EC3. Thus, these FPR agonists represent potential leads to develop for the treatment of inflammatory diseases such as rheumatoid arthritis. In the experiment, the researchers used 3-Methoxyphenylboronic acid(cas: 10365-98-7Application of 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.Application of 10365-98-7

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In 2022,Wang, Tian-Ci; Wang, Pu-Sheng; Chen, Dian-Feng; Gong, Liu-Zhu published an article in Science China: Chemistry. The title of the article was 《Access to chiral homoallylic vicinal diols from carbonyl allylation of aldehydes with allyl ethers via palladium-catalyzed allylic C-H borylation》.Synthetic Route of C9H10O2 The author mentioned the following in the article:

An asym. carbonyl allylation of aldehydes with allyl ethers proceeding via allylic C-H borylation enabled by palladium and chiral phosphoric acid sequential catalysis, providing facile access to homoallylic vicinal anti-diols such as I [R1 = n-heptyl, 4-O2NC6H4, BnOCH2, etc.; R2 = H, Me, cyclohexyl, etc.; R3 = Bn, PMB, TBSO(CH2)3, etc.] in high yields and with excellent stereoselectivity was described. This protocol enabled total synthesis of aigialomycin D to be finished within 7 steps. The results came from multiple reactions, including the reaction of 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Synthetic Route of C9H10O2)

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).Synthetic Route of C9H10O2

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Wang, Cece; Zhou, Lu; Qiu, Jian; Yang, Kai; Song, Qiuling published an article in 2022. The article was titled 《Rh-Catalyzed diastereoselective addition of arylboronic acids to α-keto N-tert-butanesulfinyl aldimines: synthesis of α-amino ketones》, and you may find the article in Organic Chemistry Frontiers.Product Details of 10365-98-7 The information in the text is summarized as follows:

A diastereoselective addition of arylboronic acids to α-keto N-tert-butanesulfinyl aldimines catalyzed by a Rh(I) catalyst was reported. This reaction provided a practical method to obtain valuable chiral α-amino ketones with excellent diastereoselectivity, featuring operational simplicity, mild reaction conditions and a broad substrate scope. In the experiment, the researchers used many compounds, for example, 3-Methoxyphenylboronic acid(cas: 10365-98-7Product Details of 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.Product Details of 10365-98-7

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You, Guirong; Chang, Zhi-Xin; Yan, Jizhong; Xia, Chengcai; Li, Fu-Rong; Li, Hong-Shuang published their research in Organic Chemistry Frontiers in 2021. The article was titled 《Rhodium-catalyzed sequential intermolecular hydroacylation and deconjugative isomerization toward diversified diketones》.Name: 2-Hydroxy-4-methoxybenzaldehyde The article contains the following contents:

A rhodium-catalyzed tandem intermol. hydroacylation of terminal alkyne-substituted secondary alcs. RCH(OH)(CH2)nCCH (R = Ph, thiophen-3-yl, Pr, etc.; n = 0, 1, 2) (I) with chelating aldehydes 2-OH-R1C6H3CHO (R1 = 3-CF3, 4-Cl, 5-NO2, etc.) and deconjugative isomerization of the resulting α,β-unsaturated ketones for the preparation of synthetically valuable 1,4-diketones 2-OH-R1C6H3C(O)CH2CH2C(O)R (II) is developed. Of note, the completely atom-economical protocol can be extended to the alkynyl alcs. (I) with appropriate carbon chain length, from which 1,5-diketone/1,6-diketone 2-OH-C6H4C(O)(CH2)nC(O)C6H5 (n = 3, 4) were obtained involving the short-range deconjugative isomerization. Given its robustness, broad substrate scope, and excellent regioselectivity, this approach provides a promising platform for the synthesis of diverse diketones (II). The experimental part of the paper was very detailed, including the reaction process of 2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3Name: 2-Hydroxy-4-methoxybenzaldehyde)

2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3) is employed in the synthesis of Schiff base ligand. It is applied as a reactant in the synthesis of LPA1R antagonists used in the inhibition of LPA-induced proliferation and contraction of normal human lung fibroblasts. Also used in the synthesis of tyrosine kinase 6 proteinase inhibitors.Name: 2-Hydroxy-4-methoxybenzaldehyde

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Zhang, Chen; Ma, Na-Na; Yu, Zi-Lun; Shen, Chuanji; Zhou, Xiaocong; Chu, Xue-Qiang; Rao, Weidong; Shen, Zhi-Liang published their research in Organic Chemistry Frontiers in 2021. The article was titled 《Palladium-catalyzed direct reductive cross-coupling of aryltrimethylammonium salts with aryl bromides》.COA of Formula: C7H7BrO The article contains the following contents:

An efficient palladium-catalyzed direct reductive cross-coupling of aryltrimethylammonium salts with aryl bromides was developed. The reactions proceeded smoothly in the presence of a palladium catalyst, magnesium turnings, LiCl, and TMEDA in THF at room temperature, leading to the corresponding biaryl compounds in moderate to good yields with reasonable functional group tolerance. The one-pot reaction using cheap and readily available aryl bromide as a coupling partner were simple to handle, thereby avoiding the use of pre-prepared organometallic reagents. In the experiment, the researchers used many compounds, for example, 1-Bromo-3-methoxybenzene(cas: 2398-37-0COA of Formula: C7H7BrO)

