Month: October 2022

In 2022,Basson, Ashley J.; Halcovitch, Nathan R.; McLaughlin, Mark G. published an article in Chemistry – A European Journal. The title of the article was 《Unified Approach to Diverse Fused Fragments via Catalytic Dehydrative Cyclization》.Synthetic Route of C7H7BrO The author mentioned the following in the article:

A range of highly functionalized polycyclic fragments have been synthesized, employing a catalytic dehydrative cyclization. A range of nucleophiles are shown to be successful, with the reaction producing numerous high value motifs. The experimental process involved the reaction of 1-Bromo-3-methoxybenzene(cas: 2398-37-0Synthetic Route of C7H7BrO)

1-Bromo-3-methoxybenzene(cas: 2398-37-0) can be used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photoinitiators and agrochemicals.Synthetic Route of C7H7BrO

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

Reference of tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamateIn 2015 ,《Protease-triggered siRNA delivery vehicles》 appeared in Journal of Controlled Release. The author of the article were Rozema, David B.; Blokhin, Andrei V.; Wakefield, Darren H.; Benson, Jonathan D.; Carlson, Jeffrey C.; Klein, Jason J.; Almeida, Lauren J.; Nicholas, Anthony L.; Hamilton, Holly L.; Chu, Qili; Hegge, Julia O.; Wong, So C.; Trubetskoy, Vladimir S.; Hagen, Collin M.; Kitas, Eric; Wolff, Jon A.; Lewis, David L.. The article conveys some information:

The safe and efficacious delivery of membrane impermeable therapeutics requires cytoplasmic access without the toxicity of nonspecific cytoplasmic membrane lysis. We have developed a mechanism for control of cytoplasmic release which utilizes endogenous proteases as a trigger and results in functional delivery of small interfering RNA (siRNA). The delivery approach is based on reversible inhibition of membrane disruptive polymers with protease-sensitive substrates. Proteolytic hydrolysis upon endocytosis restores the membrane destabilizing activity of the polymers thereby allowing cytoplasmic access of the co-delivered siRNA. Protease-sensitive polymer masking reagents derived from polyethylene glycol (PEG), which inhibit membrane interactions, and N-acetylgalactosamine, which targets asialoglycoprotein receptors on hepatocytes, were synthesized and used to formulate masked polymer-siRNA delivery vehicles. The size, charge and stability of the vehicles enable functional delivery of siRNA after s.c. administration and, with modification of the targeting ligand, have the potential for extrahepatic targeting. The results came from multiple reactions, including the reaction of tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate(cas: 139115-91-6Reference of tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate)

tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate(cas: 139115-91-6) belongs to ethers.Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. Reference of tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate

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

SDS of cas: 106685-40-9In 2020 ,《Ion Pair Strategy in Solid Lipid Nanoparticles: a Targeted Approach to Improve Epidermal Targeting with Controlled Adapalene Release, Resulting Reduced Skin Irritation》 was published in Pharmaceutical Research. The article was written by Rodrigues, Linna B. O.; Lima, Flavia A.; Alves, Camila P. B.; Martins-Santos, Elisangela; Aguiar, Marta M. G.; Oliveira, Cleida A.; Orefice, Rodrigo L.; Ferreira, Lucas A. M.; Goulart, Gisele A. C.. The article contains the following contents:

Abstract: Purpose: Adapalene (AD) is one of the main retinoids used in the topical therapy of acne, an extremely common skin disease usually associated with psychol. morbidity. However, like other retinoids, AD is frequently associated with skin irritation. To overcome the skin irritation, we proposed the encapsulation of AD in solid lipid nanoparticles (SLNs) using the ion pair strategy. Methods: The developed SLN-AD was characterized by high-performance liquid chromatog., differential scanning calorimetry, X-ray diffraction, synchrotron small-angle X-ray scattering, and transmission electron microscopy. In vitro permeation tests using porcine skin and in vivo mice skin irritation test were performed to evaluate, resp., the drug’s skin distribution and the skin irritation. Results: The characterization studies were able to demonstrate that the proposed strategy effectively provided high AD encapsulation in SLNs and its incorporation into a hydrophilic gel. Sustained release, epidermal targeting, and less skin irritation were observed for SLN-AD gel in comparison to the marketed AD gel. Conclusions: The studies demonstrated that the encapsulation of AD in SLNs through the formation of an ion pair is a valuable alternative to diminish the adverse skin reactions caused by AD and can optimize patient adherence to treatment. In the experiment, the researchers used 6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid(cas: 106685-40-9SDS of cas: 106685-40-9)

6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid(cas:106685-40-9) is a third-generation synthetic retinoid and a highly lipophilic compound derived from naphthoic acid. It is widely used in the treatment of acne.SDS of cas: 106685-40-9

