Conventional and microwave assisted synthesis of 2-amino-4,6-diaryl pyrimidine derivatives and their cytotoxic, anti-oxidant activities

Ahmad, Mohammed Rayees; Sastry, V. Girija; Prasad, Y. Rajendra; Khan, Mohammed Haseebur Rahman; Bano, Nasreen; Anwar, S. Y.

doi:10.5155/eurjchem.3.1.94-98.523

Cited by 6 publications

(3 citation statements)

References 15 publications

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“…These new hybrid molecules showed significant cytotoxic activity, with IC 50 values ranging from 2-80 µM (Kamal et al, 2014). 1,3-Diphenyl-2-propenone derivatives having cytotoxic, anti bacterial activities were also prepared (Ahmad and Bano, 2011). (Liu et al, 2014): SARS-CoV is the causative agent of Severe Acute Respiratory Syndrome (SARS).…”

Section: Intmentioning

confidence: 99%

SARS-CoV 3C-Like Protease Inhibitors of some Newly Synthesized Substituted Pyrazoles and Substituted Pyrimidines Based on 1-(3-Aminophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one

Mohamed¹,

Ibrahie²,

Amr³

et al. 2015

International J. of Pharmacology

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A series of several substituted pyrazole and pyrimidine derivatives were synthesized based on 1-(3-aminophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one (3) as starting material, which was obtained from the reaction of 3-indolaldehyde with 3-aminoacetophenone. Treatment of chalcone 3 with hydrazine hydrate or phenylhydrazine gave the corresponding pyrazole derivatives 4 and 5. Cyclization of 3 with hydroxylamine hydrochloride, thiosemicarbazide or hydrazine hydrate/acetic acid afforded the corresponding cyclized products 6-8, respectively. The reaction of 3 with guanidine hydrochloride gave the corresponding aminopyrimidine derivative 9, which was reacted with 1, 1-carbonyldiimidazole or p-flourobenzaldehyde afforded compounds 10 and 11. Condensation of 3 with urea in the presence of sodium ethoxide gave pyrimidinone derivative 12. Finally, reaction of 9 with 1, 3-indanedione afforded compound 13, which was treated with cyclopentanone or 3, 4-dimethoxybenzaldehyde to give the corresponding arylidine derivatives 14 and 15. The synthesized derivatives were tested against SARS CoV 3C-like protease and were founded active.

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Section: Intmentioning

confidence: 99%

SARS-CoV 3C-Like Protease Inhibitors of some Newly Synthesized Substituted Pyrazoles and Substituted Pyrimidines Based on 1-(3-Aminophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one

Mohamed¹,

Ibrahie²,

Amr³

et al. 2015

International J. of Pharmacology

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“…[86][87][88][89] Several other strategies have also been reported using either one-pot Flögel reaction, [90] Biginelli reaction, [91][92][93][94][95][96][97] or multipot reactions. [98,99] Besides, various conditions have been employed during the synthesis of pyrimidine (i.e., microwave, [100][101][102] ultrasonic-MW, [103] ultrasonic irradiations. [104][105][106] conventional way via reflux, [107][108][109] phase transfer, [110] stirring.…”

Section: Introductionmentioning

confidence: 99%

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

Farooq

Ngaini

2021

Journal of Heterocyclic Chem

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Chalcone-derived pyrimidine is a well-known heterocyclic compound that is commonly present in ribonucleic acid (RNA) and deoxyribonucleic acid (DNA) bio-isosteres. Pyrimidine derivatives are effective in both the electronic industry and drug industries. This review highlights the synthesis of pyrimidines, namely mono-pyrimidine, bis-pyrimidine, fused pyrimidine, symmetric, and asymmetric pyrimidine via one-pot and two-pot methods. The one-pot method is the direct reaction of amino derivatives with aldehydes and acetophenones, whereas the two-pot method is frequently reported for the synthesis of chalcone before the cyclization to a pyrimidine. This review is important in organic synthesis, particularly in the heterocyclic field, regarding pyrimidines and their significance in therapeutic and electronic industries.

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“…) still requires an efficient protocol. The existing methodologies for the synthesis of 4,6‐diarylpyrimidin‐2(1 H )‐ones lack in one or more of the following – two‐step synthesis , applicabilty to limited substrates (not investigated for heteroaryl ketones/aldehydes and bicyclic ketones/aldehydes) , and use of hazardous solvents . This tempted us to investigate the reaction under microwave conditions employing a silicated fluoroboric acid and a variety of substrates such as (i) aryl/heteroaryl ketones, (ii) aryl/heteroaryl aldehydes, (iii) bicyclic ketones, (iv) bicyclic aldehydes and (v) aldehydes and ketones with electronically diverse substituents.…”

Section: Introductionmentioning

confidence: 99%

4,6‐Diaryl/heteroarylpyrimidin‐2(1H)‐ones as a New Class of Xanthine Oxidase Inhibitors

Shukla

Kumar

Ojha

et al. 2014

Archiv der Pharmazie

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A series of 4,6-diaryl/heteroarylpyrimidones was synthesized employing silica-supported fluoroboric acid under solvent-free conditions in a microwave reactor. The catalytic influence of HBF4-SiO2 was investigated in detail to optimize the reaction conditions. The synthesized compounds were evaluated for in vitro xanthine oxidase (XO) inhibitory activity for the first time. Structure-activity relationship analyses are also presented. Among the synthesized compounds, VA-5, -9, -10, -12, -22, -23, and -25 were the active inhibitors with IC50 values ranging from 6.45 to 13.46 µM. Compound VA-25 with a pyridinyl ring as ring A and a thiophenyl ring as ring B emerged as the most potent XO inhibitor (IC50 = 6.45 µM) in comparison to allopurinol (IC50 = 12.24 µM). Some of the important interactions of VA-25 with the amino acid residues of the active site of XO were figured out by molecular modeling studies.

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Conventional and microwave assisted synthesis of 2-amino-4,6-diaryl pyrimidine derivatives and their cytotoxic, anti-oxidant activities

Cited by 6 publications

References 15 publications

SARS-CoV 3C-Like Protease Inhibitors of some Newly Synthesized Substituted Pyrazoles and Substituted Pyrimidines Based on 1-(3-Aminophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one

SARS-CoV 3C-Like Protease Inhibitors of some Newly Synthesized Substituted Pyrazoles and Substituted Pyrimidines Based on 1-(3-Aminophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

4,6‐Diaryl/heteroarylpyrimidin‐2(1H)‐ones as a New Class of Xanthine Oxidase Inhibitors

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