54585-47-6

Usage

Uses

Used in Chemical Synthesis:
3-CYANO-4,6-DIMETHYL-2-MERCAPTOPYRIDINE is used as a chemical intermediate for the synthesis of various compounds. Its distinct chemical properties make it a valuable building block in the creation of new molecules with specific functions and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-CYANO-4,6-DIMETHYL-2-MERCAPTOPYRIDINE is used as a key component in the development of new drugs. Its unique structure allows it to be incorporated into medicinal compounds that can target specific biological pathways or receptors, potentially leading to the treatment of various diseases and conditions.
Used in Agrochemical Industry:
3-CYANO-4,6-DIMETHYL-2-MERCAPTOPYRIDINE is also utilized in the agrochemical sector, where it serves as a precursor for the synthesis of pesticides and other agricultural chemicals. Its properties can be leveraged to create effective and targeted products for crop protection and enhancement of agricultural yields.
Used in Medical Research:
3-CYANO-4,6-DIMETHYL-2-MERCAPTOPYRIDINE has been studied for its potential use in the treatment of certain medical conditions. Its unique chemical structure may offer new avenues for therapeutic intervention, and ongoing research aims to explore its efficacy and safety in various medical applications.

InChI:InChI=1/C8H8N2S/c1-5-3-6(2)10-8(11)7(5)4-9/h3H,1-2H3,(H,10,11)

Upstream product

• 63913-42-8 (3E)-4-morpholin-4-yl-pent-3-en-2-one 
• 7357-70-2 Cyanothioacetamide 
• 74701-66-9 1-(prop-1-en-2-yl)pyrrolidine 
• 75-07-0 acetaldehyde 
• 67532-59-6 1-(prop-1-en-2-yl)piperidine 
• 67-64-1 acetone 
• 123-54-6 acetylacetone 

Downstream Products

• 128991-31-1 2-Cyanomethylthio-4,6-dimethyl-pyridin-3-carbonitril 
• 67795-42-0 3-amino-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide 
• 60750-75-6 4,6-dimethylisothiazolo[5,4-b]pyridin-3(2H)-one 
• 79927-21-2 4,6-dimethyl-2-mercaptonicotinic acid amide 
• 496845-20-6 N-(2,4,6-trimethylthieno[2,3-b]pyridin-3-yl)-N'-phenylthiourea 
• 72456-88-3 4,6-dimethyl-2-[(2-oxo-2-phenylethyl)sulfanyl]pyridine-3-carbonitrile 
• 443640-27-5 3-amino-4,6-dimethyl-2-phenylthieno[2,3-b]pyridine 
• 1427790-09-7 N-(4-methoxybenzyl)-6,8-dimethyl-1H-pyrazolo[3',4':4,5]thieno[2,3-b]pyridin-3-amine 

Relevant academic research and scientific papers

Synthesis, Characterization, and Antifungal Activity of Some New Thieno[2,3-b]pyridines Incorporating Quinazoline or Benzimidazole Moiety

Abstract: Reaction of 4,6-dimethyl-3-cyanopyridine-2(1H)-thione (IIIa) or 4,5,6-trisubstituted-3-cyanopyridine-2(1H)-thiones (IIIb–d) with 2-chloromethylquinazoline-4(3H)-one (IVa) furnished the corresponding 3-amino-2-(4-oxo-3,4-dihydroquinazolin-2-yl)thieno[2,3-b]pyridines (VIa–d). Reaction of aminothieno-pyridines (VIa, b, d) were reacted with triethyl orthoformate, acetic anhydride or nitrous acid to furnish pyridothienopyrimidoquinazolines (VIIIa, b, d), (IXa, b, d) or pyridothienotriazinoquinazolines (Xa, b, d). The new compound, 3-cyano-5-acetyl-6-methyl-4-styrylpyridine-2(1H)-thione (IIIe) was synthesized and reacted with 2-chloromethyl-1H-benzimadazole to give 5-acetyl-3-amino-2-(1H-benzimidazol-2-yl)-6-methyl-4-styryl-thieno[2,3-b]pyridine (XII) which was used as a key intermediate for synthesizing pyridothienopyrimidobenzimidazoles (XIII, XIV). All newly synthesized compounds were characterized on the basis of their elemental and spectral analyses. Also, most of the synthesized compounds were screened in vitro for their antifungal activity.

