Structural investigation of the new potent DNA alkylator spiro(2H-1,3,2-benzodiazaphosphole-2,2',lambda 5 [1,3,5,2,4,6] triazatriphosphorine),4',4',6',6'-tetrakis(1-aziridinyl)-1,3,4',4',6', 6',-hexahydro.
The molecular structure of spiro(2H-1,3,2-benzodiazaphosphole-2,2',lambda 5 [1,3,5,2,4,6] triazatriphosphorine), 4',4',6',6'-tetrakis(1-aziridinyl)-1,3,4',4',6',6'-hexahydro (CAS 133586-94-4), a recently synthesized potent cytostatic, was determined using X-ray diffraction method. The substance crystallizes in P2(1)2(1)2(1) orthorhombic space group. The unit cell contains 8 formal molecules coupled into 4 pseudo-centrosymmetric dimers by double intermolecular hydrogen bonds. The compound revealed, besides previously determined long-term chemical stability and good water solubility, also radiation stability. In spite of having less aziridinyl groups than 1,3,5,2,4,6-triazatriphosphorine,2,2,4,4,6,6-hexakis (1-aziridinyl)-2,2,4,4,6,6-hexahydro (N3P3Az3, Az = aziridinyl, CAS 52-46-0; Myko 63) the compound is twice more cytostatically active. Hypotheses attributing high cytostatic activity to the existence of conjugated pi-electron systems in the molecule and dimeric structures are discussed.
Regional Laboratory of Physiocochemical Analysis and Structural Research, Jagiellonian University, Kraków, Poland.
J
J
Grochowski
P
P
Serda
K
K
Brandt
D000477:Alkylating Agents / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*
D000477:Alkylating Agents; D009943:Organophosphorus Compounds; D013141:Spiro Compounds; C088093:4',4',6',6'-tetrakis(1-aziridinyl)-1,3,4',4',6',6'-hexahydrospiro(2H-1,3,2-benzodiazaphosphole-2,2'-lambda(5)(1,3,5,2,4,6)triazatriphosphorine)