Nitrogen-Containing Apigenin Analogs: Preparation and Biological Activity

Li, Rui; Zhao, Bin; Wang, Dong-En; Yao, Tianyu; Pang, Long; Tu, Qin; Ahmed, Saeed; Liu, Jianjun; Wang, Jinyi

doi:10.3390/molecules171214748

Cited by 23 publications

(16 citation statements)

References 60 publications

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“…Zhu's group also found that morpholine, benzylamine and their derivative subsituents were favorable for the antibacterial activities of a series of luteolin analogs [33]. Another study by Liu and coworkers demonstrated that the modifications of apigenin at 8-C position by nitrogen-containing cyclic or aliphatic chain substituents enhanced the antibacterial activities [34]. Notable among these apigenin analogs was the one with morpholine substituent which had potent antibacterial activities similar to those of tetracycline against gram-positive strains S. aureus and B. subtilis.…”

Section: Flavonementioning

confidence: 93%

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Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Fei¹,

Yang²,

Tang³

et al. 2014

CMC

521

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: 93%

“…Structures of antibacterial bioflavonoids. Apigenin 8-C [34] flavonoids for proteins and their biological activities [109][110][111]. For antibacterial activity, it has been revealed that flavanone showed higher activity than the corresponding flavone.…”

Section: Structure-activity Relationshipmentioning

confidence: 99%

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Fei¹,

Yang²,

Tang³

et al. 2014

CMC

521

369

View full text Add to dashboard Cite

show abstract

“…Only three Mannich bases 41 (R ¼ OH, R 1 ¼ H, R 2 ¼ 1-pyrrolidinyl, diethylamino or diisopropylamino) of apigenin ( Fig. 7) exhibited antioxidant activity greater than that of apigenin, while the rest of candidates 41 presented antioxidant activity comparable to that of apigenin [58]. Antioxidant activity of these apigenin derivatives was concentration-dependent, and DPPH radical scavenging ability of the most potent Mannich bases 41 was almost the same as that of the standard ascorbic acid at a concentration of 1.25 mg/mL.…”

Section: Antioxidant Activitymentioning

confidence: 99%

“…Aminomethylated derivatives 41 (R ¼ OH, Fig. 7) also manifested antibacterial activity in various degrees; the most active candidates were the Mannich base derived from cyclohexylamine, which was as potent as tetracycline against B. subtilis (MIC 3.9 mg/mL), and the Mannich base derived from morpholine, which had the same antibacterial activity as ampicillin against S. aureus (MIC 2 mg/mL) [58].…”

Section: Antibacterial Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

257

110

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The biological activity of Mannich bases, a structurally heterogeneous class of chemical compounds that are generated from various substrates through the introduction of an aminomethyl function by means of the Mannich reaction, is surveyed, with emphasis on the relationship between structure and biological activity. The review covers extensively the literature reports that have disclosed Mannich bases as anticancer and cytotoxic agents, or compounds with potential antibacterial and antifungal activity in the last decade. The most relevant studies on the activity of Mannich bases as antimycobacterial agents, antimalarials, or antiviral candidates have been included as well. The review contains also a thorough coverage of anticonvulsant, anti-inflammatory, analgesic and antioxidant activities of Mannich bases. In addition, several minor biological activities of Mannich bases, such as their ability to regulate blood pressure or inhibit platelet aggregation, their antiparasitic and anti-ulcer effects, as well as their use as agents for the treatment of mental disorders have been presented. The review gives in the end a brief overview of the potential of Mannich bases as inhibitors of various enzymes or ligands for several receptors.

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“…On the contrary, β-naphthoflavone derivatives containing same pharmacophore when substituted with an O-alkyl side-chain at position 1 showed decreased cytotoxic activities. Furthermore, Liu et al [267] demonstrated that nitrogen-containing apigenin analogs (R= ethylamino, propylamino, isopropylamino etc.) showed better anti-cancer and antioxidant potential (Fig.…”

Section: Phytochemicals For the Prevention/treatment Of Melanomamentioning

confidence: 99%

Phytochemicals for the Management of Melanoma

Pal¹,

Hunt²,

Diamond³

et al. 2016

MRMC

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Melanoma claims approximately 80% of skin cancer-related deaths. Its life-threatening nature is primarily due to a propensity to metastasize. The prognosis for melanoma patients with distal metastasis is bleak, with median survival of six months even with the latest available treatments. The most commonly mutated oncogenes in melanoma are BRAF and NRAS accounting approximately 60% and 20% of cases, respectively. In malignant melanoma, accumulating evidence suggests that multiple signaling pathways are constitutively activated and play an important role in cell proliferation, cell survival, epithelial to mesenchymal transition, metastasis and resistance to therapeutic regimens. Phytochemicals are gaining considerable attention because of their low toxicity, low cost, and public acceptance as dietary supplements. Cell culture and animals studies have elucidated several cellular and molecular mechanisms by which phytochemicals act in the prevention and treatment of metastatic melanoma. Several promising phytochemicals, such as, fisetin, epigallocatechin-3-gallate, resveratrol, curcumin, proanthocyanidins, silymarin, apigenin, capsaicin, genistein, indole-3-carbinol, and luteolin are gaining considerable attention and found in a variety of fresh fruits, vegetables, roots, and herbs. In this review, we will discuss the preventive potential, therapeutic effects, bioavailability and structure activity relationship of these selected phytochemicals for the management of melanoma.

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Nitrogen-Containing Apigenin Analogs: Preparation and Biological Activity

Cited by 23 publications

References 60 publications

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Mannich bases in medicinal chemistry and drug design

Phytochemicals for the Management of Melanoma

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