Sci. Pharm. 2010; 78: 1–12
Studies on the Reactivity of (9-Methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)hydrazine Towards Some Reagents for Biological Evaluation
Aymn E. RASHAD * 1, Ahmed H. SHAMROUKH 1, Randa E. ABDEL-MEGEID 1, Hayam H. SAYED 1, Nayera M. ABDEL-WAHED 2
1 Photochemistry Department, National Research Center, Elbehos Street, Dokki, Cairo, Egypt.
2 Department of Natural and Microbial Products, National Research Center, Elbehos Street, Dokki, Cairo, Egypt.
* Corresponding author. E-mail: aymnelzeny@yahoo.com (A. E. Rashad)
Abstract
(9-Methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)hydrazine (1) used as a precursor for preparation novel 1-(9-methyl-5,6- dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)-1H-pyrazoles 2–7, -1H-isoindole-1,3(2H)-dione 8, -pyridazin-3(2H)-one 9. Moreover, the acyclic C‑nucleosides 10 and 11 were prepared by treating compound 1 with D‑glucose. The in vitro antimicrobial activity of the tested compounds was evaluated by measuring the zone diameters and some of the prepared products showed potent antimicrobial activity in compared with those of well known drugs (standard). In general, the non-acetylated sugar hydrazone derivative 10 showed the highest antibacterial and antifungal potency among the tested compounds and standard with IZ = 22, 21 and 22 mm and MIC = 62.5 and 31.25 μg/ml, respectively.
Supporting Information
The scanned 1H NMR spectra of compounds 2 and 4, and the scanned 13C NMR spectra of compounds 2, 4 and 7 are available: Supporting Information (Format: PDF, Seize: ca. 0.3 MB)
Keywords
Thieno[2,3-d]pyrimidine • Pyrazole • Pyridazine • C-Nucleosides • Antimicrobial activity
Received October 20th, 2009 | Accepted November 27th, 2009 | Published Online December 11th, 2009
