34674-75-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Amino-5-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester is used as an intermediate in the synthesis of various pharmaceuticals for its potential pharmacological activities. It exhibits promising potential in the development of new drugs for the treatment of bacterial and fungal infections.
Used in Agrochemical Industry:
3-Amino-5-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester is also used in the field of agrochemicals, making it a versatile and valuable chemical compound in the agricultural industry.

Upstream product

• 16588-02-6 4-chloro-3-cyanonitrobenzene 
• 584-08-7 potassium carbonate 
• 623-51-8 ethyl 2-sulfanylacetate 
• 2365-48-2 Methyl thioglycolate 
• 34662-24-3 3-nitro-2-chlorobenzonitrile 
• 17417-09-3 2-fluoro-5-nitrobenzonitrile 
• 394-47-8 2-fluorobenzonitrile 

Downstream Products

• 348617-86-7 5-nitrobenzo[b]thiophen-3-amine 
• 348618-04-2 4-[(3-bromophenyl)amino]-8-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile 
• 348618-05-3 8-amino-4-[(3-bromophenyl)amino]-[1]benzothieno[3,2-b]pyridine-3-carbonitrile 

Relevant academic research and scientific papers

Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors

Microwave irradiation of 2-halobenzonitriles and methyl thioglycolate in the presence of triethylamine in DMSO at 130°C provides rapid access to 3-aminobenzo[b]thiophenes in 58-96% yield. This transformation has been applied in the synthesis of the thieno

Synthesis of a series of novel thieno-and benzothieno[3,2-d]pyrimidin-4(3H) -ones

A series of novel thieno- and benzothieno[3,2-d]pyrimidin-4(3H)-ones is synthesised via condensation of 3-amino(benzo)thiophene-2-carboxylates with various lactams. Georg Thieme Verlag Stuttgart New York.

Synthesis of a novel series of thieno[3,2-d]pyrimidin-4-(3H)-ones

2-Aminothieno[3,2-d]pyrimidin-4-ones were synthesized in one step by condensation of 3-amino(benzo)thiophene car-boxylate with chloroformamidine hydrochloride. Georg Thieme Verlag Stuttgart.

Structure and base catalysed cyclization of methyl (2,6-disubstituted-4-nitrophenylsulphanyl)ethanoates

The conformation of side chain - SCH2COOCH3 in title compounds in crystal agrees with the reactivity of these compounds in base catalysed ring closure in solution. In the 2,4-dinitro derivative, the side chain is oriented towards the

Structure-activity studies for a novel series of tricyclic substituted hexahydrobenz[e]isoindole α(1A) adrenoceptor antagonists as potential agents for the symptomatic treatment of benign prostatic hyperplasia (BPH)

In search of a uroselective agent that exhibits a high level of selectivity for the α(1A) receptor, a novel series of tricyclic hexahydrobenz[e]isoindoles was synthesized. A generic pharmacophoric model was developed requiring the presence of a basic amine core and a fused heterocyclic side chain separated by an alkyl chain. It was shown that the 6- OMe substitution with R, R stereochemistry of the ring junction of the benz[e]isoindole and a two-carbon spacer chain were optimal. In contrast to the highly specific requirements for the benz[e]isoindole portion and linker chain, a wide variety of tricyclic fused heterocyclic attachments were tolerated with retention of potency and selectivity. In vitro functional assays for the α1 adrenoceptor subtypes were used to further characterize these compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity.

Synthesis of [1]Benzothieno[3,2-d]pyrimidines Substituted with Electron Donating Substituents on the Benzene Ring

Various 2-fluorobenzonitriles were converted to the corresponding 3-amino[1]benzothiophenecarboxylic acid esters, which in turn were annulated with formamidine or various equivalents to produce the desired tricyclic benzothienopyrimidines. Various methoxy and nitro/amino substituants were placed on the phenyl ring, requiring several different strategies to prepare the desired benzothiophenes. Several different pyrimidone annulations were also required. The use of an electron rich 2-bromobenzonitrile in a four-step one-pot low temperature lithiation sequence to produce highly electron-rich amino[1]benzothiophenecarboxylate esters is also described. The synthesis of 7-amino-8-fluoro[1]benzothieno[3,2-d]pyrimid-4(3H)-one was relatively straightforward, but synthesis of the corresponding 7-amino-8-protio analogue proved to be very difficult, and required several approaches before a successful one was found.

TRICYCLIC SUBSTITUTED HEXAHYDROBENZ [E]ISOINDOLE ALPHA-1 ADRENERGIC ANTAGONISTS

The present invention relates to a compound of the formula STR1 and the pharmaceutically acceptable salts thereof wherein W is a tricyclic heterocyclic ring system; which is an α-1 adrenergic antagonist and is useful in the treatment of BPH; also disclosed are . alpha.-1 antagonist compositions and a method for antagonizing α-1 receptors and treating BPH.