Category: 528594-30-1

Fan, Tian-Yun published the artcileStructure-activity relationship and biological evaluation of berberine derivatives as PCSK9 down-regulating agents, Recommanded Product: 2-Methoxy-4-(2-nitroethyl)phenol, the publication is Bioorganic Chemistry (2021), 104994, database is CAplus and MEDLINE.

Proprotein convertase subtilisin/kexin type 9 (PCSK9) is a secreted protein and its deficiency markedly enhances the survival rate of patients with cardiovascular diseases (CVDs). Forty berberine (BBR) derivatives I (R¹ = H, MeO, R² = MeO, OH, PhCH₂O, EtO, R³ = MeO, OH, EtO, R²R³ = OCH₂O, R⁴ = H, MeO, R⁵ = H, Cl, MeO, PhCH₂O, cyclobutylmethoxy, etc., R⁶ = MeO, OH, R⁷ = MeO, EtO, H) were synthesized and evaluated for their activity on down-regulating the transcription of PCSK9 in HepG2 cells, taking BBR as the lead. Structure-activity relationship (SAR) anal. revealed that the 2,3-dimethoxy moiety might be beneficial for activity. Among them, I (R¹ = R⁴ = R⁷ = H, R² = R³ = R⁶ = MeO, R⁵ = p-F₃CSC₆H₄CH₂O) (II) displayed the most potent activity with an IC₅₀ value of 9.5 ± 0.5μM, better than that of BBR. Also, it significantly decreased the PCSK9 protein level at the cellular level, as well as in the liver and serum of mice in vivo. Furthermore, II markedly increased LDLR expression and LDL-C clearance via down-regulating PCSK9 protein. The mechanism of action of II is targeting HNF1α and/or Sp1 cluster modulation upstream of PCSK9, a different one from BBR. Therefore, II might have the potential to be a novel PCSK9 transcriptional inhibitor for the treatment of atherosclerosis, worthy for further investigation.

Bioorganic Chemistry published new progress about 528594-30-1. 528594-30-1 belongs to alcohols-buliding-blocks, auxiliary class Nitro Compound,Benzene,Phenol,Ether, name is 2-Methoxy-4-(2-nitroethyl)phenol, and the molecular formula is C9H11NO4, Recommanded Product: 2-Methoxy-4-(2-nitroethyl)phenol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

He, Huan published the artcileConcise total synthesis of opioids, Product Details of C9H11NO4, the publication is Organic Chemistry Frontiers (2022), 9(9), 2322-2327, database is CAplus.

Morphine and its related alkaloids are among the most representative natural medicines that have benefited human beings for over two centuries. Industrial manufacturing of these therapeutically valuable and structurally fascinating mols. relies on farming of opium poppies, causing severe soil erosion and regulation issues. Despite the advances in the development of numerous biosynthesis and chem. synthesis methods, a truly efficient approach to opioids which is competitive in terms of cost with the current manufacturing protocol remains highly desirable. Here we present a concise total synthesis of opioids exemplified by (-)-codeine, (-)-oxycodone, (-)-naloxone, and (-)-naltrexone with by far the highest overall yields (16-34%) from readily available starting materials. Remarkably, central to the success of the present synthesis is the development of a Pd-catalyzed dearomatization arene coupling reaction using an inexpensive, air stable, and robust phosphonium ligand. This bio-inspired step constructs the tetracyclic morphinan core in a manner with excellent regioselectivity, efficiency, and scalability.

Organic Chemistry Frontiers published new progress about 528594-30-1. 528594-30-1 belongs to alcohols-buliding-blocks, auxiliary class Nitro Compound,Benzene,Phenol,Ether, name is 2-Methoxy-4-(2-nitroethyl)phenol, and the molecular formula is C9H11NO4, Product Details of C9H11NO4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Luzzio, Frederick A. published the artcilePreparation of β-phenylnitroethanes having electron-donating aryl substitution, Synthetic Route of 528594-30-1, the publication is Tetrahedron Letters (2007), 48(38), 6704-6708, database is CAplus.

β-Phenyl-β-hydroxynitroethanes having activating aryl substituents are treated with Et₃SiH/F₃CCO₂H under solventless conditions to give the corresponding phenylnitroethanes. Substrates having no aryl substituents or substituents that are only mildly activating or deactivating do not result in appreciable conversion to the title compounds

Tetrahedron Letters published new progress about 528594-30-1. 528594-30-1 belongs to alcohols-buliding-blocks, auxiliary class Nitro Compound,Benzene,Phenol,Ether, name is 2-Methoxy-4-(2-nitroethyl)phenol, and the molecular formula is C9H11NO4, Synthetic Route of 528594-30-1.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Koremura, Mitsunobu published the artcileRelation between chemical structure and antimicrobial and insecticidal activities in organonitro compounds. I. Nitroalcohol derivatives, Related Products of alcohols-buliding-blocks, the publication is Takamine Kenkyusho Nenpo (1961), 198-204, database is CAplus.

