2386-26-7

Usage

Uses

It is utilized as pharmaceutical intermediate.

InChI:InChI=1/C11H15NO3/c1-5-9(14)15-11-6(2)10(8(4)13)7(3)12-11/h12H,5H2,1-4H3

Upstream product

• 2199-44-2 3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 5408-08-2 ethyl 4-iodo-3,5-dimethyl-1H-pyrrole-2-carboxylate 
• 64-19-7 acetic acid 
• 141-97-9 ethyl acetoacetate 
• 64-17-5 ethanol 
• 123-54-6 acetylacetone 
• 14369-81-4 ethyl 2,3-butadienoate 
• 107-87-9 2-Pentanone 
• 70450-66-7 2-acetyl-3-oxo-butyraldehyde 1-enol tautomer 
• 5408-04-8 ethyl 2-hydroxyimino-3-oxobutanoate 
• 815-68-9 3-acetylpentane-2,4-dione 
• 110775-00-3 (E)-2-((Z)-1-Methyl-3-oxo-but-1-enylamino)-but-2-enoic acid ethyl ester 

Downstream Products

• 517-22-6 2,4-dimethyl-3-ethyl-pyrrole 
• 2386-25-6 2,4-dimethyl-3-acetylpyrrole 
• 2199-47-5 ethyl 3,5-dimethyl-4-ethylpyrrole-2-carboxylate 
• 2386-28-9 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid 
• 5463-44-5 ethyl 3,5-dimethyl-4-nitropyrrole-2-carboxylate 
• 384797-98-2 ethyl 3,5-dimethyl-4-[1-(2-phenylhydrazono)ethyl]-1H-pyrrole-2-carboxylate 
• 1355953-56-8 ClC₄H₃NCC₆H₅C₄N(CH₃)2CH₂CH₃ 
• 1355953-59-1 3-chloro-5,7-dimethyl-6-ethyl-8-phenyl-BODIPY 

Relevant academic research and scientific papers

Discovery of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as novel and potent bromodomain and extra-terminal (BET) inhibitors with anticancer efficacy

As epigenetic readers, bromodomain and extra-terminal domain (BET) family proteins bind to acetylated-lysine residues in histones and recruit protein complexes to promote transcription initiation and elongation. Inhibition of BET bromodomains by small molecule inhibitors has emerged as a promising therapeutic strategy for cancer. Herein, we describe our efforts toward the discovery of a novel series of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as BET inhibitors. Intensive structural modifications led to the identification of compound 35f as the most active inhibitor of BET BRD4 with selectivity against BET family proteins. Further biological studies revealed that compound 35f can arrest the cell cycle in G0/G1 phase and induce apoptosis via decreasing the expression of c-Myc and other proteins related to cell cycle and apoptosis. More importantly, compound 35f showed favorable pharmacokinetic properties and antitumor efficacy in MV4-11 mouse xenograft model with acceptable tolerability. These results indicated that BET inhibitors could be potentially used to treat hematologic malignancies and some solid tumors.

Rational design of fluorescent probes for targeted: In vivo nitroreductase visualization

Nitroreductase (NTR) has been recognized as a biomarker for identifying the hypoxic status of cancers. Therefore, it is of high scientific interest to design effective fluorescent probes for tracking NTR activity. However, studies on elucidation of the structure-performance relationship of fluorescent probes and those providing valuable insight into optimized probe design have rarely been reported. Three BODIPY based fluorescent probes were made by conjugation of para-, ortho-, and meta-nitrobenzene to the BODIPY core via a thiolether bond, respectively. Our study revealed that the linkage and nitro substituent position significantly influence the capability of nitroreductase detection.

SPIROBODIPYs with spiropyran structure compound, preparation method and its use

The invention discloses a SPIROBODIPYs compound with the spiropyrane structure. The compound has the following structural general formula (refer to the Specification), wherein R1, R2, R3 and R4 are alkyl substituents or aromatic substituents, R5 is an alkyl substituent, an alcohol hydroxyl substituent or a substituent with triple bonds at the tail end. The invention further discloses the application of the SPIROBODIPYs compound to a fluorescence molecular probe. The SPIROBODIPYs compound can be applied to controllable detection of physiological and pathological process of cells, and can be used for building living cell acid organelles or used as a novel fluorescent dye of a fluorescence molecular probe for detecting the acid environment of cancer cells.

