Name: 2-(2-(2-(Prop-2-yn-1-yloxy)ethoxy)ethoxy)acetic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

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$--

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Purity

≥95%

Storage

Store at 2-8°C

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Room temperature in continental US; may vary elsewhere.

IUPACName

2-[2-(2-prop-2-ynoxyethoxy)ethoxy]acetic acid

Synonyms

Propargyl-PEG3-CH2COOH; Propargyl-PEG2-CH2COOH; Acetic acid, 2-[2-[2-(2-propyn-1-yloxy)ethoxy]ethoxy]-; 2-[2-[2-(2-Propyn-1-yloxy)ethoxy]ethoxy]acetic Acid; {2-[2-(2-Propyn-1-yloxy)ethoxy]ethoxy}acetic acid

Boiling Point

334.9±27.0°C (Predicted)

Density

1.158±0.06 g/cm3 (Predicted)

InChI Key

FWONAGPFSKACQC-UHFFFAOYSA-N

InChI

InChI=1S/C9H14O5/c1-2-3-12-4-5-13-6-7-14-8-9(10)11/h1H,3-8H2,(H,10,11)

SMILES

C#CCOCCOCCOCC(=O)O

1. Discovery of +(2-{4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}-cyclopropyl)acetic acid as potent and selective alphavbeta3 inhibitor: design, synthesis, and optimization

Srinivasan R Nagarajan, Hwang-Fun Lu, Alan F Gasiecki, et al. Bioorg Med Chem. 2007 May 15;15(10):3390-412.doi: 10.1016/j.bmc.2007.03.020.Epub 2007 Mar 13.

The integrin alpha(v)beta(3) is expressed in a number of cell types and is thought to play a major role in several pathological conditions. Various small molecules that inhibit the integrin have been shown to suppress tumor growth and retinal angiogenesis. The tripeptide Arg-Gly-Asp (RGD), a common binding motif in several ligands that bind to alpha(v)beta(3), has been depeptidized and optimized in our efforts toward discovering a small molecule inhibitor. We recently disclosed the synthesis and biological activity of several small molecules that did not contain any peptide bond and mimic the tripeptide RGD. The phenethyl group in one of the lead compounds was successfully replaced with a cyclopropyl moiety. The new lead compound was optimized for potency, selectivity, and for its ADME properties. We describe herein the discovery, synthesis, and optimization of cyclopropyl containing analogs that are potent and selective inhibitors of alpha(v)beta(3).

2-(2-(2-(Prop-2-yn-1-yloxy)ethoxy)ethoxy)acetic acid, is designed to provide a flexible polyether spacer terminating in a carboxylic acid handle. Its ether-rich backbone supports productive spatial orientation between the target-binding and E3-recruiting ligands, while the terminal acid enables robust conjugation strategies commonly used in targeted protein degradation workflows. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains a carboxylic acid and multiple ether linkages arranged in a flexible polyether chain, with a terminal propargyl ether functionality. It features an alkyne embedded in an ether substituent and a terminal carboxyl group suitable for amide or ester formation. Overall polarity and hydrogen-bonding capacity are consistent with polyether–acid linkers used in PROTAC architectures.

Reactivity: The carboxylic acid can be activated for coupling to amine- or hydrazide-bearing ligands via standard peptide-coupling chemistries, typically using carbodiimide-based activators with additives in polar aprotic solvents. The propargyl (alkyne) handle supports bioorthogonal conjugation approaches such as azide–alkyne cycloaddition under copper(I) catalysis or copper-free conditions, depending on substrate compatibility. Reaction planning should account for base sensitivity of the ether chain and the need to preserve alkyne integrity during activation steps.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