Specificities of acetoxy derivatives of coumarins, biscoumarins, chromones, flavones, isoflavones and xanthones for acetoxy drug: Protein transacetylase

Kumar, Ajit; Singh, Brajendra K.; Sharma, Nikhil; Gyanda, Kapil; Jain, Seema; Tyagi, Yogesh Kumar; Baghel, Anil Singh; Pandey, Mukesh K.; Sharma, Sunil; Prasad, Ashok K.; Jain, Subhash C.; Rastogi, R. C.; Raj, Hanumantharao G.; Watterson, Arthur C.; Eycken, Erik V. Van der; Parmar, Virinder S.

doi:10.1016/j.ejmech.2006.09.008

Cited by 22 publications

(9 citation statements)

References 24 publications

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“…Similar results were obtained when the TAase catalyzed activation of NADPH cytochrome c reductase assay and AflatoxinB1 (AFB1)-DNA binding inhibitory assay were performed with 4-phenylcoumarins and 4-methylcoumarins [96]. These results confirmed the hypothesis that DAMC was found to modulate the activities of enzymes including cytochrome P-450-linked mixed-function-oxidase (MFO), NADPH cytochrome c reductase and cytosolic GST when catalyzed by TAase [99]. To elucidate the structure activity relationship (SAR) of the phenyl ring on the benzopyran nucleus, Kumar et al compares the specificities of the acetylated coumarins, biscoumarins, chromones, flavones/isoflavones and xanthones for TAase activity.…”

Section: Anti-oxidantsupporting

confidence: 88%

“…To elucidate the structure activity relationship (SAR) of the phenyl ring on the benzopyran nucleus, Kumar et al compares the specificities of the acetylated coumarins, biscoumarins, chromones, flavones/isoflavones and xanthones for TAase activity. The results demonstrated that the presence of the phenyl ring on the pyran nucleus of polyphenolic acetates drastically reduces their specificity to TAase modification [99]. O O AcO…”

Section: Anti-oxidantmentioning

confidence: 98%

“…Raj et al,98],[Kumar et al,99] Modeling and docking: 6-hydroxyl interacts with the E802 residue of XO[Masamoto et al., 94] EsculetinThe hydroxylation at C6 is important for high selectivity of 12-LOX [Hardt et al, a hydroxyl, methoxyl or benzamido group in position 3 of coumarin decreases the anticoagulant activity; but introduction of a 8-acetyl group into 7-hydroxy-4-methlcoumarin increases the anti-coagulant activity[Arora et al,88] …”

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confidence: 99%

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The Structure and Pharmacological Functions of Coumarins and Their Derivatives

Wang²,

Xu³

et al. 2009

CMC

249

132

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Coumarins are of many different structures. They constitute an important class of pharmacological agents possessing a range of different physiological activities including anti-cancer, anti-oxidant, anti- inflammation, anti-HIV, anti-coagulant, anti-bacterial, analgesic and comparative immune-modulation. Recently, coumarins have attracted intense research interest. Of great interest is the possibility that this class of molecules could be a source of drugs for the therapy of several diseases. These include recent insights into inhibiting cell proliferation by interfering with mitotic spindle microtubule function, decrease Matrix Metalloproteinase (MMP) activity, block the cell cycle in the S or G2/M phases to interfere with processes of cell division, suppress O2(-) generation in leukocytes, inhibit different protein kinases, modulate the signalings, induce carcinogen-detoxifying enzymes glutathione S-transferases (GSTs) and/or NAD(P)H quinine oxidoreductase (NQO1), suppress the phosphorylation of Akt/PKB as a mechanism inhibiting inflammation, progress in structure modification to increase in anti-fungal action, to broaden against bacteria spectrum, to enhance inhibiting activities of nitric oxide synthase (NOS) and cyclooxygenase (COX), to strengthen anti-oxidant activity and to exhibite a much higher cytotoxicity against human umbilical vein endothelial cell (HUVEC). With fewer non-hemorrhagic side effects than the indanedione derivatives, they can be applied as an oral anticoagulant commonly for preventing venous thromboembolism following orthopedic surgery, recurrent myocardial infarction and the treatment of systemic embolism in atrial fibrillation, together with the significant advances in the basis of drug action. It is therefore useful to build up some correlations with the data available in order to better explore the molecular and cellular mechanism of coumarin action in the treatment of diseases. This review will focus on recent advances in molecular and cellular mechanisms of coumarin action involved with the relationship between structure and activity.

