Bioactive Benzofuran derivatives: A review

Khanam, Hena; Shamsuzzaman, _

doi:10.1016/j.ejmech.2014.11.039

Cited by 460 publications

(216 citation statements)

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“…[1][2][3][4] Benzofurans have been the subject of more extensive studies for the development of efficient routes for the synthesis. [5,6] The naphthofuran skeleton is present in many natural products with biological importance and its synthetic derivatives display diverse biological activities.…”

Section: Efficient and Convenient Methods For Synthesis Of Benzofuran-mentioning

confidence: 99%

Efficient and Convenient Method for Synthesis of Benzofuran-3-acetic Acids and Naphthafuran-acetic Acids

Basanagouda¹,

Narayanachar

Majati³

et al. 2015

Synthetic Communications

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Herein, we report an efficient and convenient method for synthesis of benzofuran-3-acetic acids and naphthafuran-acetic acids 5a-p by the reaction of substituted-4-bromomethylcoumarins with aqueous sodium hydroxide at refluxing temperature. The obtained products are characterized by infrared, 1 H NMR, 13 C NMR, and mass spectral data. Structures 5a and 5e are confirmed by their single x-ray diffraction studies. The advantages of this method are good yields, easy workup, and no chromatographic purifications.

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Section: Efficient and Convenient Methods For Synthesis Of Benzofuran-mentioning

confidence: 99%

Efficient and Convenient Method for Synthesis of Benzofuran-3-acetic Acids and Naphthafuran-acetic Acids

Basanagouda¹,

Narayanachar

Majati³

et al. 2015

Synthetic Communications

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“…The benzofuran ring system, although by no means as common as indole, is incorporated into many natural products and into synthetic pharmaceuticals 1,2 . Oximes are belonging to the imines, with the general formula R 1 R 2 C=NOH, where R 1 is an organic side-chain and R 2 may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and X-Ray Structural Characterization of 1-(5-Bromobenzofuran-2-Yl)-2-Mesitylethanoneoxime and 1-(5-Bromobenzofuran-2-Yl)-2-Mesitylethanone-O-(2- Phenylacetyl)oxime

Yakalı¹,

Barım²,

Kırılmış³

et al. 2016

J. Chil. Chem. Soc.

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The selected molecules of benzofuran derivatives were synthesized and their structures were studied using the X-ray crystallography and spectroscopic methods. The 1-(5-bromobenzofurane-2-yl)-2-mesitylethanoneoxime (I), C 19 H 18 BrNO 2 , and 1-(5-bromobenzofuran-2-yl)-2-mesitylethanone-O-(2-phenylacetyl) oxime (II), C 27 H 24 BrNO 3 , crystallize in the monoclinic crystal system in space group P2 1 /c with Z = 4 and in the triclinic system in space group P-1 with Z=2, respectively. The both compounds adopt Z conformation. The compound (I) consists of a dimeric arrangement of molecules around an inversion centre formed via a O-H…N intermolecular hydrogen bond linking the molecules -Along the a axis. This centrosymmetric hydrogen-bonded dimers are formed with an (6) ring motif. The compound (II) forms one dimensional infinite chain via C-H···O hydrogen bond along the a axis. Moreover, in the crystal structures of (I), (II) weak C-H..O, C-H…π and π…π interactions serve to organize formation of a two dimensional network. Moreover a short N1-N1 intermolecular contact [2.89 Å] is observed between inversion-related chains in the crystal structure of (I). The two compounds have essentialy similar bond lengths and angles. The prominent discrepancy is observed for the fragment attaching benzofuran ring with mesityl group. Benzofuran groups and other ring groups are almost planar in the crystal structures of (I) and (II).Keywords: Benzofuran derivatives; Oxime derivatives; Crystal structure; X-ray; 2D Network.e-mail addresses:gulyakali@akdeniz.edu.tr ckirilmis@adiyaman.edu.tr INTRODUCTIONBenzofuran contains a ring system obtained by the fusion of a benzene nucleus with a furan ring. The benzofuran ring system, although by no means as common as indole, is incorporated into many natural products and into synthetic pharmaceuticals 1,2 . Oximes are belonging to the imines, with the general formula R 1 R 2 C=NOH, where R 1 is an organic side-chain and R 2 may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. They exist as two geometric stereo isomers: a syn isomer and an anti isomer. Aldoximes, except for aromatic aldoximes, which exist only as anti isomers, and ketoximes can be separated almost completely and obtained as a syn isomer and an anti isomer 3 .The life threatening infections caused by pathogenic fungi have increased during the past two decades and there is need to develop new antifungals with good activity against variety of fungal species. Benzofurans and their derivates have physiological, pharmacological and toxic properties and find application as sedatives, hypnotics, agrochemicals, pharmaceuticals, cosmetics and as the building blocks of optical brighteners [4][5] . Oximes are a very effective antifungal agent so they became a matter of interest 6 . Aryl benzofuryl ketoxime sand their derivatives are highly effective compounds 7 and these some shows excellent anibacterialactivity 8 .Hydrogen-bond patterns in crystalline oximes have been analyzed by Bertolasi et al. 9 , ...

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“…Over the years many synthetic routes have been reported for the preparation of benzofurans. 1,4,5 Iodocyclization of functionalized alkynes is one of the most important and efficient synthetic methodologies for the synthesis of important heterocyclic compounds, including benzofurans.…”

Section: Introductionmentioning

confidence: 99%

“…Several compounds containing this scaffold have interesting biological activities, such as anti-cancer, anti-viral, anti-inflammatory, etc. 1 Few derivatives are even used as commercial drugs, such as Amiodarone, 2 or investigational drugs, such as Bufuralol, 3 etc. (Figure 2).…”

Section: Introductionmentioning

confidence: 99%