【药物名称】KNI-694
化学结构式(Chemical Structure):
参考文献No.610082
标题:Synthesis and biological evaluation of prodrug-type anti-HIV agents. Ester conjugates of carboxylic acid-containing dipeptide HIV protease inhibitors and a reverse transcriptase inhibitor
作者:Matsumoto, H.; Matsuda, T.; Nakata, S.; Mitoguchi, T.; Kimura, T.; Hayashi, Y.; Kiso, Y.
来源:Bioorg Med Chem 2001,9(2),417
合成路线图解说明:

In an alternative procedure, 2,2-dimethylsuccinic anhydride (II) was reacted with p-methoxybenzyl alcohol (V) in the presence of dicyclohexylamine to afford the beta,beta-dimethyl p-methoxybenzyl ester (VI) as the major product, along with minor amounts of the alpha,alpha-dimethyl regioisomer. Condensation of hemiester (VI) with AZT (IV) by using DCC and DMAP produced diester (VII). The p-methoxybenzyl group of (VII) was then removed by treatment with trifluoroacetic acid to give (VIII). Acid (VIII) was finally coupled with the dipeptide amide (I) in the presence of BOP and HOBt.

参考文献No.611007
标题:A new class of anti-HIV agents: Synthesis and activity of conjugates of HIV protease inhibitors with a reverse transcriptase inhibitor
作者:Kimura, T.; Matsumoto, H.; Matsuda, T.; Hamawaki,T.; Akaji, K.; Kiso, Y.
来源:Bioorg Med Chem Lett 1999,9(6),803
合成路线图解说明:

The title compound was prepared following two alternative synthetic sequences: Condensation of the known dipeptide amide (I) with 2,2-dimethylsuccinic anhydride (II) in the presence of DMAP produced regioselectively the succinic monoamide (III). This was then coupled to AZT (IV) by using DCC and DMAP to furnish the corresponding AZT ester.

合成路线图解说明:

In an alternative procedure, 2,2-dimethylsuccinic anhydride (II) was reacted with p-methoxybenzyl alcohol (V) in the presence of dicyclohexylamine to afford the beta,beta-dimethyl p-methoxybenzyl ester (VI) as the major product, along with minor amounts of the alpha,alpha-dimethyl regioisomer. Condensation of hemiester (VI) with AZT (IV) by using DCC and DMAP produced diester (VII). The p-methoxybenzyl group of (VII) was then removed by treatment with trifluoroacetic acid to give (VIII). Acid (VIII) was finally coupled with the dipeptide amide (I) in the presence of BOP and HOBt.

参考文献No.611009
标题:Synthesis and activity of a new type of anti-HIV agents, conjugate of HIV protease inhibitor with reverse transcriptase inhibitor
作者:Kimura, T.; Matsuda, T.; Akaji, K.; Kiso, Y.; Matsumoto, H.; Hamawaki, T.
来源:Pept Sci 1999,305
合成路线图解说明:

The title compound was prepared following two alternative synthetic sequences: Condensation of the known dipeptide amide (I) with 2,2-dimethylsuccinic anhydride (II) in the presence of DMAP produced regioselectively the succinic monoamide (III). This was then coupled to AZT (IV) by using DCC and DMAP to furnish the corresponding AZT ester.

合成路线图解说明:

In an alternative procedure, 2,2-dimethylsuccinic anhydride (II) was reacted with p-methoxybenzyl alcohol (V) in the presence of dicyclohexylamine to afford the beta,beta-dimethyl p-methoxybenzyl ester (VI) as the major product, along with minor amounts of the alpha,alpha-dimethyl regioisomer. Condensation of hemiester (VI) with AZT (IV) by using DCC and DMAP produced diester (VII). The p-methoxybenzyl group of (VII) was then removed by treatment with trifluoroacetic acid to give (VIII). Acid (VIII) was finally coupled with the dipeptide amide (I) in the presence of BOP and HOBt.

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