Synthese und cytostatische Wirkungen des 10‐ und 11‐Nitronoracronycins, Molekülvariationen des cytostatisch wirksamen Acronycins<sup>1)</sup>

1991

ChemInform

On the Synthesis of Potential Pharmaceuticals. Part 23. Synthesis and Cytostatic Activity of 10-and 11-Nitronoracronycine. Molecular Variations of Cytostatically Active Acronycine.-The nitronoracronycins (VI), synthesized as shown in the reaction scheme, possess cytotoxic activity against transplantation tumor leukemia P 388. The compounds (IIIb) and (IVa) are also active, whereas the nitroacridinones (IIIa) and (IVb) are inactive. -(REISCH, J.; DZIEMBA, P.; Arch. Pharm. (Weinheim, Ger.) 324 (1991) 2, 67-71; Inst. Pharm. Chem., Westf. Wilhelms-Univ., W-4400 Muenster, Fed. Rep. Ger.; DE)

ChemInform Abstract: On the Synthesis of Potential Pharmaceuticals. Part 23. Synthesis and Cytostatic Activity of 10‐ and 11‐Nitronoracronycine. Molecular Variations of Cytostatically Active Acronycine.

1991

ChemInform

Natural product chemistry. Part 153 . Synthesis and possible anticancer activity of 8‐nitronoracronycine

Journal of Heterocyclic Chem

1992

Since the strategy for the synthesis of 9‐, 10‐ and 11‐nitronoracronycine [3,4] could not be applied to the 8‐nitronoracronycine 9, we here report the preparation of the latter by a fusion of methyl 2‐amino‐6‐nitrobenzoate 2 and phloroglucinol 3. The fusion of 2 and 3 gave 1,3‐dihydroxy‐8‐nitro‐9(10H)‐acridinone 6. Subsequent methylation, demethylation and reaction with 2‐chloro‐2‐methyl‐3‐butyne afforded the desired 8‐nitronoracronycine 9. Compound 9, 1,3‐dimethoxy‐10‐methyl‐8‐nitro‐9(10H)‐acridinone 7 and 1,3‐dihydroxy‐10‐methyl‐8‐nitro‐9(10H)‐acridinone 8 were tested by the National Cancer Institute (NCI) for possible anticancer activity.

Natural product chemistry. Part 159. Two methods for the synthesis of 4‐azaacronycine as a potential antitumor agent

Journal of Heterocyclic Chem

Mura

et al. 1993