Synthesis, in-vitro antibacterial and anticancer screening of novel nicotinonitrile-coumarin hybrids utilizing piperazine citrate

An efficient, low-cost, high yield% and eco-friendly synthetic procedure is designed for the synthesis of novel series of nicotinonitrile-coumarin hybrid molecules bearing several aryl and/or heteroaryl moieties. Our strategy includes the synthesis of a novel series of 2-hydroxybenzaldehydes, bearing nicotinonitrile moiety, followed by its Knoevenagel reaction with ethyl acetoacetate in the presence of an organo-base. The above reaction is studied in different reaction conditions. The optimized conditions are performing the reaction in ethanol at 80 °C in the presence of 10 mol% of piperazine citrate (1:1). The in-vitro antibacterial activities of the nicotinonitrile-coumarins were evaluated against different Gram-positive and negative bacterial strains. Moreover, the in-vitro cytotoxicity of nicotinonitrile-coumarins were estimated against different eukaryotic cell lines. Compounds 5a and 5b exhibited the most promising antibacterial agents among the novel series. The structures of novel series of the target nicotinonitrile-coumarin hybrid molecules were confirmed by considering their elemental analyses and spectral data.

Discovery and optimization of thienopyridine derivatives as novel urea transporter inhibitors

Urea transporters (UTs) play an important role in the urine concentrating mechanism and are recognized as novel targets for developing small molecule inhibitors with salt-sparing diuretic activity. Thienoquinoline derivatives, a class of novel UT-B inhibitors identified by our group, play a significant diuresis in animal model. However, the poor solubility and low bioavailability limited its further development. To overcome these shortcomings, the structure modification of thienoquinoline was carried out in this study, which led to the discovery of novel thienopyridine derivatives as specific urea transporter inhibitors. Further optimization obtained the promising preclinical candidate 8n with not only excellent inhibition effect on urea transporters and diuretic activity on rat model, but also suitable water solubility and Log P value.

Experimental and theoretical study on the regioselective bis- and polyalkylation of 2-mercaptonicotinonitrile and 2-mercaptopyrimidine-5-carbonitrile derivatives

The synthetic utility of 2-mercaptonicotinonitriles 3 and 4, as well as 2-mercapto-4-oxo-6-phenyl-1,4-dihydropyrimidine-5-carbonitrile 20 as building blocks for novel bis- and poly(pyridines), along with poly(pyrimidines) via alkylation with the corresponding bis- and poy(halo) compounds was investigated. Spectroscopic and theoretical studies confirmed the S-alkylation rather than the N-alkylation.

3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells

A series of 3-amino-thieno[2,3-b]pyridines was prepared and tested in a phenotypic sea urchin embryo assay to identify potent and specific molecules that affect tubulin dynamics. The most active compounds featured a tricyclic core ring system with a fused cycloheptyl or cyclohexyl substituent and unsubstituted or alkyl-substituted phenyl moiety tethered via a carboxamide. Low nano-molar potency was observed in the sea urchin embryos for the most active compounds (1–5) suggestive of a microtubule-destabilising effect. The molecular modelling studies indicated that the tubulin colchicine site is inhibited, which often leads to microtubule-destabilisation in line with the sea urchin embryo results. Finally, the identified hits displayed a robust growth inhibition (GI50of 50–250?nM) of multidrug-resistant melanoma MDA-MB-435 and breast MDA-MB-468 human cancer cell lines. This work demonstrates that for the thieno[2,3-b]pyridines the most effective mechanism of action is microtubule-destabilisation initiated by binding to the colchicine pocket.

Synthesis of 4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile by condensation of cyanothioacetamide with acetaldehyde and 1-(Prop-1-en-2-yl)piperidine

Three-component condensation of cyanothioacetamide with acetaldehyde and 1-(prop-1-en-2-yl)-piperidine afforded 4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile which was alkylated with alkyl halides to obtain substituted 2-alkylsulfanyl-4,6-dimethylpyridine-3-carbonitriles, (3-amino-4,6-dimethylthieno-[2,3-b]pyridin-2-yl)(4-cyclohexylphenyl)methanone, and 2,2′-[ethane-1,2-diylbis(sulfanediyl)]bis(4,6-dimethylpyridine-3-carbonitrile).

Novel method of 4,6-dimethyl-2-thioxo-1,2-dihydronicotinonitrile synthesis

Condensation of acetaldehyde with cyanothioacetamide and 1-(prop-1-en-2-yl)pyrrolidine has afforded 4,6-dimethyl-2-thioxo-1,2-dihydronicotinonitrile. Alkylation of the latter with α-haloketones yields substituted 2-alkylsulfanyl-4,6-dimethylnicotinonitriles and thieno[2,3-b]pyridines.

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.

Probing structural requirements of positive allosteric modulators of the M4 muscarinic receptor

The M4 mAChR is implicated in several CNS disorders and possesses an allosteric binding site for which ligands modulating the affinity and/or efficacy of ACh may be exploited for selective receptor targeting. We report the synthesis of a focused library of putative M4 PAMs derived from VU0152100 and VU10005. These compounds investigate the pharmacological effects of previously identified methoxy and fluoro substituents, providing useful estimates of affinity (KB), cooperativity (αβ), and direct agonist properties (τB).