128918-28-5

Usage

InChI:InChI=1/C10H12N4OS/c1-4-3-5(2)13-10-6(4)7(11)8(16-10)9(15)14-12/h3H,11-12H2,1-2H3,(H,14,15)

Upstream product

• 52505-56-3 ethyl 3-amino-4,6-dimethylthieno[2,3-b]pyridine-2-carboxylate 
• 128257-06-7 2-(3-Cyano-4,6-dimethyl)pyridyl (ethoxycarbonyl)methyl sulfide 
• 14237-71-9 2-chloro-4,6-dimethylnicotinonitrile 
• 55023-72-8 3-amino-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylic acid; potassium salt 
• 54585-47-6 4,6-Dimethyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile 
• 115919-85-2 3-Amino-4,6-dimethyl-thieno<2,3-b>pyridin-2-carbonsaeure-4-nitro-phenylester 
• 58327-76-7 3-amino-2-carboxylic acid-4,6-dimethylthieno[2,3-b]pyridine 

Downstream Products

• 222538-69-4 3-amino-2-[(3,5-difurylpyrazolin-1-yl)carbonyl]-4,6-dimethylthieno[2,3-b]pyridine 
• 180793-00-4 3-amino-2-carboxybenzylidenehydrazide-4,6-dimethylthieno[2,3-b]pyridine carboxylate 
• 1299492-68-4 3-amino-4,6-dimethylthieno[2,3-b]pyridine-2-carboxylic acid (3-methyl-3H-imidazol-4-yl-methylene) hydrazide 
• 180792-90-9 3-N-benzylidene-7,9-dimethylpyrido[3',2':4,5]thieno[3,2-d]-4(3H)-pyrimidinone 

Relevant academic research and scientific papers

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.

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.

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.