209395-32-4

Basic information

• Product Name: 1H-Pyrrole-2,5-dione,1-(2-propynyl)-(9CI)
• Synonyms: 1H-Pyrrole-2,5-dione,1-(2-propynyl)-(9CI);N-Propargylmaleimide;Propargyl-Maleimide
• CAS NO: 209395-32-4
• Molecular Formula: C₇H₅NO₂
• Molecular Weight: 135.1201
• Product Categories: AMINETERTIARY
• Mol File: 209395-32-4.mol

Chemical Properties

• Melting Point: 55.0 to 60.0 °C
• Boiling Point: 88°C/2mmHg(lit.)
• Appearance: /
• Density: 1.300±0.06 g/cm3(Predicted)
• PKA: -2.63±0.20(Predicted)
• CAS DataBase Reference: 1H-Pyrrole-2,5-dione,1-(2-propynyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-2,5-dione,1-(2-propynyl)-(9CI)(209395-32-4)
• EPA Substance Registry System: 1H-Pyrrole-2,5-dione,1-(2-propynyl)-(9CI)(209395-32-4)

Safety Data

• Hazardous Substances Data: 209395-32-4(Hazardous Substances Data)

Usage

Structure

A chemical compound containing a pyrrole ring fused with a maleimide ring, with a propynyl group attached to the pyrrole ring

Type

A derivative of maleimide, which is a cyclic imide

Usage

Commonly used in organic synthesis and polymer chemistry

Reactions

Known for its ability to undergo click chemistry reactions with other molecules containing azide groups, making it useful for bioconjugation and labeling applications in biological research

Potential applications

Development of new materials and pharmaceutical compounds.

Upstream product

• 1016984-64-7 2-(2-Propynyl)-3a,4,7,7a-tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione 
• 55750-49-7 N-ethoxycarbonylmaleinimide 
• 15430-52-1 prop-2-yn-1-amine hydrochloride 
• 108-31-6 maleic anhydride 
• 2450-71-7 Propargylamine 
• 55750-48-6 N-methoxycarbonylmaleimide 
• 557-24-4 maleamic acid 
• 541-59-3 maleiimide 
• 107-19-7 propargyl alcohol 
• 925893-61-4 maleic acid N-propargylmonoamide 
• 272449-71-5 2-(2-propynyl)-3α,4,7,7α-tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione 

Downstream Products

• 1207091-96-0 C₁₃H₁₆N₂O₅S 
• 1418018-18-4 1-benzyl-5-iodo-4-maleimidomethyl-1H-[1,2,3]triazole 
• 1418018-28-6 1-benzyl-5-[¹²⁵I]iodo-4-maleimidomethyl-1H-[1,2,3]triazole 
• 10478-33-8 1-(prop-2-yn-1-yl)pyrrolidine-2,5-dione 

Relevant articles and documents

Surface-modified upconverting microparticles and nanoparticles for use in click chemistries

A method is described for modifying the surface of upconverting microparticles (UCμPs) and nanoparticles (UCNPs) such that they become amenable to click chemistry. Respective reagents are presented and used in both kinds of particles, either directly or in combination with tetraethoxysilane. The particles also were labeled by using the click reaction, a) with fluorophores to yield materials that have emission colors that depend on the wavelength of excitation ; b) with maleinimido groups (so to obtain labels for thiols), and c)with biotin (to make them useful for affinity studies based on the biotin-streptavidin system). We believe that both the UCμPs and UCNPs have the potential of being used in numerous areas including upconversion imaging, biolabeling, and derivatization, but also in encoding and security.

Catalytic Asymmetric [4+2]-Cycloadditions Using Tropolones: Developments, Scope, Transformations, and Bioactivity

An organocatalyzed asymmetric [4+2]-cycloaddition between tropolones and electron-deficient dienophiles is presented. Complex and biologically interesting dihydrohomobarrelenone scaffolds are formed through a Diels–Alder reaction utilizing bifunctional Br?nsted-base catalysis, affording the corresponding bridged bicyclic cycloadducts in up to quantitative yields with good enantio- (up to 92 % ee) and diastereoselectivity (up to >20:1 d.r.). The synthetic value of the obtained products is explored by downstream transformations, including photoisomerizations, and their biological relevancy by in vivo testing in MCF-7 cancer cells.