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

Electric Literature of C8H8O2In 2020 ,《Introduction of a new catalyst containing an ionic liquid bridge on nanoporous Na+- montmorillonite for the synthesis of hexahydroquinolines and 1,8-dioxo-decahydroacridines via Hantzsch condensation》 was published in Journal of Molecular Structure. The article was written by Mazloumi, Masoumeh; Shirini, Farhad. The article contains the following contents:

A new nanoporous catalyst formulated as Na+-MMT-[bip]-NH+2 HSO-4 was prepared via modification of Na+-MMT with bis-3-(trimethoxysilylpropyl)-amine and then addition of sulfuric acid. In continue the prepared reagent was identified with different methods including Fourier-transform IR spectroscopy (FT-IR), X-ray diffraction (XRD), field emission SEM (FESEM), thermogravimetric anal. (TGA), transmission electron microscopy (TEM), energy dispersive spectrometer (EDS) and CHN elemental anal. After identification the catalytic efficiency of this reagent was tested in the synthesis of hexahydroquinolines and 1,8-dioxo-decahydroacridines via Hantzsch condensations. All reactions were performed under mild conditions in the absence of solvent in high yields in short reaction times. The catalyst was also reusable for several times in both of the studied reactions. After reading the article, we found that the author used 2-Methoxybenzaldehyde(cas: 135-02-4Electric Literature of C8H8O2)

2-Methoxybenzaldehyde(cas: 135-02-4) is found in cassia oil, cinnamon bark, and cinnamon bark oil. It is a clear colorless liquid with a strong aroma. It has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus putrescentiae.Electric Literature of C8H8O2

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

Synthetic Route of C7H7IOIn 2019 ,《Synthetic utilization of tetrafluoroethylene-containing silyl reagent (CH2=CHCF2CF2SiEt3) in Cu(I)-mediated cross-coupling reaction with various iodoarenes》 was published in Journal of Fluorine Chemistry. The article was written by Yakushijin, Ryosuke; Yamada, Shigeyuki; Konno, Tsutomu. The article contains the following contents:

The synthetic utilization of thermally stable as well as easy-handling tri-Et (1,1,2,2-tetrafluorobut-3-en-1-yl)silane as the tetrafluoroethylenating agent through Cu(I)-mediated cross-coupling reaction with various iodoarenes, which offered a promising building block for versatile CF2CF2-containing organic mols. through easy carbon chain elongation at both ends were revealed. Specifically, the above tetrafluoroethylene-containing silyl reagent, readily prepared from com. available 4-bromo-3,3,4,4-tetrafluorobut-1-ene, smoothly reacted with various iodoarenes in the presence of Cu(I), Ag(I) and pyridine in DMF at 60° for 16 h, the corresponding CF2CF2-containing aromatic compounds being afforded in moderate to good yields. Addnl., it was revealed that the coupling reaction dramatically facilitated when iodoarenes with an ortho-directing group, e.g., COOMe, were used as an electrophile, in which the acceleration effect was theor. proved to stabilize the whole reaction system by coordination of the carbonyl oxygen to the copper atom. After reading the article, we found that the author used 1-Iodo-2-methoxybenzene(cas: 529-28-2Synthetic Route of C7H7IO)

1-Iodo-2-methoxybenzene(cas: 529-28-2) participates in palladium catalyzed enantioselective Heck arylation of 2,3-dihydrofuran in the presence of chiral ionic liquids containing L-prolinate and L-lactate anions and non-chiral quaternary ammonium cations.Synthetic Route of C7H7IO

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

Category: ethers-buliding-blocksIn 2021 ,《Modular Entry to Functionalized Tetrahydrobenzo[b]azepines via the Palladium/Norbornene Cooperative Catalysis Enabled by a C7-Modified Norbornene》 was published in Journal of the American Chemical Society. The article was written by Liu, Xin; Wang, Jianchun; Dong, Guangbin. The article contains the following contents:

