131230-76-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(((tert-butyldiMethylsilyl)oxy)Methyl)aniline is used as a key intermediate in the synthesis of immunomodulatory agents. Its unique chemical structure allows for the development of compounds that can modulate the immune system, potentially leading to the creation of new treatments for various immune-related disorders and conditions.
Used in Chemical Synthesis:
In the chemical industry, 4-(((tert-butyldiMethylsilyl)oxy)Methyl)aniline can be utilized as a versatile building block for the synthesis of a wide range of organic compounds. Its reactive functional groups and stable silyl ether linkage make it a valuable component in the development of new molecules with specific properties and applications.

Upstream product

• 623-04-1 4-aminobenzenemethanol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 135605-97-9 tert-butyldimethyl-4-nitrobenzyloxysilane 
• 16375-88-5 N-(4-hydroxymethylphenyl)acetamide 
• 619-73-8 4-nitrobenzyl chloride 
• 87736-74-1 4-(tert-butyldimethylsiloxymethyl)bromobenzene 

Downstream Products

• 195717-13-6 {(R)-1-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-2-naphthalen-2-yl-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 329349-91-9 acetic acid 2-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl ester 
• 304015-16-5 2-methoxy-4-nitrobenzyl 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenylcarbamate 
• 220299-97-8 6-cyano-naphthalene-2-carboxylic acid [4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-amide 
• 304015-65-4 (1-methyl-2-nitro-1H-imidazol-5-yl)methyl 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenylcarbamate 
• 304015-67-6 (1-methyl-5-nitro-1H-imidazol-2-yl)methyl 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenylcarbamate 
• 911359-24-5 2-bromo-N-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)acetamide 
• 858940-35-9 4-nitrobenzyl 4-(hydroxymethyl)phenylcarbamate 
• 304015-66-5 (1-methyl-2-nitro-1H-imidazol-5-yl)methyl (4-(hydroxymethyl)phenyl)carbamate 
• 304015-69-8 (1-methyl-5-nitro-1H-imidazol-2-yl)methyl 4-(hydroxymethyl)phenylcarbamate 
• 858940-36-0 4-({[(4-nitrobenzyl)oxy]carbonyl}amino)benzyl 4-nitrophenyl carbonate 
• 304015-70-1 4-({[(1-methyl-5-nitro-1H-imidazol-2-yl)methoxy]carbonyl}amino)benzyl 4-nitrophenyl carbonate 
• 304016-33-9 (1-methyl-2-nitro-1H-imidazol-5-yl)methyl (4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl)carbamate 
• 175448-32-5 epoxyquinomycin B 

Relevant academic research and scientific papers

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.

A DT-diaphorase responsive theranostic prodrug for diagnosis, drug release monitoring and therapy

A DT-diaphorase-activatable theranostic prodrug, which contains camptothecin, a self-immolative linker and a trigger group, has been developed for the detection of DT-diaphorase, tracking of drug release and selectively killing cancer cells over-expressed

Rational construction of probes rendering ratiometric response to the cancer-specific enzyme NQO1

Pursuit of fluorescent probes for identification of cancer biomarkers benefits reliable predictions of early cancer detection. Here, a strategy employing polymeric micelle assembly for encapsulation of a new enzyme (NQO1)-responsive small molecule was est

A double-triggered self-immolative spacer for increased selectivity of molecular release

A self-immolative spacer based on dissymmetricalN,N′-bis-carbamate aniline is introduced to liberate a substrate from a precursor after dual activation. The proof of principle of its exclusive selectivity for substrate liberation has been conducted on a profluorophore.

A class of intestinal lysis type co-drugs and their preparation and use

The present invention relates to a class of intestinal cleavage type co-drugs (Codrug) and preparation and use thereof, in particular, the present invention provides a co-drug compound as shown in formula I. The present invention further provides a method

Ortho-dithiol reactive treatment probe for drug release monitoring and preparation method of ortho-dithiol reactive treatment probe

The invention discloses an ortho-dithiol reactive treatment probe for drug release monitoring and a preparation method of the ortho-dithiol reactive treatment probe. The structure of a probe compound is shown as a formula I in the specification. A probe m

COMPOUND HAVING BENZO SEVEN-MEMBERED RING STRUCTURE, PREPARATION METHOD THEREFOR, AND USE THEREOF

The present invention relates to a compound having a benzo seven-membered ring structure, and a preparation method therefor, and use thereof. The compound has a structure as represented by formula (I). Provided is use of the compound having the structure and prepared with the preparation method of the present invention, enantiomers, diastereomers, racemates and mixtures thereof of the compound, as well as chemically acceptable salts, crystalline hydrates and solvent mixtures of the compound and the enantiomers, diastereomers, racemates and mixtures thereof of the compound in the preparation of drugs for treating BET Bromodomain BRD4 activity or expression level related diseases.

Turn on chemiluminescence-based probes for monitoring tyrosinase activity in conjunction with biological thiols

We report a chemiluminescent probe (CLPT1) that permits the paired detection of tyrosinase (Tyr) and biological thiols. Tyr only leads to a poor chemiluminescence response, a finding ascribed to the formation of a stableo-benzoquinone intermediate. The addition of glutathione (GSH), or ascorbate to theo-benzoquinone intermediate results in thiol conjugation or reduction to this intermediate, respectively. This produces a strong chemiluminescence response. Thiol co-dependence was demonstrated in live cells using the cell permeable analogue,CLPT3. The present chemiluminescence-based strategy allows the concurrent detection of tyrosinase activity and biological thiols.

Rational designed highly sensitive NQO1-activated near-infrared fluorescent probe combined with NQO1 substrates in vivo: An innovative strategy for NQO1-overexpressing cancer theranostics

Since NQO1 is overexpressed in many cancer cells, it can be used as a biomarker for cancer diagnosis and targeted therapy. NQO1 substrates show potent anticancer activity through the redox cycle mediated by NQO1, while the NQO1 probes can monitor NQO1 levels in cancers. High sensitivity of probes is needed for diagnostic imaging in clinic. In this study, based on the analysis of NQO1 catalytic pocket, the naphthoquinone trigger group 13 rationally designed by expanding the aromatic plane of the benzoquinone trigger group 10 shows significantly increased sensitivity to NQO1. The sensitivity of the naphthoquinone trigger group-based probe A was eight times higher than that of benzoquinone trigger group-based probe B in vivo. Probe A was selectively and efficiently sensitive to NQO1 with good safety profile and plasma stability, enabling its combination with NQO1 substrates in vivo for NQO1-overexpressing cancer theranostics for the first time.

Discovery of a novel class of norovirus inhibitors with high barrier of resistance

Human noroviruses (HuNoVs) are the most common cause of viral gastroenteritis resulting in ~219,000 deaths annually and a societal cost of ~USD60 billion. There are no antivirals or vaccines available to treat and/or prevent HuNoV. In this study, we performed a large-scale phe-notypical antiviral screening using the mouse norovirus (MNV), which included ~1000 drug-like small molecules from the Drug Design and Synthesis Centre (Sapienza University, Rome). Compound 3-((3,5-dimethylphenyl)sulfonyl)-5-chloroindole-N-(phenylmethanol-4-yl)-2.carboxamide (compound 1) was identified as an inhibitor of MNV replication with an EC50 of 0.5 ± 0.1 μM. A series of 10 analogs were synthesized of which compound 6 showed an improved potency/selectiv-ity (EC50 0.2 ± 0.1 μM) against MNV; good activity was also observed against the HuNoV GI replicon (EC50 1.2 ± 0.6 μM). Time-of-drug-addition studies revealed that analog 6 acts at a time point that coincides with the onset of viral RNA replication. After six months of selective pressure, two compound 6res variants were independently selected, both harboring one mutation in VPg and three mutations in the RdRp. After reverse engineering S131T and Y154F as single mutations into the MNV backbone, we did not find a markedly compound 6res phenotype. In this study, we present a class of novel norovirus inhibitors with a high barrier to resistance and in vitro antiviral activity.