144072-29-7

Usage

Uses

Used in Pharmaceutical Industry:
BOC-4-aminobenzyl alcohol is used as a key intermediate in the synthesis of various drugs and biologically active molecules for the following reasons:
Its structure allows for the creation of complex organic compounds that can target specific biological pathways.
The BOC protecting group facilitates selective reactions, preventing unwanted side reactions during the synthesis process.
It contributes to the development of new therapeutic agents with improved efficacy and reduced side effects.
Used in Medicinal Chemistry:
BOC-4-aminobenzyl alcohol is employed as a versatile reagent in medicinal chemistry for the following purposes:
It aids in the preparation of a wide range of organic compounds, expanding the scope of potential drug candidates.
Its presence in the synthesis process can enhance the stability and solubility of the resulting compounds, which is crucial for their pharmaceutical applications.
It supports the exploration of novel chemical spaces, enabling the discovery of innovative drug molecules with unique mechanisms of action.
Used in Drug Discovery:
BOC-4-aminobenzyl alcohol is utilized as a valuable component in drug discovery for the following reasons:
It enables the design and synthesis of molecules with specific pharmacological properties, contributing to the advancement of personalized medicine.
Its use in combinatorial chemistry allows for the rapid generation of diverse compound libraries, accelerating the identification of potential drug candidates.
It plays a role in the optimization of lead compounds, refining their potency, selectivity, and pharmacokinetic properties to enhance their therapeutic potential.

InChI:InChI=1/C12H17NO3/c1-12(2,3)16-11(15)13-10-6-4-9(8-14)5-7-10/h4-7,14H,8H2,1-3H3,(H,13,15)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 150-13-0 4-amino-benzoic acid 
• 110969-44-3 4-tert-butyloxycarbonylaminobenzoic acid ethyl ester 
• 94-09-7 p-aminoethylbenzoate 
• 144072-30-0 4-((tert-butoxycarbonyl)amino)benzaldehyde 
• 66493-39-8 4-(N-tert-butoxycarbonyl)aminobenzoic acid 
• 1239374-04-9 tert-butyl 4-(hydroxymethyl)phenyl(3-perfluorooctylpropoxy)carbamate 
• 34619-03-9 tert-butyldicarbonate 
• 623-04-1 4-aminobenzenemethanol 

Downstream Products

• 866005-62-1 (4-isothiocyanatomethyl-phenyl)-carbamic acid tert-butyl ester 
• 1346771-64-9 C₁₇H₂₃N₃O₄S 
• 1346771-63-8 C₁₈H₂₃N₃O₄S 
• 1346771-62-7 C₁₇H₂₂ClN₃O₄S 
• 1346771-61-6 C₁₇H₂₂BrN₃O₄S 
• 220298-96-4 4‐(tert‐butoxycarbonylamino)benzylamine 

Relevant academic research and scientific papers

Synthesis of rigid photoswitchable hemithioindigo ω-amino acids

The synthesis of novel N-Boc- and N-Fmoc protected hemithioindigo-based ω-amino acids is described. An approach to modulate the thermal stability of a hemithioindigo subunit is presented. Placing the amino-group in the stilbene part from the para- to meta

NON-ATP/CATALYTIC SITE P38 MITOGEN ACTIVATED PROTEIN KINASE INHIBITORS

Compounds that inhibit p38a MAPK protein, and methods of using the same, are provided for treating or preventing diseases such as cancer or inflammatory diseases.

Methanesulfinylation of Benzyl Halides with Dimethyl Sulfoxide

A phenyltrimethylammonium tribromide-mediated nucleophilic substitution/oxygen transformation reaction of benzyl halides with DMSO has been developed. In this transition-metal-free reaction, DMSO acts as not only a solvent but also a "S(O)Me" source, thus providing a convenient method for the efficient and direct synthesis of various benzyl methyl sulfoxides.

NON-ATP/CATALYTIC SITE p38 MITOGEN ACTIVATED PROTEIN KINASE INHIBITORS

Compounds that inhibit p38α MAPK protein, and methods of using the same, are provided for treating or preventing diseases such as cancer or inflammatory diseases.

CHROMENOPYRIDINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS

The invention relates to inhibitors of PI5P4K inhibitors useful in the treatment of cancers, neurodegenerative diseases, inflammatory disorders, and metabolic diseases, having the Formula (I); where A1, A2, G, R1, R2, R3, R4, and W are described herein.

Development of a self-immolative linker for tetrazine-triggered release of alcohols in cells

Bioorthogonal decaging reactions are a promising strategy for prodrug activation because they involve bond cleavage to release a molecule of interest. The trans-cyclooctene (TCO)-tetrazine inverse electron-demand Diels-Alder reaction has been widely applied in vivo for decaging of amine prodrugs, however, the release of alcohol-containing bioactive compounds has been less well studied. Here, we report a TCO-carbamate benzyl ether self-immolative linker for the release of OH-molecules upon reaction with a tetrazine trigger. The benzyl ether linker proved to be highly stable and can rapidly liberate alcohols under physiological conditions upon reaction with tetrazines. The mechanism and decaging yield were systematically examined by fluorescence and HPLC analysis by using a fluorogenic TCO-benzyl ether-coumarin probe and different 3,6-substituted tetrazine derivatives. This study revealed that decaging occurs rapidly (t1/2 = 27 min) and the cycloaddition step happens within seconds (t1/2 = 7 s) with reaction rates of ≈100 M-1 s-1. Importantly, the reaction is compatible with living organisms as demonstrated by the decaging of a prodrug of the antibacterial compound triclosan in the presence of live E. Coli, that resulted in complete cell killing by action of the released "OH-active drug". Overall, this work describes a new linker for masking alcohol functionality that can be rapidly reinstated through tetrazine-triggered decaging.

Synthesis of Nitrogen-Containing Goniothalamin Analogues with Higher Cytotoxic Activity and Selectivity against Cancer Cells

Two series of racemic goniothalamin analogues displaying nitrogen-containing groups were designed and synthesized. A total of 19 novel analogues were evaluated against a panel of four different cancer cell lines, along with the normal prostate cell line PNT2 to determine their selectivity. Among them, goniothalamin chloroacrylamide 13 e displayed the lowest IC50 values for both MCF-7 (0.5 μm) and PC3 (0.3 μm) cells, about 26-fold more potent than goniothalamin (1). Besides its higher potency, compound 13 e also displayed much higher selectivity than goniothalamin. In contrast, goniothalamin isobutyramide 13 c was the most potent analogue against Caco-2 cells (IC50=0.8 μm), about 10-fold more potent and 17-fold more selective than 1. These results reveal the potential of compounds 13 c and 13 e for further in vivo studies, representing the first goniothalamin analogues with IC50 values in the low micromolar range and high selectivity against MCF-7, Caco-2, and PC3 cancer cell lines.

Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers

A simple method for the dimerization of phenylpropenoid derivatives is reported. It leverages electrochemical oxidation of p-unsaturated phenols to access the dimeric materials in a biomimetic fashion. The mild nature of the transformation provides excellent functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical-trapping antioxidants; more so than the phenols from which they are derived—or transformed to—despite the fact that they do not possess a labile H-atom for transfer to the peroxyl radicals that propagate autoxidation.

Efficient and expeditious chemoselective BOC protection of amines in catalyst and solvent-free media

A green and eco-friendly route for the almost quantitative BOC protection of a large variety of aliphatic and aromatic amines, amino acids, and amino alcohols is reported in catalyst and solvent-free media under mild reaction conditions. The products were confirmed by 1H, 13C NMR, IR spectroscopy, and in some cases, elemental analysis. This protocol does not require any water quenches, solvent separations, and purification steps, such as recrystallization and column chromatography.

DRUG-LINKER CONJUGATE PHARMACEUTICAL COMPOSITIONS

Compositions are disclosed having a cytotoxic and/or vascular disrupting agent (VDA) payload attached to a linker. The linker can be a cathepsin B protease cleavable linker or a non-cleavable linker that may degrade intracellularly. Methods for making and using the compositions are also provided. The compositions can be provided to a patient in need thereof with the composition coming into contact with a cancer cell to activate or release the cytotoxic and/or vascular disrupting agent payload.