Synthesis of new series of pyrazolo[4,3-d]pyrimidin-7-ones and pyrido[2,3-d]pyrimidin-4-ones for their bacterial and cyclin-dependent kinases (CDKs) inhibitory activities

被引:25
作者
Geffken, Detlef [2 ]
Soliman, Raafat [1 ]
Soliman, Farid S. G. [1 ]
Abdel-Khalek, Magdi M. [1 ]
Issa, Doaa A. E. [1 ]
机构
[1] Univ Alexandria, Fac Pharm, Dept Pharmaceut Chem, Alexandria, Egypt
[2] Univ Hamburg, Dept Pharmaceut Chem, Inst Pharm, Hamburg, Germany
关键词
Pyrazole; Pyrazolo[4,3-d]pyrimidin-7-one; Pyrido[2,3-d]pyrimidin-4-one; Hydrazono-pyridazine; Antibacterial activity; ANTIBACTERIAL ACTIVITY; SILDENAFIL ANALOGS; PHENYL RING; DERIVATIVES; ACID; OLOMOUCINE; POTENT; MOIETY; CDC2;
D O I
10.1007/s00044-010-9328-z
中图分类号
R914 [药物化学];
学科分类号
100705 [微生物与生化药学];
摘要
Two series of pyrazolo[4,3-d]pyrimidin-7-ones and pyrido[2,3-d]pyrimidin-4-ones were designed, synthesised, and evaluated for their antibacterial activities and CDKs inhibitory activities. The pyridazine derivative: 6-phenyl-5-phenylhydrazono-2,3,4,5-tetrahydropyridazine-3,4-dione (3a) revealed activity against Staphylococcus aureus as Gram-positive bacteria while compound 2-(2-Ethoxyphenyl-5-Phenylpiperazinosulfonamido)-3H-pyrido[2,3-d]pyrimidin-4-one (13c) was showing moderate antifungal activity against Candida albicans.
引用
收藏
页码:408 / 420
页数:13
相关论文
共 33 条
[1]
DEVELOPMENT OF ETHYL 3,4-DIHYDRO-4-OXOPYRIMIDO[4,5-B]QUINOLINE-2-CARBOXYLATE, A NEW PROTOTYPE WITH ORAL ANTIALLERGY ACTIVITY [J].
ALTHUIS, TH ;
MOORE, PF ;
HESS, HJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (01) :44-48
[2]
Bell A. S., 1992, Pyrazolopyrimidinone antianginal agents, Eur. Pat. Appl, Patent No. [463756, 463756 A1]
[3]
Slow-binding inhibition of 2-keto-3-deoxy-6-phosphogluconate (KDPG) aldolase [J].
Braga, R ;
Hecquet, L ;
Blonski, C .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (11) :2965-2972
[4]
ACYLPYRUVATES AS POTENTIAL ANTIFUNGAL AGENTS [J].
BURCH, HA ;
GRAY, JE .
JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (04) :429-&
[5]
A novel and efficient synthesis of pyrimido[4,5-d]pyrimidine-2,4,7-trione and pyrido[2,3-d:6,5-d] dipyrimidine-2,4,6,8-tetrone derivatives [J].
Dabiri, Minoo ;
Arvin-Nezhad, Harnid ;
Khavasi, Hamid Reza ;
Bazgir, Ayoob .
TETRAHEDRON, 2007, 63 (08) :1770-1774
[6]
Crystal structure of human cyclin-dependent kinase 2 in complex with the adenine-derived inhibitor H717 [J].
Dreyer, MK ;
Borcherding, DR ;
Dumont, JA ;
Peet, NP ;
Tsay, JT ;
Wright, PS ;
Bitonti, AJ ;
Shen, J ;
Kim, SH .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (04) :524-530
[7]
Enantio- and regiospecific reduction of ethyl 4-phenyl-2.4-dioxobutyrate with baker's yeast:: preparation of (R)-HPB ester [J].
Fadnavis, NW ;
Radhika, KR .
TETRAHEDRON-ASYMMETRY, 2004, 15 (21) :3443-3447
[8]
SYNTHESIS OF 5-SUBSTITUTED 3-ISOXAZOLECARBOXYLIC ACID HYDRAZIDES AND DERIVATIVES [J].
GARDNER, TS ;
LEE, J ;
WENIS, E .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (05) :1514-&
[9]
Exploiting chemical libraries, structure, and genomics in the search for kinase inhibitors [J].
Gray, NS ;
Wodicka, L ;
Thunnissen, AMWH ;
Norman, TC ;
Kwon, SJ ;
Espinoza, FH ;
Morgan, DO ;
Barnes, G ;
LeClerc, S ;
Meijer, L ;
Kim, SH ;
Lockhart, DJ ;
Schultz, PG .
SCIENCE, 1998, 281 (5376) :533-538
[10]
Haesslein Jean-Luc, 2002, Current Topics in Medicinal Chemistry, V2, P1037, DOI 10.2174/1568026023393291