Synthesis and Antimicrobial Activity of 2-Aryl-4H-3,1-benzoxazin-4-ones

Khan, Zulfiqar Ali; Naqvi, Syed Ali Raza; Shahzad, Sohail Anjum; Mahmood, Nasir; Yar, Muhammad; Zahoor, Ameer Fawad

doi:10.14233/ajchem.2013.12846

Cited by 11 publications

(8 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On refluxing the acid 1 with acetic anhydride, the title compound 2 was obtained in 59% yield as a result of ring closure (Chart 1). Structure of 4(H)-3,1-benzoxazin-4-one derivative 2 was elucidated from its analytical data, IR (showed ν C=O at 1749 cm −1 which is characteristic for the benzoxazinone moiety) and 1 H-NMR spectrum which displayed peaks at δ 6.71 for CH=, 7.28-7.77 (10, Ar-H), 8.20, 8.37 (2s, 2H, Ar-H benzoxazinone), 10.22 exchangeable with D 2 O for NH. The 13 C-NMR spectrum contained 14 signals; the most important, at δ 118.10, 120.30 and 161.60, 163.40 ppm for (C=C) and (2 C=O).…”

Section: Resultsmentioning

confidence: 99%

“…They are of considerable interest on account of the diverse range of biological properties such as antimicrobial, herbicidal, anti-inflammatory, anticancer, antibacterial, antifungal, central nervous system (CNS), antimalarial, antitumor, and adenosine receptor antagonistic activities. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] In continuation of our interested in the synthesis of some of heterocyclic nitrogen compounds having biological and pharmacological activities, [15][16][17][18][19][20][21][22][23][24][25] and through our program [26][27][28][29] aiming to explore the chemical reactivity of the oxazinone moiety present in 4(H)-3,1-benzoxazin-4-one derivatives, we have decided to synthesize a series of novel 3-substituted quinazolin-4(3H)-one, with two bromine atoms in the benzene ring using 2-[α-benzoylaminostyryl]-6,8-dibromo-3,1-benzoxain-4(H)-one (2) as a versatile starting material. Compound 2 was subjected for the reaction with some nitrogen nucleophiles and other reactions.…”

mentioning

confidence: 99%

“…Compound 2 was subjected for the reaction with some nitrogen nucleophiles and other reactions. The structures of the newly synthesized compounds were elucidated through their IR, 1 H-NMR, 13 C-NMR and mass spectroscopic data. The new products showed remarkable antibacterial, antifungal and anti-inflammatory activities upon screening for biological activity tests.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, Antimicrobial and Anti-inflammatory Activity of Some New Benzoxazinone and Quinazolinone Candidates

et al. 2016

View full text Add to dashboard Cite

Benzoxazinones and quinazolinones have a wide spectrum of biological activity. In this paper we focused on studying the antimicrobial and anti-inflammatory activities of some newly synthesized benzoxazinone and quinazolinone derivatives. Thus we prepared 2-[α-benzoylaminostyryl]-6,8-dibromo-3,1-benzoxazin-4(H)-one 2 which underwent a reaction with primary and secondary amines, and hydrazine hydrate to give compounds 3, 4 and 5, respectively. Treatment of 2 with hydroxylamine hydrochloride, formamide and/or NaN 3 / AcOH afforded compounds 7, 8, 11 and 12, respectively. Also, compound 2 reacted with maleic anhydride, aromatic hydrocarbons and/or active methylene compounds to produce compounds 13, 15a-c and 16, respectively. Most of the newly synthesized compounds showed significant antimicrobial and anti-inflammatory activities comparable to ampicillin, mycostatine and indomethacin positive controls.

show abstract

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Antimicrobial and Anti-inflammatory Activity of Some New Benzoxazinone and Quinazolinone Candidates

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The compounds are isolated from natural products, such as dianthalexin ( Dianthus caryophyllus ), [2] Avenalumins (oat leaves), [3] Cephalandoles A ( Cephalanceropsis gracilis ) [4] are 4 H ‐3,1‐benzoxazin‐4‐one derivatives (Figure 1). They own countless biological activities including anticancer, [5] anti‐bacterial, [6] antifungal, [7] analgesic, [8] anti‐inflammatory [9] and herbicidal activity [10] . Some of them act as inhibitors of serine proteases [11] and human leukocyte elastase [12] .…”

