82782-85-2

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE, 97+% is used as a building block for the synthesis of complex organic molecules, particularly in the development of new drugs. Its unique structure and reactivity may contribute to the discovery of novel therapeutic agents with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, METHYL 4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE, 97+% may be utilized as a key intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical properties can be harnessed to create new compounds with enhanced pesticidal or herbicidal activity.
Used in Material Science:
METHYL 4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE, 97+% can be employed in material science for the development of novel materials with unique properties. Its heterocyclic structure and reactivity may be leveraged to create new polymers, coatings, or other materials with improved performance characteristics, such as enhanced stability, conductivity, or biocompatibility.

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 1816-92-8 Methyl azidoacetate 
• 39793-31-2 4H-thieno[3,2-b]pyrrole-5-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 439113-19-6 methyl 2-azido-3-(thiophen-2-yl)acrylate 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 368442-47-1 3-(tert-butoxycarbonylamino)-2-thiophenecarboxaldehyde 
• 102244-89-3 β-(2-Thienyl-)-α-azidoacrylsaeuremethylester 

Downstream Products

• 892404-18-1 4-(2-oxo-2-phenyl-ethyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid methyl ester 
• 892406-73-4 methyl 4-(2-oxopropyl)-4H-thieno[3,2-b]pyrrole-5-carboxylate 
• 1007388-64-8 methyl 6-[(dimethylamino)methyl]-4H-thieno[3,2-b]pyrrole-5-carboxylate 
• 1007388-98-8 methyl 2-[(dimethylamino)methyl]-4H-furo[3,2-b]pyrrole-5-carboxylate 
• 1163132-87-3 [4-(4-Fluorobenzyl)-4H-thieno[3,2-b]pyrrol-5-yl][4-(morpholine-4-carbonyl)piperidin-1-yl]methanone 
• 1047023-77-7 ethyl 1-(4-(4-fluorobenzyl)-4H-thieno[3,2-b]pyrrole-5-carbonyl)-piperidine-4-carboxylate 
• 903165-55-9 C₂₀H₁₉FN₂O₃S 
• 897774-27-5 C₁₄H₁₀FNO₂S 
• 897767-45-2 methyl N-(4-fluoro)benzyl-4H-thieno[3,2-b]pyrrole carboxylate 
• 1369487-28-4 (S)-1-(4-(4-fluorobenzyl)-4H-thieno[3,2-b]pyrrole-5-carbonyl)-N-(1-phenylethyl)piperidine-4-carboxamide 
• 1369487-29-5 (R)-1-(4-(4-fluorobenzyl)-4H-thieno[3,2-b]pyrrole-5-carbonyl)-N-(1-phenylethyl)piperidine-4-carboxamide 
• 1369487-30-8 (R)-N-benzyl-1-(4-(1-(4-fluorophenyl)ethyl)-4H-thieno[3,2-b]pyrrole-5-carbonyl)piperidine-4-carboxamide 
• 1369487-31-9 (S)-N-benzyl-1-(4-(1-(4-fluorophenyl)ethyl)-4H-thieno[3,2-b]pyrrole-5-carbonyl)piperidine-4-carboxamide 
• 924643-46-9 4-(4-chlorobenzyl)-4H-thieno[3,2-b] pyrrole-5-carboxylic acid 

Relevant academic research and scientific papers

Synthesis of Photochromic 1,2-Dihetarylethene Using Regioselective Acylation of Thienopyrroles

(Matrix Presented) The influence of catalysts, acid chlorides, and solvents in the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. Conditions for the regioselective acylation processes were found. Thienopyrrole-based photoc

Discovery of thienopyrrolotriazine derivatives to protect mitochondrial function against Aβ-induced neurotoxicity