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Section: Anti-oxidantsupporting

confidence: 88%

Section: Anti-oxidantmentioning

confidence: 98%

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confidence: 99%

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The Structure and Pharmacological Functions of Coumarins and Their Derivatives

Wang²,

Xu³

et al. 2009

CMC

249

132

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“…Biscoumarins' properties are similar to those of coumarins and exhibit various biological activities such as anticoagulants, antioxidants, antitumor, and antifungal agents. Essential and not well studied is their role a s inhibitors of various enzymes-urease, anti-HIV-1 protease and integrase, DNA polymerase, and protein kinase [3,4,5,6,7]. Bis-coumarins were usually prepared by the condensation of carbonyl compounds with 4-hydroxycoumarin in organic solvents [8,9] which employs large amounts of hazardous and toxic solvents associated with catalysts.…”

Section: Introductionmentioning

confidence: 99%

Grape juice catalyzed synthesis of Bis-coumarin derivatives by Grindstone Technique: A Green chemistry Approach.

Nazeruddin¹,

Mulani²,

Shaikh³

et al. 2019

JCPR

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Biscoumarins' properties are similar to those of coumarins and exhibit various biological activities. Bis-coumarins were usually prepared by the condensation of carbonyl compounds with 4-hydroxycoumarin in organic solvents which employs large amounts of hazardous and toxic solvents associated with catalysts. However, these protocols were not environmentally benign. Thus, the introduction of efficient new methods based on green methodology is still in great demand. In the course of our investigation to develop new green synthetic method we wish to report here in a simple, efficient and eco-friendly procedure for the synthesis of bis-coumarin derivatives by grinding the aromatic aldehyde and 4-hydroxy coumarin in the presence of grape juice as a natural catalyst. This is a convenient and facile one pot synthesis of bis-coumarin with a greener approach. Thus facilitating efficient synthesis of bioactive compounds in environmentally benign way with shorter reaction time, mild reaction conditions, easy workup, and more over less expensive with excellent yield of the product.

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“…Owing to their plethora of pharmacological activities [1,2], coumarins have been a subject of extensive research over many decades [3,4]. In recent years, our laboratories have been actively engaged in studying the synthesis and biological activities of a wide range of coumarin derivatives [5][6][7][8]. We have previously isolated 8-acetyl-7-hydroxy-6-methoxycoumarin and 8-methoxycoumarin from Fraxinus floribunda leaves [9], trigoforin (3,4,7-trimethylcoumarin) and trigocoumarin [3-(ethoxycarbonyl)methyl-4-methyl-5,8-dimethoxycoumarin] from Trigonella foenumgraecum stems [10,11], and troupin (4-methyl-6-hydroxy-7,8-dimethoxycoumarin) from Tamarix troupii [12] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic Synthesis of Novel Partial Esters of a Bioactive Dihydroxy 4-Methylcoumarin by Rhizopus oryzae Lipase (ROL)

et al. 2016

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Abstract:Highly regioselective acylation has been observed in 7,8-dihydroxy-4-methylcoumarin (DHMC) by the lipase from Rhizopus oryzae suspended in tetrahydrofuran (THF) at 45 • C using six different acid anhydrides as acylating agents. The acylation occurred regioselectively at one of the two hydroxy groups of the coumarin moiety resulting in the formation of 8-acyloxy-7-hydroxy-4-methylcoumarins, which are important bioactive molecules for studying biotansformations in animals, and are otherwise very difficult to obtain by only chemical steps. Six monoacylated, monohydroxy 4-methylcoumarins have been biocatalytically synthesised and identified on the basis of their spectral data and X-ray crystal analysis.

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Specificities of acetoxy derivatives of coumarins, biscoumarins, chromones, flavones, isoflavones and xanthones for acetoxy drug: Protein transacetylase

Cited by 22 publications

References 24 publications

The Structure and Pharmacological Functions of Coumarins and Their Derivatives

The Structure and Pharmacological Functions of Coumarins and Their Derivatives

Grape juice catalyzed synthesis of Bis-coumarin derivatives by Grindstone Technique: A Green chemistry Approach.

Biocatalytic Synthesis of Novel Partial Esters of a Bioactive Dihydroxy 4-Methylcoumarin by Rhizopus oryzae Lipase (ROL)

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