Here, the authors report a straightforward method to synthesize THBAs (tetrahydrobenzo[b]azepines), e.g., I, directly from simple aryl iodides RI (R = 3-chlorophenyl, quinolin-6-yl, 4-(morpholinyl)-2-methylphenyl, etc.) via palladium/norbornene (Pd/NBE) cooperative catalysis. Capitalizing on an olefin-tethered electrophilic amine reagent, an ortho amination followed by 7-exo-trig Heck cyclization furnishes the seven-membered heterocycle. To overcome the difficulty with ortho-unsubstituted aryl iodide substrates, a unique C7-bromo-substituted NBE, II, to offer the desired reactivity and selectivity was discovered. In addition to THBAs, synthesis of other benzo-seven-membered ring compounds e.g., III, can also be promoted by II. Combined exptl. and computational studies show that the C7-bromo group in II plays an important and versatile role in this catalysis, including promoting β-carbon elimination, suppressing benzocyclobutene formation, and stabilizing reaction intermediates. The mechanistic insights gained could guide future catalyst design. The synthetic utility has been demonstrated in a streamlined synthesis of tolvaptan (IV) and forming diverse pharmaceutically relevant THBA derivatives Finally, a complementary and general catalytic condition to access C6-substituted THBAs from ortho-substituted aryl iodides has also been developed.1-Iodo-2-methoxybenzene(cas: 529-28-2Category: ethers-buliding-blocks) was used in this study.

1-Iodo-2-methoxybenzene(cas: 529-28-2) participates in palladium catalyzed enantioselective Heck arylation of 2,3-dihydrofuran in the presence of chiral ionic liquids containing L-prolinate and L-lactate anions and non-chiral quaternary ammonium cations.Category: ethers-buliding-blocks

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

Electric Literature of C9H12O2On October 22, 2015 ,《Navigating CYP1A Induction and Arylhydrocarbon Receptor Agonism in Drug Discovery. A Case History with S1P1 Agonists》 was published in Journal of Medicinal Chemistry. The article was written by Taylor, Simon J.; Demont, Emmanuel H.; Gray, James; Deeks, Nigel; Patel, Aarti; Nguyen, Dung; Taylor, Maxine; Hood, Steve; Watson, Robert J.; Bit, Rino A.; McClure, Fiona; Ashall, Holly; Witherington, Jason. The article contains the following contents:

This article describes the finding of substantial upregulation of mRNA and enzymes of the cytochrome P 450 1A family during a lead optimization campaign for small mol. S1P1 agonists. Fold changes in mRNA up to 10 000-fold for CYP1A1 in vivo in rat and cynomolgus monkey and up to 45-fold for CYP1A1 and CYP1A2 in vitro in rat and human hepatocytes were observed Challenges observed with correlating induction in vitro and induction in vivo resulted in the implementation of a short, 4 day in vivo screening study in the rat which successfully identified noninducers. Subtle structure-activity relationships in this series of S1P1 agonists are described extending beyond planarity and lipophilicity, and the impact and considerations of AhR and CYP1A induction in the context of drug development are discussed. In addition to this study using (3-Methoxy-2-methylphenyl)methanol, there are many other studies that have used (3-Methoxy-2-methylphenyl)methanol(cas: 33797-34-1Electric Literature of C9H12O2) was used in this study.

(3-Methoxy-2-methylphenyl)methanol(cas: 33797-34-1) belongs to ethers.The C-O bonds that comprise simple ethers are strong. They are unreactive toward all but the strongest bases. Although generally of low chemical reactivity, they are more reactive than alkanes. Electric Literature of C9H12O2

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

Magee, Thomas V.; Ripp, Sharon L.; Li, Bryan; Buzon, Richard A.; Chupak, Lou; Dougherty, Thomas J.; Finegan, Steven M.; Girard, Dennis; Hagen, Anne E.; Falcone, Michael J.; Farley, Kathleen A.; Granskog, Karl; Hardink, Joel R.; Huband, Michael D.; Kamicker, Barbara J.; Kaneko, Takushi; Knickerbocker, Michael J.; Liras, Jennifer L.; Marra, Andrea; Medina, Ivy; Nguyen, Thuy-Trinh; Noe, Mark C.; Obach, R. Scott; O’Donnell, John P.; Penzien, Joseph B.; Reilly, Usa Datta; Schafer, John R.; Shen, Yue; Stone, Gregory G.; Strelevitz, Timothy J.; Sun, Jianmin; Tait-Kamradt, Amelia; Vaz, Alfin D. N.; Whipple, David A.; Widlicka, Daniel W.; Wishka, Donn G.; Wolkowski, Joanna P.; Flanagan, Mark E. published their research in Journal of Medicinal Chemistry on December 10 ,2009. The article was titled 《Discovery of Azetidinyl Ketolides for the Treatment of Susceptible and Multidrug Resistant Community-Acquired Respiratory Tract Infections》.Name: 5-Methoxy-4-methylpyridin-3-amine The article contains the following contents:

Respiratory tract bacterial strains are becoming increasingly resistant to currently marketed macrolide antibiotics. The current alternative telithromycin (1) from the newer ketolide class of macrolides addresses resistance but is hampered by serious safety concerns, hepatotoxicity in particular. We have discovered a novel series of azetidinyl ketolides that focus on mitigation of hepatotoxicity by minimizing hepatic turnover and time-dependent inactivation of CYP3A isoforms in the liver without compromising the potency and efficacy of 1. The experimental process involved the reaction of 5-Methoxy-4-methylpyridin-3-amine(cas: 77903-28-7Name: 5-Methoxy-4-methylpyridin-3-amine)

