title: Synthesis and biological properties of new phosmidosine analogs having an N-acylsulfamate linkage.
abstract: 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.
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama, Japan.
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Taguchi
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ohkubo
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Sekine
authors.forename: Kohji
authors.initials: K
authors.lastname: Seio
authors.forename: Hideaki
authors.initials: H
authors.lastname: Kakeya
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Osada
authors.forename: Takuma
authors.initials: T
authors.lastname: Sasaki
mesh_terms: 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*
chemical_list: D000970:Antineoplastic Agents; D011685:Purine Nucleotides; D013451:Sulfonic Acids; C068885:phosmidosine; C005741:sulfamic acid