Toyo Jozo Kabushiki Kaisha

Masatoshi Tsujino

Kiyofumi Fukukawa

Tadashiro Fujii

Satoshi Yaginuma

Satoshi Shuto

Naoki Muto

Takao Hirano

Tetsu Saito

Masaru Otani

Hiromichi Itoh

Tooru Ueda

Hideo Sakakibara

Hiromichi Ito

Novel nucleoside-phospholipid conjugates of the formula ##STR1## wherein R.sub.1 is C.sub.14-24 long chain aliphatic acyl or C.sub.1-24 aliphatic alkyl, R.sub.2 is C.sub.2-10 aliphatic acyl or C.sub.1-24 aliphatic alkyl and N.sub.s is a nucleoside residue; and pharmacologically acceptable salts thereof are prepared in a one-step reaction by reacting the corresponding nucleoside and glycerophospholipid derivative in the presence of phospholipase D-P.

Novel nucleoside-phospholipid conjugate

Novel nucleoside-phospholipid conjugates of the formula ##STR1## wherein R.sub.1 is C.sub.14-24 long chain aliphatic acyl or C.sub.1-24 aliphatic alkyl and N.sub.s is a nucleoside residue; and pharmacologically acceptable salts thereof are prepared in a one-step reaction by reacting the corresponding nucleoside and glycerophospholipid derivative in the presence of phospholipase D-P.

Nucleoside-phospholipid conjugate

Neplanocin A derivatives of the formula ##STR1## wherein R.sub.1 is hydrogen or benzoyl, R.sub.4 is hydrogen or halogen, hydroxy, acetoxy, acetylthio, amino or azide, R.sub.5 is hydrogen or acetyl, and R.sub.6 is hydrogen or acetyl. The compounds of the present invention have inhibitory action for the growth of L 5178 Y cells and have the same or superior activity as neplanocin A.

2'-(R)-substituted-2'-deoxyneplanocin A derivatives

A compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are long-chain fatty acid residue, and Ns is nucleoside residue selected from the group consisting of 5-fluorouridine-5'-yl, 5-fluoro-2'-deoxyuridine-5'-yl-, bredinin-5'-yl, tubercidine-5'-yl-, neplanocin A-6'-yl-, 5-fluorocytidine-5'-yl-, arabinosylcytosine-5'-yl, arabinocyl-5-fluorocytosine-5'-yl-, arabinosyladenine-5'-yl- and arabinosylthymine-5 '-yl-, and pharmacologically acceptable salts thereof, having antitumor activity.

Neplanocin A derivatives of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or benzoyl, R.sub.3 is hydrogen or OR.sub.8, R.sub.5 is hydrogen or acetyl, R.sub.6 is hydrogen, acetyl or benzoyl, when R.sub.3 is hydrogen, R.sub.4 is hydrogen or halogen, hydroxy, acetoxy, acetylthio, amino or azide, and when R.sub.3 is OR.sub.8, R.sub.4 is hydrogen, R.sub.8 is hydrogen or acetyl, or R.sub.8 and R.sub.5 together form benzylidene, and at least one of R.sub.8, R.sub.5 and R.sub.6 is other than hydrogen. The compounds of the present invention have inhibitory action for the growth of L 5178 Y cells and have the same or superior activity as neplanocin A, and hence are useful as antitumor agents.

Neplanocin A derivatives

Antibiotic neplanocin A of the formula ##STR1## is produced by culturing Ampullariella sp. A 11079 FERM-P No. 4494 in a nutrient medium and then separating the neplanocin A thus produced from the culture medium.

Antibiotic neplanocin A

Neplanocin-B and -F of the formula ##STR1## in which Y is oxygen or a valence bond, are produced by culturing Ampullariella sp. A 11079 FERM-P No. 4494 in a nutrient medium and then separating the neplanocin-B and -F thus produced from the culture medium.

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Shizuoka, Japan

Masatoshi Tsujino