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2-[(3-氨丙基)硫代]腺苷5'-二磷酸的简便合成:腺苷5'-二磷酸功能分子探针合成的关键中间体。

Facile synthesis of 2-[(3-aminopropyl)thio]adenosine 5'-diphosphate: a key intermediate for the synthesis of molecular probes of adenosine 5'-diphosphate function.

作者信息

Jefferson J R, Hunt J B, Jamieson G A

机构信息

American Red Cross Cell Biology Laboratory, Rockville, Maryland 20855.

出版信息

J Med Chem. 1987 Nov;30(11):2013-6. doi: 10.1021/jm00394a015.

DOI:10.1021/jm00394a015
PMID:3669009
Abstract

Adenosine 5'-diphosphate (ADP) and, uniquely, its C-2 derivatized analogues are able to induce platelet activation. We here report the synthesis of 2-[(3-aminopropyl)thio]-ADP from ADP itself via 1,N6-etheno-ADP. 2-[(3-Aminopropyl)thio]-ADP induced platelet aggregation with a potency about one-seventh that of ADP itself and should prove a useful intermediate in the synthesis of other probes of platelet function.

摘要

5'-二磷酸腺苷(ADP)及其独特的C-2衍生类似物能够诱导血小板活化。我们在此报告了通过1,N6-乙烯基-ADP从ADP本身合成2-[(3-氨基丙基)硫基]-ADP的方法。2-[(3-氨基丙基)硫基]-ADP诱导血小板聚集的效力约为ADP本身的七分之一,应被证明是合成其他血小板功能探针的有用中间体。

相似文献

1
Facile synthesis of 2-[(3-aminopropyl)thio]adenosine 5'-diphosphate: a key intermediate for the synthesis of molecular probes of adenosine 5'-diphosphate function.2-[(3-氨丙基)硫代]腺苷5'-二磷酸的简便合成:腺苷5'-二磷酸功能分子探针合成的关键中间体。
J Med Chem. 1987 Nov;30(11):2013-6. doi: 10.1021/jm00394a015.
2
ADP induces desensitisation of equine platelet aggregation responses: studies using ADP beta S, a stable analogue of ADP.二磷酸腺苷(ADP)可诱导马血小板聚集反应脱敏:使用ADPβS(一种ADP的稳定类似物)的研究。
Res Vet Sci. 1993 Mar;54(2):235-43. doi: 10.1016/0034-5288(93)90063-l.
3
Differential effects of adenine nucleotide analogues on shape change and aggregation induced by adnosine 5-diphosphate (ADP) in human platelets.腺嘌呤核苷酸类似物对人血小板中5-二磷酸腺苷(ADP)诱导的形态变化和聚集的不同作用。
Br J Pharmacol. 1999 Jul;127(6):1359-66. doi: 10.1038/sj.bjp.0702690.
4
Competitive inhibition by adenosine 5'-triphosphate of the actions on human platelets of 2-chloroadenosine 5'-diphosphate, 2-azidoadenosine 5'-diphosphate and 2-methylthioadenosine 5'-diphosphate.5'-三磷酸腺苷对2-氯-5'-二磷酸腺苷、2-叠氮基-5'-二磷酸腺苷和2-甲硫基-5'-二磷酸腺苷作用于人类血小板的竞争性抑制作用。
Br J Pharmacol. 1982 Oct;77(2):329-33. doi: 10.1111/j.1476-5381.1982.tb09302.x.
5
Differential inhibition by adenosine or by prostaglandin E1 of human platelet aggregation induced by adenosine 5'-O-(1-thiodiphosphate) and adenosine 5'-O-(2-thiodiphosphate).腺苷或前列腺素E1对5'-O-(1-硫代二磷酸)腺苷和5'-O-(2-硫代二磷酸)腺苷诱导的人血小板聚集的差异抑制作用。
Br J Pharmacol. 1982 Feb;75(2):257-9. doi: 10.1111/j.1476-5381.1982.tb08781.x.
6
Partial agonist behaviour of adenosine 5'-O-(2-thiodiphosphate) on human platelets.腺苷5'-O-(2-硫代二磷酸)对人血小板的部分激动剂行为。
Br J Pharmacol. 1981 Jun;73(2):405-8. doi: 10.1111/j.1476-5381.1981.tb10436.x.
7
Specific but noncompetitive inhibition by 2-alkylthio analogues of adenosine 5'-monophosphate and adenosine 5'-triphosphate of human platelet aggregation induced by adenosine 5'-diphosphate.5'-二磷酸腺苷诱导的人血小板聚集受到5'-单磷酸腺苷和5'-三磷酸腺苷的2-烷硫基类似物的特异性而非竞争性抑制。
Br J Pharmacol. 1982 Feb;75(2):397-400. doi: 10.1111/j.1476-5381.1982.tb08800.x.
8
Sulfhydryl analogues of adenosine diphosphate: chemical synthesis and activity as platelet-aggregating agents.二磷酸腺苷的巯基类似物:化学合成及其作为血小板聚集剂的活性
Can J Biochem. 1976 Jun;54(6):529-33. doi: 10.1139/o76-077.
9
Characterization of the effects of adenosine 5'-[beta-thio]-diphosphate in rat liver.5'-[β-硫代]-二磷酸腺苷对大鼠肝脏作用的特征研究
Br J Pharmacol. 1993 Mar;108(3):663-8. doi: 10.1111/j.1476-5381.1993.tb12858.x.
10
Effects of RP and SP diastereoisomers of adenosine 5'-O-(1-thiodiphosphate) on human platelets.腺苷5'-O-(1-硫代二磷酸)的RP和SP非对映异构体对人血小板的作用。
Br J Pharmacol. 1981 Jun;73(2):409-12. doi: 10.1111/j.1476-5381.1981.tb10437.x.

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