By Alan C. Sartorelli (Eds.)
content material: improvement of [alpha]-(N)-heterocyclic carboxaldehyde thiosemicarbazones with medical strength as antineoplastic brokers / Alan C. Sartorelli and Krishna C. Agrawal --
Adriamycin / David W. Henry --
Biochemical pharmacology of the anthracycline antibiotics / Nicholas R. Bachur --
strength bioreductive alkylating brokers / Ai Jeng Lin, Lucille A. Cosby, and Alan C. Sartorelli --
A overview of stories at the mechanism of motion of nitrosoureas / Glynn P. Wheeler.
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Extra resources for Cancer Chemotherapy
P h y s i c a l data on the adriamycin d e r i v a t i v e are not y e t a v a i l a b l e but both 30 and 31 can be accommodated by the model receptor complex. S u r p r i s i n g l y the adriamycin quaternary r e t a i n e d a p p r e c i a b l e i n v i v o a c t i v i t y while the daunomycin d e r i v a t i v e was i n a c t i v e . However q u a t e r n i z a t i o n i s c l e a r l y d e t r i m e n t a l to i n v i v o a c t i v i t y i n both cases. Before l e a v i n g the subject of d e r i v a t i v e s the work of Trouet et a l .
Adriamycin 41 the d i a s t e r i o m e r i c p a i r of analogs 44 and 45. Compound 44 now resembles the parent a n t i b i o t i c s q u i t e c l o s e l y , possessing a chromophore w i t h very s i m i l a r e l e c t r o n i c c h a r a c t e r , c o r r e c t stereochemistry a t the 7 - p o s i t i o n and only l a c k i n g the 9 - p o s i t i o n s u b s t i t u e n t s and the 4-methoxy group. These seeming advances toward the parent a n t i b i o t i c s improved the DNA/RNA i n h i b i t o r y c h a r a c t e r o f the drug somewhat but by a f a c t o r of l e s s than two over anthraquinone 43.
The l a t t e r authors employed a conformation f o r the daunomycin A r i n g s i m i l a r to that found i n the c r y s t a l s t r u c t u r e o Figure 3. Possible conformations of ring A of daunomycin I f another conformation of r i n g A i s p o s t u l a t e d (Figure 3b) a model i s p o s s i b l e which s i m i l a r l y permits the chromophore to i n t e r c a l a t e between base p a i r s and the protonated amino sugar i n the major groove to form an e l e c t r o s t a t i c bond w i t h a DNA phosphate l o c a t e d one n u c l e o t i d e away from the i n t e r c a l a t i o n s i t e .
Cancer Chemotherapy by Alan C. Sartorelli (Eds.)