Synthesis, and Evaluation of Coumarin Hybrids as Antimycobacterial Agents

Hassan, Mohd. Zaheen; Alsayari, Abdulrhman; Osman, Hasnah; Ali, Mohamed Ashraf; Muhsinah, Abdullatif Bin; Ahsan, Mohamed Jawed

doi:10.32383/appdr/112406

Cited by 4 publications

(4 citation statements)

References 16 publications

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“…The starting blocking unit 2-thiouracil derivative (1) was prepared [31,34] from the classic Biginelli condensation of ethyl cyanoacetate, 2,4dichlorobenzaldehyde and thiourea in basic medium of anhydrous K2CO3.The IR-spectrum of this compound showed absorption at (2227 cm -1 and 1662 cm -1 ) for C≡N and C=O respectively. 1 HNMR spectrum showed a singlet signal at δ 9.70 and δ 11.30 for 2 hydrogens of pyrimidine ring (2NH).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of The Antiviral Activity of Novel 2-Thiopyrimidine-5-Carbonitrile Derivatives

et al. 2022

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2-Thiouracil-5-carbonitriles are promising compounds that have been prepared in the last twenty years and have proven to have a diversity of biological activity. In line with this approach, our new compounds were prepared starting from Biginilli condensation of thiourea, ethyl cyanoacetate and 2,4-dichlorobenzaldehyde in basic medium to give a thiouracil derivative (1) which was subjected to chlorination at4 th position by POCl3/PCl5 mixture producing chloropyrimidine (2) which in turns was reacted with m-aminoacetophenone in pyridine yielding acetyl derivative (3) which was condensed with a series of four aromatic aldehydes in alcoholic sodium hydroxide producing chalcones (4a-d) which were used as starting materials for the preparation of many heterocyclic nuclei by their reaction with hydrazine, phenyl hydrazine, hydroxylamine HCl, thiourea, ethyl cyanoacetate /ammonium acetate, malononitrile, ethyl cyanoacetate/acetic acid/sodium acetate to give pyrazoline, phenyl pyrazoline, isoxazoline, thiopyrimidine, pyridinone, aminopyridine and aminopyran derivatives (5a-d) to (11a-d) respectively . Some of the newly synthesized compounds were investigated as antiviral agents. Compounds (2), (7a), and (7c) show promising antiviral activity against Bovine Viral Diarrhea Virus (BVDV). The structures of the newly synthesized compounds were confirmed by elemental analysis in addition to spectral data and physical methods.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of The Antiviral Activity of Novel 2-Thiopyrimidine-5-Carbonitrile Derivatives

et al. 2022

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“…These products form Scheme 16. Mechanism for the 2H-chromen-thiazol-pyrazol-2H-chromen-2one synthesis (68). [81] (The mechanism was redrawn from literature.)…”

Section: Chemistryselectmentioning

confidence: 99%

“…[80] The reaction of 3-bromoacetylcoumarin (2), 3-(acetoacetyl)coumarin derivatives (67) and thiosemicarbazide (58) under reflux conditions in ethanol was identified as a onepot, multicomponent reaction for the synthesis of 2H-chromenthiazol-pyrazol-2H-chromen-2-one (68) in good yields (Scheme 15). [81] Scheme 16 shows a proposed mechanism [81] pathway for final product production (68). First, the thiosemicarbazide (58) reacts with 3-bromoacetylcoumarin (2), releasing HBr in the process.…”

Section: Chemistryselectmentioning

confidence: 99%

3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

et al. 2022

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Compounds containing the coumarin scaffold are widely used in the pharmaceutical and medicinal industries. The biological activities of coumarin containing derivatives make the attractive for the develop new drugs. Different methods and techniques are developed to synthesize new drugs using coumarin as a starting material. This review summarized various methods, techniques and reaction conditions for synthesis of coumarins containing compounds from 3‐bromoacetylcoumarin. A total of 79 coumarin intermediates and products are reported herein. The different reactions include nucleophilic substitutions, one‐pot and multi‐step synthesis for preparation of coumarin containing compounds through different mechanisms and the outcomes achieved through such reactions are discussed. The prepared compounds showed a range of activities resulting in antifungal, antimicrobial, anti‐inflammatory, antidiabetic and cholinesterase inhibitors. The nucleophilic substitution reactions involving urea related compounds, followed by intramolecular cyclization lead to imidazole and thiazole moieties, which exhibit antibacterial activities. It is hoped that this review provides useful insight for researchers engaged in this field to expand the knowledge gained in this area.

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Recently, a molecular hybridization method offered a promising strategy to design new potent hybrid molecules with multi-targeting synergistic effects. 12 Previous studies showed that molecular hybrids containing pyrazole and azo (-N=N-)/hydrazo (=N-NH-) pharmacophores in a single molecular framework resulted in improved antimicrobial potentials. 13,14 In continuation of our endeavors to develop potent and effective antimicrobial agents, 15 this study deals with the optimization of pyrazole-azo/hydrazo molecular hybrid leads as potential antimicrobial agents.

Results and discussion

ChemistrySo far, the majority of previously reported syntheses of arylhydrazono pyrazoles (AHPs) and aryldiazenyl pyrazoles

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confidence: 99%

Synthesis and antimicrobial activity of aryldiazenyl/arylhydrazono pyrazoles

Alsayari

Asiri

Muhsinah

et al. 2021

Journal of Chemical Research

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We report the design, synthesis, and in vitro antimicrobial evaluation of functionalized pyrazoles containing a hydrazono/diazenyl moiety. Among these newly synthesized derivatives, 4-[2-(4-chlorophenyl)hydrazono]-5-methyl-2-[2-(naphthalen-2-yloxy)acetyl]-2,4-dihydro-3 H-pyrazol-3-one is a promising antimicrobial agent against Staphylococcus aureus (minimum inhibitory concentration 0.19 μg mL−1). Structure–activity relationship studies reveal that the electronic environment on the distal phenyl ring has a considerable effect on the antimicrobial potential of the hybrid analogues. Molecular docking studies into the active site of S. aureus dihydrofolate reductase also prove the usefulness of hybridizing a pyrazole moiety with azo and hydrazo groups in the design of new antimicrobial agents.

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Synthesis, and Evaluation of Coumarin Hybrids as Antimycobacterial Agents

Cited by 4 publications

References 16 publications

Synthesis and Evaluation of The Antiviral Activity of Novel 2-Thiopyrimidine-5-Carbonitrile Derivatives

Synthesis and Evaluation of The Antiviral Activity of Novel 2-Thiopyrimidine-5-Carbonitrile Derivatives

3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

Synthesis and antimicrobial activity of aryldiazenyl/arylhydrazono pyrazoles

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