Category: 1370732-71-0

Hagen, Helen published the artcileAminoferrocene-Based Prodrugs Activated by Reactive Oxygen Species, COA of Formula: C14H21BO3, the publication is Journal of Medicinal Chemistry (2012), 55(2), 924-934, database is CAplus and MEDLINE.

Cancer cells generally generate higher amounts of reactive oxygen species than normal cells. On the basis of this difference, prodrugs have been developed (e.g., hydroxyferrocifen), which remain inactive in normal cells, but become activated in cancer cells. In this work we describe novel aminoferrocene-based prodrugs, which, in contrast to hydroxyferrocifen, after activation form not only quinone methides (QMs), but also catalysts (iron or ferrocenium ions). The released products act in a concerted fashion. In particular, QMs alkylate glutathione, thereby inhibiting the antioxidative system of the cell, whereas the iron species induce catalytic generation of hydroxyl radicals. Since the catalysts are formed as products of the activation reaction, it proceeds autocatalytically. The most potent prodrug described here is toxic toward cancer cells (human promyelocytic leukemia (HL-60), IC₅₀ = 9 μM, and human glioblastoma-astrocytoma (U373), IC₅₀ = 25 μM), but not toxic (up to 100 μM) toward representative nonmalignant cells (fibroblasts).

Journal of Medicinal Chemistry published new progress about 1370732-71-0. 1370732-71-0 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester, name is (3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol, and the molecular formula is C14H21BO3, COA of Formula: C14H21BO3.

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

Li, Renhe published the artcileRedox-Neutral ortho Functionalization of Aryl Boroxines via Palladium/Norbornene Cooperative Catalysis, Category: alcohols-buliding-blocks, the publication is Chem (2019), 5(4), 929-939, database is CAplus and MEDLINE.

A redox-neutral ortho functionalization of aryl boroxines via Pd/NBE catalysis was reported. An electrophile, such as carboxylic acid anhydrides or O-benzoyl hydroxylamines, was coupled at the boroxine ortho position, and a proton as the second electrophile was introduced at the ipso position. This reaction did not require extra oxidants or reductants and avoided stoichiometric bases or acids, thereby tolerating a wide range of functional groups. In particular, orthogonal chemoselectivity between aryl iodide and boroxine moieties was demonstrated, which could be used to control reaction sequences. Finally, a deuterium-labeling study supported the ipso protonation pathway. This unique mechanistic feature could inspire the development of a new class of Pd/NBE-catalyzed transformations.

Chem published new progress about 1370732-71-0. 1370732-71-0 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester, name is (3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol, and the molecular formula is C14H21BO3, Category: alcohols-buliding-blocks.

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

Marzenell, Paul published the artcileAminoferrocene-Based Prodrugs and Their Effects on Human Normal and Cancer Cells as Well as Bacterial Cells, Product Details of C14H21BO3, the publication is Journal of Medicinal Chemistry (2013), 56(17), 6935-6944, database is CAplus and MEDLINE.

Aminoferrocene-based prodrugs are activated under cancer-specific conditions (high concentration of reactive oxygen species, ROS) with the formation of glutathione scavengers (p-quinone methide) and ROS-generating iron complexes. Herein, the authors explored three structural modifications of these prodrugs to improve their properties: (a) the attachment of a -COOH function to the ferrocene fragment leads to the improvement of water solubility and reactivity in vitro but also decreases cell-membrane permeability and biol. activity, (b) the alkylation of the N-benzyl residue does not show any significant affect, and (c) the attachment of the second arylboronic acid fragment improves the toxicity (IC₅₀) of the prodrugs toward human promyelocytic leukemia cells (HL-60) from 52 to 12 μM. Finally, the authors demonstrated that the prodrugs are active against primary chronic lymphocytic leukemia (CLL) cells, with the best compounds exhibiting an IC₅₀ value of 1.5 μM. The most active compounds were found to not affect mononuclear cells and representative bacterial cells.

Journal of Medicinal Chemistry published new progress about 1370732-71-0. 1370732-71-0 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester, name is (3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol, and the molecular formula is C14H21BO3, Product Details of C14H21BO3.

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

Peiro Cadahia, Jorge published the artcileSynthesis and Evaluation of Hydrogen Peroxide Sensitive Prodrugs of Methotrexate and Aminopterin for the Treatment of Rheumatoid Arthritis, COA of Formula: C14H21BO3, the publication is Journal of Medicinal Chemistry (2018), 61(8), 3503-3515, database is CAplus and MEDLINE.

A series of novel hydrogen peroxide sensitive prodrugs I (11–13; R = H, Me, F) of methotrexate (MTX) and aminopterin (AMT) were synthesized and evaluated for therapeutic efficacy in mice with collagen induced arthritis (CIA) as a model of chronic rheumatoid arthritis (RA). The prodrug strategy selected is based on ROS-labile 4-methylphenylboronic acid promoieties linked to the drugs via a carbamate linkage or a direct C-N bond. Activation under pathophysiol. concentrations of H₂O₂ proved to be effective, and prodrug candidates were selected in agreement with relevant in vitro physicochem. and pharmacokinetic assays. Selected candidates showed moderate to good solubility, high chem. and enzymic stability, and therapeutic efficacy comparable to the parent drugs in the CIA model. Importantly, the prodrugs displayed the expected safer toxicity profile and increased therapeutic window compared to MTX and AMT while maintaining a comparable therapeutic efficacy, which is highly encouraging for future use in RA patients.

Journal of Medicinal Chemistry published new progress about 1370732-71-0. 1370732-71-0 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester, name is (3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol, and the molecular formula is C14H21BO3, COA of Formula: C14H21BO3.

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