5-Methoxy-4-methylpyridin-3-amine(cas: 77903-28-7) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.Name: 5-Methoxy-4-methylpyridin-3-amine

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

In 2019,Journal of Medicinal Chemistry included an article by Yokoyama, Takeshi; Mizuguchi, Mineyuki. Electric Literature of C10H20O5. The article was titled 《Crown Ethers as Transthyretin Amyloidogenesis Inhibitors》. The information in the text is summarized as follows:

Transthyretin (TTR) is a tetrameric protein found in human serum and associated with amyloid diseases. Because the tetramer dissociation and misfolding of the monomer precede amyloid fibril formation, development of a small mol. that binds to TTR and stabilizes the TTR tetramer is an efficient strategy for the treatment of amyloidosis. Here, we report our discovery of the anti-TTR amyloidogenesis activities of crown ethers. X-ray crystallog. anal., binding assay, and chem. crosslinking assay showed that 4′-carboxybenzo-18C6 (4) stabilized the TTR tetramer by binding to the allosteric sites on the mol. surface of the TTR tetramer. In addition, 4 synergistically increased the stabilization activity of diflunisal, one of the most potent TTR amyloidogenesis inhibitors. These exptl. evidences establish that 4 is a valuable template compound as an allosteric inhibitor of TTR amyloidogenesis. The results came from multiple reactions, including the reaction of 1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5Electric Literature of C10H20O5)

1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5) is a member of crown ether Ligands. Crown-ethers are macrocyclic polyethers capable of forming host-guest complexes, especially with inorganic and organic cations. Crown-ethers can incorporate protonated primary amine compounds by formation of ion-dipole bonds with the oxygen atoms of the chiral selector. Crown-ethers have been widely used for the separation of several pharmaceuticals both in aqueous and non-aqueous media. Electric Literature of C10H20O5

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

In 2019,Plant Cell, Tissue and Organ Culture included an article by Ahmad, Zishan; Shahzad, Anwar; Sharma, Shiwali. Recommanded Product: 673-22-3. The article was titled 《Chitosan versus yeast extract driven elicitation for enhanced production of fragrant compound 2-hydroxy-4-methoxybenzaldehyde (2H4MB) in root tuber derived callus of Decalepis salicifolia (Bedd. ex Hook.f.) Venter》. The information in the text is summarized as follows:

Decalepis salicifolia (Bedd. ex Hook.f.) Venter is a new source of the com. important flavor compound 2-hydroxy-4-methoxybenzaldehyde (2H4MB), a structural isomer of vanillin, with high pharmacol. value and used as a flavoring agent at industrial level for making soft drink and bakery products. The natural availability of this high-valued plant is not able to meet the ever-increasing demands due to limited studies. Considering the importance of suspension culture over excised root culture, present communication provides a protocol for the suspension culture of root tuber derived callus of D. salicifolia for the first time. Maximum frequency (84.8%) callus induction was obtained on Murashige and Skoog (MS) medium augmented with (1.0μM) thidiazuron (TDZ) + (1.0μM) α-naphthalene acetic acid (NAA). Two important biotic elicitors, chitosan (CH) and yeast extract (YE) at different concentrations (50, 100, 200 and 300μM) were used as elicitor to investigate the effects on biomass content, 2H4MB content, total phenolic content (TPC), total flavonoid content (TFC) and antioxidant activity in cell suspension culture with different contact periods i.e. 24, 48 72 and 96 h. The results showed the supremacy of CH over YE and maximum biomass was 9.7 DW g/l at optimum contact period of 72 h when suspension culture was treated with 200μM CH. Maximum content of 2H4MB was14.8μg/g at 200μM CH and it was found to be 1.4-fold increase in relation to the control (10.8μg/g). The maximum TPC and TFC were 4.8 mg/g and 4.0 mg/g resp. at 200μM CH and 72 h of the contact period. The DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity (RSA) had also been evaluated and most of the suspension culture showed the correlation with TPC and TFC. The maximum RSA (63.8%) and hydroxyl radical scavenging activity (HRSA) (55.2%) were revealed the ability of plant as a potent antioxidant agent. Thus, a new protocol has been developed for the elicitors-induced enhancement of metabolites and antioxidant activity in suspension culture of D. salicifolia. The experimental process involved the reaction of 2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3Recommanded Product: 673-22-3)

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.Recommanded Product: 673-22-3

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