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The stereoselectivity of antitumor active [1,2-diamino-1-phenylpropane]dichloroplatinum(II) complexes

Gust, Ronald and Gelbcke, Michael and Angermaier, Bernhard and Bachmann, Helmut and Krauser, Rudolf and Schönenberger, Helmut (1997) The stereoselectivity of antitumor active [1,2-diamino-1-phenylpropane]dichloroplatinum(II) complexes. Inorganica chimica acta 264 (1-2), pp. 145-160.

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Abstract

The syntheses of enantiomeric threo- and erythro-1,2-diamino-1-phenylpropanes (Ph/Me) and of racemic 1,2-diaminophenylethane (Ph/H) are described. These diamines and related N2-methyl- and N1,N2-dimethyl-1,2-diamino-1-phenylpropanes were transformed into dichloroplatinum(II) complexes I [R1 = R2 = R3 = H (Ph/H-PtCl2); R1 = Me, R2 = R3 = Me (Ph/Me-PtCl2); R1 = R3 = Me, R2 = H (Ph/Me-Me-PtCl2); R1 ...

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Item Type:Article
Date:1997
Additional Information (public):CAN 127:365319 78-7 Inorganic Chemicals and Reactions 71027-87-7P (trans-2,4-Dimethyl-5-phenyl-3-oxazoline); 93431-15-3P Role: BYP (Byproduct), PREP (Preparation) (byproduct in prepn. of erythro 1,2-diamino-1-phenylpropane ligand); 10025-99-7 (Dipotassium tetrachloroplatinate) Role: RCT (Reactant), RACT (Reactant or reagent) (complexation with 1,2-diamino-1-phenylpropanes and analogs); 130827-42-8; 130827-43-9; 130857-96-4; 130857-97-5; 198221-87-3; 198221-89-5; 198221-93-1; 198221-95-3 Role: RCT (Reactant), RACT (Reactant or reagent) (complexation with tetrachloroplatinate); 18486-69-6 ((R)-(-)-Myrtenal) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation with erythro 1,2-diamino-1-phenylpropane to check optical purity); 492-41-1 ((1R,2S)-2-Amino-1-phenylpropanol); 37577-28-9 ((1S,2R)-2-Amino-1-phenylpropanol) Role: RCT (Reactant), RACT (Reactant or reagent) (for prepn. of chiral 1,2-diamino-1-phenylpropane ligand); 81703-29-9P; 93860-66-3P; 198221-71-5P; 198221-72-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (for prepn. of erythro 1,2-diamino-1-phenylpropane ligand); 100-42-5 Role: RCT (Reactant), RACT (Reactant or reagent) (for prepn. of racemic 1,2-diamino-1-phenylethane ligand); 61091-41-6P; 198473-93-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (for prepn. of threo 1,2-diamino-1-phenylpropane ligand); 87-69-4; 147-71-7 Role: RCT (Reactant), RACT (Reactant or reagent) (for purifn. of threo 1,2-diamino-1-phenylpropane ligand); 16635-94-2P (1,2-Diamino-1-phenylethane dihydrochloride); 61091-42-7P ((1S,2S)-2-Amino-1-chloro-1-phenylpropane hydrochloride); 107912-48-1P ((1R,2R)-2-Amino-1-chloro-1-phenylpropane hydrochloride); 198221-73-7P ((1R,2S)-1,2-Diamino-1-phenylpropane dihydrochloride); 198221-74-8P ((1S,2R)-1,2-Diamino-1-phenylpropane dihydrochloride) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and complexation with tetrachloroplatinate); 198221-75-9P; 198221-76-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and condensation with (R)-(-)-myrtenal to check optical purity); 198221-78-2P; 198473-99-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. for purifn. of threo 1,2-diamino-1-phenylpropane ligand); 198221-82-8P; 198221-83-9P; 198221-84-0P; 198221-85-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 72426-83-6P; 198221-79-3P; 198221-80-6P; 198221-81-7P; 198292-24-9P; 198292-25-0P; 198292-26-1P; 198292-27-2P; 198292-28-3P; 198292-29-4P; 198292-30-7P; 198292-31-8P; 198292-32-9P Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), PRP (Properties), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (prepn., conformation, and stereoselectivity of antitumor active [1,2-diamino-1-phenylpropane]dichloroplatinum(II) complexes); 198221-77-1P ((1R,2R)-1,2-Diamino-1-phenylpropane); 198473-98-2P ((1S,2S)-1,2-Diamino-1-phenylpropane) Role: PUR (Purification or recovery), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., purifn. as tartrate, and complexation with tetrachloroplatinate); 96-09-3P (Styrene oxide); 22710-73-2P (1,2-Diazido-1-phenylethane); 67464-41-9P (2-Azido-2-phenylethanol); 198221-70-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (racemic; for prepn. of racemic 1,2-diamino-1-phenylethane ligand); 5700-56-1P (1,2-Diamino-1-phenylethane) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (racemic; prepn. and conversion to hydrochloride for complexation with tetrachloroplatinate)
Institutions:Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Schönenberger
Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer)
Projects:SFB 234
Identification Number:
ValueType
1997:679452Other
Keywords:Conformation Stereochemistry (antitumor potency of diastereomeric and enantiomeric platinum diaminophenylpropane dichloro complexes in relation to) Structure-activity relationship (antitumor stereoselectivity of antitumor active [1,2-diamino-1-phenylpropane]dichloroplatinum(II) complexes) Amines Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (diamines, platinum complexes prepn. and stereoselectivity in antitumor activity of [1,2-diamino-1-phenylpropane]dichloroplatinum(II) complexes) Antitumor agents (prepn. and stereoselectivity in antitumor activity of [1,2-diamino-1-phenylpropane]dichloroplatinum(II) complexes) platinum diaminophenylpropane chloro prepn antitumor activity stereoselectivity antitumor activity platinum diaminophenylpropane chloro phenylpropanediamine platinum chloro prepn antitumor activity diamine platinum chloro prepn antitumor activity conformation platinum diaminophenylpropane chloro isomer
Dewey Decimal Classification:500 Science > 540 Chemistry & allied sciences
Status:Published
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Yes
Deposited On:09 Nov 2010 14:19
Last Modified:09 Nov 2010 14:23
Item ID:17716
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