Synthesis and biological activity of arylsulfonamide derivatives containing 2-arylamino-4(3&lt;i&gt;H&lt;/i&gt;)-quinazolinone

Zeng, Zhigang; Gao, Tao; Li, Yan; Wang, Xiang; Yang, Xu-Hong; Wu, Minghu

doi:10.1584/jpestics.d16-053

Cited by 6 publications

(2 citation statements)

References 19 publications

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“…In that reaction, 2-methyl-4H-benzo[d] [1,3]oxazin-4one [7] (0.1 M) and obtained compounds [5] (0.1 M) was suspended in glacial acetic acid [7] and refluxed for 4 h. After completion of reaction, the reaction mixture was cooled at room temperature, and then it was poured into crushed ice and kept overnight in the refrigerator. [16] The obtained solid product [8] was filtered, washed with cold water and recrystallized from hot ethanol (75%). The synthesis was monitored by the TLC for the completion of the reaction.…”

Section: Step 2: Synthesis Of 3-(5-((substitutedamino)methyl)-134-tmentioning

confidence: 99%

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2020

IJPBA

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Objective: The objective of the paper was to evaluate the antifungal and antibacterial potential of new derivatives of ((E)-3-(5-((substitutedphenylamino)methyl)-1,3,4-thiadiazol-2-yl)-2-styryl quinazolin-4(3H)one. Materials and Methods: Various syntheses of (E)-3-(5-(substitutedaminomethyl)-1,3,4-thiadiazol-2yl)-2-styrylquinazolin-4(3H)-one derivatives have been synthesized by reacting 2-substituted benzoxazin-4one with (E)-2-(4-Substituedstyryl)-4H-benzo[d] [1,3]oxazin-4-one. All synthesized compounds have been characterized by the infrared, 1HNMR, and mass spectral analysis. Proposed compounds have been evaluated for antifungal and antibacterial activity. The antimicrobial activity of synthesized compounds (QNM-1 to QNM-15) has been carried through the serial dilution method. For bacterial screening, bacterial species were taken includes Staphylococcus aureus (MTCC-96), Bacillus subtilis (MTCC-441), Pseudomonas aeruginosa (MTCC-424), and Escherichia coli (MTCC-40). Norfloxacin (1-Ethyl-6-fluoro-1,4,dihydro-4-oxo-7-(1-piperazinyl)-3quinoline carboxylic acid) was used as the standard drug for antibacterial study. For antifungal screening, the following fungal species were used includes Aspergillus niger (MTCC-281), Candida albicans (MTCC-227), and Fusarium oxysporum (MTCC-284). Clotrimazole was selected as a standard drug for antifungal study. Results and Discussion: QNM-1, QNM-2, QNM-3, QNM-5, QNM-7, QNM-9, QNM-12, QNM-14, and QNM-15 were the most active compounds [Table 1] in the synthesized series which were active against both Gram-positive and Gram-negative organisms by the antibacterial screening. In the case of antibacterial activity, the presence of electronegative group (Cl, Br, F, and NO 2) at both R may enhance the activity when they are p-substituted, but the compounds QNM-6 (R1=-C 6 H 5 Br (o); Ar=-C 6 H 5), QNM-10 (R 1 =-C 6 H 5 F (o); Ar=-C 6 H 5 F), QNM-11 (R1 =-C 6 H 5 NO 2 (p); Ar=-C 6 H 5 F), and QNM-4 (R1 =-C 6 H 5 F (m); Ar=-C 6 H 5) with given substitution may result in diminishing the activity. In case of antifungal activity, compounds QNM-1, QNM-5, QNM-7, QNM-9, QNM-11, QNM-12, QNM-14, and QNM-15 were the most active compounds in the synthesized series which were active against both Gram-positive and Gram-negative organisms. In that series, compounds QNM-14, QNM-11, QNM-5, and QNM-7 have shown the highest activity. Compounds QNM-3, QNM-6, QNM-10, and QNM-13 have the least active. This result has also concluded that o-substituted compounds, i.e.,-C 6 H 5 Cl(o),-C 6 H 5 Cl (m),-C 6 H 5 Br(o),-C 6 H 5 F (o),-C 6 H 5 F (p) at R 1 position my resulted in diminishing or lower the activity.

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Section: Step 2: Synthesis Of 3-(5-((substitutedamino)methyl)-134-tmentioning

confidence: 99%

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2020

IJPBA

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“…Since the seminal preparation of the trifluoromethoxy group by Yagupolskii in 1955 [ 1 ], the interest in this very specific organic moiety has grown continuously, in particular for life sciences purposes [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. Such interest can be explained by the conjunction of its multiple advantages: the “pseudohalogen” character of this entity which makes it comparable to a fluorine atom in terms of electronic properties, and the deep modifications of the conformation as well as the physico-chemical behavior induced in molecules linked to this group [ 10 , 11 , 12 , 13 , 14 ].…”

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confidence: 99%

Dichlorotrifluoromethoxyacetic Acid: Preparation and Reactivity

et al. 2017

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Experimental and Computational Insights into the Water‐Mediated Decomposition of N‐Sulfonylhydrazones: A Catalyst‐Free Synthesis of γ‐Keto/Nitrile Sulfones

et al. 2020

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This work is an example of water‐mediated decomposition of N‐sulfonylhydrazones used as sulfonyl‐transferring reagents in the selective sulfa‐Michael reaction in the absence of any base or catalyst. A wide range of substituted N‐sulfonylhydrazones were tested as sources of sulfonyl anions with enones or acrylonitrile, which in turn provided the γ‐ keto/nitrile sulfones in very good yields. Additionally, we have performed a rigorous computational mechanistic study to investigate the role of water which demonstrates the key role of water in the hydrogen abstraction from N‐tosylhydrazone to initiate the reaction.

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Synthesis and biological activity of arylsulfonamide derivatives containing 2-arylamino-4(3<i>H</i>)-quinazolinone

Cited by 6 publications

References 19 publications

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Dichlorotrifluoromethoxyacetic Acid: Preparation and Reactivity

Experimental and Computational Insights into the Water‐Mediated Decomposition of N‐Sulfonylhydrazones: A Catalyst‐Free Synthesis of γ‐Keto/Nitrile Sulfones

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