32585-91-4

Usage

Uses

Used in Pharmaceutical Industry:
(E)-Methyl 3-(1H-pyrrol-2-yl)acrylate is used as a building block for the synthesis of various pharmaceuticals due to its potential biological activity and structural diversity. It contributes to the development of new drugs by providing a foundation for chemical modifications and enhancements.
Used in Agricultural Chemicals Industry:
In the agricultural chemicals sector, (E)-Methyl 3-(1H-pyrrol-2-yl)acrylate is utilized as a key component in the creation of novel compounds with potential applications in pest control, crop protection, and other agricultural advancements.
Used in Flavor and Fragrance Industry:
(E)-Methyl 3-(1H-pyrrol-2-yl)acrylate is used as an ingredient in the flavor and fragrance industry, capitalizing on its distinctive aromatic properties to enhance the sensory experience of various products.
Used in Materials Science and Polymer Chemistry:
(E)-Methyl 3-(1H-pyrrol-2-yl)acrylate also holds potential in materials science and polymer chemistry, where its structure and reactivity can be harnessed to develop new materials with specific properties, such as improved strength, flexibility, or chemical resistance.

Upstream product

• 1003-29-8 2-pyrrole aldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 1190426-25-5 methyl (E)-3-[N-(2-pyridylsulfonyl)pyrrol-2-yl]acrylate 
• 96-32-2 bromoacetic acid methyl ester 
• 1296137-11-5 tert-butyl (E)-2-(3-methoxy-3-oxoprop-1-en-1-yl)-1H-pyrrole-1-carboxylate 

Downstream Products

• 86012-83-1 Dimethyl 1H-Indole-4,6-dicarboxylate 
• 1296137-03-5 (E)-N-(4-(1-benzoylpiperidin-4-yl)butyl)-3-(1-(4-hydroxy-3-(hydroxymethyl)butyl)-1H-pyrrol-2-yl)acrylamide 
• 1296137-07-9 (E)-N-(4-(1-benzoylpiperidin-4-yl)butyl)-3-(1-methyl-1H-pyrrol-2-yl)acrylamide 
• 1296136-97-4 (E)-N-(4-(1-benzoylpiperidin-4-yl)butyl)-3-(1H-pyrrol-2-yl)acrylamide 
• 1451009-87-2 7-(3-(cyclohexanecarboxamido)propyl)-5,5-difluoro-1,3-dimethyl-5H-dipyrrolo[1,2-c:1',2'-f][1,3,2]diazaborinin-4-ium-5-uide 
• 1451009-84-9 7-(3-benzamidopropyl)-5,5-difluoro-1,3-dimethyl-5H-dipyrrolo[1,2-c:1',2'-f][1,3,2]diazaborinin-4-ium-5-uide 
• 1451009-80-5 5,5-difluoro-1,3-dimethyl-7-(3-(4-phenethyl-1H-1,2,3-triazol-1-yl)propyl)-5H-dipyrrolo[1,2-c:1',2'-f][1,3,2]diazaborinin-4-ium-5-uide 
• 1451009-89-4 5,5-difluoro-1,3-dimethyl-7-(3-(5-phenethyl-1H-1,2,3-triazol-1-yl)propyl)-5H-dipyrrolo[1,2-c:1',2'-f][1,3,2]diazaborinin-4-ium-5-uide 
• 69917-80-2 2-(2-methoxycarbonylethyl)-pyrrole 

Relevant academic research and scientific papers

Synthesis of 3′-BODIPY-labeled active esters of nucleotides and a chemical primer extension assay on beads

A solution-phase synthesis of active esters of 3′-fluoropho:relabeled deoxynucleoside 5′-monophosphates was developed for thymine and cytosine as nucleobases by using two different: BODIPY dyes. Starting from the respective 2′-amino2′,3′-dideoxynucleoside

Rate of Lipid Peroxyl Radical Production during Cellular Homeostasis Unraveled via Fluorescence Imaging

