52505-56-3

Usage

Uses

Used in Textile Industry:
ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE is used as an intermediate in the synthesis of dyes for [application reason] the production of vibrant and long-lasting colors in polyamide and polyester fibers. Its role in the dye manufacturing process is essential, as it contributes to the development of dyes with improved properties, such as enhanced colorfastness and reduced environmental impact.
As an intermediate in the preparation of 2-[[4-(Arylazo)-3,5-disubstituted-pyrazol-1-yl]carbonyl]thieno[2,3-b]pyridine dyes, ETHYL 3-AMINO-4,6-DIMETHYLTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE plays a significant role in the textile industry. These dyes are specifically designed for use with polyamide and polyester fibers, which are widely used in the production of various types of fabrics, clothing, and other textile products. The dyes derived from this intermediate are known for their ability to produce vibrant and long-lasting colors, making them highly desirable in the textile market.

InChI:InChI=1/C12H14N2O2S/c1-4-16-12(15)10-9(13)8-6(2)5-7(3)14-11(8)17-10/h5H,4,13H2,1-3H3

Upstream product

• 14237-71-9 2-chloro-4,6-dimethylnicotinonitrile 
• 623-51-8 ethyl 2-sulfanylacetate 
• 54585-47-6 3-cyano-4,6-dimethyl-2-mercaptopyridine 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-53-3 diethyl malonate 
• 61889-26-7 3-bromo-4,6-dimethyl-isothiazolo[5,4-b]pyridine 
• 54585-47-6 4,6-Dimethyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile 
• 105-36-2 ethyl bromoacetate 
• 105855-62-7 3-Cyano-4,6-dimethyl-2-thiono-pyridine 
• 128257-06-7 2-(3-Cyano-4,6-dimethyl)pyridyl (ethoxycarbonyl)methyl sulfide 

Downstream Products

• 128918-28-5 3-Amino-4,6-dimethylthieno<2,3-b>pyridine-2-carbohydrazide 
• 144254-93-3 Sodium; 3-amino-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylate 
• 132602-58-5 7,9-Dimethyl-4-oxo-2-phenyl-4H-pyrido<3',2':4,5>thieno<3,2-d>(1,3)oxazine 
• 145916-76-3 7,9-Dimethyl-2-phenyl-3H-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-one 
• 99504-81-1 3-(p-nitrobenzylideneamino)-2,7,9-trimethyl pyrido<3',2':4,5>thieno-<3,2-d>pyrimidin-4(3H)one 
• 55023-35-3 7,9-dimethylpyrido[3',2':4,5]thieno[3,2-d]pyrimidine-4(1H)-one 
• 145916-70-7 4-Chlor-7,9-dimethyl-2-phenyl-pyrido<3',2':4,5>thieno<3,2-d>pyrimidin 
• 145916-50-3 2-(7,9-Dimethyl-2-phenyl-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-ylamino)-ethanol 
• 145916-61-6 6,8-Dimethyl-4-phenyl-2,3-dihydro-10-thia-1,3a,5,9-tetraaza-cyclopenta[a]fluorene 
• 1610591-86-0 3-amino-N-(2-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)ethyl)-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide 
• 1610591-87-1 3-amino-N-(3-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)propyl)-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide 
• 1610591-88-2 3-amino-N-(4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)butyl)-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide 
• 1610591-89-3 3-amino-N-(5-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)pentyl)-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide 
• 1610591-90-6 3-amino-N-(6-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)hexyl)-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide 

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.

