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Molecules 2011, 16(12), 10187-10201; doi:10.3390/molecules161210187
Article

Synthesis and Analgesic Activity of Some New Pyrazoles and Triazoles Bearing a 6,8-Dibromo-2-methylquinazoline Moiety

1,3,* , 2
 and 3
Received: 10 October 2011; in revised form: 1 December 2011 / Accepted: 2 December 2011 / Published: 7 December 2011
(This article belongs to the Section Organic Synthesis)
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Abstract: 2-(6,8-Dibromo-2-methylquinazolin-4-yloxy)-acetohydrazide (4) was prepared by the reaction of 6,8-dibromo-2-methylbenzo-[d][1,3]oxazin-4-one with formamide to afford quinazolinone 2, followed by alkylation with ethyl chloroacetate to give the ester 3. Treatment of ester 3 with hydrazine hydrate and benzaldehyde afforded 4 and styryl quinazoline 5. The hydrazide was reacted with triethyl orthoformate, acetylacetone and ethyl acetoacetate and benzaldehyde derivatives to afford the corresponding pyrazoles 6, 7, 9 and hydrazone derivatives 10a-c. Cyclization of hydrazones 10a-c with thioglycolic acid afforded the thiazole derivatives 11a-c. Reaction of the hydrazide with isothiocyanate derivatives afforded hydrazinecarbothioamide derivatives 12a-c, which cyclized to triazole-3-thiols and thiadiazoles 13a-c and 14a-c, respectively. Fusion of the hydrazide with phthalimide afforded the annelated compound 1,2,4-triazolo[3,4-a]isoindol-5-one (15). The newly synthesized compounds were characterized by their spectral (IR, 1H-, 13C-NMR) data. Selected compounds were screened for analgesic activity.
Keywords: isoindol-5-one; pyrazole; quinazolin-4(3H)-one; thiazole; 1,2,4-triazole; 1,3,4-thiadiazole; analgesic activity isoindol-5-one; pyrazole; quinazolin-4(3H)-one; thiazole; 1,2,4-triazole; 1,3,4-thiadiazole; analgesic activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Saad, H.A.; Osman, N.A.; Moustafa, A.H. Synthesis and Analgesic Activity of Some New Pyrazoles and Triazoles Bearing a 6,8-Dibromo-2-methylquinazoline Moiety. Molecules 2011, 16, 10187-10201.

AMA Style

Saad HA, Osman NA, Moustafa AH. Synthesis and Analgesic Activity of Some New Pyrazoles and Triazoles Bearing a 6,8-Dibromo-2-methylquinazoline Moiety. Molecules. 2011; 16(12):10187-10201.

Chicago/Turabian Style

Saad, Hosam A.; Osman, Nermen A.; Moustafa, Ahmed H. 2011. "Synthesis and Analgesic Activity of Some New Pyrazoles and Triazoles Bearing a 6,8-Dibromo-2-methylquinazoline Moiety." Molecules 16, no. 12: 10187-10201.



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