272-14-0

Usage

Uses

Used in Pharmaceutical Industry:
Thieno[3,2-c]pyridine is used as an intermediate for the synthesis of Ticlopidine, a medication primarily used to reduce the risk of stroke and blood clots in patients with certain medical conditions. It functions as an antagonist of the platelet membrane glycoprotein IIb/IIIa receptor, inhibiting platelet aggregation and thus reducing the likelihood of clot formation.
Additionally, Thieno[3,2-c]pyridine derivatives are employed as intermediates in the development of drugs for the treatment of inflammatory disorders. These derivatives have demonstrated potential in modulating the immune response and reducing inflammation, making them valuable in the treatment of conditions such as arthritis, asthma, and other autoimmune diseases.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 13, p. 1347, 1976 DOI: 10.1002/jhet.5570130643

InChI:InChI=1/C7H5NS/c1-3-8-5-6-2-4-9-7(1)6/h1-5H

Upstream product

• 58754-96-4 N-(2,2-dimethoxyethyl)-4-methyl-N-3-(thienylmethyl)benzenesulfonamide 
• 55390-13-1 C₉H₁₃NO₂S 
• 58754-97-5 (2,2-dimethoxy-ethyl)-thiophen-3-ylmethyl-amine 
• 41057-09-4 2-Vinylthiophene-3-carbaldehyde 
• 92642-98-3 2-Vinylthiophene-3-carbaldehyde Ethylene Acetal 
• 60249-07-2 ethyl thieno<3,2-c>pyridine-6-carboxylate 
• 61962-72-9 7-methoxy-4,5,6,7-tetrahydro-thieno(3,2-c)pyridine hydrochloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 73099-88-4 5-(2-chloro-benzyl)-thieno[3,2-c]pyridinium; bromide 
• 58754-98-6 N-(2,2-dimethoxyethyl)-4-methyl-N-(thiophen-2-ylmethyl)benzenesulfonamide 
• 58754-99-7 dimethoxy-N-(thiophen-2-ylmethyl)ethanamine 
• 98-03-3 thiophene-2-carbaldehyde 
• 28783-41-7 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride 
• 54903-50-3 4,5,6,7-tetrahydrothieno[3,2-c]pyridine 

Downstream Products

• 55142-80-8 5-(3-methyl-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 55142-97-7 5-(3,5-dimethoxy-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 55142-79-5 5-(2-methyl-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 55142-90-0 5-(3,4-dichloro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 55143-02-7 5-(2-nitro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 55142-78-4 5-benzyl-4,5,6,7-tetrahydro-thieno[3,2-c]-pyridine 
• 55157-56-7 5-(4-chloro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 53885-46-4 5-(2-fluoro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 54943-17-8 5-(2-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 55142-82-0 5-(4-methyl-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 55142-93-3 5-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 55142-92-2 5-(3-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 55142-86-4 5-(3-chloro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 55142-84-2 5-(4-fluoro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 

Relevant academic research and scientific papers

Design, synthesis, and antifibrosis evaluation of 4-(benzo-[c][1,2,5]thiadiazol-5-yl)-3(5)-(6-methyl- pyridin-2-yl)pyrazole and 3(5)-(6-methylpyridin- 2-yl)-4-(thieno-[3,2,-c]pyridin-2-yl)pyrazole derivatives

Six series of 4-(benzo[c][1,2,5]thiadiazol-5-yl)-3(5)-(6-methylpyridin-2-yl)- pyrazoles 18a–d, 19a–d, 22a–d and 3(5)-(6-methylpyridin-2-yl)-4-(thieno[3,2,-c]- pyridin-2-yl)pyrazoles 20a–d, 21a–d, 23c, 23d have been synthesized and evaluated for their activin receptor-like kinase 5 (ALK5) and p38α mitogen activated protein (MAP) kinase inhibitory activities in enzymatic assays. Among these compounds, the most active compound, 22c, inhibited ALK5 phosphorylation with an IC50 value of 0.030 μM in the enzymatic assay. Compound 22c showed four-fold more potent activity against ALK5 kinase than the clinical candidate, compound LY-2157299. The selectivity index of 22c against p38α MAP kinase is 235, which is much higher than that of LY-2157299 (4) and equally selective to that of EW-7197 (218). Compound 22c effectively suppressed protein and mRNA expression of collagen I and α-SMA in TGF-β-induced LX-2 human hepatic stellate cell (HSC), this result shows that compound 22c has the ability to inhibit the activation of HSC. Compound 22c is expected to be a preclinical candidate for the treatment of hepatic fibrosis.

