scholarly journals AntiHIV, antitubercular and antibacterial activities of novel 1-substituted-3-(3-(4-methylphenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-yl amino) isothioureas

2019 ◽  
Vol 10 (3) ◽  
Author(s):  
Narendhar B ◽  
Chitra K ◽  
Alagarsamy V
Keyword(s):  
Dimethyl Sulphate ◽  
Antitubercular Activity ◽  
Antibacterial Activities ◽  
Alkyl Aryl ◽  
Aryl Isothiocyanates ◽  
Anti Hiv

In this research, substituted thiosemicarbazide group was placed at 2nd position & 4-methylphenyl group was placed at 3rd position of condensed pyrimidine nucleus. Entire prepared title analogues were examined for its antibacterial, antitubercular, & anti HIV activities against selected bacteria & virus. The target compounds 1-substituted-3-(3-(4-methylphenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-ylamino)isothioureas (TTS01 – TTS10) were synthesized from 2-hydrazino-3-(4-methylphenyl)benzopyrimidin-4(3H)-one (5) by reacting with various alkyl/aryl isothiocyanates followed by methylation with dimethyl sulphate. Among the test compounds, 2-methyl-3-(3-(4-methylphenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-ylamino)-1-(3-chlorophenyl) isothiourea (TTS09) and 2-methyl-3-(3-(4-methylphenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-yl amino)-1-(4-nitrophenyl) isothiourea (TTS06) shown most potent activity against S. epidermidis, S. Aureus, and P. vulgaris 3 µg/ml MIC. Compounds TTS06 & TTS09 exhibited the antitubercular activity with 12.5 µg/ml MIC and antiHIV activity at 9.06 and 8.56 µg/ml, respectively against HIV1 and HIV2. Thus for further optimization & development of novel antitubercular and antiHIV drugs, compounds TTS06 & TTS09 may act as a pilot derivative.

Design and Synthesis of Novel 1-substituted-3-(3-(3-nitrophenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-yl amino) Isothioureas for their Anti-HIV, Antibacterial Activities, Graph Theoretical Analysis, Insilico Modeling, Prediction of Toxicity and Metabolic Studies

Drug Research ◽  
2020 ◽  
Vol 70 (08) ◽  
pp. 348-355
Author(s):  
Bandi Narendhar ◽  
Veerachamy Alagarsamy ◽  
Chitra Krishnan
Keyword(s):  
Antitubercular Activity ◽  
Antibacterial Activities ◽  
Dilution Method ◽  
Agar Dilution Method ◽  
Gram Positive ◽  
Alkyl Aryl ◽  
Design And Synthesis ◽  
Modeling Prediction ◽  
Anti Hiv Agents ◽  
Anti Hiv

AbstractIn the present study, we have placed the substituted thiosemicarbazide moiety at the C-2 position and 3-nitrophenyl group at N-3 position of benzopyrimidines and studied their antitubercular, anti-HIV and antibacterial activities against selected gram positive and negative bacteria. The target compounds 1-substituted-3-(3-(3-nitrophenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-ylamino) isothioureas (PTS1 – PTS15 ) were obtained by the reaction of 2-hydrazino-3-(3-nitrophenyl) benzopyrimidin-4(3 H)-one (5) with different alkyl/aryl isothiocyanates followed by methylation with dimethyl sulphate. All synthesized compounds were screened for their antitubercular, anti-HIV and antibacterial activity against selective gram positive and gram negative bacteria by agar dilution method. Among the series, compound 2-methyl-3-(3-(3-nitrophenyl)-4-oxo-3,4-dihydrobenzopyrimidin-2-ylamino)-1-(3-chlorophenyl)isothiourea (PTS14) shown most potent activity against Klebsiella pneumoniae, Proteus vulgaris and Staphylococcus aureus; PTS14 exhibited the antitubercular activity at the minimum microgram of 1.56 µg/mL and anti-HIV activity at 0.96 µg/mL against HIV1 and HIV2 and offers potential for further optimization and development to new antitubercular and anti-HIV agents. The results obtained from this study confirm that the synthesized and biologically evaluated benzopyrimidines showed promising antimicrobial, antitubercular and anti-HIV activities and are new scaffolds for antimicrobial activity.