Compounds (23) including nitroparaffins, nitroalkyl alcs., dinitroparaffins, nitro Ph alcs., ω-nitroacetophenone, and diphenylnitroethane were synthesized and tested for their biol. activities. Most of the alkyl nitro compounds except dinitroparaffins were inactive against plant pathogens and insects, whereas among the α-phenyl-β-nitro alcs. tested, 1-phenyl-2-nitroethanol had high antimicrobial activities against plant pathogens such as Xanthomonas oryzae and Glomerella cingulata and had insecticidal activity against housefly. This tendency applied similarly to the ω-nitro-acetophenone derivatives, where insecticidal activity was lost. The biol. activities of Ph nitro compounds were very low except 1-phenyl-2-nitroethanol, which indicated a possible effect of the partition coefficient of the compound between H₂O and lipid on the biol. activity. It was presumed that the presence of the Ph radical was necessary for antimicrobial and insecticidal activities of the β-nitro compounds

Takamine Kenkyusho Nenpo published new progress about 528594-30-1. 528594-30-1 belongs to alcohols-buliding-blocks, auxiliary class Nitro Compound,Benzene,Phenol,Ether, name is 2-Methoxy-4-(2-nitroethyl)phenol, and the molecular formula is C9H11NO4, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Nagasawa, Shota published the artcileChromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols, Product Details of C9H11NO4, the publication is Journal of Organic Chemistry (2021), 86(9), 6952-6968, database is CAplus and MEDLINE.

We describe an aerobic intramol. dearomative coupling reaction of tethered phenols such as I using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products such as II including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

Journal of Organic Chemistry published new progress about 528594-30-1. 528594-30-1 belongs to alcohols-buliding-blocks, auxiliary class Nitro Compound,Benzene,Phenol,Ether, name is 2-Methoxy-4-(2-nitroethyl)phenol, and the molecular formula is C9H11NO4, Product Details of C9H11NO4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Wang, Jianjun published the artcileTotal Synthesis of (-)-Melanthioidine by Copper-Mediated Cyclodimerization, Product Details of C9H11NO4, the publication is Organic Letters (2016), 18(15), 3542-3545, database is CAplus and MEDLINE.

An efficient asym. total synthesis of the dimeric macrocyclic diaryl ether phenethyltetrahydroisoquinoline alkaloid (-)-melanthioidine is reported. Key steps of the synthesis include an efficient Noyori asym. transfer hydrogenation to access the enantioenriched phenethyltetrahydroisoquinoline monomeric subunit and a copper-mediated cyclodimerization to form the two diaryl ether linkages with concomitant macrocyclization.

Organic Letters published new progress about 528594-30-1. 528594-30-1 belongs to alcohols-buliding-blocks, auxiliary class Nitro Compound,Benzene,Phenol,Ether, name is 2-Methoxy-4-(2-nitroethyl)phenol, and the molecular formula is C6H16OSi, Product Details of C9H11NO4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Faverio, Chiara published the artcileAmmonia-Borane-Mediated Reduction of Nitroalkenes, Safety of 2-Methoxy-4-(2-nitroethyl)phenol, the publication is SynOpen (2020), 4(4), 116-122, database is CAplus.

Ammonia-borane was successfully employed in the reduction of nitroalkenes. A variety of nitrostyrenes and alkyl-substituted nitroalkenes were chemoselectively reduced to the corresponding nitroalkanes, in short reaction time, with an atom-economic, simple exptl. procedure that also worked with α- and β-substituted nitroolefins.

SynOpen published new progress about 528594-30-1. 528594-30-1 belongs to alcohols-buliding-blocks, auxiliary class Nitro Compound,Benzene,Phenol,Ether, name is 2-Methoxy-4-(2-nitroethyl)phenol, and the molecular formula is C9H11NO4, Safety of 2-Methoxy-4-(2-nitroethyl)phenol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Li, Yu-Hsun published the artcileDirect Transformation of Nitroalkanes to Nitriles Enabled by Visible-Light Photoredox Catalysis and a Domino Reaction Process, Name: 2-Methoxy-4-(2-nitroethyl)phenol, the publication is Organic Letters (2019), 21(19), 7750-7754, database is CAplus and MEDLINE.

A mild and convenient process for direct transformation of nitroalkanes to the corresponding nitriles was developed using a visible-light photoredox catalysis strategy with household decorative blue LEDs and the additives of Et₃N and DIPIBA (or DIPEA). Application of the process in secondary nitroalkanes bearing a β-alc. resulted in a domino process of the retro-Henry reaction and the subsequent acetalization, aldol, cyanohydrin, and ring-contraction reactions with stereoselectivities. The photocatalytic reaction was demonstrated by a continuous flow method.

Organic Letters published new progress about 528594-30-1. 528594-30-1 belongs to alcohols-buliding-blocks, auxiliary class Nitro Compound,Benzene,Phenol,Ether, name is 2-Methoxy-4-(2-nitroethyl)phenol, and the molecular formula is C9H11NO4, Name: 2-Methoxy-4-(2-nitroethyl)phenol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts