Reactivity of 3-Cyanoacetylindole Derivatives: Synthesisof 3-Hydrazonopyrazolyl and 3-Thiadiazolyl Indole Derivatives

Hassaneen, Hamdi M.; Gomaa, Zakaria Ahmed

doi:10.4236/ijoc.2011.13015

Cited by 9 publications

(5 citation statements)

References 25 publications

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“…The entire carbon skeleton was assigned by 13 C-NMR spectra. Notice that all the compounds synthesized retain signals similar to the cyanoacetylindole skeleton, similar to those reported previously [68,69] as well as a typical NH absorption in the IR spectrum (]; 3,400-3,300 cm −1 ).…”

Section: Resultssupporting

confidence: 85%

Synthesis of New (E)-2-(1H-Indole-3-ylcarbonyl)-3-heteroaryl-acrylonitriles via Microwave-Assisted Knoevenagel Condensation

Treuer

De-la-Torre

Gutiérrez

2017

Journal of Chemistry

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Given the broad spectrum of biological uses of heteroaryl-acrylonitrile derivatives, it is necessary to find simple methods to synthesize and diversify this family of compounds. We report a stereoselective synthesis of a series of new (E)-2-(1H-indole-3-ylcarbonyl)-3-heteroaryl-acrylonitriles ( a-i) obtained from 3-(cyanoacetyl)indole and heteroaryl-aldehydes under microwaveassisted Knoevenagel reaction at 300 W of potency and 100 ∘ C. The desired derivatives ( a-i) were obtained with variable yields (30-94%) and time reactions (8-90 min). All the heteroaryl-acrylonitriles were characterized by physicoanalytical techniques such IR, 1 H, 13 C NMR, and electrospray mass spectrometry.

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Section: Resultssupporting

confidence: 85%

Synthesis of New (E)-2-(1H-Indole-3-ylcarbonyl)-3-heteroaryl-acrylonitriles via Microwave-Assisted Knoevenagel Condensation

Treuer

De-la-Torre

Gutiérrez

2017

Journal of Chemistry

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“…Hydrazinolysis of ester 4a and then condensation with 3-chlorobenzaldehyde provided carbohydrazide 56 with a unique linker in 61% yield over two steps . To mask the ketone group, pyrazole 57 was prepared by cyclization of the linker of 1 with hydrazine hydrate in refluxing ethanol in 64% yield …”

Section: Resultsmentioning

confidence: 99%

Structure–Activity Relationship Studies of Substituted 2-(Isoxazol-3-yl)-2-oxo-N′-phenyl-acetohydrazonoyl Cyanide Analogues: Identification of Potent Exchange Proteins Directly Activated by cAMP (EPAC) Antagonists

Zhu

Chen

et al. 2015

J. Med. Chem.

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Exchange proteins directly activated by cAMP (EPAC) as guanine nucleotide exchange factors mediate the effects of the pivotal second messenger cAMP, thereby regulating a wide variety of intracellular physiological and pathophysiological processes. A series of novel 2-(isoxazol-3-yl)-2-oxo-N′-phenyl-acetohydrazonoyl cyanide EPAC antagonists was synthesized and evaluated in an effort to optimize properties of the previously identified high-throughput (HTS) hit 1 (ESI-09). Structure–activity relationship (SAR) analysis led to the discovery of several more active EPAC antagonists (e.g., 22 (HJC0726), 35 (NY0123), and 47 (NY0173)) with low micromolar inhibitory activity. These inhibitors may serve as valuable pharmacological probes to facilitate our efforts in elucidating the biological functions of EPAC and developing potential novel therapeutics against human diseases. Our SAR results have also revealed that further modification at the 3-, 4-, and 5-positions of the phenyl ring as well as the 5-position of the isoxazole moiety may allow for the development of more potent EPAC antagonists.

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“…Finally, compound 3 was used to synthesize the pyrazolotriazine derivatives (39-41) via coupling with the corresponding 3-pyrazole diazonium chlorides (35)(36)(37)(38) [ [35][36][37], followed by heating the formed hydrazones (35)(36)(37) in acetic acid (Scheme 5). The structures of the products 35-38 and 39-41 were determined from spectroscopic and elemental analytical data.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antioxidant Evaluation of Some Novel Thiophene, Pyrazole, Chromene, Pyrazolotriazine Derivatives Bearing Sulfonamide Moiety

Gouda

2015

Journal of Heterocyclic Chem

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As a part of ongoing studies in developing new potent antioxidant agents, N‐[4‐(aminosulfonyl)phenyl]‐2‐cyanoacetamide (3) was utilized as key intermediate for the synthesis of some new thiophene, chromene, and pyrazolotriazine pyridine derivatives. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1H‐NMR, and mass spectral data. Representative compounds of the synthesized products were tested and evaluated as antioxidant. Compounds 7 and 30 are promising compounds.

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Reactivity of 3-Cyanoacetylindole Derivatives: Synthesisof 3-Hydrazonopyrazolyl and 3-Thiadiazolyl Indole Derivatives

Cited by 9 publications

References 25 publications

Synthesis of New (E)-2-(1H-Indole-3-ylcarbonyl)-3-heteroaryl-acrylonitriles via Microwave-Assisted Knoevenagel Condensation

Synthesis of New (E)-2-(1H-Indole-3-ylcarbonyl)-3-heteroaryl-acrylonitriles via Microwave-Assisted Knoevenagel Condensation

Structure–Activity Relationship Studies of Substituted 2-(Isoxazol-3-yl)-2-oxo-N′-phenyl-acetohydrazonoyl Cyanide Analogues: Identification of Potent Exchange Proteins Directly Activated by cAMP (EPAC) Antagonists

Synthesis and Antioxidant Evaluation of Some Novel Thiophene, Pyrazole, Chromene, Pyrazolotriazine Derivatives Bearing Sulfonamide Moiety

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