Synthesis and biological evaluation of a novel class of β-carboline derivatives

Chen, Hao; Gao, Pengchao; Zhang, Meng; Liao, Wei; Zhang, Jianwei

doi:10.1039/c4nj00262h

Cited by 36 publications

(15 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Various aromatic β-carbolines has been accessed by oxidative dehydrogenation of their heterocyclic precursors using metal-based reagents. For example selenium dioxide (SeO 2 , 10 equiv) has been used in the presence of an acid for oxidative dehydrogenation of tetrahydro-β-carbolines 49 to afford aromatic β-carbolines 50 ( Scheme 15 ) [ 65 ]. Bhutania et al [ 66 ] has also reported a similar synthesis of 1-aryl-β-carboline derivative 52 starting from 51 ( Scheme 15 ).…”

Section: Reviewmentioning

confidence: 99%

See 1 more Smart Citation

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

Hati¹,

Holzgrabe²,

Sen³

2017

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Nitrogen heteroarenes form an important class of compounds which can be found in natural products, synthetic drugs, building blocks etc. Among the diverse strategies that were developed for the synthesis of nitrogen heterocycles, oxidative dehydrogenation is extremely effective. This review discusses various oxidative dehydrogenation strategies of C–C and C–N bonds to generate nitrogen heteroarenes from their corresponding heterocyclic substrates. The strategies are categorized under stoichiometric and catalytic usage of reagents that facilitate such transformations. The application of these strategies in the synthesis of nitrogen heteroarene natural products and synthetic drug intermediates are also discussed. We hope this review will arouse sufficient interest among the scientific community to further advance the application of oxidative dehydrogenation in the synthesis of nitrogen heteroarenes.

show abstract

Section: Reviewmentioning

confidence: 99%

“… Selenium dioxide and potassium dichromate-mediated oxidative dehydrogenation of tetrahydro-β-carbolines [ 65 – 66 ]. …”

Section: Reviewmentioning

confidence: 99%

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

Hati¹,

Holzgrabe²,

Sen³

2017

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…This derivative is a potent cytotoxic agent against chronic myeloid leukemia cells (K562) among the series of β-carbolines (Scheme 28). 124 L-Tryptophan (174) has also been used for the preparation of other β-carboline derivatives with different bioactive properties. The β-carboline 185 is prepared from 174 and 4-nitrobenzaldehyde (181) via tandem C-N/C-C bond formation followed by the decarboxylation/oxidation process to produce intermediate 183.…”

Section: Syn Thesismentioning

confidence: 99%

Recent Advances for the C–C and C–N Bond Formation in the Synthesis of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine, and β-Carboline Alkaloids

Galvis

Kouznetsov

2017

Synthesis

View full text Add to dashboard Cite

Among the existing methods for the synthesis of bioactive and/or complex small molecules, organic transformations such as C–C and C–N bond formation have been significantly developed and exploited for the synthesis of diverse synthetic and natural fused aza-polycycles. The abundance and biological and physical activities of 1-phenethyl-tetrahydroisoquinolines, aporphines, homoaporphines, and β-carbolines have inspired many organic chemists to seek sustainable and efficient protocols for their preparation. However, these methodologies involve multiple steps and in most cases the key reaction step is based on the formation of new C–C and/or C–N bonds, and this is usually the critical step that lowers the yields and selectivity. This review is focused on the advances made in recent years regarding the synthesis of these selected natural fused aza-polycycles, overviewing the substrate scope, limitations, regioselectivity, and chemoselectivity, as well as related control strategies of these reactions, concentrating on developments from 2010 to 2016.1 Introduction2 1-Phenethyl-tetrahydroisoquinolines; Dysoxylum Alkaloids3 Aporphines, Homoaporphines, and Semisynthetic Derivatives4 Harmala and Eudistomin Alkaloids and Their Biological Properties5 Metal-Catalyzed C–C Bond Formation6 Pd-Catalyzed C–C and C–N Bond Formation7 Metal-Catalyzed C–N Bond Formation8 [4+2] Cycloaddition in the Synthesis Of Aporphines9 Tandem C–N/C–C Bond Formation: The Pictet–Spengler Reaction10 Miscellaneous Methods11 Conclusions

show abstract

“…12,13 Among the reported properties, it is worth mentioning the potential of β-carboline derivatives as anticancer agents, which has stimulated studies on their synthesis and structure-activity relationship (SAR). [14][15][16][17][18][19][20][21][22][23] These studies revealed that the introduction of appropriate substituents at the 1-, 3-and 9-positions of the β-carboline ring can result in more potent drugs with reduced toxicity and neurotoxic effects.…”

mentioning

confidence: 99%

Synthesis and Antitumor Activity of Novel 1-Substituted 3-(4,5-Substituted 1,2,4-Triazol-3-yl)-β-carboline Derivatives

et al. 2018

View full text Add to dashboard Cite

Schiff bases, 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazoles, and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles carrying the β-carboline nucleus were synthesized from 3-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-β-carbolines. The compounds were evaluated for their in vitro antitumor activity against eight human cancer cell lines. The 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazole derivatives showed a broad spectrum of antitumor activity, with GI50 values lower than 13 μM for all cell lines tested. In general, all tested compounds showed potent activity against the breast (MCF-7) cancer cell line, with GI50 values in the range of 2.07 to 4.58 μM.

show abstract

Synthesis and biological evaluation of a novel class of β-carboline derivatives

Abstract: β-Carboline was modified with amino acids and several novel β-carboline analogues were obtained.

Cited by 36 publications

References 48 publications

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

Recent Advances for the C–C and C–N Bond Formation in the Synthesis of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine, and β-Carboline Alkaloids

Synthesis and Antitumor Activity of Novel 1-Substituted 3-(4,5-Substituted 1,2,4-Triazol-3-yl)-β-carboline Derivatives

Contact Info

Product

Resources

About

Synthesis and biological evaluation of a novel class of β-carboline derivatives

Abstract: β-Carboline was modified with amino acids and several novel β-carboline analogues were obtained.

Cited by 36 publications

References 48 publications

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

Recent Advances for the C–C and C–N Bond Formation in the Synthesis­ of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine­, and β-Carboline Alkaloids

Synthesis and Antitumor Activity of Novel 1-Substituted 3-(4,5-Substituted 1,2,4-Triazol-3-yl)-β-carboline Derivatives

Contact Info

Product

Resources

About

Recent Advances for the C–C and C–N Bond Formation in the Synthesis of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine, and β-Carboline Alkaloids