Preparation, spectral and thermal properties of Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) complexes with iodosubstituted 2,2′-dipyrrolylmethene

Complexes [ML2] of cobalt(II), nickel(II), copper(II), zinc(II), and cadmium(II) with asymmetrically substituted (E)-3-ethyl-5-[(4-iodo-3,5- dimethyl-2H-pyrrol-2-ylidene)methyl]-2,4-dimethyl-1H-pyrrole (HL) have been prepared and characterized for the first time. The spectral properties, stability in solutions and in the solid phase at elevated temperature of the complexes have been studied. The effects of complexing metal ion and the reaction medium on the spectral luminescent properties (absorptivity, quantum yield, fluorescence lifetime, and the radiation constant) and on thermal destruction of the [ML2] complexes have been discussed.

Vinyl azides derived from allenes: Thermolysis leading to multisubstituted 1,4-pyrazines and Mn(III)-catalyzed photochemical reaction leading to pyrroles

Thermolysis of phosphorus-based vinyl azides under solvent- and catalyst-free conditions furnished a new route for 1,4-pyrazines. A simple one-pot, Mn(III)-catalyzed photochemical route has been developed for multisubstituted pyrroles starting from allenes and 1,3-dicarbonyls via in situ-generated vinyl azides. The utility of new phosphorus-based pyrroles is also demonstrated in the Horner reaction. The structures of key products are unequivocally confirmed by X-ray crystallography.

Synthesis and spectral properties of new 3,3'-bis(dipyrrolylmethene) with acetylene spacer

Bis(2,4,7,9-tetramethyl-8-ethyldipyrrolylmethen-3-yl)acetylene dihydrobromide (H2L·2HBr), new bis(dipyrrolylmethene), in whose molecule dipyrrolylmethene domains were connected through 3,3'-carbon atoms of internal pyrrole nuclei by acetylene spacer, were synthesized by original procedure. The compound was characterized by element analysis, IR, 1H NMR, and electronic spectroscopy. The comparative analysis of spectral properties shows the reduction of the basicity of H2L ligand in comparison with the structural analogs, which contain internal methylene spacer. The quantum-chemical simulation showed that the rigid acetylene spacer gives linear structure to the H2L molecule in contrast to the spiral-shaped geometry of structural analogs with-CH2-spacer. Pleiades Publishing, Ltd., 2010.

Design and development of a new pyrromethene dye with improved photostability and lasing efficiency: Theoretical rationalization of photophysical and photochemical properties

(Chemical Equation Presented) In an attempt to develop a photostable and efficient pyrromethene compound for use in liquid dye lasers, three congeners of the commercially available pyrromethene 567 (PM567) laser dye were synthesized and their photophysical properties, lasing efficiencies, and photochemical stabilities were studied. In general the presence of an aryl group at C-8 of the pyrromethene chromophore increased the photostability. One of the congeners possessing a C-8 trimethoxyphenyl moiety showed significantly improved lasing parameters than PM567. Compared to PM567, the photochemical stability of the new dye was 2-fold, while it showed an equivalent lasing efficiency to that of PM567 at a significantly lower concentration. The increased photostability of these new dye molecules could be explained by theoretical calculation on their capacity to generate singlet oxygen (1O2) and probability of reaction with 1O2. Our calculations were in agreement with the experimental results and indicated that a systematic design of new derivatives of pyrromethene chromophore might lead to improved laser dye molecules.

Phosphoric acid-promoted synthesis of 4-acylpyrrole-2-carboxylic esters and dipyrryl ketones from mixed anhydrides

An efficient synthesis of 4-acylpyrrole-2-carboxylic esters utilizing a phosphoric acid-catalyzed mixed anhydride system is described. The new route also enables the preparation of dipyrryl ketones and N-confused dipyrryl ketones.

Thermochemistry of substituted pyrroles

The heats of solution of a series of substituted pyrroles in benzene, carbon tetrachloride, chloroform, DMF, and pyridine were measured by a calorimetric method at 298.15 K.The influence of substituents in the pyrrole molecule on the energy parameters of solvation by organic solvents is discussed.

An efficient route to dipyrrinones: Synthesis of xanthobilirubic acid methyl ester

Structurally interesting and complicated dipyrrinones, such as xanthobilirubic acid methyl ester (9), can be synthesized on a large scale from simple, inexpensive starting materials like ethyl acetoacetate, 2,4-pentanedione (1) and ethyl acrylate in 8 steps with an average yield of 80% at each step and an overall 17% yield.