Synthesis and biological evaluation of novel C (7) modified chrysin analogues as antibacterial agents

Babu, K. Suresh; Babu, T. Hari; Srinivas, P.; Kishore, K. Hara; Murthy, U. S. N.; Rao, J. Madhusudana

doi:10.1016/j.bmcl.2005.09.009

Cited by 116 publications

(27 citation statements)

References 19 publications

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“…More over, nitrogencontaining flavone analogs have been increasingly prepared and studied on their antibacterial potentials. Babu et al [31], synthesized a series of chrysin derivatives in which chrysin ring system linked to the alkyl amines by different spacers at C-7 position, and evaluated their antibacterial activities. All the derivatives showed higher antibacterial effects than chrysin and the ones with morpholine or N,N-dimethyl amine substituents even inhibited the growth of the tested gram positive bacteria with the same minimum inhibitory concentrations (MIC) as streptomycin.…”

Section: Flavonementioning

confidence: 99%

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Fei¹,

Yang²,

Tang³

et al. 2014

CMC

600

369

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Flavonoids are well known as antibacterial agents against a wide range of pathogenic microorganism. With increasing prevalence of untreatable infections induced by antibiotic resistance bacteria, flavonoids have attracted much interest because of the potential to be substitutes for antibiotics. In this review, the structure-relationship of flavonoids as antibacterial agents is summarized, and the recent advancements on the antibacterial mechanisms of flavonoids are also discussed. It is concluded that hydroxyls at special sites on the aromatic rings of flavonoids improve the activity. However, the methylation of the active hydroxyl groups generally decreases the activity. Besides, the lipopholicity of the ring A is vital for the activity of chalcones. The hydrophobic substituents such as prenyl groups, alkylamino chains, alkyl chains, and nitrogen or oxygen containing heterocyclic moieties usually enhance the activity for all the flavonoids. The proposed antibacterial mechanisms of flavonoids are as follows: inhibition of nucleic acid synthesis, inhibition of cytoplasmic membrane function, inhibition of energy metabolism, inhibition of the attachment and biofilm formation, inhibition of the porin on the cell membrane, alteration of the membrane permeability, and attenuation of the pathogenicity.

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Section: Flavonementioning

confidence: 99%

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Fei¹,

Yang²,

Tang³

et al. 2014

CMC

600

369

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“…Chrysin (5,7-dihydroxyflavone), a natural flavonoid widely distributed in plants, has a variety of pharmacological effects, including antiviral [3], antiinflammation [4], antioxidant [5], anticancer [6], and antibacterial effect [7]. In order to improve the biological activities of chrysin, a number of its derivatives have been prepared [8][9][10].…”

Section: Discussionmentioning

confidence: 99%

The crystal structure of benzenaminium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate hydrate, C₂₁H₁₉NO₈S

Min-yan

Zhang

2018

Zeitschrift Für Kristallographie - New Crystal Structures

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C 21 H 19 NO 8 S, triclinic, P1 (no. 2), a = 7.2884(9) Å, b = 11.9469(15) Å, c = 12.2002(16) CCDC no.:1836578 Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialA solution of chrysin (3.7 mmol) in concentrated sulfuric acid (6.0 mL) was stirred at room temperature for 15 h, the mixture was poured into aniline hydrochloride saturated aqueous

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“…(−)-Cytisine 9 alone had minimal effect on cancer cell proliferation at these concentrations (<15% inhibition at 10μM, Table S1). Several groups reported isoflavonoids with amine substituents as antineoplastic agents, 18 antibacterials, 19 and antipsychotics, 20 and still other groups explored the linkage of (−)-cytisine to known drugs such as the phenothiazines. 21 The work reported here is the first to explore covalently linked cytisine-isoflavonoids as antineoplastic agents.…”

Section: Discussionmentioning

confidence: 99%

Developing antineoplastic agents that target peroxisomal enzymes: cytisine-linked isoflavonoids as inhibitors of hydroxysteroid 17-beta-dehydrogenase-4 (HSD17B4)

et al. 2017

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Cytisine-linked isoflavonoids (CLIFs) inhibited PC-3 prostate and LS174T colon cancer cell proliferation by inhibiting a peroxisomal bifunctional enzyme. A pull-down assay using a biologically active, biotin-modified CLIF identified the target of these agents as the bifunctional, peroxisomal enzyme, hydroxysteroid 17β-dehydrogenase-4 (HSD17B4). Additional studies with truncated versions of HSD17B4 established that CLIFs specifically bind the C-terminus of HSD17B4 and selectively inhibited the enoyl CoA hydratase but not the D-3-hydroxyacyl CoA dehydrogenase activity. HSD17B4 was overexpressed in prostate and colon cancer tissues, knocking down HSD17B4 inhibited cancer cell proliferation, suggesting that HSD17B4 is a potential biomarker and drug target and that CLIFs are potential probes or therapeutic agents for these cancers.

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Synthesis and biological evaluation of novel C (7) modified chrysin analogues as antibacterial agents

Cited by 116 publications

References 19 publications

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

The crystal structure of benzenaminium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate hydrate, C₂₁H₁₉NO₈S

Developing antineoplastic agents that target peroxisomal enzymes: cytisine-linked isoflavonoids as inhibitors of hydroxysteroid 17-beta-dehydrogenase-4 (HSD17B4)

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Synthesis and biological evaluation of novel C (7) modified chrysin analogues as antibacterial agents

Cited by 116 publications

References 19 publications

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

The crystal structure of benzenaminium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate hydrate, C21H19NO8S

Developing antineoplastic agents that target peroxisomal enzymes: cytisine-linked isoflavonoids as inhibitors of hydroxysteroid 17-beta-dehydrogenase-4 (HSD17B4)

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The crystal structure of benzenaminium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate hydrate, C₂₁H₁₉NO₈S