Efficient synthesis and biological evaluation of some 2,4-diamino-furo[2,3- d]pyrimidine derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 21, 2010, Pages 6188-6190

  Hu, Yang Gen ^a,b   Wang, Yan ^a   Du, Shi Ming ^b   Chen, Xiao Bao ^a   Ding, Ming Wu ^c  

^a WUHAN UNIVERSITY   (China)

^b Medical University   (China)

^c CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

Antitumor activity; Aza Wittig reactions; Ethyl 4 alkylamino 2 arylamino 6 methyl furo 2,3 d pyrimidine 5 carboxylate

Indexed keywords

AMINE; AMMONIA; ANTINEOPLASTIC AGENT; CARBOXYLIC ACID DERIVATIVE; CYANAMIDE; ETHYL 2 (M TOLYLAMINO) 4 (BUTYLAMINO) 6 METHYLFURO[2,3 D]PYRIMIDINE 5 CARBOXYLATE; ETHYL 2 (M TOLYLAMINO) 4 (DIETHYLAMINO) 6 METHYLFURO [2,3 D]PYRIMIDINE 5 CARBOXYLATE; ETHYL 2 (M TOLYLAMINO) 4 (ISOPROPYLAMINO) 6 METHYLFURO[2,3 D]PYRIMIDINE 5 CARBOXYLATE; ETHYL 2 (M TOLYLAMINO) 6 METHYL 4 (4 METHYLPIPERAZIN 1 YL) FURO[2,3 D]PYRIMIDINE 5 CARBOXYLATE; ETHYL 2 (M TOLYLAMINO) 6 METHYL 4 MORPHOLINO FURO[2,3 D]PYRIMIDINE 5 CARBOXYLATE; ETHYL 4 (2 HYDROXYETHYLAMINO) 6 METHYL 2 (PHENYLAMINO) FURO[2,3 D]PYRIMIDINE 5 CARBOXYLATE; ETHYL 4 (BUTYLAMINO) 6 METHYL 2 (PHENYLAMINO) FURO[2,3 D]PYRIMIDINE 5 CARBOXYLATE; ETHYL 4 (ISOPROPYLAMINO) 6 METHYL 2 (PHENYLAMINO) FURO[2,3 D]PYRIMIDINE 5 CARBOXYLATE; ETHYL 4 ALKYLAMINO 2 ARYLAMINO 6 METHYL FURO[2,3 D]PYRIMIDINE 5 CARBOXYLATE; ETHYL 6 METHYL 4 (4 METHYLPIPERAZIN 1 YL) 2 (PHENYLAMINO)FURO[2,3 D]PYRIMIDINE 5 CARBOXYLATE; ETHYL 6 METHYL 4 MORPHOLINO 2 (PHENYLAMINO) FURO[2,3 D]PYRIMIDINE 5 CARBOXYLATE; ISOCYANATE; PHOSPHORANE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; CYTOTOXICITY; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; LUNG CANCER; PROTON NUCLEAR MAGNETIC RESONANCE; WITTIG REACTION; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; FURANS; HUMANS; INDICATORS AND REAGENTS; LUNG NEOPLASMS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PYRIMIDINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; X-RAY DIFFRACTION;

EID: 77957912107     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.122     Document Type: Article

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16. 4 (327.33): C, 62.38; H, 5.23; N, 12.84. Found: C, 62.21; H, 5.17; N, 12.75.
17. 3 (345.78): C, 59.05; H, 4.66; N, 12.15. Found: C, 58.96; H, 4.60; N, 12.03.
18. 3, 100 MHz) δ
19. 0). X-ray structure showed that all ring atoms in the furo[2,3-d]pyrimidine moiety are nearly coplanar and the phenyl ring is twisted with respect to the pyrimidine ring system by 8.00(7)°. Crystallographic data for 5b have been deposited in the Cambridge Crystallographic Data Center as supplementary publication numbers CCDC 778650. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ).
20. Cytotoxic activities were evaluated by using standard MTT assay after exposure of cells to the tested compounds for 48 h. Results are presented as mean values of two independent experiments done in quadruplicates. Coefficients of variation were <10%.