3D-QSAR studies on chromone derivatives as HIV-1 protease inhibitors

Ungwitayatorn, Jiraporn; Samee, Weerasak; Pimthon, Jutarat

doi:10.1016/j.molstruc.2003.10.036

Cited by 32 publications

(11 citation statements)

References 25 publications

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“…Chromone derivatives were synthesized by one-pot cyclization reaction with 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) as catalyst [25]. The antioxidant activities of the synthesized compounds were assessed on the basis of the radical scavenging effect on the DPPH free radicals as described previously [16].…”

Section: Methodsmentioning

confidence: 99%

3D-QSAR Investigation of Synthetic Antioxidant Chromone Derivatives by Molecular Field Analysis

Samee

Nunthanavanit

Ungwitayatorn

2008

IJMS

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A series of 7-hydroxy, 8-hydroxy and 7,8-dihydroxy synthetic chromone derivatives was evaluated for their DPPH free radical scavenging activities. A training set of 30 synthetic chromone derivatives was subject to three-dimensional quantitative structure-activity relationship (3D-QSAR) studies using molecular field analysis (MFA). The substitutional requirements for favorable antioxidant activity were investigated and a predictive model that could be used for the design of novel antioxidants was derived. Regression analysis was carried out using genetic partial least squares (G/PLS) method. A highly predictive and statistically significant model was generated. The predictive ability of the developed model was assessed using a test set of 5 compounds (r

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Section: Methodsmentioning

confidence: 99%

3D-QSAR Investigation of Synthetic Antioxidant Chromone Derivatives by Molecular Field Analysis

Samee

Nunthanavanit

Ungwitayatorn

2008

IJMS

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“…3D-QSAR studies using CoMFA and CoMSIA on chromone derivatives as a new class of HIV-1 PR inhibitors has recently been reported by Ungwitayatorn et al [90]. The HIV-1 PR activity measured at a fixed concentration (12.5 µg/ml) and reported as % inhibition was used as the dependent variable.…”

Section: Hiv-1 Protease (Pr) As Targetmentioning

confidence: 99%

Application of 3D-QSAR Techniques in Anti-HIV-1 Drug Design - An Overview

Debnath¹

2005

CPD

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Despite the availability of several classes of drugs against acquired immunodeficiency syndrome (AIDS) caused by human immunodeficiency virus type 1(HIV-1), this deadly disease showing very little sign of containment, especially in Sub-Saharan Africa and South-East Asia. More than 20 million people died since the first diagnosis of AIDS more than twenty years ago and almost 40 million people are currently living with HIV/AIDS. Structure-based drug design effort was immensely successful in identifying several drugs that are currently available for the treatment of HIV-1. Many applications have been reported on the use of quantitative structure-activity relationship (QSAR) studies to understand the drug-receptor interactions and help in the design of more effective analogs. Extensive application was also reported on the application of 3D-QSAR techniques, such as, Comparative Molecular Field Analysis (CoMFA), Comparative Molecular Similarity Analysis (CoMSIA), pharmacophore generation using Catalyst/HypoGen, free-energy binding analysis, GRID/GOLPE, HINT-based techniques, etc. in anti-HIV-1 drug discovery programs in academia and industry. We have attempted to put together a comprehensive overview on the 3D-QSAR applications in anti-HIV-1 drug design reported in the literature during the last decade.

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“…Chromones are well-known natural and synthetic products that possess diverse biological activities [1], including anticancer [2][3][4], antitumor [5], antiproliferative [6], neuroprotective [7], HIV-inhibitory [8,9], antimicrobial [10,11], antioxidant [12], anti-inflammatory [13], and antibiotic [14]. Heteroannulated chromones showed significant biological activity including pharmacological [15], antiplatelet [16], antiallergic [17], antiangiogenic [18], antirheumatic [19], antibacterial [20], anti-inflammatory, and analgesic [21].…”

Section: Introductionmentioning

confidence: 99%

“…and 4(6)-aminouracil were supplied by Merck and 5-amino-3methyl-1H-pyrazole by Aldrich. 4-Hydroxy-1-methylquinolin-2(1H)-one (4)[27], 2-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one (6)[28], and 4-hydroxy-2H-pyrano[3,2-c]quinoline-2,5(6H)dione(8) [27] were prepared according to literature.10-Methyl-6H,8H-dichromeno[2,3-b:3′,4′-e]pyridine-6,8dione(3). A mixture of 2-amino-6-methylchromone-3-carboxaldehyde (1), (0.61 g, 3 mmol) and 4-hydroxycoumarin (2), (0.49 g, 3 mmol), in DMF (10 mL) containing a few drops of DBU, was heated under reflux for 2 h. The yellow crystals obtained after cooling were filtered off and crystallized from DMF/H 2 O to give compound 3 as yellow crystals, mp > 300°C, yield 0.53 g (54%).…”

mentioning

confidence: 99%