Bridging cells of three colors with two bio-orthogonal click reactions

Cell-cell interactions play a crucial role in the development and function of multicellular organisms. To study cell-cell interactions in vitro, it is a big challenge for researchers to artificially build up cell junctions to bridge different types of cells for this purpose. Herein, by employing two orthogonal click reactions, we rationally designed four click reagents Mal-CBT, Mal-Cys, Mal-Alkyne, and Mal-N3 and successfully applied them to bridge cells of three colors. Orthogonality between these two click reactions was validated in solution and characterized with HPLC and ESI-MS analyses. After modifications of fluorescent protein-expressing prokaryotic Escherichia coli (E. coli) cells (or eukaryotic HEK 293T cells) of three colors with the reagents Mal-Cys, Mal-CBT and Mal-Alkyne, or Mal-N3, the cells were sequentially bridged. The HEK 293T cells showed a higher efficiency of cell bridging than the E. coli cells. Finally, using optical tweezers, we quantitatively measured the bridging probability between Mal-Cys-modified and Mal-CBT-modified HEK 293 cells, as well as the rupture force between two bridged cells. We found that the CBT-Cys click reaction markedly improved the efficiency of cell bridging and the rupture force between two bridged cells was measured to be 153.8 pN at a force-loading rate of 49 pN s-1. Our results demonstrate that it is possible to use two (or n) orthogonal click reactions to bridge three (or n + 1) types of cells. Taking the biological importance of cell junctions into consideration, we anticipate that our method of bridging three types of cells with two bio-orthogonal click reactions will be a useful tool for biologists to study cell-cell interactions with more convenience and efficiency.

Diacetylene-Based C 2h-Symmetric Monomers for Two-Dimensional-Polymer Synthesis

Two linear monomers with two terminal photoreactive groups (anthracene or maleimide) embedded in a diacetylene skeleton were synthesized for two-dimensional-polymer synthesis. Both of them were crystallized and their single-crystal structures were solved. It was found that the size of terminal groups can be critical for diacetylene's arrangement. The crystal structure of dimaleimide monomer revealed that maleimide groups strongly stacking in antiparallel and the photo-induced [2+2] cycloaddition of stacked maleimides was preliminary studied.

Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes

The ligation of gold(I) metalloamphiphiles with biomolecules is reported, using water-soluble AuI-N-alkynyl substituted maleimide complexes. For this purpose, two different polar ligands were applied: 1) a neutral, dendritic tetraethylene glycol-functionalized phosphane and 2) a charged, sulfonated N-heterocyclic carbene (NHC). The retro Diels–Alder reaction of a furan-protected maleimide gold(I) complex, followed by cycloaddition with a diene-functionalized biotin under mild conditions leads to a novel gold(I) metalloamphiphile. The strong streptavidin–biotin binding affinity in buffered aqueous solution of the resulting biotin alkynyl gold(I) phosphane conjugate remains intact. The cytotoxicity of the biotinylated gold(I) complex against a T47D human breast cancer cell line is higher than for cisplatin.

Rationally Designed Solvatochromic Fluorescent Indoline Derivatives for Probing Mitochondrial Environment

A new class of solvatochromic, robust, and multifunctional fluorescent probes derived from indoline is presented. Specificity of mitochondria targeting was achieved and utilized for probing polarity under normal and apoptotic conditions. A large Stokes shift, high quantum yield, thermal, photochemical, and pH stability, tolerance to buffer compositions, and a bioconjugation tool-kit make it a promising candidate for live-cell fluorescence imaging.

AMATOXIN DERIVATIVES AND CONJUGATES THEREOF AS INHIBITORS OF RNA POLYMERASE

The invention disclosed herein relates to cytotoxic cyclic peptides of Formula (A), methods of inhibiting RNA polymerase with such cyclic peptides, immunoconjugates comprising such cyclic peptides (i.e Antibody Drug Conjugates), pharmaceutical compositions comprising such cyclic peptides immunoconjugates, compositions comprising such cyclic peptides immunoconjugates with a therapeutic co-agent and methods of treatment using such cyclic peptides immunoconjugates.

AMATOXIN DERIVATIVES AND CONJUGATES THEREOF AS INHIBITORS OF RNA POLYMERASE

The invention disclosed herein relates to cytotoxic cyclic peptides of Formula (I), methods of inhibiting RNA polymerase with such cyclic peptides, immunoconjugates comprising such cyclic peptides (i.e Antibody Drug Conjugates), pharmaceutical compositions comprising such cyclic peptides immunoconjugates, compositions comprising such cyclic peptides immunoconjugates with a therapeutic co-agent and methods of treatment using such cyclic peptides immunoconjugates: Formula (I).

Chemo- And diastereoselectivities in the electrochemical reduction of maleimides

The electrochemical cathodic reduction of cyclic imides (maleimides) to succinimides can be achieved chemoselectively in the presence of alkene, alkyne, and benzyl groups. The efficiency of the system was demonstrated by using a 3D electrode in a continuous flow reactor. The reduction of 3,4-dimethylmaleimides to the corresponding succinimides proceeds with a 3:2 diastereomeric ratio, which is independent of the nitrogen substituent and electrode surface area. The stereoselectivity of the process was rationalized by using DFT calculations, involving an acid-catalyzed tautomerization of a half-enol occurring through a double hydrogen-transfer mechanism.

HIGH MOLECULAR WEIGHT ZWITTERION-CONTAINING POLYMERS

The present invention provides multi-armed high MW polymers containing hydrophilic groups and one or more functional agents, and methods of preparing such polymers.