146137-95-3

Usage

Uses

Used in Pharmaceutical Industry:
6-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with unique molecular structures. Its incorporation into drug molecules can potentially enhance their therapeutic effects and selectivity.
Used in Agrochemical Industry:
In the agrochemical sector, 6-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is utilized as a building block for the creation of novel agrochemicals, aiming to improve the efficacy and selectivity of pesticides and other agricultural chemicals.
Used in Organic Chemistry Research:
6-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER serves as a valuable compound in organic chemistry research, where it is employed to explore new reactions and mechanisms, potentially leading to the discovery of innovative synthetic pathways and the creation of new organic molecules.
Used in Drug Discovery:
6-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is used as a starting material in drug discovery processes, where its unique structural features and reactivity are leveraged to design and develop new pharmaceutical agents with potential therapeutic benefits.
These applications highlight the versatility and importance of 6-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER in various scientific and industrial fields, emphasizing its role in advancing chemical knowledge and contributing to the development of new and improved products.

InChI:InChI=1/C11H7NO2S/c1-14-11(13)10-5-8-3-2-7(6-12)4-9(8)15-10/h2-5H,1H3

Upstream product

• 2365-48-2 Methyl thioglycolate 
• 105942-10-7 3-fluoro-4-formylbenzonitrile 
• 90178-78-2 2-nitro-4-cyano-benzaldehyde 
• 403-54-3 m-Fluorobenzonitrile 
• 181282-72-4 3-amino-6-cyanobenzo[b]thiophene-2-carboxylic acid methyl ester 
• 146137-82-8 3-fluoro-4-formyl-2-(trimethylsilyl)benzonitrile 

Downstream Products

• 105212-28-0 6-Cyanbenzothiophen-2-carbonsaeure 
• 154650-81-4 benzo[b]thiophene-6-carbonitrile 
• 634903-62-1 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-(5-phenyl-1,2,4-oxadiazol-3-yl)-1-benzothiophene-2-carboxamide hydrochloride 
• 634903-63-2 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-(5-benzyl-1,2,4-oxadiazol-3-yl)-1-benzothiophene-2-carboxamide hydrochloride 

Relevant academic research and scientific papers

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.

GEMINAL SUBSTITUTED QUINUCLIDINE AMIDE COMPOUNDS AS AGONISTS OF ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTORS

The present invention relates to novel geminal substituted quinuclidine amide compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of α7- nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

Benzo[b]thiophene-2-carboxamide derivatives as potent urotensin-II receptor antagonists

Members of a series of benzo[b]thiophene-2-carboxamide derivatives, possessing an N-(1-(3-bromo-4-(piperidin-4-yloxy)benzyl)piperidin-4-yl) group, were synthesized and evaluated as urotensin-II receptor antagonists. The results show that these substances have potent UT binding affinities. Observations made in a systematic SAR investigation of the effects of a variety of substituents (R1and R2) at the 5- and 6-positions in the benzo[b]thiophene-2-carboxamide moiety on UT binding affinities led to identification of the 5-cyano analog 7f as a highly potent UT antagonist with an IC50value of 25?nM. Despite having a good metabolic stability, 7f is a potent inhibitor of CYP isozyme and displays an unsuitable PK profile.

AMIDE COMPOUNDS, COMPOSITIONS AND USES THEREOF

Compounds are provided according to formula (1 ) : where A, B, W, X', L, R1, R3, R4b, and m' are as defined herein. Provided compounds and pharmaceutical compositions thereof are useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, cognitive disorders, anxiety, depression, and others.

Discovery of a new series of potent and selective linear tachykinin NK 2 receptor antagonists

Starting from 1 (MEN 14268), a selective tachykinin NK2 receptor antagonist with an interesting in vitro pharmacological profile, a family of numerous antagonists was obtained through an optimization process focused on iterated structural modifications. The effects of the introduction of a wide variety of substituents on the lipophilic aromatic part of the molecule and the modulation of the structural constraint through the insertion of different achiral α,α-dialkylamino acids were investigated. In particular, aromatic and benzofused heteroaromatic moieties were introduced at the pseudo-N-terminal residue to replace the 2-benzothiophene moiety, and a systematic investigation of the best positioning of substituents onto the aromatic platform was reported for the benzothiophene core. Studies on the modulation of the length and the rigidity of the hydrophilic pseudo-C-terminal pendant are presented. Many heteroaliphatic groups are well tolerated by the receptor in this part of the ligand. The product 48f (MEN15596), bearing a methyl substituent on the benzothiophene and a tetrahydropyranylmethylpiperidine pendant, was finally selected for its good in vivo activity after intravenous, intraduodenal, and oral administration in guinea pigs.

2-HETEROARYL CARBOXAMIDES

The invention relates to the novel 2-heteroaryl carboxamides according to formula (I), wherein R1 represents 1-aza-bicyclo [2.2.2]oct-3-yl, which is optionally replaced via the nitrogen atom by a group selected from the family C1-C4 alkyl, benzyl and oxy, A represents oxygen or sulfur, the ring B represents benzo or pyrido that are optionally replaced by the groups from the family of halogen, cyano, formyl, trifluoromethyl, trifluoromethoxy, nitro, amino, C1-C6 alkyl and C1-C6 alkoxy, E represents C=C, aryl and heteroaryl, wherein aryl and heteroaryl may be replaced by groups from the family of halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, amino, C1-C6 alkoxy and C1-C6 alkyl, and to the solvents, salts or solvents of salts of said compounds. The invention also relates to the use of said compounds in the production of drugs for the treatment and/or the prophylaxis of diseases and for improving perception, power of concentration, learning power and/or retentiveness of memory.

UROKINASE INHIBITORS

Disclosed are benzothiophene and thienothiophene derivatives useful for inhibiting urokinase activity.

Fluorine as an ortho-directing group in aromatic metalation: A two step preparation of substituted benzo[b] thiophene-2-carboxylates

A simple 2-step synthesis of B-ring substituted benzo[b]thiophene-2-carboxylates from aryl fluorides has been developed. The route involves a selective lithiation ortho to fluorine, followed by formylation, and subsequently, displacement of fluorine with