Recovery of mitochondrial dysfunction has gained increasing attention as an alternative therapeutic strategy for Alzheimer's disease (AD). Recent studies suggested that the 18 kDa mitochondrial translocator protein (TSPO) has the potential to serve as a drug target for the treatment of AD. In this study, we generated a structure-based pharmacophore model and virtually screened a commercial library, identifying SVH07 as a virtual hit, which contained a tricyclic core structure, thieno[2′,3’:4,5]pyrrolo[1,2-d][1,2,4]triazine group. A series of SVH07 analogues were synthesized and their effects on the mitochondrial membrane potential and ATP production were determined by using neuronal cells under Aβ-induced toxicity. Among these analogues, compound 26 significantly recovered mitochondrial membrane depolarization and ATP production. In vitro binding assays indicated that SVH07 and 26 showed high affinities to TSPO with the IC50 values in a nanomolar range. We believe that compound 26 is a promising lead compound for the development of TSPO-targeted mitochondrial functional modulators with therapeutic potential in AD.

Regioselective acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5- carboxylate

The influence of catalysts, acid chlorides, and solvents on the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. The use of AlCl3 allows the regioselective introduction of the acyl group into position 3 to be performed, whereas the acyl group is regioselectively introduced into position 6 of thienopyrrole when SnCl4 is used.

SUBSTITUTED BICYCLIC HETEROARYL COMPOUNDS

Disclosed are compounds of Formula (I) N-oxides, or salts thereof, wherein X, Y, A, G, R1, and R5 are defined herein. Also disclosed are methods of using such compounds as inhibitors of signaling through Toll-like receptor 7, or 8, or 9, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating inflammatory and autoimmune diseases.

Synthesis and characterization of S,N-heterotetracenes

The synthesis and optoelectronic properties of novel S,N-heterotetracenes consisting of fused heterocyclic thiophene and pyrrole rings are presented. Tetracyclic and benzannulated derivatives with a varying number and sequence of sulfur and nitrogen heteroatoms were synthesized in multistep synthetic routes. A Buchwald-Hartwig amination of brominated precursors, thermolysis of azide precursors, and a Cadogan reaction of nitro-substituted precursors were successfully applied to eventually build-up pyrrole rings to stable and soluble fused systems. The various obtained heteroatom sequences 'SSNS' (SN4), 'SNNS' (SN4''), and 'NSSN' (SN4') allowed for evaluation of structure-property relationships relative to the sulfur analogue tetrathienoacene ('SSSS'). In line with the results for the whole series of S,N-heteroacenes, we find that replacement of sulfur by nitrogen atoms in the tetra- and hexacyclic systems leads to a red-shift in absorption, a decrease in oxidation potential and energy gap. On the other hand, the replacement of a thiophene ring by benzene leads to the opposite effects.

Divergent synthesis of indole-2-carboxylic acid derivatives via ligand-free copper-catalyzed ullmann coupling reaction

— This article describes a ligand-free copper-catalyzed Ullmami coupling reaction for the preparation of divergent indole-2-carboxylic acid derivatives including esters, amides and anhydrides. Various compounds 3, which could be synthesized from aldehydes conveniently, were used as substrate to provide the corresponding indole-2-carboxylic acid derivatives in moderate to good vields.

Chemical Evolution of a Bacterial Proteome

We have changed the amino acid set of the genetic code of Escherichia coli by evolving cultures capable of growing on the synthetic noncanonical amino acid L-β-(thieno[3,2-b]pyrrolyl)alanine ([3,2]Tpa) as a sole surrogate for the canonical amino acid L-tryptophan (Trp). A long-term cultivation experiment in defined synthetic media resulted in the evolution of cells capable of surviving Trp→[3,2]Tpa substitutions in their proteomes in response to the 20 899 TGG codons of the E. coli W3110 genome. These evolved bacteria with new-to-nature amino acid composition showed robust growth in the complete absence of Trp. Our experimental results illustrate an approach for the evolution of synthetic cells with alternative biochemical building blocks.

