1820717-35-8

Basic information

• Product Name: Azido-PEG1-CH2CO2tBu
• Synonyms: Azido-PEG1-CH2CO2tBu;Azido-PEG1-CH2CO2-t-butyl ester;tert-Butyl 2-(2-azidoethoxy)acetate;Azido-PEG1-t-butyl acetate
• CAS NO: 1820717-35-8
• Molecular Formula: C8H15N3O3
• Molecular Weight: 201.223
• Mol File: 1820717-35-8.mol

Chemical Properties

• Appearance: /
• Solubility: Soluble in DCM, DMF
• CAS DataBase Reference: Azido-PEG1-CH2CO2tBu(CAS DataBase Reference)
• NIST Chemistry Reference: Azido-PEG1-CH2CO2tBu(1820717-35-8)
• EPA Substance Registry System: Azido-PEG1-CH2CO2tBu(1820717-35-8)

Safety Data

• Hazardous Substances Data: 1820717-35-8(Hazardous Substances Data)

Usage

Uses

Used in Bioconjugation Applications:
Azido-PEG1-CH2CO2tBu is used as a bioconjugation agent for the covalent attachment of biomolecules to various surfaces or other molecules. The azide group allows for efficient and site-specific coupling through Click Chemistry, while the t-butyl protected carboxyl group provides a means to control the reactivity and timing of the deprotection process.
Used in Drug Delivery Systems:
In the pharmaceutical industry, Azido-PEG1-CH2CO2tBu is used as a component in drug delivery systems to improve the solubility, stability, and bioavailability of therapeutic agents. The PEGylation of drugs can reduce immunogenicity and increase circulation time, while the azide group facilitates the attachment of drug molecules or targeting ligands through Click Chemistry.
Used in Materials Science:
Azido-PEG1-CH2CO2tBu is utilized in the development of functional materials, such as hydrogels, nanoparticles, and surfaces, for various applications in tissue engineering, diagnostics, and sensors. The combination of PEG's biocompatibility and the azide group's reactivity allows for the creation of stimuli-responsive materials and the incorporation of multiple functionalities.
Used in Chemical Synthesis:
In organic synthesis, Azido-PEG1-CH2CO2tBu serves as a versatile building block for the synthesis of complex molecules and macromolecules. The azide group can be used for various transformations, such as the Staudinger ligation or the reduction to amines, while the t-butyl protected carboxyl group can be selectively deprotected to introduce new functional groups or enable further reactions.

Upstream product

• 1643957-24-7 tert-butyl 2-(2-[[(4-methylbenzene)sulfonyl]oxy]ethoxy)acetate 
• 287174-32-7 (2-hydroxyethoxy)acetic acid tert-butyl ester 
• 1309451-06-6 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 1517-05-1 2-azidoethanol 

Downstream Products

• 1155811-37-2 tert-butyl 2-(2-aminoethoxy)acetate 

Relevant articles and documents

Development of small-molecule BRD4 degraders based on pyrrolopyridone derivative

Bromodomain-containing protein 4 (BRD4) plays a crucial role in the epigenetic regulation of gene transcription and some BRD4 inhibitors have been advanced to clinical trials. Nevertheless, the clinical application of BRD4 inhibitors could be limited by drug resistance. As an alternative strategy, the emerging Proteolysis Targeting Chimeras (PROTACs) technology has the potential to overcome the drug resistance of traditional small-molecule drugs. Based on PROTACs approaches, several BRD4 degraders were developed and have been proved to degrade BRD4 protein and inhibit tumor growth. Herein, we present the design, synthesis, and biological evaluation of pyrrolopyridone derivative-based BRD4 degraders. Four synthesized compounds displayed comparative potence against BRD4 BD1 with IC50 at low nanomolar concentrations. Anti-proliferative activity of 32a against BxPC3 cell line (IC50 = 0.165 μM) was improved by about 7-fold as compared to the BRD4 inhibitor ABBV-075. Furthermore, degrader 32a potently induced the degradation of BRD4 and inhibited the expression of c-Myc in BxPC3 cell line in a time-dependent manner. The exploration of intracellular antitumor mechanism showed 32a induced cell cycle arrest and apoptosis effectively. All the results demonstrated that compound 32a could be considered as a potential BRD4 degrader for further investigation.

Discovery of a new class of PROTAC BRD4 degraders based on a dihydroquinazolinone derivative and lenalidomide/pomalidomide

BRD4 has emerged as an attractive target for anticancer therapy. However, BRD4 inhibitors treatment leads to BRD4 protein accumulation, together with the reversible nature of inhibitors binding to BRD4, which may limit the efficacy of BRD4 inhibitors. To address these problems, a protein degradation strategy based on the proteolysis targeting chimera (PROTAC) technology has been developed to target BRD4 recently. Herein, we present our design, synthesis and biological evaluation of a new class of PROTAC BRD4 degraders, which were based on a potent dihydroquinazolinone-based BRD4 inhibitor compound 6 and lenalidomide/pomalidomide as ligand for E3 ligase cereblon. Gratifyingly, several compounds showed excellent inhibitory activity against BRD4, and high anti-proliferative potency against human monocyte lymphoma cell line THP-1. Especially, compound 21 (BRD4 BD1, IC50 = 41.8 nM) achieved a submicromolar IC50 value of 0.81 μM in inhibiting the growth of THP-1 cell line, and was 4 times more potent than compound 6. Moreover, the mechanism study established that 21 could effectively induce the degradation of BRD4 protein and suppression of c-Myc. All of these results suggested that 21 was an efficacious BRD4 degrader for further investigation.

Identification of New Small-Molecule Inducers of Estrogen-related Receptor α (ERRα) Degradation

A series of (E)-3-(4-((2,4-bis(trifluoromethyl)benzyl)oxy)-3-methoxyphenyl)-2-cyanoacrylamide derivatives were designed and synthesized as new estrogen-related receptor α (ERRα) degraders based on the proteolysis targeting chimera (PROTAC) concept. One of the representative compounds 6c is capable of specifically degrading ERRα protein by >80% at a relatively low concentration of 30 nM, becoming one of the most potent and selective ERRα degraders to date. Compound 6c could be utilized as a new powerful research tool for further biological investigation of ERRα.

Pyrrolopyridone double-functional molecule compound based on Cereblon ligand induced BET degradation

The invention relates to a novel pyrrolopyridone double-functional molecule, and pharmaceutically acceptable salts, hydrates, prodrug thereof, and a pharmaceutical composition taking the novel pyrrolopyridone double-functional molecule as an active component, and applications of the above compounds and the pharmaceutical composition in treatment or prevention of tumor, inflammation, and immunity diseases. The double-functional molecule is a proteolytic targeting chimera (PROTAC); the preparation method is mature; connecting arms are adopted to connect BET protein small molecular inhibitors andCereblon protein ligand in E3 ubiquitin ligase complex so as to obtain the double-functional molecule; the obtained compound is capable of realizing selective induction of BET protein degradation; and the tumor prevention effect is obvious.

Pyrrolopyridone bifunctional molecular compound based on VHL ligand-induced BET degradation

The invention relates to a novel kind of pyrrolopyridone bifunctional molecule and its pharmaceutically acceptable salt, hydrate and prodrug and a pharmaceutical composition using the compounds as active ingredients, and application in the preparation of these compounds and their pharmaceutical composition and in the treatment or prevention of tumors, inflammation, diseases related immunity, etc.The bifunctional molecule involved in the invention is a proteolytic targeting chimera (PROTAC). A small molecule inhibitor of BET protein and a Von Hippel-Lindau (VHL) protein ligand in E3 ubiquitinligase complex are linked by a connecting arm to obtain the bifunctional molecule. The obtained compound can selectively induce the degradation of BET protein, and has significant anti-tumor effect.

Cereblon ligand mediated novel BET protein degradation bifunctional molecules, preparation and application thereof

The invention relates to a preparation method of new bifunctional small molecules and pharmaceutically acceptable salts, hydrates or prodrugs thereof, and application of the compounds and pharmaceutical compositions thereof in treatment of tumors, inflammation, immunity and other diseases. The bifunctional small molecules involved in the invention are protein degradation targeting chimeras (PROTACs), and can selectively induce BET protein degradation. According to the invention, a connecting arm is employed to connect a BET protein small molecule inhibitor and a cereblon protein ligand in theE3 ubiquitin ligase complex so as to obtain the bifunctional small molecules.

Cereblon ligand-induced BET degradation-based bifunctional molecule and preparation and application thereof

The invention relates to a novel preparation method of a bifunctional molecule and a pharmaceutically acceptable salt, hydrate or prodrug thereof and application of these compounds and a medicinal composition thereof in treatment of diseases such as tumors, inflammation and immunity. The bifunctional molecule is a protein degradation-targeted complex (PROTACs), and is capable of selectively inducing BET protein degradation. A BET protein small-molecule inhibitor is connected with a cereblon protein ligand in an E3 ubiquitin ligase complex to obtain the bifunctional molecule.