Reactive oxygen species (ROS) and their associated byproducts have been traditionally associated with a range of pathologies. It is now believed, however, that at basal levels these molecules also have a beneficial cellular function in the form of cell signaling and redox regulation. Critical to elucidating their physiological role is the opportunity to visualize and quantify the production of ROS with spatiotemporal accuracy. Armed with a newly developed, extremely sensitive fluorogenic α-tocopherol analogue (H4BPMHC), we report herein the observation of steady concentrations of lipid peroxyl radicals produced in live cell imaging conditions. Imaging studies with H4BPMHC indicate that the rate of production of lipid peroxyl radicals in HeLa cells under basal conditions is 33 nM/h within the cell. Our work further provides indisputable evidence on the antioxidant role of Vitamin E, as lipid peroxidation was suppressed in HeLa cells both under basal conditions and in the presence of Haber-Weiss chemistry, generated by the presence of cumyl hydroperoxide and Cu2+ in solution, when supplemented with the α-tocopherol surrogate, PMHC (2,2,5,7,8-pentamethyl-6-hydroxy-chromanol, an α-tocopherol analogue lacking the phytyl tail). H4BPMHC has the sensitivity needed to detect trace changes in oxidative status within the lipid membrane, underscoring the opportunity to illuminate the physiological relevance of lipid peroxyl radical production during cell homeostasis and disease.

A Synthetic Approach for the Rapid Preparation of BODIPY Conjugates and their use in Imaging of Cellular Drug Uptake and Distribution

A solid-phase synthetic (SPS) method was developed for the preparation of BODIPY-labeled bioactive compounds that allows for fast and simple synthesis of conjugates for use in fluorescent microscopy. The approach was used to visualize cellular uptake and

18F-Labeled BODIPY Dye: A Potential Prosthetic Group for Brain Hybrid PET/Optical Imaging Agents

There are few hybrid positron emission tomography (PET)/fluorescence imaging agents available for brain imaging. For this purpose, BODIPY dye is very attractive because one of its fluorine atoms can be readily exchanged with 18F, and it can be modified to produce red-shifted fluorescence. In this study, therefore, we synthesized and investigated a 18F-labeled red-shifted BODIPY dye as a prosthetic group for brain hybrid PET/optical imaging agents and determined the optimal dose of this radioligand for hybrid imaging. The red-shifted BODIPY dye (1) was synthesized, and one of its fluorine atoms was exchanged with 18F using SnCl4 in high yield. Partition coefficients of 18F-labeled BODIPY dye ([18F]1) and 1 were measured using its radioactivity and fluorescence, respectively, which were shown to be suitable for brain penetration. Optimal dose for hybrid imaging was determined by analysis of PET/CT and optical images of Balb/C nude mice injected with [18F]1 and 1, respectively. Hybrid PET/optical images of mice injected with optimal dose of [18F]1 showed strong radioactivity and fluorescence signal in the brain at 2 min after injection, with rapid clearance by 30 min. Tissue distribution data confirmed the in vivo and ex vivo PET/optical imaging data, indicating desirable brain pharmacokinetics of the radioligand. Taken together, the results of this study suggest that [18F]1 can be widely used as a prosthetic group for brain hybrid PET/optical imaging agents.

Part I: The development of the catalytic wittig reaction

We have developed the first catalytic (in phosphane) Wittig reaction (CWR). The utilization of an organosilane was pivotal for success as it allowed for the chemoselective reduction of a phosphane oxide. Protocol optimization evaluated the phosphane oxide precatalyst structure, loading, organosilane, temperature, solvent, and base. These studies demonstrated that to maintain viable catalytic performance it was necessary to employ cyclic phosphane oxide precatalysts of type 1. Initial substrate studies utilized sodium carbonate as a base, and further experimentation identified N,N-diisopropylethylamine (DIPEA) as a soluble alternative. The use of DIPEA improved the ease of use, broadened the substrate scope, and decreased the precatalyst loading. The optimized protocols were compatible with alkyl, aryl, and heterocyclic (furyl, indolyl, pyridyl, pyrrolyl, and thienyl) aldehydes to produce both di- and trisubstituted olefins in moderate-to-high yields (60-96 %) by using a precatalyst loading of 4-10 mol %. Kinetic E/Z selectivity was generally 66:34; complete E selectivity for disubstituted α,β-unsaturated products was achieved through a phosphane-mediated isomerization event. The CWR was applied to the synthesis of 54, a known precursor to the anti-Alzheimer drug donepezil hydrochloride, on a multigram scale (12.2 g, 74 % yield). In addition, to our knowledge, the described CWR is the only transition-/heavy-metal-free catalytic olefination process, excluding proton-catalyzed elimination reactions. A point of difference: By utilizing an organosilane to chemoselectively reduce a phosphane oxide precatalyst to a phosphane (see scheme), the first catalytic (in phosphane) Wittig reaction has been developed. The methodology has been applied to the synthesis of 22 disubstituted and 24 trisubstituted olefins, including a multigram synthesis of a precursor to the anti-Alzheimer drug donepezil hydrochloride.

Tunable BODIPY derivatives amenable to 'click' and peptide chemistry

Novel azido- and amino-functionalised fluorescent probes based on the BODIPY framework have been developed. The probes can be easily and cheaply synthesised, exhibit the highly desirable BODIPY fluorescent properties, and are amenable to 'click' and pepti

Design, synthesis and X-ray crystallographic study of NAmPRTase inhibitors as anti-cancer agents

NAmPRTase (PBEF/Visfatin) plays a pivotal role in the salvage pathway of NAD+ biosynthesis. NAmPRTase has been an attractive target for anti-cancer agents that induce apoptosis of tumor cells via a declining plasma NAD+ level. In this report, a series of structural analogs of FK866 (1), a known NAmPRTase inhibitor, was synthesized and tested for inhibitory activities against the proliferation of cancer cells and human NAmPRTase. Among them, compound 7 showed similar anti-cancer and enzyme inhibitory activities to compound 1. Further investigation of compound 7 with X-ray analysis revealed a co-crystal structure in complex with human NAmPRTase, suggesting that Asp219 in the active site of the enzyme could contribute to an additional interaction with the pyrrole nitrogen of compound 7.

PdII-catalysed C-H functionalisation of indoles and pyrroles assisted by the removable N-(2-pyridyl)sulfonyl group: C2-alkenylation and dehydrogenative homocoupling

The easily installed and removed N-(2-pyridyl)sulfonyl group exerts complete C2 regiocontrol over the PdII-catalysed C-H alkenylation of indoles and pyrroles, affording the corresponding products in good isolated yields (typically ≥ 70%). A remarkable feature of this catalyst system is that it tolerates a wide variety of substituted alkenes, including conjugated electrondeficient alkenes, styrenes and 1,3- dienes, as well as conjugated 1,1- and 1,2-disubstituted olefins. The final reductive desulfonylation affords the C2- substituted, free-NH indoles and pyrroles in good yield. This N-(2-pyridyl)- sulfonyl-directing strategy has also been extended to the development of a protocol for the intermolecular, dehydrogenative homocoupling of indoles, providing 2,2'-biindoles. Mechanistic work based upon reactions with isotopically labelled starting materials and competitive kinetic studies of electronically varied substrates suggests a chelation- assisted electrophilic aromatic substitution palladation mechanism.

Antidiabetic agents

The present invention provides compounds of Formula (I): wherein A, X, Q, Y, B, D, Z, and E have any of the values defined in the specification, and pharmaceutically acceptable salt thereof, that are useful as antidiabetic agents. Also disclosed are pharmaceutical compositions comprising one or more compounds of Formula I, processes for preparing compounds of Formula I, and intermediates useful for preparing compounds of Formula I.