【药物名称】Eptaplatin, Heptaplatin, NSC-644591, NSC-D-644591, SKI-2053R, Sunpla
化学结构式(Chemical Structure):
参考文献No.273735
标题:Synthesis and antitumor activity of a series of [2-substituted-4,5-bis(aminomethyl)-1,3-dioxolane]platinum(II) complexes
作者:Kim, D.-K.; Kim, G.; Gam, J.; Cho, Y.-B.; Kim, H.-T.; Tai, J.-H.; Kim, K.H.; Hong, W.-S.; Park, J.-G.
来源:J Med Chem 1994,37(10),1471-85
合成路线图解说明:

Reaction of D-tartaric acid (I) with EtOH in the presence of an acid catalyst gives diethyl D-tartrate (II), which is treated with isobutyraldehyde and anhydrous CuSO4 in the presence of methanesulfonic acid yielding diethyl 2,3-O-isobutylidene-D-tartrate (III). The 1,3-dioxolane diester (III) was then reduced with LAH to afford (4R,5R)-4,5-bis(hydroxymethyl)-2-isopropyl-1,3-dioxolane (IV), which is treated with methanesulfonyl chloride in pyridine yielding (4R,5R)-4,5-bis(methylsulfonyloxymethyl)-2-isopropyl-1,3-dioxolane (V). The bis(methanesulfonate) (V) is reacted with NaN3 in DMF to give (4R,5R)-4,5-bis(azidomethyl)-2-isopropyl-1,3-dioxolane (VI), which is reduced with hydrogen in the presence of 10% Pd/C in EtOH to afford (4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane (VII). The diamine (VII) is reacted with an equimolar amount of in situ generated K2PtI4 to afford cis-diiodo[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane] platinum(II) (VIII), which is finally treated with malonic acid disilver salt in H2O to obtain (IX).

参考文献No.323247
标题:SKI-2053R
作者:Kim, D.-K.; Kim, K.H.
来源:Drugs Fut 1995,20(11),1128
合成路线图解说明:

Reaction of D-tartaric acid (I) with EtOH in the presence of an acid catalyst gives diethyl D-tartrate (II), which is treated with isobutyraldehyde and anhydrous CuSO4 in the presence of methanesulfonic acid yielding diethyl 2,3-O-isobutylidene-D-tartrate (III). The 1,3-dioxolane diester (III) was then reduced with LAH to afford (4R,5R)-4,5-bis(hydroxymethyl)-2-isopropyl-1,3-dioxolane (IV), which is treated with methanesulfonyl chloride in pyridine yielding (4R,5R)-4,5-bis(methylsulfonyloxymethyl)-2-isopropyl-1,3-dioxolane (V). The bis(methanesulfonate) (V) is reacted with NaN3 in DMF to give (4R,5R)-4,5-bis(azidomethyl)-2-isopropyl-1,3-dioxolane (VI), which is reduced with hydrogen in the presence of 10% Pd/C in EtOH to afford (4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane (VII). The diamine (VII) is reacted with an equimolar amount of in situ generated K2PtI4 to afford cis-diiodo[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane] platinum(II) (VIII), which is finally treated with malonic acid disilver salt in H2O to obtain (IX).

参考文献No.801543
标题:Synthesis of carbon-14 labelled cis-malonato[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane] platinum(II) (SKI 2053R)
作者:Kim, Y.; Rim, J.; Yoo, K.; Kim, G.; Gam, J.; Kim, K.H.; Kim, D.-K.; Song, S.
来源:J Label Compd Radiopharm 1994,34(2),157-64
合成路线图解说明:

Reaction of D-tartaric acid (I) with EtOH in the presence of an acid catalyst gives diethyl D-tartrate (II), which is treated with isobutyraldehyde and anhydrous CuSO4 in the presence of methanesulfonic acid yielding diethyl 2,3-O-isobutylidene-D-tartrate (III). The 1,3-dioxolane diester (III) was then reduced with LAH to afford (4R,5R)-4,5-bis(hydroxymethyl)-2-isopropyl-1,3-dioxolane (IV), which is treated with methanesulfonyl chloride in pyridine yielding (4R,5R)-4,5-bis(methylsulfonyloxymethyl)-2-isopropyl-1,3-dioxolane (V). The bis(methanesulfonate) (V) is reacted with NaN3 in DMF to give (4R,5R)-4,5-bis(azidomethyl)-2-isopropyl-1,3-dioxolane (VI), which is reduced with hydrogen in the presence of 10% Pd/C in EtOH to afford (4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane (VII). The diamine (VII) is reacted with an equimolar amount of in situ generated K2PtI4 to afford cis-diiodo[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane] platinum(II) (VIII), which is finally treated with malonic acid disilver salt in H2O to obtain (IX).

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