52505-57-4

Usage

Uses

Used in Pharmaceutical Industry:
3-AMINO-4,6-DIMETHYL-THIENO[2,3-B]PYRIDINE-2-CARBONITRILE is used as a building block for the synthesis of various pharmaceutical drugs, contributing to the development of new therapeutics for the treatment of a range of diseases.
Used in Organic Synthesis:
In the field of organic synthesis, 3-AMINO-4,6-DIMETHYL-THIENO[2,3-B]PYRIDINE-2-CARBONITRILE serves as an intermediate, enabling the preparation of a diverse array of chemical compounds.
Due to its unique structure and properties, 3-AMINO-4,6-DIMETHYL-THIENO[2,3-B]PYRIDINE-2-CARBONITRILE has attracted significant interest in research and development for creating innovative drugs and materials.

Upstream product

• 67795-42-0 3-amino-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide 
• 14237-71-9 2-chloro-4,6-dimethylnicotinonitrile 
• 54585-47-6 4,6-Dimethyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile 
• 107-14-2 chloroacetonitrile 
• 128991-31-1 2-Cyanomethylthio-4,6-dimethyl-pyridin-3-carbonitril 
• 54585-47-6 3-cyano-4,6-dimethyl-2-mercaptopyridine 

Downstream Products

• 1427790-09-7 N-(4-methoxybenzyl)-6,8-dimethyl-1H-pyrazolo[3',4':4,5]thieno[2,3-b]pyridin-3-amine 
• 1243541-74-3 7,9-dimethyl-5-phenyl-2,3,5,6-tetrahydroimidazo[1,2-c]pyrido[3',2':4,5]thieno[2,3-e]pyrimidine 
• 1243541-80-1 1-(9,11-dimethyl-2,3-dihydroimidazo[1,2-c]pyrido[3',2':4,5]thieno[3,2-e]pyrimidin-5-yl)sulfanylacetyl-4-phenylthiosemicarbazide 

Relevant academic research and scientific papers

Novel M4 positive allosteric modulators derived from questioning the role and impact of a presumed intramolecular hydrogen-bonding motif in β-amino carboxamide-harboring ligands

This letter describes a focused exercise to explore the role of the β-amino carboxamide moiety found in all of the first generation M4 PAMs and question if the NH2 group served solely to stabilize an intramolecular hydrogen bond (IMHB) and enforce planarity. To address this issue (and to potentially find a substitute for the β-amino carboxamide that engendered P-gp and contributed to solubility liabilities), we removed the NH2, generating des-amino congeners and surveyed other functional groups in the β-position. These modifications led to weak M4 PAMs with poor DMPK properties. Cyclization of the β-amino carboxamide moiety by virtue of a pyrazole ring re-enforced the IMHB, led to potent (and patented) M4 PAMs, many as potent as the classical bicyclic β-amino carboxamide analogs, but with significant CYP1A2 inhibition. Overall, this exercise indicated that the β-amino carboxamide moiety most likely facilitates an IMHB, and is essential for M4 PAM activity within classical bicyclic M4 PAM scaffolds.

SUBSTITUTED 1H-PYRAZOLO[3',4',4,5]THIENO[2,3-B]PYRIDIN-3-AMINE ANALOGS AS POSITIVE ALLOSTERIC MODULATIORS OF THE MUSCARINIC ACETYCHOLINE RECEPTOR M4

In one aspect, the invention relates to substituted lH-pyrazolo[3',4':4,5]thieno[2,3- b]pyridin-3 -amine analogs, derivatives thereof, and related compounds, which are useful as positive allosteric modulators of the muscarinic acetylcholine receptor M4 (m

Studies on the Synthesis of Some Styryl-3-cyano-2(1H)-pyridinethiones and Polyfunctionally Substituted 3-Aminothienopyridine Derivatives

The 3-cyano-4,6-dimethyl-2(1H)-pyridinethione was condensed with benzaldehyde in basic solution leads to styryl-3-cyano-2(1H)-pyridinethiones.Treatment of cinnamicaldehyde with cyanothioacetamide to give cinnamylidencyanothioacetamide, which can be cyclized with the appropriate ketones to afford the 3-cyano-5,6-polymethylene-4-styryl-2(1H)-pyridinethione derivatives.The polyfunctionally substituted 3-aminothienopyridine derivatives were obtained in good yield by cyclization of 3-cyano-2(1H)-pyridinethione derivatives with appropriate α-halogeno carbonyl compounds and nitrile, respectively.

Synthesis and antifungal activity of pyrido[3',2':4,5]thieno[3,2-d]-1,2,3-triazine derivatives

The antimicrobical activity of some pyrido[3'2':4,5]thieno[3,2d]-1,2,3-triazine derivatives has been studied. Some compounds proved effective against microorganisms in vitro, compounds 3a and 3c in particular exhibited antifungal activity, comparable to M

SYNTHESIS AND REACTIONS OF SOME THIENOPYRIDINE DERIVATIVES

Substituted thienopyridines (VIII-XII) were prepared by ring closure of the corresponding S-alkylated derivatives (II-VI).Thienopyridine-2-carbohydrazide XIII was interacted with some reagents afforded the expected pyridothienopyrimidines (XIV-XVI).Also, the carboazide XVII undergo Curtius rearrangement giving imidazolothienopyridine (XVIII).The carboxamide derivatives (X-XII) interacted with CS2 giving pyridothienopyrimidines (XX-XXII), while interaction with nitrous acid, pyridothienotriazines (XXIII-XXV) were produced.