Regioselective Synthesis and Bioactivity of New 5-Amino-6-arylamino-pyrazolo[3,4-d]-pyrimidin-4(5H)-one Derivatives

A novel approach to regioselective synthesis of new 5-amino-6-arylamino-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 5 derivatives via a tandem aza-wittig and annulation reaction of iminophosphorance 2, aromatic isocyanates and hydrazine in 69.6-94.7% isolated yields is reported. The compound 5 reacted wit...

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Published inJournal of heterocyclic chemistry Vol. 46; no. 2; pp. 256 - 260
Main Authors Wang, Hong-Qing, Zhou, Wei-Ping, Wang, Yu-Yuan, Lin, Can-Rong, Liu, Zhao-Jie
Format Journal Article
LanguageEnglish
Published MALDEN Wiley 01.03.2009
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTIMICROBIAL AGENTS
DESIGN
INHIBITORS
ANTIFUNGAL ACTIVITY
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Summary:A novel approach to regioselective synthesis of new 5-amino-6-arylamino-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 5 derivatives via a tandem aza-wittig and annulation reaction of iminophosphorance 2, aromatic isocyanates and hydrazine in 69.6-94.7% isolated yields is reported. The compound 5 reacted with triethyl orthoformate to give compound 6 in good yield (65.8-82.8%). Their structure was clearly confirmed by spectroscopy data (IR, (1)H NMR, MS, elemental analysis) and the results of preliminary bioassay indicated that compounds 5 and 6 possess high antifungal activity against Botrytis cinerea Pers and Sclerotinia sclerotiorum, and compound 5h showed 100, 96.4, and 90.2% inhibitory rate to Botrytis cinerea Pers, Pyricularia oryzae, and Sclerotinia sclerotiorum at the concentration of 50 mg/L. The antifungal activities of compound 6 were generally higher than those of compound 5.
ISSN:0022-152X
DOI:10.1002/jhet.26