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质量水平
方案
99%
mp
>300 °C (dec.) (lit.)
官能团
chloro
SMILES字符串
Clc1ncnc2[nH]cnc12
InChI
1S/C5H3ClN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H,7,8,9,10)
InChI key
ZKBQDFAWXLTYKS-UHFFFAOYSA-N
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一般描述
6-Chloropurine (6-CIPH), a 6-substituted purine derivative, is an antileukemic drug. It can be prepared by the chlorination of hypoxanthine with phosphorus oxychloride in the presence of dimethylaniline. The NMR-based conformational analysis of the products formed during the reaction of 6-CIPH with 3,4-di-O-acetyl-D-xylal and 3,4-di-O-acetyl-L-arabinal have been reported. 6-CIPH can undergo palladium-catalyzed cross coupling with organostannanes at 6-position to form the corresponding arylated or alkylated products.
应用
6-Chloropurine may be used:
- To prepare purine via catalytic dehydrogenation.
- To prepare 9-alkylated adenines via Mitsunobu reaction with various alcohols.
- As a starting material to synthesize dihydroisoxazole 6-chloropurine.
Synthesis and anti-HIV activity of dihydroisoxazole 6-chloropurine and adenine.
Xiang Y, et al.
Bioorganic & Medicinal Chemistry Letters, 6(9), 1051-1054 (1996)
6-Chloropurines and organostannanes in palladium catalyzed cross coupling reactions.
Gundersen LL.
Tetrahedron Letters, 35(19), 3155-3158 (1994)
Synthesis of Nucleosides and Related Compounds. Part XXV. The Alkylation of 6-Chloropurine with Alcohols by Mitsunobu Reaction.
Toyota A, et al.
Chemical & Pharmaceutical Bulletin, 40(4), 1039-1041 (1992)
The Synthesis and Properties of 6-Chloropurine and Purine1.
Bendich A, et al.
Journal of the American Chemical Society, 76(23), 6073-6077 (1954)
REACTIONS OF RIBONUCLEOTIDE DERIVATIVES OF PURINE ANALOGUES AT THE CATALYTIC SITE OF INOSINE 5'-PHOSPHATE DEHYDROGENASE.
A HAMPTON
The Journal of biological chemistry, 238, 3068-3074 (1963-09-01)
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