7-Azaindole. VI. Preparation of 5- and 6-Substituted 7-Azaindoles<sup>1</sup>

Robison, Michael M.; Robison, Bonnie L.; Butler, Florence P.

doi:10.1021/ja01512a058

Cited by 27 publications

(9 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction of 1 with 69% nitric acid and concentrated sulfuric acid at low temperature produced the 1-nitro compound 2 in 95% yield. The 1-nitro compound 2 in concentrated sulfuric acid was converted to the 5-nitro isomer 3 in 35% yield ( 27 ). The selective reduction reaction of the nitro group of 3 was then carried out in the presence of 10% Pd on carbon under a hydrogen atmosphere in order to obtain the intermediate 16a .…”

Section: Resultsmentioning

confidence: 99%

Modification of the aminopyridine unit of 2′-deoxyaminopyridinyl-pseudocytidine allowing triplex formation at CG interruptions in homopurine sequences

Wang

Taniguchi

Okamura

et al. 2018

Nucleic Acids Research

View full text Add to dashboard Cite

The antigene strategy based on site-specific recognition of duplex DNA by triplex DNA formation has been exploited in a wide range of biological activities. However, specific triplex formation is mostly restricted to homo-purine strands within the target duplex DNA, due to the destabilizing effect of CG and TA inversion sites where there is an absence of natural nucleotides that can recognize the CG and TA base pairs. Hence, the design of artificial nucleosides, which can selectively recognize these inversion sites with high affinity, should be of great significance. Recently, we determined that 2-amino-3-methylpyridinyl pseudo-dC (3MeAP-ΨdC) possessed significant affinity and selectivity toward a CG inversion site and showed effective inhibition of gene expression. We now describe the design and synthesis of new modified aminopyridine derivatives by focusing on small chemical modification of the aminopyridine unit to tune and enhance the selectivity and affinity toward CG inversion sites. Remarkably, we have newly found that 2-amino-4-methoxypyridinyl pseudo-dC (4OMeAP-ΨdC) could selectively recognize the CG base pair in all four adjacent base pairs and form a stable triplex structure against the promoter sequence of the human gene including multiple CG inversion sites.

show abstract

Section: Resultsmentioning

confidence: 99%

Modification of the aminopyridine unit of 2′-deoxyaminopyridinyl-pseudocytidine allowing triplex formation at CG interruptions in homopurine sequences

Wang

Taniguchi

Okamura

et al. 2018

Nucleic Acids Research

View full text Add to dashboard Cite

show abstract

“…Molecular orbital calculations were performed with the MOPAC program (PM3 method) on a CAChe Work System (SONY Tektronix). 7-Azaindole derivatives, 3 (Robison and Robison, 1956), 4 (Herbert and Wibberley, 1969), 5 and 6 (Robison et al, 1959) , and 7 (Ga ´lvez and Viladoms, 1982), were prepared using methods reported in the literature. Compounds 8, 12, and 13 (Minakata et al, 1992a) and 9 and 10 ( Minakata et al, 1992b) were synthesized using procedures developed in Osaka University.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Activity of 1H-Pyrrolo[2,3-b]pyridine Derivatives: Correlation between Inhibitory Activity against the Fungus Causing Rice Blast and Ionization Potential

Minakata¹,

Hamada²,

Komatsu³

et al. 1997

J. Agric. Food Chem.

View full text Add to dashboard Cite

Synthesis and biological activity of a variety of 3- and 6-substituted 1H-pyrrolo[2,3-b]pyridine (7-azaindole) derivatives are described. Many of the synthesized 7-azaindoles exhibited considerable fungicidal activity toward Pyricularia oryzae, a fungus which causes rice blast, in vivo. When quantum parameters of the tested 7-azaindoles were evaluated by semiempirical molecular orbital calculations, a relationship was observed between the activity and the calculated ionization potentials of the 7-azaindole derivatives. Keywords: 1H-Pyrrolo[2,3-b]pyridine; fungicidal activity; ionization potential; rice blast

show abstract

“…Evaporation of the appropriate fractions gave 5-nitro-7-azaindoline as a light brown solid (950 mg, 35%); mp 155-160 °C [Lit. 1…”

Section: -Nitro-7-azaindoline (7)mentioning

confidence: 99%

“…The appropriate fractions were evaporated, and the residue triturated with i-hexane to give 2-amino-5-nitro-3-[(trimethylsilyl)ethynyl]pyridine as a yellow solid (1.65 g, 93%); mp 200-202 °C. 1 Amino-7-azaindole (3) from 11 2-Amino-5-nitro-3-[(trimethylsilyl)ethynyl]pyridine (700 mg, 2.98 mmol) and copper(I) iodide (114 mg, 0.60 mmol) were dissolved in NMP (14 mL). The mixture was irradiated in an Emrys Optimiser focused microwave at 190 °C for 30 min.…”

Section: -Amino-5-nitro-3-[(trimethylsilyl)ethynyl]pyridine (11)mentioning

confidence: 99%

“…However, the key intermediate 3 is not easily accessible. There is only one previously reported literature synthesis, 1 giving the product in 21% overall yield in 4 steps from 7-azaindoline (5). A recent patent application by Bristol-Myers Squibb 2 describes the introduction of the 5-amino-7-azaindole moiety into a molecule indirectly, involving lithiation and protecting group chemistry.…”

mentioning

confidence: 99%

See 1 more Smart Citation

A Practical, Efficient Synthesis of 5-Amino-7-azaindole

Pearson¹,

Nandan²

2005

Synthesis

View full text Add to dashboard Cite

show abstract

7-Azaindole. VI. Preparation of 5- and 6-Substituted 7-Azaindoles¹

Cited by 27 publications

References 2 publications

Modification of the aminopyridine unit of 2′-deoxyaminopyridinyl-pseudocytidine allowing triplex formation at CG interruptions in homopurine sequences

Modification of the aminopyridine unit of 2′-deoxyaminopyridinyl-pseudocytidine allowing triplex formation at CG interruptions in homopurine sequences

Synthesis and Biological Activity of 1H-Pyrrolo[2,3-b]pyridine Derivatives: Correlation between Inhibitory Activity against the Fungus Causing Rice Blast and Ionization Potential

A Practical, Efficient Synthesis of 5-Amino-7-azaindole

Contact Info

Product

Resources

About

7-Azaindole. VI. Preparation of 5- and 6-Substituted 7-Azaindoles1

Cited by 27 publications

References 2 publications

Modification of the aminopyridine unit of 2′-deoxyaminopyridinyl-pseudocytidine allowing triplex formation at CG interruptions in homopurine sequences

Modification of the aminopyridine unit of 2′-deoxyaminopyridinyl-pseudocytidine allowing triplex formation at CG interruptions in homopurine sequences

Synthesis and Biological Activity of 1H-Pyrrolo[2,3-b]pyridine Derivatives: Correlation between Inhibitory Activity against the Fungus Causing Rice Blast and Ionization Potential

A Practical, Efficient Synthesis of 5-Amino-7-azaindole

Contact Info

Product

Resources

About

7-Azaindole. VI. Preparation of 5- and 6-Substituted 7-Azaindoles¹