221006-70-8 Usage
Description
2,6-Dimethoxypyridine-3-boronic acid is an organic compound that features a pyridine ring with two methoxy groups at the 2nd and 6th positions and a boronic acid group at the 3rd position. 2,6-Dimethoxypyridine-3-boronic acid is known for its reactivity and utility in organic synthesis, particularly in the formation of various heterocyclic compounds and pharmaceutical agents.
Uses
Used in Pharmaceutical Synthesis:
2,6-Dimethoxypyridine-3-boronic acid is used as a key reactant for the preparation of benzopyranone derivatives, which serve as positive GABAA receptor modulators. These modulators are important in the development of medications targeting neurological disorders and anxiety conditions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2,6-Dimethoxypyridine-3-boronic acid is utilized as a building block for the synthesis of pyrazine derivatives. These derivatives have potential applications as orally active corticotropin-releasing factor-1 (CRF-1) receptor antagonists, which can be beneficial in the treatment of stress-related disorders and anxiety.
Used in Microwave-Assisted Organic Synthesis:
2,6-Dimethoxypyridine-3-boronic acid is employed as a reactant in microwave-enhanced synthesis processes, specifically for the preparation of trisubstituted pyridazines. The use of microwaves accelerates the reaction, leading to more efficient and cleaner synthesis of these complex heterocyclic compounds.
Used in Cross-Coupling Reactions:
This boronic acid is used as a reactant in the preparation of biaryl derivatives through palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. The cross-coupling process allows for the formation of carbon-carbon bonds between aryl or heteroaryl halides, facilitating the synthesis of biaryl compounds with potential applications in materials science and pharmaceuticals.
Used in the Synthesis of 3-Arylpyridines:
2,6-Dimethoxypyridine-3-boronic acid is also used in the synthesis of 3-arylpyridines via palladium-P Phos catalyzed Suzuki cross-coupling. The resulting 3-arylpyridines are valuable intermediates in the development of pharmaceuticals and agrochemicals, given their diverse biological activities and potential as ligands in coordination chemistry.
Check Digit Verification of cas no
The CAS Registry Mumber 221006-70-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,2,1,0,0 and 6 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 221006-70:
(8*2)+(7*2)+(6*1)+(5*0)+(4*0)+(3*6)+(2*7)+(1*0)=68
68 % 10 = 8
So 221006-70-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H10BNO4/c1-12-6-4-3-5(8(10)11)7(9-6)13-2/h3-4,10-11H,1-2H3
221006-70-8Relevant articles and documents
Synthetic studies to help elucidate the metabolism of the preclinical candidate TBAJ-876—a less toxic and more potent analogue of bedaquiline
Choi, Peter J.,Conole, Daniel,Sutherland, Hamish S.,Blaser, Adrian,Tong, Amy S.T.,Cooper, Christopher B.,Upton, Anna M.,Palmer, Brian D.,Denny, William A.
, (2020/03/26)
Bedaquiline is a novel drug approved in 2012 by the FDA for treatment of drug-resistant tuberculosis (TB). Although it shows high efficacy towards drug-resistant forms of TB, its use has been limited by the potential for significant side effects. In particular, bedaquiline is a very lipophilic compound with an associated long terminal half-life and shows potent inhibition of the cardiac potassium hERG channel, resulting in QTc interval prolongation in humans that may result in cardiac arrhythmia. To address these issues, we carried out a drug discovery programme to develop an improved second generation analogue of bedaquiline. From this medicinal chemistry program, a candidate (TBAJ-876) has been selected to undergo further preclinical evaluation. During this evaluation, three major metabolites arising from TBAJ-876 were observed in several preclinical animal models. We report here our synthetic efforts to unequivocally structurally characterize these three metabolites through their independent directed synthesis.
ANTIBACTERIAL COMPOUNDS AND USES THEREOF
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Paragraph 0111, (2017/09/28)
The present invention relates to compounds of formula (I) including any stereochemically isomeric form thereof, or pharmaceutically acceptable salts thereof, for the treatment of tuberculosis.
Towards compatibility between ruthenium sensitizers and cobalt electrolytes in dye-sensitized solar cells
Polander, Lauren E.,Yella, Aswani,Curchod, Basile F. E.,Ashari Astani, Negar,Teuscher, Joel,Scopelliti, Rosario,Gao, Peng,Mathew, Simon,Moser, Jacques-E.,Tavernelli, Ivano,Rothlisberger, Ursula,Graetzel, Michael,Nazeeruddin, Md. Khaja,Frey, Julien
supporting information, p. 8731 - 8735 (2013/09/12)
Ruthenium and Co: Ruthenium(II) complexes remain prime candidates for dye-sensitized solar applications; however, current ruthenium sensitizers are not compatible with cobalt(II/III) electrolytes. Herein, the effect of surface insulation on device efficiency is studied by comparing two cyclometalated tris-heteroleptic ruthenium(II) complexes. This approach demonstrates a general principle that leads to unprecedented efficiency for a ruthenium(II) sensitizer used in combination with a cobalt electrolyte. Copyright
