Synthesis of 3-Bromo Derivatives of Flavones

Rho, Ho Sik; Ko, Byoung‐Seob; Kim, Ho Kyoung; Ju, Young-Sung

doi:10.1081/scc-120003625

Cited by 28 publications

(11 citation statements)

References 23 publications

(10 reference statements)

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“…Data for compounds 6 (Moon et al 2005), 8 (Shen et al 1993), 9 (Rho et al 2002), 11 (Marder et al 1996) and 13 (Khan & Goswami 2005) were in accordance with that reported in literature. 105.7, 107.4, 108.3, 114.6, 129.2, 132.0, 132.7, 139.5, 155.8, 161.9, 176 6,7, 300 mg of 17 (0.7 mmol) gave 275 mg (92%) of a yellow solid that was difficult to manipulate because of its low 20.4, 20.8, 21.1, 105.8, 108.1, 110.9, 116.7, 122.5, 127.8, 147.1, 150.7, 153.2, 153.7, 161.8, 166.1, 167.9, 168.7, 175.0, 183.4…”

Section: Typical Procedures For the Oxidation Of Flavanones To Flavonessupporting

confidence: 87%

Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones

Bovicelli

D'Angelo

Collalto

et al. 2007

Journal of Pharmacy and Pharmacology

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Flavonoids are constituents of the human diet (they are present in many beverages and food), and in organisms they are responsible for several biological functions, including that of antioxidant. Because of the increasing interest in these molecules, methods for their synthesis and structural modification are of great importance; studies on the biological activities of many of these compounds are insufficient because of their scarcity and/or high cost. We have developed an expeditious synthesis of polyoxygenated flavones, starting from available and inexpensive flavanones, using a bromination-methoxylation procedure. A series of flavonoids that are not otherwise accessible can be prepared using this method. As an example, 3'-demethoxysudachitin, a limited flavone possessing antimicrobial activity against methicillin-resistant Staphylococcus aureus and Helicobacter pylori and acting as a 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenger, was prepared in fairly satisfactory yield.

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Section: Typical Procedures For the Oxidation Of Flavanones To Flavonessupporting

confidence: 87%

Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones

Bovicelli

D'Angelo

Collalto

et al. 2007

Journal of Pharmacy and Pharmacology

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“…Several attempts to introduce the bromine group to 20 using ammonium bromide and ammonium persulphate at room temperature by grinding in a solvent-free condition via green synthesis were unsuccessful and did not yield the target product [27]. Several other preparation methods were referred [28][29][30][31] to obtain the target product 3-bromoflavone which is an important intermediate for the C-3 modification, and it was found that the treatment of 20 with Bu 4 NBr/PhI(OAc) 2 in CH 2 Cl 2 at room temperature under nitrogen atmosphere successfully produced 3-bromoflavone, 21 in high yield, 98% [32].…”

Section: Chemical Synthesismentioning

confidence: 99%

Molecular characterization, biological activity, and in silico study of 2-(3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-6-methoxy-4H-chromen-4-one as a novel selective COX-2 inhibitor

Rullah

Aluwi

Yamin

et al. 2015

Journal of Molecular Structure

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“…There was, however, a high field shift for the ethyl protons of di-thioketone 42 (Table 1). Bromination of 40a (R = Et, Ar = naphthyl) with nBu 4 NBr in the presence of PhI(OAc) 2 9 afforded 3-bromo derivative 43 , which was converted to 44 by demethylation with BBr 3 . Meanwhile, flavanone analogue 48 was prepared by the treatment of 39 with HI in HOAc.…”

Section: Chemistrymentioning

confidence: 99%

Antitumor Agents. 284. New Desmosdumotin B Analogues with Bicyclic B-Ring as Cytotoxic and Antitubulin Agents

Nakagawa‐Goto

Lai

et al. 2011

J. Med. Chem.

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We previously reported that the biological activity of analogues of desmosdumotin B (1) was dramatically changed depending on the B-ring system. A naphthalene B-ring analogue 3 exerted potent in vitro activity against a diverse panel of human tumor cell lines with GI50 values of 0.8–2.1 μM. In contrast, 1-analogues with a phenyl B-ring showed unique selective activity against P-glycoprotein (P-gp) overexpressing multidrug resistance cell line. We have now prepared and evaluated 1-analogues with bicyclic or tricyclic aromatic B-ring systems as in vitro inhibitors of human cancer cell line proliferation. Among all synthesized derivatives, 21 with a benzo[b]thiophenyl B-ring was highly active, with GI50 values of 0.06–0.16 μM, and this activity was not influenced by overexpression of P-gp. Furthermore, 21 inhibited tubulin assembly in vitro with an IC 50 value of 2.0 μM and colchicine binding by 78% as well as cellular microtubule polymerization and spindle formation.

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Synthesis of 3-Bromo Derivatives of Flavones

Cited by 28 publications

References 23 publications

Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones

Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones

Molecular characterization, biological activity, and in silico study of 2-(3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-6-methoxy-4H-chromen-4-one as a novel selective COX-2 inhibitor

Antitumor Agents. 284. New Desmosdumotin B Analogues with Bicyclic B-Ring as Cytotoxic and Antitubulin Agents

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