Ellipticine analogue

Photolysis of derivatives of compounds 4 and 5 has been further studied as a route to azacarbazoles. The example 264 shows normal behavior as well as elimination of an alkoxy group, and the report includes examples of derivatives of compound 5 as well as references to earlier work (93JCS(P1)1261). Production of an intermediate for an anti-tumour ellipticine analogue is shown by example 265 (84MI1), and incorporation of acetonitrile solvent by example 266 (91TL323). 

The range of these aza-ellipticine analogues, although by now extensive, is still insufficient to permit a systematic evaluation of their structure-activity relationships. It is established, however, that the three methylated compounds 11-13 are all less active than ellipticine toward a range of tumor cell lines <2004AP434>. 

O N +, HSO4- Inhibitor of reverse transcriptase (Ellipticin analogue) 1996BML2831... 

LM Shi, Y Fan, TG Myers, PM O Connor, KD Pauli, SH Friend, JN Weinstein. Mining the NCI anticancer drug discovery databases genetic function approximation for the QSAR study of anticancer ellipticine analogues. J Chem Inf Comput Sci 38 189-199, 1998. 

Base-catalyzed condensations on 2-alkyl functions in indoles seems to be rather general and the ellipticine analogue 16 is readily available by this route, 2 as outlined in Scheme 6. 

Condensation of the readily available N-pivaloyl ketone 259 (Scheme 77) with N-acetyl indolin-3-one (558) under acid conditions provides good yields of 1 l-azapyrido[3,4-6]carbazole 559, which represents an aza analogue of ellipticine (Scheme 168) (89JHC105). 

The synthesis of novel 2-cyanothiazolecarbazole analogues of ellipticine has been reported. The 3-aminocarbazole 36 was treated with 4,5-dichloro-l,2,3-dithiazolium chloride (Appel s salt 37) to give the imino-l,2,3-dithiazole 38. Rearrangement of 38 under thermal conditions gave 39 in moderate yield <02TL2482>. 

The Graebe-Ullmann methodology has proved especially valuable in the synthesis of ellipticine and analogues. Using flash vacuum pyrolysis, Miller and StoweU... 

Tandem Directed ortho Metalation-Metal - Halogen Exchange Route to Antitumor Ellipticine Alkaloids and Analogues... 

Vilarem MF, Charcosset JY, Primaux F, Gras MP et al. 1985 Differential effects of ellipticine and aza-analogue derivatives on cell cycle progression and survival of balb/C 3t3 cells released from serum starvation. Cancer Res 458 3906-3911... 

---