Iron-catalyzed aryl-aryl cross coupling route for the synthesis of 1-(2-amino)-phenyl)dibenzo[b,d]furan-2-ol derivatives and their biological evaluation

Chiranjeevi, Barreddi; Koyyada, Ganesh; Prabusreenivasan, S.; Kumar, Vanaja; Sujitha, Pombala; Kumar, C. Ganesh; Sridhar, Balasubramanian; Shaik, S; Chandrasekharam, Malapaka

doi:10.1039/c3ra43345e

Cited by 23 publications

(12 citation statements)

References 28 publications

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“…Furthermore, 2-dibenzofuranol instead of 2-naphthol could also be employed for this reaction system and gave the corresponding 1-(2-aminophenyl)dibenzo [b,d] furan-2-ol derivatives in good to high yields (Scheme 40) [65]. Some of the compounds synthesized show anti-tubercular and cytotoxic activities.…”

Section: Other C-c Cdc Reactionmentioning

confidence: 97%

Iron-Catalyzed Cross-Dehydrogenative-Coupling Reactions

Itazaki

Nakazawa

2015

Topics in Organometallic Chemistry

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Cross-dehydrogenative-coupling (CDC) reactions involving C-H bond activation are powerful tools for C-C bond formation and are highly significant from the perspective of atom economy. A variety of carbon-carbon bond-forming reactions utilizing various coupling partners are known today. Iron-catalyzed organic syntheses have attracted considerable attention because iron is an abundant, inexpensive, and environmentally benign metal. This chapter summarizes the development of iron-catalyzed CDC reactions, the reaction mechanism, and the role of the Fe species in the catalytic cycle in the period from 2007 to 2014.

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Section: Other C-c Cdc Reactionmentioning

confidence: 97%

Iron-Catalyzed Cross-Dehydrogenative-Coupling Reactions

Itazaki

Nakazawa

2015

Topics in Organometallic Chemistry

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“…Natural products and their structurally diverse derivatives play a major role in drug discovery and development (Cragg et al, 1997). Derivatives of dibenzofuran, a three-ring fused system, have shown interesting biological activities as therapeutics for diseases such as cancer, thombosis, tuberculosis, etc (Yurtasş et al, 2016; Kantevari et al, 2011; Chiranjeevi et al, 2013). Our lab is studying the design and synthesis of new inhibitors of P450 enzymes, which are a superfamily of heme proteins involved in the metabolism and detoxification of endogenous and exogenous compounds (Sridhar et al, 2017).…”

Section: Structure Descriptionmentioning

confidence: 99%

A dibenzofuran derivative: 2-(pentyloxy)dibenzo[b,d]furan

Goyal

Donahue

et al. 2018

IUCr Data

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The title compound, C17H18O2, crystallizes in two-dimensional sheets, in which the 2-(pentyloxy)dibenzo[b,d]furan molecules are arranged in a head-to-head and tail-to-tail fashion that enables hydrophobic interactions between fully extended 2-pentoxy chains and π–π stacking between dibenzofuran rings in adjacent rings. Nearest intermolecular π-π stacking contacts are 3.3731 (12) Å. The molecule is nearly planar with an r.m.s. deviation of 0.0803 Å from the mean plane defined by the nineteen non-hydrogen atoms.

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“…Considering these facts, the development of new chemotherapeutic scaffolds which selectively act on the target has become a primary objective of medicinal chemists. In continuation of our efforts on transition metal catalyzed reactions and green technologies for organic transformations and their applications for the synthesis of biologically active compounds, we aimed to focus on a green approach for the synthesis of dibenzofuranol derivatives. Further, arylamine containing compounds also have important biological significance.…”

Section: Introductionmentioning

confidence: 99%

“…Further, arylamine containing compounds also have important biological significance. In our previous work, we described the iron catalyzed aryl–aryl regioselective cross coupling of dibenzofuranol and dialkyl aniline where the amino group is not a part of the heterocycle . The resulting dibenzofuranol derivatives showed antimicrobial and anticancer activities (Fig.…”

Section: Introductionmentioning

confidence: 99%

Molecular Engineering of Tetracyclic 2,3‐Dihydro‐1H‐benzo[2,3]‐benzofuro[4,5‐e][1,3]oxazine Derivatives: Evaluation for Potential Anticancer Agents

Botla

Pilli

Koude

et al. 2017

Archiv der Pharmazie

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Water-mediated one-pot Mannich type condensation of dibenzo[b,d]furan-2-ol with different amines resulted in a large library of novel 2,3-dihydro-1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazine derivatives in moderate to excellent yields. The ortho-aminomethylation of the dibenzofuranols proceeded smoothly in the presence of various aromatic/aliphatic amines and paraformaldehyde, followed by cyclization. All the newly synthesized tetracyclic 2,3-dihydro-1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazine derivatives were chemically characterized and screened for their cytotoxicity activity by cell viability assay (MTT test) against three human cancer cell lines and antibacterial activity by determining the minimum inhibitory concentration (MIC) against four bacterial strains. Among all the derivatives, MCV-24 showed promising anticancer activity by inhibiting the cell proliferation of an ovarian cancer cell line (SKOV3) with an IC value at 7.5 µM, whereas MCV-24 to MCV-30 derivatives showed moderate activity against a lung cancer cell line (A549) with an IC value ranging from 11 to 15.9 µM. Besides MCV-29, -30, and -31 also exhibited broad-spectrum antibacterial activity. Among all new compounds, MCV-24-30 showed promising anticancer and MCV-29-31 antibacterial activity.

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Iron-catalyzed aryl-aryl cross coupling route for the synthesis of 1-(2-amino)-phenyl)dibenzo[b,d]furan-2-ol derivatives and their biological evaluation

Cited by 23 publications

References 28 publications

Iron-Catalyzed Cross-Dehydrogenative-Coupling Reactions

Iron-Catalyzed Cross-Dehydrogenative-Coupling Reactions

A dibenzofuran derivative: 2-(pentyloxy)dibenzo[b,d]furan

Molecular Engineering of Tetracyclic 2,3‐Dihydro‐1H‐benzo[2,3]‐benzofuro[4,5‐e][1,3]oxazine Derivatives: Evaluation for Potential Anticancer Agents

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