Synthesis and biological screening of pyrazole moiety containing analogs of podophyllotoxin

Umesha, Basavaiah; Basavaraju, Y. B.; Mahendra, C.

doi:10.1007/s00044-014-1100-3

Cited by 13 publications

(9 citation statements)

References 16 publications

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“…1The literature survey approaching to synthesis of benzofuran linked with tetralone moiety indicate the lack of reference available. In view of this, on continuation of our research interest in the synthesis and biological evaluation of podophyllotoxin analogous 22 , we have synthesized benzofuran linked tetralones in one compact structure for the purpose of increasing the antimitotic activity.…”

Section: Research Articlementioning

confidence: 99%

Synthesis and Bioevaluation Study of Benzofuran Linked Tetralones as Antimitotic Agent

2018

Chem Sci Trans

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A series of new benzofuran linked tetralones (5a-h) have been prepared by chalcone route of Claisen-Schmidt condensation reaction in the presence of sodium hydroxide, 1-(benzofuran-6-yl)ethanone (1) reacts with substituted benzaldehyde (2a-h) followed by cyclopropanation of 1-(benzofuran-6-yl)-3-phenylprop-2-en-1-one (3a-h) with trimethylsulfoxonium iodide (TMSOI) in the presence of sodium hydride and Friedel-Craft's intramolecular cyclization reaction of benzofuran-6-yl(2-phenylcyclopropyl)methanone (4a-h) in the presence of anhyd. stannic chloride and acetic anhydride. The target molecules were characterized by spectral and elemental analysis and also screened for their antimitotic activity by onion root method. Taken together, our results indicated that among the entire synthesized analogues, the two new compounds 5e and 5f bearing electron donating methoxy group on para and 3,4,5-position of the phenyl moiety respectively exhibits even good antimitotic activity than other compounds.

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Section: Research Articlementioning

confidence: 99%

Synthesis and Bioevaluation Study of Benzofuran Linked Tetralones as Antimitotic Agent

2018

Chem Sci Trans

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“…Podophyllotoxin ( PPT, 1 , Scheme 1), a well-known naturally occurring aryltetralin lignan, is mainly isolated from the roots of the North American Podophyllum peltatum Linnaeus , the Tibetan P. emodi Wall, or the Taiwanese species Podophyllum peltatum 5. It shows strong cytotoxic activity against various cancer cell lines and acts at the colchicine-binding site on tubulin 6Scheme 1Structure of compounds 1 – 6: podophyllotoxin ( 1 ), etoposide ( 2 ), teniposide ( 3 ), etopophos ( 4 ), NK-611 ( 5 ), and podophyllotoxin glucosides ( 6 ).…”

Section: Introductionmentioning

confidence: 99%

<p>Glucoside Derivatives Of Podophyllotoxin: Synthesis, Physicochemical Properties, And Cytotoxicity</p>

Liu

Kong

et al. 2019

DDDT

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BackgroundWidespread concern of the side effects and the broad-spectrum anticancer property of podophyllotoxin as an antitumor agent highlight the need for the development of new podophyllotoxin derivatives. Although some per-butyrylated glucosides of podophyllotoxin and 4β-triazolyl-podophyllotoxin glycosides show good anticancer activity, the per-acetylated/free of podophyllotoxin glucosides and their per-acetylated are not well studied.MethodsA few glucoside derivatives of PPT were synthesized and evaluated for their in vitro cytotoxic activities against five human cancer cell lines, HL-60 (leukemia), SMMC-7721 (hepatoma), A-549 (lung cancer), MCF-7 (breast cancer), and SW480 (colon cancer), as well as the normal human pulmonary epithelial cell line (BEAS-2B). In addition, we investigated the structure–activity relationship and the physicochemical property–anticancer activity relationship of these compounds.ResultsCompound 6b shows the highest cytotoxic potency against all five cancer cell lines tested, with IC50 values ranging from 3.27±0.21 to 11.37±0.52 μM. We have also found that 6b displays higher selectivity than the etoposide except in the case of HL-60 cell line. The active compounds possess similar physicochemical properties: MSA > 900, %PSA < 20, ClogP > 2, MW > 700 Da, and RB > 10.ConclusionWe synthesized several glucoside derivatives of PPT and tested their cytotoxicity. Among them, compound 6b showed the highest cytotoxicity. Further studies including selectivity of active compounds have shown that the selectivity indexes of 6b are much greater than the etoposide except in the case of HL-60 cell line. The active compounds possessed similar physicochemical properties. This study indicates that active glucoside analogs of podophyllotoxin have potential as lead compounds for developing novel anticancer agents.

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“…The biologically active and less cytotoxic new tetralone intermediates of podophyllotoxin have been synthesized. The modification of podophyllotoxin structure might enhance the biological activity with favorable solubility and reduced toxicity [5,6]. Some synthesized analogues of podophyllotoxin showed better antibacterial activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Aryl Tetralone Derivatives by Chalcone Route

Chaitramallu¹,

Dakshayinich²,

rashekarachar³

et al. 2016

Med chem (Los Angeles)

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The tetralone analogues of podophyllotoxin were synthesized by the chalcone route. This route attracts the attention because of its simple operating conditions and easy availability of the chemicals. Initially, chalcones were prepared in high yields by Claisen-Schmidt reaction of acetophenones derivatives with 3,4,5-trimethylthoxybenzaldehyde. The cyclopropyl ketones were prepared in good yields by Simmon-Smith reaction of chalcones with diiodomethane with Zn-Cu couple in presence of ether. Tetralones were prepared in good yields by the intramolecular cyclization reaction of cyclopropyl ketones in the presence of p-toluene sulphonic acid and acetic anhydride. The structures of the synthesized compounds were confirmed by IR, 1 H NMR and Mass spectral technique. The title compounds were screened for their antimitotic and antimicrobial activities.

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Synthesis and biological screening of pyrazole moiety containing analogs of podophyllotoxin

Cited by 13 publications

References 16 publications

Synthesis and Bioevaluation Study of Benzofuran Linked Tetralones as Antimitotic Agent

Synthesis and Bioevaluation Study of Benzofuran Linked Tetralones as Antimitotic Agent

<p>Glucoside Derivatives Of Podophyllotoxin: Synthesis, Physicochemical Properties, And Cytotoxicity</p>

Synthesis of Aryl Tetralone Derivatives by Chalcone Route

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