169744-02-9

Basic information

• Product Name: Carbamic acid, [2-[2-(2-aminoethoxy)ethoxy]ethyl]-, phenylmethyl ester
• CAS NO: 169744-02-9
• Molecular Formula: C14H22N2O4
• Molecular Weight: 282.34
• Mol File: 169744-02-9.mol

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [2-[2-(2-aminoethoxy)ethoxy]ethyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [2-[2-(2-aminoethoxy)ethoxy]ethyl]-, phenylmethyl ester(169744-02-9)
• EPA Substance Registry System: Carbamic acid, [2-[2-(2-aminoethoxy)ethoxy]ethyl]-, phenylmethyl ester(169744-02-9)

Safety Data

• Hazardous Substances Data: 169744-02-9(Hazardous Substances Data)

Upstream product

• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 929-59-9 3,6-dioxa-1,8-diaminooctane 
• 86520-52-7 2-[2-(2-azidoethoxy)ethoxy]ethanol 
• 205535-92-8 2-[2-{2-(N-benzyloxycarbonyl)aminoethoxy}ethoxy]ethanol 
• 6338-55-2 2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 885313-16-6 {2-[2-(2-benzyloxycarbonylamino-ethoxy)-ethoxy]-ethylamino}-acetic acid tert-butyl ester 
• 1590422-26-6 (8'-((2-boronobenzyl)amino)-3′,6′-dioxaaminooctyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide 

Relevant articles and documents

Microwave-Assisted Synthesis and Physicochemical Characterization of Tetrafuranylporphyrin-Grafted Reduced-Graphene Oxide

This work describes the design of a modified porphyrin that bears four furan rings linked by 1,2-bis-(2-aminoethoxy)ethane spacers. This unit is a well-suited scaffold for a Diels-Alder reaction with commercial reduced-graphene oxide, which is also described in this paper. A new hybrid material is obtained, thanks to efficient grafting under microwave irradiation, and fully characterized in terms of structure (UV, TGA, Raman) and morphology (HR-TEM and AFM). Potential applications in photo- and sonodynamic therapy are envisaged.

A MedChem toolbox for cereblon-directed PROTACs

A modular chemistry toolbox was developed for cereblon-directed PROTACs. A variety of linkers was attached to a CRBN ligand via the 4-amino position of pomalidomide. We used linkers of different constitution to modulate physicochemical properties. We equipped one terminus of the linker with a set of functional groups, e.g. protected amines, protected carboxylic acids, alkynes, chloroalkanes, and protected alcohols, all of which are considered to be attractive for PROTAC design. We also highlight different opportunities for the expansion of the medicinal chemists' PROTAC toolbox towards heterobifunctional molecules, e.g. with biotin, fluorescent, hydrophobic and peptide tags.

CONJUGATES COMPRISING SELF-IMMOLATIVE GROUPS AND METHODS RELATED THERETO

In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and an active agent. The antibody-drug conjugate may comprise a self- immolative group. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

CONJUGATES COMPRISING PEPTIDE GROUPS AND METHODS RELATED THERETO

In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and at least two active agents. In preferred embodiments, the linker comprises a peptide sequence of a plurality of amino acids, and at least two of the active agents are covalently coupled to side chains of the amino acids. The antibody-drug conjugate may comprise a self-immolative group, preferably two-self-immolative groups. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

Polylysine dendrimer contrast agent

The present invention relates generally to branched macromolecules and their use as imaging or contrast agents. In particular, the invention relates to dendrimers, derived from lysine or lysine analogs, bearing a plurality of functional moieties and their application to imaging techniques in which a disease state may be imaged with a targeted contrast agent.

Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

The molecular recognition of carbohydrates and proteins mediates a wide range of physiological processes and the development of synthetic carbohydrate receptors ("synthetic lectins") constitutes a key advance in biomedical technology. In this article we report a synthetic lectin that selectively binds to carbohydrates immobilized in a molecular monolayer. Inspired by our previous work, we prepared a fluorescently labeled synthetic lectin consisting of a cyclic dimer of the tripeptide Cys-His-Cys, which forms spontaneously by air oxidation of the monomer. Amine-tethered derivatives of N-acetylneuraminic acid (NANA), β-D-galactose, β-Dglucose and α-D-mannose were microcontact printed on epoxide-terminated self-assembled monolayers. Successive prints resulted in simple microarrays of two carbohydrates. The selectivity of the synthetic lectin was investigated by incubation on the immobilized carbohydrates. Selective binding of the synthetic lectin to immobilized NANA and β-D-galactose was observed by fluorescence microscopy. The selectivity and affinity of the synthetic lectin was screened in competition experiments. In addition, the carbohydrate binding of the synthetic lectin was compared with the carbohydrate binding of the lectins concanavalin A and peanut agglutinin. It was found that the printed carbohydrates retain their characteristic selectivity towards the synthetic and natural lectins and that the recognition of synthetic and natural lectins is strictly orthogonal.

MCR DENDRIMERS

The invention relates to a method for producing peptoidic, peptidic and chimeric peptidic-peptoidic dendrimers by multiple iterative multi-component reactions (MCR), in particular Ugi or Passerini multi-component reactions, to compounds produced in this way and to the use thereof.

Synthesis and characterization of well-defined lactic acid-PEG cooligomers and its tricarbonyl rhenium conjugates

This article describes the synthesis and characterization of hydroxyl tailored, molecularly defined biodegradable cooligomers capable of chelating rhenium for potential radiopharmaceuticals. New insights were gained during the synthesis of lactide based on dimethylaminopyridine-catalyzed transesterification.

Design and photophysical properties of new RGD targeted tetraphenylchlorins and porphyrins

The synthesis, characterization, fluorescence, and singlet oxygen quantum yields of tetraphenylporphyrin and tetraphenylchlorin coupled to RGD type peptide are reported. C-terminus protected RGD derivatives were synthesized in liquid phase at the gram scale via an efficient convergent process. C-terminus unprotected RGD derivatives were synthesized on solid support. The UV-vis, fluorescence, and singlet emission spectra showed that the photophysical properties of the photosensitizers were retained in all compounds and some of them are very promising for potential PDT applications.

Double functionalisation of carbon nanotubes for multimodal drug delivery

Multi-walled carbon nanotubes have been covalently functionalised via 1,3-dipolar cycloaddition of azomethine ylides with orthogonally protected amino functions that can be selectively deprotected and subsequently modified with drugs and fluorescent probe