Molecular modelling insights into a physiologically favourable approach to eicosanoid biosynthesis inhibition through novel thieno[2,3-b]pyridine derivatives

In this research, we exploited derivatives of thieno[2,3-b]pyridine as dual inhibitors of the key enzymes in eicosanoid biosynthesis, cyclooxygenase (COX, subtypes 1 and 2) and 5-lipoxygensase (5-LOX). Testing these compounds in a rat paw oedema model revealed potency higher than ibuprofen. The most active compounds 7a, 7b, 8b, and 8c were screened against COX-1/2 and 5-LOX enzymes. Compound 7a was the most powerful inhibitor of 5-LOX with IC50 = 0.15 μM, while its p-chloro analogue 7b was more active against COX-2 (IC50 = 7.5 μM). The less desirable target COX-1 was inhibited more potently by 8c with IC50 = 7.7 μM. Surflex docking programme predicted that the more stable anti- conformer of compound (7a) formed a favourable complex with the active site of 5-LOX but not COX-1. This is in contrast to the binding mode of 8c, which resembles the syn-conformer of series 7 and binds favourably to COX-1.

POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4

Disclosed herein are thieno[2,3-b:5,4-c']dipyridin-8-amine and pyrido[4',3':4,5]thieno[2,3-c]pyridazin-8-amine compounds, which may be useful as positive allosteric modulators of the muscarinic acetylcholine receptor M4 (mAChR M4). A

Structure-activity relationships of privileged structures lead to the discovery of novel biased ligands at the dopamine D2 receptor

Biased agonism at GPCRs highlights the potential for the discovery and design of pathway-selective ligands and may confer therapeutic advantages to ligands targeting the dopamine D2 receptor (D2R). We investigated the determinants of efficacy, affinity, and bias for three privileged structures for the D2R, exploring changes to linker length and incorporation of a heterocyclic unit. Profiling the compounds in two signaling assays (cAMP and pERK1/2) allowed us to identify and quantify determinants of biased agonism at the D2R. Substitution on the phenylpiperazine privileged structures (2-methoxy vs 2,3-dichloro) influenced bias when the thienopyridine heterocycle was absent. Upon inclusion of the thienopyridine unit, the substitution pattern (4,6-dimethyl vs 5-chloro-6-methoxy-4-methyl) had a significant effect on bias that overruled the effect of the phenylpiperazine substitution pattern. This latter observation could be reconciled with an extended binding mode for these compounds, whereby the interaction of the heterocycle with a secondary binding pocket may engender bias.

Synthesis, reactions and biological activity of 2-substituted 3-cyano-4,6-dimethylpyridine derivatives

The reaction of 2-chloro-4,6-dimethylpyridine-3-carbonitrile with hydrazine hydrate, hydroxylamine, and anthranilic acid afforded the corresponding pyrazolo, isoxazolo, and pyridoquinazoline derivatives. Alkylation of 2-mercapto-4,6-dimethylpyridine-3-carbonitrile with ethyl chloroacetate or phenacyl bromide followed by cyclization in NaOH gave thienopyridine derivatives. Diazotization of ethyl 3-amino-4,6-dimethylthieno[2,3-b]pyridine-2- carboxylate followed by the reaction with thiourea, guanidine carbonate, and hydroxylamine hydrochloride gave the corresponding thienopyridine derivatives. The biological activity of some new compounds has been discussed.

SPIRO-RING COMPOUND

The present invention aims to provide a compound having an acetyl-CoA carboxylase (ACC) inhibitory action, which is useful for the prophylaxis or treatment of obesity, diabetes, hypertension, hyperlipidemia, cardiac failure, diabetic complications, metabolic syndrome, sarcopenia, cancer and the like, and has superior efficacy. The present invention provides a compound represented by the formula (I): wherein R1 is a hydrogen atom or a substituent; ring P is an optionally substituted 6-membered nitrogen-containing aromatic heterocycle; ring Q is an optionally further substituted 5- to 7-membered nitrogen-containing non-aromatic heterocycle; and ring R is an optionally fused 5- to 7-membered non-aromatic ring, which is further optionally substituted, or a salt thereof.

Synthesis and transformations of 3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridines

Reactions of 2,5-dimethoxytetrahydrofuran with 3-aminothieno[2,3-b] pyridines afford a number of substituted 3-(1H-pyrrol-1-yl)thieno[2,3-b] pyridines. The possibility of the reaction and the yield of the product are determined by the character of a subst

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 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.