SYNTHESIS AND ANTILEUKEMIC ACTIVITY OF CHYMOTRYPSIN-ACTIVATED DERIVATIVES OF 3'-AMINO-2',3'-DIDEOXYCYTIDINE - (SYNTHETIC NUCLEOSIDES AND NUCLEOTIDES .33.)

被引：0

作者：

KAWAGUCHI, T

SAKAIRI, H

KIMURA, S

YAMAGUCHI, T

SANEYOSHI, M

机构：

[1] HOKKAIDO UNIV, FAC PHARMACEUT SCI, SAPPORO, HOKKAIDO 060, JAPAN

[2] NISHI TOKYO UNIV, DEPT SCI BIOL, YAMANASHI 40901, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1995年 / 43卷 / 03期

关键词：

3'-AMINO-2'; 3'-DIDEOXYCYTIDINE; PHENYLALANINE; CHYMOTRYPSIN; ENZYMATIC ACTIVATION; PRODRUG; P388;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

3'-Amino-2',3'-dideoxycytidine (8) was directly synthesized from 2'-deoxycytidine. 2',3'-Dideoxy-3'-(N-acyl-L-phenylalanylamino)cytidines (acyl = butoxycarbonyl (9a), acetyl (9b), benzoyl (9c), and n-hexanoyl (9d)) were synthesized as chymotrypsin-activated prodrugs of 8. This N-protection was required for activation by chymotrypsin to 8. In vitro, compound 8 showed high cytotoxic activity against P388 cells, but the prodrugs 9a-d were ineffective. In vivo, however, these prodrugs showed much higher activity than 8 in mice bearing P388 cells.

引用

页码：501 / 504

页数：4

共 50 条

[41] Synthesis and anticonvulsant activity of a class of 2-amino 3-hydroxypropanamide and 2-aminoacetamide derivatives
Ghidini, E
Delcanale, M
De Fanti, R
Rizzi, A
Mazzuferi, M
Rodi, D
Simonato, M
Lipreri, M
Bassani, F
Battipaglia, L
Bergamaschi, M
Villetti, G
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (10) : 3263 - 3274
[42] Design, Synthesis and Antiviral Activity of 2-(3-Amino-4-piperazinylphenyl)chromone Derivatives
Kim, Mi Kyoung
Yoon, Hyunjun
Barnard, Dale Lynn
Chong, Youhoon
CHEMICAL & PHARMACEUTICAL BULLETIN, 2013, 61 (04) : 486 - 488
[43] SYNTHESIS AND ANXIOLYTIC ACTIVITY OF 2-METHYL-3- AMINO-4QUINAZOLINONE ACETAMIDE DERIVATIVES
Patil, J. P.
Amrutkar, S. V.
Borole, R. N.
HETEROCYCLIC LETTERS, 2014, 4 (03): : 363 - 370
[44] SYNTHESIS AND ANTIFUNGAL ACTIVITY OF SOME 1-AMINO-3-(2-BENZIMIDAZOLYL)-GUANIDINES AND THEIR DERIVATIVES
SAWHNEY, SN
GUPTA, A
VIR, D
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1991, 30 (06): : 584 - 588
[45] Synthesis and evaluation of antimitotic activity of alkylated 2-amino-1,3,4-oxadiazole derivatives
Rai, KML
Linganna, N
FARMACO, 2000, 55 (05): : 389 - 392
[46] Synthesis and biological activity of 5-substituted-2-amino-1,3,4-oxadiazole derivatives
Kumar, Sanjeev
TURKISH JOURNAL OF CHEMISTRY, 2011, 35 (01) : 99 - 108
[47] Synthesis and anti HCMV activity of 3,4-disubstituted tetrahydrofuran derived nucleosides and nucleotides: a tethered series of PME derivatives (vol 7, pg 2567, 1997)
Wang, W
Jin, H
Fuselli, N
Mansour, TS
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (02) : 203 - 203
[48] STUDY OF LACTAMS .33. SYNTHESIS OF 2-OXO-1H,2,3,4,5-TETRAHYDROAZEPINO[4,5-B]-INDOLE DERIVATIVES
GLUSHKOV, RG
ZASOSOVA, IM
OVCHAROVA, IM
SOLOVYOVA, NP
SHEINKER, YN
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1979, (07): : 954 - 960
[49] Synthesis, reactions, and antiviral activity of 6′-amino-2′-thioxo-1′,2′-dihydro-3,4′-bipyridine-3′,5′-dicarbonitrile
Attaby, Fawzy A.
Elghandour, A. H. H.
Ali, M. A.
Ibrahem, Yasser M.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (04) : 695 - 709
[50] AMINOACYL DERIVATIVES OF NUCLEOSIDES NUCLEOTIDES AND POLYNUCLEOTIDES .2. SYNTHESIS OF 2'(3')-O-GLYCYL DERIVATIVES OF URIDYLYL-(3'-]5')-URIDINE CYTIDYLYL-(3'-]5')-ADENOSINE AND URIDYLYL-(3'-]5')-ADENOSINE USING CORRESPONDING RIBONUCLEOSIDE 2',3'-CYCLIC ORTHOESTERS AS KEY INTERMEDIATES
CHLADEK, S
ZEMLICKA, J
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1967, 32 (05) : 1776 - &

← 1 2 3 4 5 →