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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: |
| ||||
| 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 | ||||
| Item ID: | 17716 |
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 ...
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 = R2 = R3 = Me (Ph/Me-Dime-PtCl2)]. For the 1H NMR spectroscopic detn. of their optical purity the diamines (Ph/Me) were converted with (R)-myrtenal into their diimines. In the test on the MCF-7 breast cancer cell line (R,R)-Ph/Me-PtCl2 produced the strongest effect of all new complexes, comparable with that of the std. cisplatin and of other Pt complexes. Its enantiomer (S,S)-Ph/Me-PtCl2 possessed a distinctly weaker inhibitory potency while the erythro-configurated counterparts were even less active [(R,R)>(S,S)>(S,R) = (R,S)]. All N2-methylated and N1,N2-dimethylated complexes (Ph/Me-Me-PtCl2, Ph/Me-Dime-PtCl2) showed comparable activities equaling those of (R,S)- and (S,R)-Ph/Me-PtCl2. The mol. reasons for the differing potencies of the diastereomeric and enantiomeric Ph/Me-PtCl2 complexes are discussed in consideration of the complex conformation.
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