scholarly journals Anti-HIV, Antitubercular and Antibacterial Activities of Novel 3-(Substituted Quinazolinylamino)-2-phenyl quinazolin-4(3H)ones

2019 ◽  
Vol 32 (2) ◽  
pp. 281-286
Author(s):  
M.T. Sulthana ◽  
K. Chitra ◽  
V. Alagarsamy
Keyword(s):  
Antibacterial Activity ◽  
Antitubercular Activity ◽  
Antibacterial Activities ◽  
Primary Amines ◽  
Dilution Method ◽  
Agar Dilution Method ◽  
E Coli ◽  
Agar Dilution ◽  
Anti Hiv Agents ◽  
Anti Hiv

In the present study, we have synthesized a series of novel 2-phenyl-3-(substituted quinazolinylamino)quinazolin-4(3H)-ones by the reaction of 3-(substituted)-2-hydrazinoquinazoline-4(3H)-ones with 2-phenyl-3,1-benzoxazin-4-one. The starting material 3-(substituted)-2-hydrazinoquinazolin-4(3H)-ones were synthesized from various primary amines. All the synthesized compounds were screened for their antitubercular, anti-HIV and antibacterial activity against different Grampositive and Gram-negative strains by agar dilution method. Among the test compounds, 3-(4-nitrophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (BQZ6) and 3-(4-chlorophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (BQZ7) shown most potent antibacterial activity against E. coli, P. aeruginosa and S. aureus with the MIC of 3 μg/mL. The compound BQZ7 exhibited the antitubercular activity with the MIC of 25 μg/mL and anti-HIV activity with the MIC of 35.4 μg/mL against HIV1 and HIV2 and offers potential lead for further optimization and development to new antitubercular and anti-HIV agents. The results from this study confirm that the synthesized and biologically evaluated quinazolines showed promising antimicrobial, antitubercular and anti-HIV activities and are new scaffolds for antimicrobial activity

Design, Synthesis, Pharmacological evaluation, in silico modeling, prediction of toxicity and metabolism studies of novel 1-(substituted)-2-methyl-3-(4-oxo-2-phenyl quinazolin-3(4H)-yl)isothioureas

2020 ◽  
Vol 16 ◽  
Author(s):  
M. T. Sulthana ◽  
V. Alagarsamy ◽  
K. Chitra
Keyword(s):  
Antitubercular Activity ◽  
Assay Method ◽  
Dilution Method ◽  
Agar Dilution Method ◽  
Drug Resistant ◽  
Alkyl Aryl ◽  
Design Synthesis ◽  
Hiv Drugs ◽  
Anti Hiv

Background: Although exhaustive efforts to prevent and treat tuberculosis (TB) was taken the problem still continues due to multi-drug-resistant (MDR) and extensively drug resistant TB (XDR-TB). It clearly highlights the urgent need to develop novel “druggable” molecules for the co-infection treatment and strains of MDR-TB and XDR-TB. Objective: In this approach a hybrid molecule was created by merging two or more pharmacophores. Active site of targets may be addressed by each of the pharmacophores and proffers the opportunity for selectivity. In addition, it also reduced the undesirable side effects and drug-resistant. Methods: In this study, a novel quinazolinone analog was designed and synthesized by substituting thiourea nucleus and phenyl ring at N-3 and C-2 position of quinazoline ring respectively. All title compounds were tested for antitubercular activity by in-vitro M. tuberculosis and anti-human immunodeficiency virus (HIV) activity by MT-4 cell assay method. The agar dilution method was used to test the antibacterial potency of entire prepared derivatives against various strains of gram positive and gram-negative microorganism. Results: The title compounds, 1-(substituted)-2-methyl-3-(4-oxo-2-phenyl quinazolin-3(4H)-yl) isothioureas (QTS1 – QTS15) are synthesized by reaction between key intermediate 3-amino-2-phenylquinazolin-4(3H)-one with various alkyl/aryl isothiocyanates followed by methylation with dimethyl sulphate. Among the series, compound 1-(3-chlorophenyl)-2-methyl-3-(4-oxo-2-phenyl quinazolin- 3(4H)-yl) isothioureas (QTS14) shown highest potency against B. subtilis, K. pneumonia and S. aureus at 1.6 µg/mL. The compound QTS14 exhibited the most potent antitubercular activity at with the MIC of 0.78 µg/mL and anti-HIV activity at 0.97µg/mL against HIV1 and HIV2. Conclusion: The results obtained from this study confirm that the synthesized and biologically evaluated quinazolines showed promising antimicrobial, antitubercular and anti-HIV activities. The new scaffolds for proffers plausible lead for further development and optimization to novel antitubercular and anti-HIV drugs.

ChemInform Abstract: Synthesis of Zidovudine Derivatives with anti-HIV-1 and Antibacterial Activities.

ChemInform ◽  
2009 ◽  
Vol 40 (30) ◽  
Author(s):  
Palaniappan Senthilkumar ◽  
Jing Long ◽  
Raparla Swetha ◽  
Vaidyanathan Shruthi ◽  
Rui-Rui Wang ◽  
...  
Keyword(s):  
Antibacterial Activities ◽  
Anti Hiv ◽  
Hiv 1

scholarly journals Structure–Activity Relationships and Organ Specificity in the Induction of GST and NQO1 by Alkyl-Aryl Isothiocyanates

2008 ◽  
Vol 25 (9) ◽  
pp. 2164-2170 ◽  
Author(s):  
Rex Munday ◽  
Yuesheng Zhang ◽  
Christine M. Munday ◽  
Meghana V. Bapardekar ◽  
Joseph D. Paonessa
Keyword(s):  
Organ Specificity ◽  
Alkyl Aryl ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Aryl Isothiocyanates

Design, Synthesis and Biological Evaluation of Carbazole Derivatives as Antitubercular and Antibacterial Agents

2019 ◽  
Vol 15 (1) ◽  
pp. 83-97
Author(s):  
Satheeshkumar Sellamuthu ◽  
Mohammad F. Bhat ◽  
Ashok Kumar ◽  
Gopal Nath ◽  
Sushil K. Singh
Keyword(s):  
Structural Similarity ◽  
Antitubercular Activity ◽  
Vero Cells ◽  
Antibacterial Activities ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Antitubercular Drugs ◽  
Carbazole Derivatives ◽  
Antipsychotic Activity ◽  
Bbb Permeability

Background:The neuroleptic chlorpromazine has been reported for antitubercular activity but the associated antipsychotic activity restricted its clinical presentation.Objectives:Novel derivatives of carbazole having structural similarity with chlorpromazine were designed, in an attempt to reduce the associated side effects, while retaining the antitubercular activity.Materials and Methods:The designed molecules were synthesized and screened for antitubercular and antibacterial activities. The blood-brain barrier (BBB) permeability and mammalian cell (VERO) cytotoxicity (CC50) were examined to determine the safety of compounds.Results:Among the developed compounds, 14c, 15c, 16c and 17c were found to be promising against Mtb H37Rv at MIC of 1.56 µg/ml. They were also effective against S. aureus and E. coli at MIC of 0.98 and 7.81 µg/ml, respectively. The BBB permeability of the compounds was found to be less than chlorpromazine. Therefore, the developed compounds are expected to have diminished antipsychotic effect. The compounds were further marked safe against mammalian VERO cells at CC50 > 90 µg/ml.Conclusion:The profound antitubercular activity with a concomitant reduction in BBB permeability of carbazole derivatives can pave new vista in the discovery of antitubercular drugs.

scholarly journals Anthraquinone Derivatives from a Marine-Derived Fungus Sporendonema casei HDN16-802

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 334 ◽  
Author(s):  
Xueping Ge ◽  
Chunxiao Sun ◽  
Yanyan Feng ◽  
Lingzhi Wang ◽  
Jixing Peng ◽  
...  
Keyword(s):  
Chlorine Atom ◽  
Anticoagulant Activity ◽  
Antitubercular Activity ◽  
Antibacterial Activities ◽  
Cytotoxic Activities ◽  
Spectroscopic Techniques ◽  
Addition Compound ◽  
Anthraquinone Derivatives ◽  
Ic50 Values ◽  
First Time

Five new anthraquinone derivatives, auxarthrols D–H (1–5), along with two known analogues (6–7), were obtained from the culture of the marine-derived fungus Sporendonema casei. Their structures, including absolute configurations, were established on the basis of NMR, HRESIMS, and circular dichroism (CD) spectroscopic techniques. Among them, compound 4 represents the second isolated anthraquinone derivative with a chlorine atom, which, with compound 6, are the first reported anthraquinone derivatives with anticoagulant activity. Compounds 1 and 3 showed cytotoxic activities with IC50 values from 4.5 μM to 22.9 μM, while compounds 1, 3–4, and 6–7 showed promising antibacterial activities with MIC values from 12.5 μM to 200 μM. In addition, compound 7 was discovered to display potential antitubercular activity for the first time.

scholarly journals Synthesis, biological evaluation and molecular docking studies of new 2-ethoxy-4-{[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonate derivatives on human aldose reductase enzyme

2021 ◽  
Author(s):  
Gül Özdemir ◽  
Namık Kılınç ◽  
Sevda Manap ◽  
Murat Beytur ◽  
Muzaffer Alkan ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Antibacterial Activities ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Binding Energies ◽  
Diffusion Method ◽  
Alkyl Aryl ◽  
Molecular Docking Studies ◽  
New Compounds

A series of 2-ethoxy-4-{[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonates (3) were synthesized from the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with 2-ethoxy-4-formyl-phenyl benzenesulfonate (2). N-acetyl derivatives (4) of compounds 3 were also obtained. Then, the compounds 3 have been treated with morpholine and 2,6-dimethylmorpholine in the presence of formaldehyde to synthesize 2-ethoxy-4-{[1-(morpholine-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonates (5) and 2-ethoxy-4-{[1-(2,6-dimethylmorpholine-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonates (6), respectively. The structures of twenty-six new compounds were identified by using elemental analysis, IR, 1H NMR, 13C NMR, and MS spectral data. In addition, in vitro antibacterial activities of the new compounds were evaluated against six bacteria such as Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Bacillus cereus and Klepsiella pneumonia according to agar well diffusion method. Furthermore, in order to determine the possible antidiabetic properties of the synthesized 1,2,4-triazole derivatives, inhibition effects on the AR enzyme were investigated and molecular docking studies were carried out to determine the receptor-ligand interactions of these compounds. IC50 values of triazole-derived compounds (6a, 6b, 6d-g) against AR enzyme were determined as 0.95 µM, 0.75 µM, 1.83 µM, 0.62 µM, 1.05 µM, 1.06 µM, respectively. Considering the docking scores and binding energies obtained docking studies, it has been shown that molecules fit very well to the active site of the AR enzyme.

Anti-HIV and Antibacterial Activities of Novel 2-(3-Substituted-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-diones

2021 ◽  
Vol 47 (1) ◽  
pp. 112-121
Author(s):  
M. T. Sulthana ◽  
K. Chitra ◽  
V. Alagarsamy ◽  
G. Saravanan ◽  
V. Raja Solomon
Keyword(s):  
Antibacterial Activities ◽  
Anti Hiv
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