Preparation method of thienopyridine-type ionic rod-like liquid crystal and ionic liquid compound

The invention discloses a preparation method of a thienopyridine-type ionic rod-like liquid crystal and ionic liquid compound. The thienopyridine-type ionic rod-like liquid crystal and ionic liquid compound have structures as shown in a general formula I, a general formula II and a general formula III. Asymmetric compounds represented by the general formula I show a liquid crystal phase in a certain temperature range, and different inorganic ions and organic ions can be regulated and controlled for carrying out ion exchange. On one hand, storage and release of the inorganic ions and organic ions can be realized in a liquid crystal phase range according to needs; on the other hand, conversion between ionic liquid crystals and ionic liquid is realized through ion regulation and control, anda directional reference is provided for design and application of ion battery materials, special molecular devices and the like. The compounds represented by the general formula II and the general formula III provides another probable design and synthesis idea for the thienopyridine-type rod-like (ion) liquid crystal (plastic crystal) compound. The preparation method is short in route and high inyield.

Preparation method of thienopyridine heterocyclic compound and derivatives thereof

The invention discloses a preparation method of a thienopyridine heterocyclic compound and derivatives thereof. The provided preparation method is different from reported methods. According to the preparation method, 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride is taken as the raw material and is cheap and easily available; the reaction conditions of all steps are mild; the operation of post treatment is simple; the reaction yield is high, and the requirements of industrial production are met. The thienopyridine heterocyclic compound and derivatives thereof have a wide application value in fields such as ionic liquid, ionic liquid crystal, organic semiconductor materials, and the like.

Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal-Free Catalyst under Air

Graphene oxide (GO) has been developed as an inexpensive, environmental friendly, metal-free carbocatalyst for the dehydrogenation of nitrogen heterocycles. Valuable compounds, such as quinoline, 3,4-dihydroisoquinoline, quinazoline, and indole derivatives, have been successfully used as substrates. The investigation of various oxygen-containing molecules with different conjugated systems indicated that both the oxygen-containing groups and large π-conjugated system in GO sheets are essential for this reaction. (Figure presented.).

Rho-kinase inhibitors

Disclosed are compounds and derivatives thereof, their synthesis, and their use as Rho-kinase inhibitors. These compounds of the present invention are useful for inhibiting tumor growth, treating erectile dysfunction, and treating other indications mediated by Rho-kinase, e.g., coronary heart disease.

Evolution of products in the combustion of scrap tires in a horizontal, laboratory scale reactor

A horizontal laboratory reactor was used to study the evolution of byproducts from the combustion of scrap tires at five nominal temperatures (ranging from 650 to 1050 °C) and different oxygen:sample ratios A model was used to calculate the bulk air ratio (λ), and the oxygen consumption was discussed considering this ratio λ. More than 100 volatile and semivolatile compounds were identified and quantified by gas chromatography mass spectrometry, plotting their yields vs the bulk air ratio and temperature. Five different behaviors considering the bulk air ratio and the temperature were identified.

A Convenient Synthesis of the Thienopyridine Nucleus

The unsubstituted thienopyridine ring system was prepared from thiophene-3-carboxaldehyde in 4 steps. The sequence is suitable for scale-up.

Process for the preparation of thieno(3,2-c) pyridine and derivatives thereof

This invention relates to a process for the preparation of compounds having the formula: STR1 in which R1 is H or lower alkyl and R2 is H or lower alkyl, or phenyl or benzyl optionally substituted with at least one halogen or a lower alkyl, lower alkoxy, trifluoromethyl or nitro group. According to this method, a compound of the formula: STR2 in which R1 and R2 are as defined above and R3 is H or optionally substituted alkyl or benzyl, is reacted with a derivative Hal--SO2 --R (III) in which Hal is halogen and R is optionally substituted alkyl, aryl or aralkyl, to give a derivative of the formula: STR3 in which the various symbols have the above-defined meanings, and the sulfonated derivative of the formula (IV) is heated in the presence of an acid, to give the compound of the formula (I).