Synthesis, biological evaluation and molecular docking of novel series of spiro [(2H,3H) quinazoline-2,1′- cyclohexan]-4(1H)- one derivatives as anti-inflammatory and analgesic agents

Amin, Kamelia M.; Kamel, Mona M.; Anwar, Manal M.; Khedr, Mohammed A.; Syam, Yasmin M.

doi:10.1016/j.ejmech.2009.12.078

Cited by 131 publications

(57 citation statements)

References 37 publications

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“…The signals at 8.70, 6.60 ppm and 8. 40,6.80 ppm are attributed to thiazole and pyrimidine protons, respectively. Also, the spectra exhibit a characteristic singlet at 11.7-11.6 ppm due to SO 2 NH proton.…”

Section: Spectral Data Analysis Of Spiro Compounds 4a-umentioning

confidence: 99%

“…Spiro heterocyclic compounds possess various pharma-cological properties and hence their synthesis is of interest to organic chemists. Such compounds display pronounced antimicrobial [5], analgesic [6], anti-inflammatory [6], antimycobacterial [7], antifungal [8], antitumor [9,10] and antiviral [9,10] activities. Among these heterocycles, spiro azoles have been identified as privileged structures in medicinal chemistry and have attracted increasing interest in the recent years [11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Biological Activities Evaluation of New Spiro Heterocycles Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties

2016

International Journal of Advanced Research in Chemical Science

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Section: Spectral Data Analysis Of Spiro Compounds 4a-umentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activities Evaluation of New Spiro Heterocycles Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties

2016

International Journal of Advanced Research in Chemical Science

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“…The first step of our strategy was focused on ring transformation of oxazin to thieno [3,2-d]pyrimidine (28,29) Refluxing compound 3 with the appropriate aldehyde and malononitrile or ethyl cyanoacetate in the presence of excess ammonium acetate in n-butanol afforded the corresponding aminopyridine 5a-e and pyridone derivatives 6a-e, respectively. Also, treatment of acetyl derivative 3 with appropriate aldehydes in 5 % ethanolic sodium hydroxide solution, afforded the corresponding α,β-unsaturated ketones 7a-e in moderate yields (Scheme 3).…”

Section: Chemistrymentioning

confidence: 99%

Simple approach to thieno[3,2-d]pyrimidines as new scaffolds of antimicrobial activities

2016

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6ʹ-(4-Chlorophenyl)-spiro[cyclohexane-1,2ʹ-thieno[3,2-d][1,3] oxazin]-4ʹ(1ʹH)-one (1) was synthesized and used as a starting material for the synthesis of a novel series of spiro compounds having biologically active sulfonamide 2a-e and 3ʹ-(4-acetylphenyl)-6ʹ- (4-chlorophenyl)-1ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d] pyrimidine-4ʹ(3ʹH)-one (3). Compound 2a was used as a key intermediate for the synthesis of sulfonyl carbothioamide derivatives 4a-c. Also, compound 3 was used as an intermediate for the synthesis of 3ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d]pyrimidin]-3ʹ-yl] phenyl}-2-imino-4-(substituted phenyl and/or thienyl)-1,2-dihydropyridine- 3-carbonitrile derivatives 5a-e, 3ʹH-spiro[cyclohexane- 1,2ʹ- thieno[3,2-d]pyrimidin]-3ʹ-yl]phenyl}-2-oxo-4-(substituted phenyl and/or thienyl)-1,2-dihydropyridine-3-carbonitrile derivatives 6a-e, and 4-[(2Z)-3-substituted-arylprop-2-enoyl] phenyl-1ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d]pyrimidine derivatives 7a-e. Cyclocondensation of 7a-e with hydrazine hydrate produced 6ʹ-(4-chlorophenyl)-3ʹ-[4-(5-substituted aryl-4,5-dihydro- 1H-pyrazol-3-yl)phenyl]-1ʹH-spiro[cyclohexane-1,2ʹ-thieno- [3,2-d]pyrimidin]-4ʹ(3ʹH)-ones 8a-e but with hydroxylamine hydrochloride afforded the corresponding isoxazoline derivatives 9a-e. Also, cyclocondensation by thiourea afforded 2-thioxo-1,2- dihydropyrimidin-4-yl)-phenyl-spiro-{cyclohexanethieno[3,2-d] pyrimidin}-4-one derivatives 10a-e. The new compounds were investigated for antimicrobial activity. Compounds 2c, 8b,c, 9b and 10b were the most potent ones against both Gram-negative and Gram-positive bacteria. Compound 8c exhibited higher antifungal activity towards the examined fungi with MIC of 1-2 μmol mL-1 compared to ketoconazole (MIC 2-3 μmol mL-1 ).

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“…Other mechanisms that may contribute to NSAID mediated anti-inflammatory activity include the reduction of superoxide radicals, induction of apoptosis, inhibition of adhesion molecule expression, decrease of nitric oxide synthase, decrease of proinflammatory cytokine levels (tumornecrosis factor-α, interleukin-1), modification of lymphocyte activity, and alteration of cellular membrane functions (6). However, long term clinical usages of NSAIDs are associated with significant side effects such as severe gastrointestinal ulceration, bleeding, intolerance and nephrotoxicity (7,8). Therefore, investigation of new NSAIDs is still a major challenge and production of safer and more active NSAIDs and analgesic drugs are needed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, analgesic, anti-inflammatory and ulcerogenic properties of some novel N'-((1-(substituted amino)methyl)-2-oxoindolin-3-ylidene)-4-(2-(methyl/phenyl)-4-oxoquinazolin-3(4H)-yl)benzohydrazide derivatives

Saravanan¹

2012

Drug Discov Ther

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A new series of N'-((1-(substituted amino)methyl)-2-oxoindolin-3-ylidene)-4-(2-(methyl/ phenyl)-4-oxoquinazolin-3(4H)-yl)benzohydrazide derivatives 4a-4l were designed and synthesized from anthranilic acid. All the synthesized compounds were characterized by spectroscopic means and elemental analyses. The tail-flick technique and the carrageenaninduced foot paw edema test were performed for screening analgesic and anti-inflammatory activity, respectively. All of the compounds were also examined for their ulcerogenicity. Some of the compounds showed significant activity. Among the test compounds, 4b exhibited 53% and 69% analgesic activity at a dose of 10 and 20 mg/kg, respectively. It also displayed 47% (10 mg/kg) and 65% (20 mg/kg) anti-inflammatory activity with one-fourth of ulcer index of the reference drugs diclofenac and aspirin.

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Synthesis, biological evaluation and molecular docking of novel series of spiro [(2H,3H) quinazoline-2,1′- cyclohexan]-4(1H)- one derivatives as anti-inflammatory and analgesic agents

Cited by 131 publications

References 37 publications

Synthesis and Biological Activities Evaluation of New Spiro Heterocycles Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties

Synthesis and Biological Activities Evaluation of New Spiro Heterocycles Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties

Simple approach to thieno[3,2-d]pyrimidines as new scaffolds of antimicrobial activities

Synthesis, analgesic, anti-inflammatory and ulcerogenic properties of some novel N'-((1-(substituted amino)methyl)-2-oxoindolin-3-ylidene)-4-(2-(methyl/phenyl)-4-oxoquinazolin-3(4H)-yl)benzohydrazide derivatives

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