28900-10-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-6-methyl-3-pyridinecarbonitrile is used as a synthetic building block for the preparation of biologically active compounds. It plays a significant role in the development of new potent anticancer agents, such as 2-(Alkoxycarbonyl)-3-Anilinobenzo[b]thiophenes and Thieno[2,3-b]pyridines. These compounds have shown potential in combating cancer by targeting specific cellular pathways and mechanisms.
Additionally, 2-Chloro-6-methyl-3-pyridinecarbonitrile may be used in the preparation of methyl-2-nitropyridinecarboxamides, which are also of interest in the pharmaceutical industry due to their potential applications in drug development.
Used in Chemical Industry:
In the chemical industry, 2-Chloro-6-methyl-3-pyridinecarbonitrile is utilized as an intermediate in the synthesis of various organic compounds. Its unique structure and functional groups make it a versatile building block for creating a wide range of products, from pharmaceuticals to specialty chemicals.

InChI:InChI=1/C7H5ClN2/c1-5-2-3-6(4-9)7(8)10-5/h2-3H,1H3

Upstream product

• 4241-27-4 2-hydroxy-6-methylnicotinonitrile 
• 18619-97-1 ethyl 3-cyano-2-hydroxy-6-methylisonicotinate 
• 40108-12-1 ethyl 2-chloro-3-cyano-6-methyl-4-pyridine carboxylate 
• 500546-18-9 2-chloro-3-cyano-6-methyl-isonicotinic acid amide 
• 3222-48-8 6-methylnicotinonitrile 
• 31795-59-2 6-methylpyridine-3-carbonitrile 1-oxide 
• 4241-27-4 1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile 
• 500545-40-4 2-chloro-3-cyano-6-methyl-isonicotinic acid 

Downstream Products

• 368426-79-3 6-(bromomethyl)-2-chloropyridine-3-carbonitrile 
• 66690-78-6 3-aza-N,4-dimethylisatoic anhydride 
• 97484-82-7 1-allyl-7-methyl-2H-pyrido<2,3-d><1,3>oxazine-2,4(1H)-dione 
• 97484-94-1 2-allylamino-6-methylnicotinic acid sodium salt 
• 69407-72-3 1,7-dimethyl-1,2-dihydro-4-hydroxy-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester 
• 69407-71-2 1-allyl-4-hydroxy-7-methyl-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 955-63-5 2-[(4-chlorophenyl)thio]-6-methylnicotinonitrile 

Relevant academic research and scientific papers

Novel 3-pyridinecarbonitriles incorporating sulfonamide moieties as anti-breast cancer agents

A novel series of 3-pyridinecarbonitrile derivatives incorporating sulfonamide moieties and sulfonyl derivatives was synthesized using 2-chloro-6-methylnicotinonitrile as a strategic starting material. The structures of the synthesized compounds were eluc

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.

KINASE INHIBITOR

[Problem] To provide a novel PIM-3 inhibitor and a novel cancer therapeutic drug, in particular, a therapeutic drug for pancreatic cancer. [Solution] A PIM-3 kinase inhibitor comprising a compound represented by general formula (I) or a pharmacologically acceptable salt, hydrate or solvate thereof.

Pyridine C-region analogs of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists

A series of pyridine derivatives in the C-region of N-((6-trifluoromethyl-pyridin-3-yl)methyl) 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides were investigated as hTRPV1 antagonists. The SAR analysis indicated that 6-difluorochloromethyl pyridine derivatives were the best surrogates of the C-region for previous leads. Among them, compound 31 showed excellent antagonism to capsaicin as well as to multiple hTRPV1 activators. It demonstrated stronganalgesic activity in the formalin test in mice with full efficacy and it blocked capsaicin-induced hypothermia in vivo.

Synthesis of methyl 3-azidothieno[2,3-b]pyridine-2-carboxylates and application of the huisgen reaction

The preparation of new substituted methyl 3-azidothieno[2,3-b]pyridine carboxylates by azotization of methyl 3-aminothieno[2,3-b]pyridine and subsequent treatment with sodium azide is described. Via Huisgen's 1,3-dipolar cycloaddition between substituted alkynes and the prepared azides, methyl 1,2,3-triazolo-thieno[2,3-b]pyridine carboxylates have been obtained.

Synthesis, in vitro and in vivo activity of thiamine antagonist transketolase inhibitors

Tumor cells extensively utilize the pentose phosphate pathway for the synthesis of ribose. Transketolase is a key enzyme in this pathway and has been suggested as a target for inhibition in the treatment of cancer. In a pharmacodynamic study, nude mice with xenografted HCT-116 tumors were dosed with 1 ('N3′-pyridyl thiamine'; 3-(6-methyl-2-amino-pyridin-3-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium chloride hydrochloride), an analog of thiamine, the co-factor of transketolase. Transketolase activity was almost completely suppressed in blood, spleen, and tumor cells, but there was little effect on the activity of the other thiamine-utilizing enzymes α-ketoglutarate dehydrogenase or glucose-6-phosphate dehydrogenase. Synthesis and SAR of transketolase inhibitors is described.

POLYCYCLIC N-HETEROCYCLIC COMPOUNDS. 46 SYNTHESIS OF THIENONAPHTHYRIDINES FROM 2-(3-CYANOPROPYLTHIO)PYRIDINE-3-CARBONITRILE

An efficient methodology for the synthesis of thienonaphthyridine skeleton via Smiles type rearrangement reaction followed by cyclization is described.Synthesis of its derivatives is also described.

Pyridylthio-acylanilide herbicides

Novel herbicidally active pyridylthio-acylanilides of the formula STR1 in which R1, R2 and R3, independently of one another, represent hydrogen, halogen, cyano or trifluoromethyl or alkyl, alkoxy and alkylthio having 1 to 4 carbon atoms in each case, R4 represents halogen, methyl or methoxy, n represents a number 0, 1 or 2, z represents the group (Ia) STR2 or the group (Ib) STR3 where X represents oxygen, sulphur, an N--R10 or N--O--R11 group, or X and Rg tpgether represent the STR4 radical, and the other radicals can have various meanings. Intermediates of the formulae STR5 are also new.

Synthesis of Azaanthraquinones: Homolytic Substitution of Pyridines

Synthesis of specific di- and tri-hydroxyazaanthraquinones by Friedel-Crafts procedures is limited by orientational ambiguity and by the lack of reactivity of pyridine derivatives in electrophilic acylation processes; however, suitable pyridines have been made to undergo radical benzoylation and benzylation at unsubstituted positions 2, 4 and 6.In particular, derivatives of pyridine-3-carbonitrile have been benzoylated at positions 2 and 4.Ring closure by intramolecular Houben-Hoesch reaction has then led to specifically substituted 1- and 2-azaanthraquinones and thence to the antibiotic bostrycoidin (1).