Synthesis and properties of semiconducting bispyrrolothiophenes for organic field-effect transistors

A series of new highly soluble bispyrrolothiophenes were synthesized from vinyl azides by using transition-metal-catalyzed C-H-bond functionalization. In addition to modifying the substituents present on the end-pyrrolothiophene moieties, the arene linker in between the two units was also varied. The solution-state properties and field-effect-transistor (FET) electrical behavior of these bispyrrolothiophenes was compared. Our investigations identified that the optical properties and oxidation potential of our compounds were dominated by the pyrrolothiophene unit with a λmax value of approximately 400 nm and oxidation at approximately 1 V. FET devices constructed with thin films of these bispyrrolothiophenes were also fabricated by means of thin-film solution processing. One of these compounds, a bispyrrolothiophene linked with benzothiodiazole, exhibits a mobility of approximately 0.3 cm 2V-1s-1 and the Ion/Ioff value is greater than 106. Highly soluble bispyrrolothiophenes have been synthesized from vinyl azides by using transition-metal-catalyzed C-H bond functionalization (see scheme; TFT=thin-film transistor). The solution-state properties and field-effect-transistor (FET) electrical behavior of these compounds were investigated.

Novel inhibitors of neurotropic alphavirus replication that improve host survival in a mouse model of acute viral encephalitis

Arboviral encephalitis is a potentially devastating human disease with no approved therapies that target virus replication. We previously discovered a novel class of thieno[3,2-b]pyrrole-based inhibitors active against neurotropic alphaviruses such as western equine encephalitis virus (WEEV) in cultured cells. In this report, we describe initial development of these novel antiviral compounds, including bioisosteric replacement of the 4H-thieno[3,2-b]pyrrole core with indole to improve metabolic stability and the introduction of chirality to assess target enantioselectivity. Selected modifications enhanced antiviral activity while maintaining low cytotoxicity, increased stability to microsomal metabolism, and also revealed striking enantiospecific activity in cultured cells. Furthermore, we demonstrate improved outcomes (both symptoms and survival) following treatment with indole analogue 9h (CCG-203926) in an in vivo mouse model of alphaviral encephalitis that closely correlate with the enantiospecific in vitro antiviral activity. These results represent a substantial advancement in the early preclinical development of a promising class of novel antiviral drugs against virulent neurotropic alphaviruses.

HETEROCYCLIC INHIBITORS OF AN Hh-SIGNAL CASCADE, MEDICINAL COMPOSITIONS BASED THEREON AND METHODS FOR TREATING DISEASES CAUSED BY THE ABERRANT ACTIVITY OF AN Hh-SIGNAL SYSTEM

The invention relates to novel heterocyclic compounds and to the use thereof, to pharmaceutical compositions containing said chemical compounds as an active ingredient and to the use thereof for producing medicinal preparations for the human being and warm-blood animals for treating diseases caused by the aberrant activity of an Hedgehog (Hh)-signal system, in particular oncological diseases. The invention also relates to the use of the above-mentioned compounds in the form of ‘molecular pharmacological tools’ for examining (in vitro and in vivo) the biochemical features of the Hh-signal system, in particular, the interaction of Hh protein and transmembrane proteins, namely, suppressor Patched (Ptc) and protooncogenic proteins. The eight groups of the claimed compounds comprise the derivatives of 2,6-dihydro-7H-pyrazolo[3,4-d]pyridazine-7-one and 1,4-dihydropyrazolo[3,4-b][1,4]thiazine-5-one; N-acidylated 4-imidazo[1,2-a]pyrimidine-2-il-anilines; ([4H-thino[3,2-b]pyrrol-5-il) carbonyl]piperidine-4-carbonic acid amides; 2-(4carbomoilpyperidine-1-il)-isonicotinic acid amides; N-sylphonyl-1,2,3,4-tetrahydroquinoline-6-carbonic acid amides; and pyridine 2-amino-4,5,6,7-tetrahydrothieno[2,3-c] N-acidylated 3-azole derivatives.