Antitumor agents. 207. Design, synthesis, and biological testing of 4β-anilino-2-fluoro-4′-demethylpodophyllotoxin analogues as cytotoxic and antiviral agents

Journal of Medicinal Chemistry

Volumn 44, Issue 9, 2001, Pages 1422-1428

  VanVliet, D S ^a   Tachibana, Y ^a   Bastow, K F ^a   Huang, E S ^b   Lee, K H ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUOROPODOPHYLLOTOXIN; 2'' DEOXY 2'' (DIMETHYLAMINO)ETOPOSIDE; 4BETA ANILINO 2 FLUORO 4' O NORPODOPHYLLOTOXIN; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; CYTOTOXIC AGENT; ETOPOSIDE; PODOPHYLLOTOXIN; TENIPOSIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING SITE; DRUG DESIGN; DRUG SCREENING; FLUORINATION; NONHUMAN; POLYMERIZATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CERCOPITHECUS AETHIOPS; DNA; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HERPESVIRUS 1, HUMAN; HERPESVIRUS 2, HUMAN; HUMANS; MICROBIAL SENSITIVITY TESTS; NUCLEIC ACID HYBRIDIZATION; PODOPHYLLOTOXIN; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED; VERO CELLS;

EID: 0035953324     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000377f     Document Type: Article

References (40)

1. Antitumor agents. 206. Anti-AIDS agents. 39. Molecular modifications of lead compounds to develop potent antitumor and anti-HIV agents
2. Activity of a new glycosidic lignan derivative (VP-16-213) related to podophyllotoxin in experimental tumors
3. 4′-demethylepipodophyllotoxin thenylidene glucoside (VM 26), a podophyllum compound with a new mechanism of action
4. Clinical and pharmacokinetic phase I trial of oral dimethylaminoetoposide (NK611) administered for 21 days every 35 days
5. Antitumor agents 194. Synthesis and biological evaluations of 4β-mono-, di-, and trisubstituted aniline-4′-O-demethyl-podophyllotoxin and related compounds with improved pharmacological profiles
6. Phase I evaluation of a water-soluble etoposide prodrug, etoposide phosphate, given as a 5-minute infusion on days 1, 3, and 5 in patients with solid tumors
7. A fluorescence stopped flow study of the competition and displacement kinetics of podophyllotoxin and the colchicine analogue 2-methoxy-5-(2′,3′,4′-trimethoxyphenyl)tropone on Tubulin
8. Activation of CDC25 phosphatase and CDC2 kinase involved in GL331-induced apoptosis
9. Unscheduled activation of cyclin B1/CDC2 kinase in human promyelocytic leukemia cell line HL60 cells undergoing apoptosis induced by DNA damage
10. Mechanism of action of antitumor drug etoposide: A review
11. Metal and photoinduced cleavage of DNA by podophyllotoxin, etoposide, and their related compounds
12. E-ring desoxy analogues of etoposide
13. Metabolism of plant-derived anticancer agents
14. Biliary clearance and hepatic metabolism of etoposide (VP-16)
15. Clinical pharmacology of etoposide by radioimmunoassay
16. The podophyllotoxin-picropodophyllin equilibrium
17. Preparation of 2-substituted podophyllotoxin derivatives
18. Synthesis of 2-azapodophyllotoxin
19. Synthesis and antitumor activity of podophyllotoxin aza-analogues
20. Nonenolizable podophyllotoxin derivatives
21. 1H NMR spectra, and activity of delactonized derivatives of the anticancer drug etoposide
22. Clinical studies with podophyllum compounds SPI-77 (NSC-72274) and SPG-827 (NSC-42076)
23. A high yield preparation of 2-fluoropodophyllotoxin
24. A new silyl protecting group
25. N-fluoro-O-benzenedisulfonimide: A useful new fluorinating reagent
26. N-fluorobenzenesulfonimide: A practical reagent for electrophilic fluorinations
27. A one-pot, efficient synthesis of the potent cytotoxic podophyllotoxin derivative NPF
28. Recent progress in the development of novel antitumor etoposide analogues
29. Susceptibility of phosphonoformic acid-resistant herpes simplex virus variants to arabinosylnucleosides and aphidicolin. antimicrob
30. 1,3-Dihydroxy-acridone derivatives as inhibitors of herpes virus replication
31. Clinical manifestations of AIDS in the era of pneumocystis prophylaxis
32. Neuroradiographic findings in the newborn period and long-term outcome in children with symptomatic congenital cytomegalovirus infection
33. Inhibitory effect of 4-(4-fluorophenyl-2-(4-hydroxyphenyl)-5-(4-pyridyl)1H-imidazole on HCMV DNA replication
34. Irreversible inhibition of human cytomegalovirus replication by topoisomerase II inhibitor, etoposide: A new strategy for the treatment of human cytomegalovirus infection
35. Antitumor agents. 163. Three-dimensional quantitative structure-activity relationship study of 4′-O-demethylepipodophyllotoxin analogues using the modified CoMFA/q2-GRS approach