Synthesis and biological properties of new phosmidosine analogs having an N-acylsulfamate linkage.
A new phosmidosine analog 10, in which the proline and 8-oxoadenosine moieties were linked by an N-acyl sulfamate linkage, was successfully synthesized by the sulfamoylation of an 8-oxoadenosine derivative 5 followed by coupling with an L-proline derivative 8. An L-alanine-substituted derivative 13 and its derivative 14 without the alanyl residue were also synthesized. The morphological reversion activity of these synthetic compounds in v-src(ts) NRK cells and their antitumor activity in L1210 and KB cells were studied. As the result, neither L-proline- nor L-alanine-substituted phosmidosine analogs 10 and 13 showed any antitumor activity. Contrary to these results, the derivative 14 lacking the amino acid residue showed potent antitumor activities against cancer cells.
Taguchi
Haruhiko
H
Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama, Japan.
Ohkubo
Akihiro
A
Sekine
Mitsuo
M
Seio
Kohji
K
Kakeya
Hideaki
H
Osada
Hiroyuki
H
Sasaki
Takuma
T
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011685:Purine Nucleotides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000737:chemistry*
D000970:Antineoplastic Agents; D011685:Purine Nucleotides; D013451:Sulfonic Acids; C068885:phosmidosine; C005741:sulfamic acid