Unexpected Regiospecific Reduction of the Double Bond by NaBH<sub>4</sub>in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile

Dubey, P. K.; Reddy, P. V. V. Prasada

doi:10.1080/00397910701397177

Cited by 7 publications

(4 citation statements)

References 19 publications

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“…Bauerine C (1), 1-Oxo-β-carboline RET Inhibitor (2), CLK Inhibitor (3), and 3-Aminobauerine C (4) 6,7-dichloroindole-2-carboxylate (13) 10 was alkylated with methyl iodide in DMF after deprotonation with sodium hydride to give Nmethylated indole 14 (Scheme 1A). Formylation of 14 using Vilsmeier conditions afforded carbaldehyde 15 which was cyclized with hydrazine, yielding 3-azabauerine C (16).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In order to address the importance of the 9-methyl substituent in the tetracyclic spiro series, 22 was prepared from 21 and cyclohexanone using our general procedure (Scheme A). By employment of triethylbenzylammonium chloride (TEBAC) mediated phase-transfer catalysis, 22 can be alkylated with dimethyl sulfate and potassium carbonate in acetonitrile, yielding 9-methyl derivative 9 . This protocol allows for the selective alkylation of the indole nitrogen without affecting the lactam nitrogen and constitutes a feasible alternative to our previously reported procedure for selective N-methylation of 1-oxo-β-carbolines .…”

Section: Resultsmentioning

confidence: 99%

“…6,7-Dichloro-5-methyl-3H-pyridazino [4,5-b]indol-4(5H)-one Hemihydrate (16). Compound 15 (474 mg, 1.6 mmol) and hydrazine hydrate (192 mg, 4.8 mmol) were dissolved in 1,4-dioxane (50 mL), and the mixture was heated to reflux for 3 h. After the mixture was cooled, the crude precipitated product was filtered off and recrystallized from ethyl acetate to give 241 mg (56%) of 16 as a yellow solid.…”

Section: ■ Conclusionmentioning

confidence: 99%

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7,8-Dichloro-1-oxo-β-carbolines as a Versatile Scaffold for the Development of Potent and Selective Kinase Inhibitors with Unusual Binding Modes

et al. 2012

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Development of both potent and selective kinase inhibitors is a challenging task in modern drug discovery. The innate promiscuity of kinase inhibitors largely results from ATP-mimetic binding to the kinase hinge region. We present a novel class of substituted 7,8-dichloro-1-oxo-β-carbolines based on the distinct structural features of the alkaloid bauerine C whose kinase inhibitory activity does not rely on canonical ATP-mimetic hinge interactions. Intriguingly, cocrystal structures revealed an unexpected inverted binding mode and the presence of halogen bonds with kinase backbone residues. The compounds exhibit excellent selectivity over a comprehensive panel of human protein kinases while inhibiting selected kinases such as the oncogenic PIM1 at low nanomolar concentrations. Together, our biochemical and structural data suggest that this scaffold may serve as a valuable template for the design and development of specific inhibitors of various kinases including the PIM family of kinases, CLKs, DAPK3 (ZIPK), BMP2K (BIKE), and others.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

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7,8-Dichloro-1-oxo-β-carbolines as a Versatile Scaffold for the Development of Potent and Selective Kinase Inhibitors with Unusual Binding Modes

et al. 2012

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“…In continuation of our earlier work, [17][18][19][20][21] we now wish to report our studies on the condensation of 3,4-pyridinediamines with aromatic aldehydes and the unambiguous structural assignment for the products based purely on chemical methods.…”

Section: Introductionmentioning

confidence: 99%

Unambiguous structural assignment of monoanils of 3,4-pyridinedi- amine via regioselective synthesis

Dubey¹,

Chowdary²,

Ramesh³

et al. 2008

Arkivoc

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Condensation of 3,4-pyridinediamine 1 with aromatic aldehydes results in the selective formation of the regioisomer 4-amino-3-benzylideneamino pyridine 2, which on reduction with NaBH 4 affords 3-benzylamino-4-aminopyridine 4. The structure of the compound 4 was established by an unambiguous synthesis of another regioisomer 3-amino-4-benzylaminopyridine 5 via another sequence of reactions. Based on the Regiospecific chemical synthesis of 5, the structures of 2 and 4 were established. The structures of all the new compounds have been confirmed by spectral studies (IR, 1 H NMR and Mass spectroscopy).

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ChemInform Abstract: Unexpected Regiospecific Reduction of the Double Bond by NaBH₄ in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile.

Dubey

Reddy

2007

ChemInform

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Unexpected Regiospecific Reduction of the Double Bond by NaBH₄in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile

Cited by 7 publications

References 19 publications

7,8-Dichloro-1-oxo-β-carbolines as a Versatile Scaffold for the Development of Potent and Selective Kinase Inhibitors with Unusual Binding Modes

7,8-Dichloro-1-oxo-β-carbolines as a Versatile Scaffold for the Development of Potent and Selective Kinase Inhibitors with Unusual Binding Modes

Unambiguous structural assignment of monoanils of 3,4-pyridinedi- amine via regioselective synthesis

ChemInform Abstract: Unexpected Regiospecific Reduction of the Double Bond by NaBH₄ in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile.

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Unexpected Regiospecific Reduction of the Double Bond by NaBH4in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile

Cited by 7 publications

References 19 publications

7,8-Dichloro-1-oxo-β-carbolines as a Versatile Scaffold for the Development of Potent and Selective Kinase Inhibitors with Unusual Binding Modes

7,8-Dichloro-1-oxo-β-carbolines as a Versatile Scaffold for the Development of Potent and Selective Kinase Inhibitors with Unusual Binding Modes

Unambiguous structural assignment of monoanils of 3,4-pyridinedi- amine via regioselective synthesis

ChemInform Abstract: Unexpected Regiospecific Reduction of the Double Bond by NaBH4 in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile.

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Unexpected Regiospecific Reduction of the Double Bond by NaBH₄in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile

ChemInform Abstract: Unexpected Regiospecific Reduction of the Double Bond by NaBH₄ in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile.