ChemInform Abstract: Facile One‐Pot Synthesis and Antimycobacterial Evaluation of Pyrazolo[3,4‐d]pyrimidines.

Trivedi, Anjali; Dodiya, Dipti K.; Surani, Janak J.; Jarsania, Samir H.; Mathukiya, Hitesh; Ravat, N. R.; Shah, V. H.

doi:10.1002/chin.200844167

Cited by 7 publications

(10 citation statements)

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“…In our proposed investigation, it was extended to synthesize some novel pyrimidines from 2,5-dichloro-3-acetylthienyl chalcones, which has highly reactive dielectrophilic ketovinyl side chain to condense with guanidine hydrochloride in presence of KOH to produce twenty novel pyrimidine derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) at room temperature and refluxed for 6 h (Scheme-I). The spectral characterizations were carried out on the synthesized pyrimidine derivatives using suitable IR, 1 H NMR, 13 C NMR, mass spectra and elemental analysis data.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of chalcone was reported and performed by condensing 2-(4-carboxyphenylazo)acetoacetate with aromatic aldehydes to produce modified chalcones and these chalcones were treated with urea in ethanolic KOH to form a series of pyrimidine derivatives. They were also screened for antimycobacterial activity against Mycobacterium tuberculosis H37Rv stain using microplate alamar blue assay [12]. 4-Acetyl pyridine was treated with a substituted benzaldehyde to synthesize new chalcones and pyrimidine derivatives are produced by the reaction of new chalcones with guanidine and urea in ethanolic KOH.…”

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confidence: 99%

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Novel Pyrimidine Derivatives from 2,5-Dichloro-3-acetylthienyl Chalcones as Antifungal, Antitubercular and Cytotoxic Agents: Design, Synthesis, Biological Activity and Docking Study

2019

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Twenty novel pyrimidine derivatives were synthesized from 2,5-dichloro-3-acetylthienyl chalcones by reacting with guanidine HCl in presence of KOH and ethanol under reflux for 6 h. Their structural characterizations were evaluated by ATR-FTIR, 1H NMR, 13C NMR, mass spectroscopy. They were also screened for antifungal, antitubercular and cytotoxicity activities. They were displayed good antifungal activity (MIC = 32-125 μg/mL) against Aspergillus niger and Candida tropicalis fungal species except compound 15 with 4"-pyridinyl moiety (MIC = 8.00 μg/mL) being more potent. Compound 5 with 2",4"-dichlorophenyl moiety was shown with good antitubercular activity (MIC = 6.2 μg/mL) against Mycobacterium tuberculosis H37Rv (MTB) stain. They have also tested for in vitro cytotoxicity activity against DU-145 prostate cancer cell lines. In which the compound 15 with 4"-pyridinyl moiety (IC50 = 2.0 ± 0.1 μg/mL) and compound 17 with 2"-pyrrolyl moiety (IC50 = 6.0 ± 0.1 μg/mL) possess highly potent antiprostate cancer properties. The molecular docking was done with the crystalline structure of mitochondrial 2-enoyl thioester reductase Etr1p/Etr2p heterodimer from Candida tropicalis fungal species with compound 15 (-7.80 kcal/mol) and shown greater binding affinity than fluconazole (-7.60 kcal/mol). Docking was performed with protein crystalline structure (PDB ID: 2WEE) of Mycobacterium tuberculosis H37Rv (MTB) stain and among all, compound 5 was exhibited good binding affinity (-6.90 kcal/mol), compared to pyrazinamide (-4.10 kcal/mol). The protein crystalline structure of a mutant androgen receptor (AR) ligand-binding domain (LBD) (PDB file: 1GS4) was tested with compounds 15 and 17 (-7.60 and -8.20 kcal/mol). They were exhibited good binding properties compared to methotrexate (-5.10 kcal/mol). Hence, these novel pyrimidine compounds are as lead compounds as antifungal, antitubercular and cytotoxic agents.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Novel Pyrimidine Derivatives from 2,5-Dichloro-3-acetylthienyl Chalcones as Antifungal, Antitubercular and Cytotoxic Agents: Design, Synthesis, Biological Activity and Docking Study