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.COA of Formula: C7H7BrO

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Komkov, A. V.; Baranin, S. V.; Dmitrenok, A. S.; Kolotyrkina, N. G.; Zavarzin, I. V. published their research in Russian Chemical Bulletin in 2021. The article was titled 《A new route to the synthesis of 4-amino-substituted pyrido[2,3-d]pyrimidin-5-one derivatives》.Category: ethers-buliding-blocks The article contains the following contents:

The reaction of 6-(R-amino)-5-acetyl-4-methylsulfonyl-2-phenylpyrimidines with amines was studied. 6-Arylamino derivatives reacted with alkylamines to form 6-alkylamino-4-arylamino-5-acetyl-2-phenylpyrimidines, which upon refluxing in benzene with DMF dimethylacetal are converted to 4-alkylamino-8-aryl-2-phenylpyrido[2,3-d]pyrimidin-5(8H)-ones, e.g. I. The cyclization proceeded selectively with participation of the arylamino group only, the alkylamino group being not involved. At the same time, refluxing of 5-acetyl-4,6-dibenzylamino-2-phenylpyrimidine with DMF dimethylacetal in toluene affords the product of condensation on the acetyl group, which upon refluxing in o-xylene transforms to 4-benzylamino-8-benzyl-2-phenylpyrido[2,3-d]pyrimidin-5(8H)-one. In the experiment, the researchers used N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5Category: ethers-buliding-blocks)

N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Category: ethers-buliding-blocks

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《Simultaneous determination of nine perfluoroalkyl carboxylic acids by a series of amide acetals derivatization and gas chromatography tandem mass spectrometry》 was written by Ji, Yongyan; Cui, Zongyan; Li, Xuemin; Wang, Zhibin; Zhang, Jinjie; Li, Adan. Category: ethers-buliding-blocks And the article was included in Journal of Chromatography A in 2020. The article conveys some information:

A novel and simple derivatization method using a series of amide acetals as derivatization reagents, along with gas chromatog. tandem mass spectrometry (GC-MS/MS) anal., were developed and validated for simultaneous determination of 9 perfluoroalkyl carboxylic acids (PFCAs) in this study. The structures and fragmentation pathway of PFCAs derivatives were deduced and verified. The derivatization method developed in this study improved the sensitivity of the detection of PFCAs by GC. The applicability of 6 amide acetals for the derivatization of PFCAs was demonstrated. Derivatization conditions for 9 PFCAs were optimized with addition of 20μL of derivatization reagent and reaction at 35°C for 30 min. 9 PFCAs derivatives were confirmed to be stable over 15 days. The instrument detection limits (IDLs) were lower than 0.01 pg/μL. The intra and inter-day precisions were below 4.06% and 5.48%, resp. To demonstrate the utility of the derivatization method, the level of PFCAs in the marine products were detected. The alk. digestion followed by solid-phase extraction (SPE) cleanup method was used for pretreatment. The method detection limits (MDLs) ranged from 0.04 to 0.10 ng/g, and the spiked recoveries ranged between 54.72% and 107.29%, with relative standard deviation (RSD) of 1.53%-11.89%. Five PFCAs were detected in the range of 0.66 to 499.03 ng/g dry weight The experimental process involved the reaction of N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5Category: ethers-buliding-blocks)

N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Category: ethers-buliding-blocks

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Ether – Wikipedia,
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《Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source》 was published in Journal of Organic Chemistry in 2020. These research results belong to Lim, Taeho; Ryoo, Jeong Yup; Han, Min Su. COA of Formula: C7H7BrO The article mentions the following:

The authors developed a simple and atom-economic transition-metal-free borylation reaction of aryl bromides. An atom-economic and com. available diboron source, bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps, and the functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway. This simple borylation reaction will be useful for the synthesis of valuable arylboronic acids. The experimental process involved the reaction of 1-Bromo-3-methoxybenzene(cas: 2398-37-0COA of Formula: C7H7BrO)

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.COA of Formula: C7H7BrO

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《Visible light-induced green synthesis of 2-amino-4H-chromenes》 was published in Environmental Chemistry Letters in 2020. These research results belong to Chen, Lu; Lin, Chuyuan; Lan, Yongyin; Li, Zhenzhen; Huang, Dandan; Yang, Wei; Li, Yibiao. Name: 2-Methoxybenzaldehyde The article mentions the following:

An efficient and green synthesis of 2-amino-4H-chromenes I [R = 4-MeC6H4, 4-ClC6H4, 3-MeOC6H4, etc.], II [R1 = 3-HOC6H4, 4-HOC6H4, 3-O2NC6H4, 4-O2NC6H4, 4-NCC6H4, 3-MeO-4-HOC6H3] and III [R2 = Ph, 4-FC6H4, 4-BrC6H4, etc.] via a photochem. transformation via a multicomponent reaction of malononitrile, benzaldehydes and naphthols/hydroxycoumarins/hydroxy-methyl-pyrones using 9-mesityl-10 methylacridinium perchlorate (Acr+-Mes ClO4-) as a photocatalyst was reported. This procedure possessed several advantages over other reported methods in that it employs a green and sustainable solvent, gave the desired products in excellent yields and avoids the inconvenient preparation of catalyst. The results came from multiple reactions, including the reaction of 2-Methoxybenzaldehyde(cas: 135-02-4Name: 2-Methoxybenzaldehyde)

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.Name: 2-Methoxybenzaldehyde

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