Section: Introductionmentioning

confidence: 99%

Pyrazolyl‐Benzoxazinone Derivatives as Dual Hsp Inhibitors in Human Breast Cancer

et al. 2022

View full text Add to dashboard Cite

Heat Shock Proteins (Hsps) play major role on the onset of several cancers. Metabolic rates of cancer cells are higher compared to that of untransformed cells. This accelerated rate force functional substrate proteins to fold faster than normal folding rate. Although, the process leads cell cycle halting and eventually induces apoptosis, Hsps help cell survival and inhibit apoptosis and fold substrate proteins especially signaling proteins. When cancer cells accelerate the metabolism for invasion and metastasis, substrate proteins must fold to their native state rapidly. Since, functional forms of the proteins must be folded properly, cancer cells overexpress Hsps to fold substrate proteins and avoid apoptosis. Hsp90 and Hsp70 play key role in these processes. Inhibition of either Hsp90 or Hsp70 display complementary function. Therefore, dual inhibition of Hsp70 and Hsp90 potentially provides anticancer affect. In silico studies showed that pyrazolyl‐benzoxazine derivatives display binding activity for both Hsps. For this purpose, pyrazole‐3‐carbonyl chloride were converted to pyrazolyl‐benzoxazine derivatives via reactions of anthranilic acids in good yields (68–83 %). The structures of the newly synthesized compounds were elucidated by IR‐NMR spectroscopy, elemental analysis, and single‐crystal X‐ray diffraction. Binding of the compounds inhibit function of Hsps and cause cytotoxic effect over MCF‐7 cells. The compounds display potential anticancer effects.

show abstract

“…Thus, the design and synthesis of novel and potential antibacterial, flame retardant, and reinforcement coating materials for textile fabrics are a much appreciated and required research trend. On the other hand, derivatives of 2-substituted-4H-3,1-benzoxazin-4-one have been attracted significant attention from chemists and pharmacologists because of their broad spectrum in biological activities and antibacterial applications [15][16][17][18]. One of the most important features of 4H-3,1-benzoxazinones chemistry is their use as key starting materials for further transformations in the design and synthesis of biologically active compounds [15][16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Facile Route for Synthesis of Novel Flame Retardant, Reinforcement and Antibacterial Textile Fabrics Coatings

2020

View full text Add to dashboard Cite

New and innovative textile fabrics coatings were facilely developed. The coating was developed based on synthesis of novel charring and antibacterial organic agent in conjunction with chitosan. N-[2,3-dibromo-4-(4-methoxy-3-methylphenyl)-4-oxobutanoyl]anthranilic acid was synthesized as organic antibacterial, reinforcement, and charring agent (OA) and then, dispersed in chitosan solution followed by coating on textile fabrics using immersion route forming new flame retardant coating layer. The developed organic molecule structure was elucidated using spectroscopic techniques. The mass loadings of developed organic agent dispersed in chitosan solution were varied between 20–60 wt.%. The coated textile fabrics have special surface morphology of fiber shape aligned on textile fibers surface. The thermal stability and charring residues of the coated textile fabrics were enhanced when compared to blank and organic agent free coated samples. Furthermore, the flammability properties were evaluated using LOI (limiting oxygen index) and UL94 tests. Therefore, the coated textile fabrics record significant enhancement in flame retardancy achieving first class flame retardant textile of zero mm/min rate of burning and 23.8% of LOI value compared to 118 mm/min. rate of burning and 18.2% for blank textile, respectively. The tensile strength of the coated textile fabrics was enhanced, achieving 51% improvement as compared to blank sample. Additionally, the developed coating layer significantly inhibited the bacterial growth, recording 18 mm of clear inhibition zone for coated sample when compared to zero for blank and chitosan coated ones.

show abstract

Synthesis and Antimicrobial Activity of 2-Aryl-4H-3,1-benzoxazin-4-ones

Cited by 11 publications

References 8 publications

Synthesis, Antimicrobial and Anti-inflammatory Activity of Some New Benzoxazinone and Quinazolinone Candidates

Synthesis, Antimicrobial and Anti-inflammatory Activity of Some New Benzoxazinone and Quinazolinone Candidates

Pyrazolyl‐Benzoxazinone Derivatives as Dual Hsp Inhibitors in Human Breast Cancer

Facile Route for Synthesis of Novel Flame Retardant, Reinforcement and Antibacterial Textile Fabrics Coatings

Contact Info

Product

Resources

About