Quinoline, quinazoline and acridone alkaloids (July 1999 to June 2000)

Novel 4-aminoquinazoline derivatives as new leads for anticancer drug discovery

“…The starting material 4-chloro-2-phenylquinazoline was purchased from Sigma (USA) and was directly used for the preparation of target compounds. nyl)quinazolin-4-amune (7), 2-phenyl-N- (2,4,6-trichlorophenyl)quinazolin-4-amine (8), N-(4-bro mophenyl)-2-phenylquinazolin-4-amine (9) (25), N-(2,4-dichlorophenyl)-2-phenylquinazolin-4-amine (10), N-(adamantan-1-yl)-2-phenylquinazolin-4-amine (11), phenyl (4-(2-phenylquinazolin-4-ylamino)phenyl)methanone (12), 2-((2-phenylquinazolin-4-yl)amino)anthracene-9,10-dione (13) (26). General procedure.…”

“…IR spectra (KBr disc) were recorded using an FT-IR spectrophotometer (Perkin Elmer, USA). 1 H NMR spectra were scanned on a NMR spectrophotometer (Bruker AXS Inc., Switzerland) operating at 500 MHz for 1 H-and 125.76 MHz for 13 C. Chemical shift s are expressed in d-values (ppm) relative to TMS as an internal standard, using DMSO-d 6 as a solvent. Elemental analyses were done on a model 2400 CHNSO analyser (Perkin Elmer, USA).…”

“…On the other hand, 1 H NMR spectrum of compound 11 revealed the presence of a multiple peer at 1.5-2.3 ppm for adamantane moiety. 13 C NMR spectrum of compound 12 showed a singlet at 195.1 ppm att ributed to C=O group. Scheme 2 In vitro anti-breast cancer activity and SAR Doxorubicin [CAS 23214-92-8], the reference drug used in this study an anthracycline antibiotic is commonly used in the treatment of a wide range of cancers such as acute leukemia's Hodgkin's disease and other lymphomas and cancers of the breast, adrenal cortex, endometrial, lung, ovary, and other sites.…”

“…Interaction of 4-chloro-2-phenylquinazoline with diff erent amines in dry dimethylformamide yielded the corresponding 4-aminoquinazoline derivatives 1-13. All the synthesized compounds were established on the basis of elemental analyses, IR, 1 H NMR, 13 C NMR and mass spectral data. IR spectra of compounds 1-13 revealed the presence of bands characteristic of NH at 3423 to 3240 cm H NMR spectrum of compound 1 revealed a triplet at 1.2 ppm assigned to CH 3 group and at 2.7 ppm due to CH 2 group.…”

“…croorganisms (11)(12)(13). In the light of these facts, and as a continuation of our previous reported work on the synthesis of novel anticancer agents (14-23), we planned to synthesize a novel series of 4-aminoquinazoline derivatives carrying biologically active moieties as analogues to bioactive compounds I-IV, hoping that the new compounds might show signifi cant cytotoxic activity.…”