Unusual reactivity of β-(3-indolyl)-α,β-unsaturated ketones. 2-Acetylvinyl group removal by phenylhydrazine hydrochloride

Бутин, А. В.; Uchuskin, Maxim G.; Pilipenko, Arkady S.; Serdyuk, Olga V.; Trushkov, Igor V.

doi:10.1016/j.tetlet.2011.07.136

Cited by 8 publications

(3 citation statements)

References 58 publications

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“…Control experiments showed that the dihydroquinazolinone 6a in the EtOAc, CH 2 Cl 2 , and ethanol solutions was oxidized to key quinazolinone 3a upon standing in air. Moreover, the deformylation reaction and its related cleavage processes are well known and widely used as a key step for the preparation of natural and synthetic compounds [ 42 , 43 , 44 , 45 ]. Finally, the desired product 3a was obtained in a quantitative yield when the reaction was performed in N , N -dimethylacetamide (DMAC) in the presence of Na 2 S 2 O 5 at 150 °C ( Scheme 1 c).…”

Section: Resultsmentioning

confidence: 99%

The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives

Mendogralo,

Nesterova,

Nasibullina

et al. 2023

Molecules

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The treatment of many bacterial diseases remains a significant problem due to the increasing antibiotic resistance of their infectious agents. Among others, this is related to Staphylococcus aureus, especially methicillin-resistant S. aureus (MRSA) and Mycobacterium tuberculosis. In the present article, we report on antibacterial compounds with activity against both S. aureus and MRSA. A straightforward approach to 2-(1H-indol-3-yl)quinazolin-4(3H)-one and their analogues was developed. Their structural and functional relationships were also considered. The antimicrobial activity of the synthesized compounds against Mycobacterium tuberculosis H37Rv, S. aureus ATCC 25923, MRSA ATCC 43300, Candida albicans ATCC 10231, and their role in the inhibition of the biofilm formation of S. aureus were reported. 2-(5-Iodo-1H-indol-3-yl)quinazolin-4(3H)-one (3k) showed a low minimum inhibitory concentration (MIC) of 0.98 μg/mL against MRSA. The synthesized compounds were assessed via molecular docking for their ability to bind long RSH (RelA/SpoT homolog) proteins using mycobacterial and streptococcal (p)ppGpp synthetase structures as models. The cytotoxic activity of some synthesized compounds was studied. Compounds 3c, f, g, k, r, and 3z displayed significant antiproliferative activities against all the cancer cell lines tested. Indolylquinazolinones 3b, 3e, and 3g showed a preferential suppression of the growth of rapidly dividing A549 cells compared to slower growing fibroblasts of non-tumor etiology.

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Section: Resultsmentioning

confidence: 99%

The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives

Mendogralo,

Nesterova,

Nasibullina

et al. 2023

Molecules

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“…The reaction represents a common approach to 3-unsubstituted 2-arylindoles 125 with antibacterial activity. 79…”

Section: Syn Thesismentioning

confidence: 99%

Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

et al. 2019

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Indolylvinyl ketones are valuable building blocks that can be utilized for the synthesis of numerous natural products and bioactive molecules containing an indole core motif. Herein, we describe their application for the total synthesis of some alkaloids, their analogues, and a variety of other important compounds, with an emphasis on biologically active examples.1 Introduction2 Functionalization of the Enone C=C Bond2.1 Reduction2.2 Michael Addition2.3 Cycloaddition3 Transformation of the Carbonyl Group3.1 Reduction3.2 Knoevenagel Reaction3.3 Addition of Organometallic Compounds3.4 Olefination4 Reactions Involving the Enone Conjugate System С=С–С=О4.1 Reactions with 1,2-Dinucleophiles4.2 Reactions with Compounds Bearing an Active Methylene Group4.3 Reactions with 1,3-Dinucleophiles4.4 Reactions with 1,4-Dinucleophiles5 Functionalization of the Enone Methylene Group C(O)–CH2R5.1 Acylation/Crotonic Condensation and Related Transformations5.2 Enolization6 Functionalization of the Indole Core6.1 [4+2] Cycloaddition6.2 [3+3] Annulation6.3 Electrocyclic Reactions7 Miscellaneous8 Conclusions

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“…Instead of the expected products, deacylvinylated indoles 103 were obtained. This was explained by the protonation of the initially formed pyrazoline K followed by the elimination of pyrazole from the intermediate L to produce two aromatic species (Scheme ) 43…”

Section: Synthesis Of Azaheterocycles By Furan Reactions With Elecmentioning

confidence: 99%

Furan's Gambit: Electrophile‐Attack‐Triggered Sacrifice of Furan Rings for the Intramolecular Construction of Azaheterocycles

2015

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Unusual reactivity of β-(3-indolyl)-α,β-unsaturated ketones. 2-Acetylvinyl group removal by phenylhydrazine hydrochloride

Cited by 8 publications

References 58 publications

The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives

The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives

Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

Furan's Gambit: Electrophile‐Attack‐Triggered Sacrifice of Furan Rings for the Intramolecular Construction of Azaheterocycles

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