2019

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“…Dihydropyrimidines are not represented in the current clinical antitubercular regimens, suggesting that this class of compounds may target new biochemical mechanisms, potentially allowing treatment of MDR-TB and there are very few investigatory reports on dihydropyrimidines as antitubercular agents 7,8 . Recognizing these facts and in continuation of work on pyrimidine derivatives [9][10][11] , we set upon a programme of making dihydropyrimidine as the template and adding versatile substituents on the various positions of dihydropyrimidine ring.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel 2-Mercapto-4-(p-Aminophenyl Sulphonylamino)-6-(Aryl)-Pyrimidine-5-Carboxamide Derivatives via the Biginelli Reaction

Bhuva

Gothalia

Singala

et al. 2014

ILCPA

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Series of 2-mercapto-4-(p-aminophenylsulphonylamino)-6-(aryl)-pyrimidine-5-carboxamide A a-h were synthesized via the biginelli condensation. 2-mercapto-4-amino-6-(aryl)-pyrimidine-5-carboxamide react with p-acetamidophenylsulphonylchloride in the presence of pyridine 2 to form 2-mercapto-4-(p-acetamidophenylsulphonylamino)-6-(aryl)-pyrimidine-5-carboxamide 3. It was treated with diluted HCl under reflux afforded 2-mercapto-4-(p-aminophenylsulphonylamino)-6-(aryl)-pyrimidine-5-carboxamide A a-h. . The newly synthesized compounds were characterized by elemental analyses, infrared (IR), 1 H NMR and 13 C NMR spectroscopic investigation.

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“…Pyrimidine derivatives are of interest because of their pharmacological properties including antimicrobial [11,12], anticancer [13 -15], antitubercular [16], antimalarial [17], and anti-inflammatory activity [18 -20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial and antifungal activity of some new pyrimidin-2(5H)-one/thione and 4H-chromen-4-one derivatives

Ansari¹,

Gawale²

2011

Pharm Chem J

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A new synthesis of 2-substituted-4H-chromen-4-ones (IVa-c) and 4-(2-hydroxyphenyl)-6-substituted pyrimidin-2(5H)-one/thiones (Va -Vc)/(VIa -VIc) derivatives is reported. First, benzoyloxy esters are converted into their 1,3-diones (IIIa -IIIc) by using dry KOH in pyridine via the Baker -Venkataraman transformation reaction. Then, 1,3-diones thus obtained are cyclised into 2-substituted-4H-chromen-4-ones (IVa -IVc) and 4-(2-hydroxyphenyl)-6-substituted pyrimidin-2(5H)-one/thiones (Va -Vc)/(VIa -VIc) by refluxing in acetic acid and urea/thiourea in ethanol, respectively. The newly synthesized compounds were characterized by IR, 1 H NMR, and mass spectroscopy and elemental analysis and tested for their antibacterial and antifungal activity.

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ChemInform Abstract: Facile One‐Pot Synthesis and Antimycobacterial Evaluation of Pyrazolo[3,4‐d]pyrimidines.

Cited by 7 publications

References 1 publication

Novel Pyrimidine Derivatives from 2,5-Dichloro-3-acetylthienyl Chalcones as Antifungal, Antitubercular and Cytotoxic Agents: Design, Synthesis, Biological Activity and Docking Study

Novel Pyrimidine Derivatives from 2,5-Dichloro-3-acetylthienyl Chalcones as Antifungal, Antitubercular and Cytotoxic Agents: Design, Synthesis, Biological Activity and Docking Study

Synthesis of Novel 2-Mercapto-4-(p-Aminophenyl Sulphonylamino)-6-(Aryl)-Pyrimidine-5-Carboxamide Derivatives via the Biginelli Reaction

Synthesis and antibacterial and antifungal activity of some new pyrimidin-2(5H)-one/thione and 4H-chromen-4-one derivatives

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