Antineoplastic agents 429. Syntheses of the combretastatin A-1 and combretastatin B-1 prodrugs

Anti-Cancer Drug Design

Volumn 15, Issue 3, 2000, Pages 203-216

  Pettit, G R ^a   Lippert III, J W ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

Antineoplastic activity; Combretastatin A 1 prodrug; Combretastatin B 1 prodrug; Phosphate esters

Indexed keywords

COMBRETASTATIN; COMBRETASTATIN A1; COMBRETASTATIN B1; PRODRUG; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CHEMICAL REACTION; CIS ISOMER; DEPHOSPHORYLATION; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGENATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

AMMONIUM COMPOUNDS; ANIMAL; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL DIVISION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMAN; PHOSPHORIC ACID ESTERS; PRODRUGS; SOLUBILITY; STILBENES; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.; TUMOR CELLS, CULTURED;

EID: 0033814533     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (94)

1. P-glycoprotein resistance to 5'-nor-anhydro-vinblastine (Navelbine®)
2. Oxidative demethylation with chromium trioxide in acetic acid
3. Antiangiogenic tumour therapy: Will it work?
4. Reaction of iodine with olefins. Kinetics and mechanism of iodine addition to pentene isomers
5. Deprotection of masked steroidal alcohols by hydride transfer
6. 4-Hydroxybenzylidenemalo-naonitrile: A useful matrix for MALDI of water-insoluble analytes
7. Manganous ion binding to tubulin
8. N,N-Diisopropyl-bis[2-(trimethylsilyl)ethyl]phosphoramidite. An attractive phosphitylating agent compatible with the Fmoc/t-butyl strategy for the synthesis of phosphotyrosine containing peptides
9. Thaliblastine, a plant alkaloid circumvents multidrug resistance by direct binding to P-glycoprotein
10. Treatment of nocturnal leg cramps
11. Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anti-cancer agents that inhibit tubulin polymerization
12. (Z)-1-(4-Methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents
13. Combretastatin A-4, an agent that displays potent and selective toxicity toward tumor vasculature
14. Critical tests and safety studies on a levamisole-piperazine mixture as an anthelminthic in the horse
15. Determination of quinine in serum, plasma, red blood cells and whole blood in healthy and Plasmodium falciparum malaria cases by high-performance liquid chomatography
16. Rapid removal of protecting groups from peptides by catalytic transfer hydrogenation with 1,4-cyclohexadiene
17. Phase-transfer-catalysed halogenation of di-t-butyl phosphite. Preparation of di-t-butyl phosphorohalidate
18. Zinc ion-induced assembly of tubulin
19. In vitro microtubule assembly regulation by divalent cations and nucleotides
20. Cinchonine per os: Efficient circumvention of p-glycoprotein-mediated multidrug resistance
21. A convenient method for the phosphorylation of phenols with diethyl cyanophosphonate
22. Polymerization and depolymerization of microtubules in vitro as studied by flow birefringence
23. Interactions of tubulin with small ligands
24. Chemistry of the glycosidic linkage. Direct conversion of glycosides into 1-thioglycosides by use of [alkyl (or aryl)-thio]trimethylsilanes
25. A simple synthesis of (+)-isocarbacyclin via convergent process
26. A controlled synthesis of α-(E)-1 -alkenyl ketones from β-keto benzyl esters
27. Tubulin assembly induced by cobalt and zinc
28. Stereochemistry of halogen azide additions to olefins. The stability of three-membered iodonium vs. bromonium ions
29. Analytical profile of papaverine hydrochloride
30. Shikonin, an ingredient of Lithospermum erythrorhizon, inhibits angiogenesis in vivo and in vitro
31. Cleavage of esters and ethers with iodotrimethylsilane
32. Determination of verapamil and norverapamil in human biological material
33. Triphenylcarbenium and tris(p-bromo-phenyl)ammoniumyl ion induced lactoniations of ω-benzyloxy and ω-p-methoxy-benzyloxy methyl esters
34. Differential effects of magnesium on tubuilin-nucleotide interactions
35. Influence of the site of stimulation on atrioventricular nodal refractory periods and the effect of verapamil
36. Divalent cation-nucleotide complex at the exchangeable nucleotide binding site of tubulin
37. Quantitative dealkylation of alkyl ethers via treatment with trimethylsilyliodide. A new method for ether hydrolysis
38. Selective demethylations in 2,3,4-trimethoxyaryl carbonyl compounds
39. Effect of α-interferon on P-glycoprotein expression and function and on verapamil modulation of doxorubicin resistance
40. Use of ferric chloride in carbohydrate reactions. IV. Acetolysis of benzyl ethers of sugars
41. Microbubules from mammalian brain: Some properties of their depolymerization products and a proposed mechanism of assembly and disassembly
42. 4-phopho-L-tyroside-containing peptides
43. Chloroquine or quinine is an effective therapy of uncomplicated Plasmodium falciparum malaria in children from Gabon
44. 2+
45. The in vitro polymerization of tubulin from beef brain
46. Interactions of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin: A structure-activity study
47. 14C]verapamil
48. + in tubulin
49. Novel method for dealkylation of esters, ethers, and acetals by chlorotrimethylsilane-sodium iodide
50. Studies on total syntheses of antitumor styryllactones: Stereoselective total syntheses of (+)-goniofufurone, (+)-goniobutenolide A, and (-)-goniobutenolide B
51. Selective deprotection of silyl ethers
52. Synthetic methods and reactions. 62. Transformations with chlorotrimethylsilane/sodium iodide, a convenient in situ iodotrimethylsilane reagent
53. Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)
54. Cell growth inhibitor constituents from Combretum kraussi
55. A new convenient and efficient general procedure for the conversion of alcohols into their dibenzyl phosphorotriester using N,N-diethyl dibenzyl phosphoramidite
56. Di-tert-butyl-N,N-diethylphosphoramidite. A new phosphitylating agent for the efficient phosphorylation of alcohols
57. Antineoplastic agents. New syntheses of the combretastatin A-4 prodrug
58. Isolation, structure and synthesis of combretastatin A-2, A-3, and B-2
59. Isolation, structure, and synthesis of combretastatins A-1 and B-1, potent new inhibitors of microtubule assembly, derived from Combretum caffrum
60. Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4
61. Antineoplastic agents 322. Synthesis of combretastatin A-4 prodrugs
62. Antineoplastic agents 320. Synthesis of a practical pancratistatin prodrug
63. Antineoplastic agents 393. Synthesis of the trans-isomer of combretastatin A-4 prodrug
64. Intravenous quinidine for the treatment of severe falciparum malaria
65. Synthesis, NMR, and structure of oligonucleotide phosphorodithioates
66. The kinetics of halogen addition to unsaturated compounds. Part XVIII. Iodine addition
67. Synthesis of D-myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate analogues and their membrane-permeant derivatives
68. Podophyllotoxin, steganacin and combretastatin: Natural products that bind at the colchicine site of tubulin
69. Recent developments in chemical deprotection of ester functiional groups
70. Reversal of multidrug resistance by a novel quinoline derivative, MS-209
71. Synthesis of etoposide phosphate, BMY-40481: A water-soluble clinically active prodrug of etoposide
72. A simple, rapid, and efficient protocol for the selective phosphorylation of phenols with dibenzyl phosphite
73. Calcium antagonists: Clinical use in the treatment of arrhythmias
74. Desilylation of tert-butyldimethylsilyl ethers of phenols
75. Stereospecific trans photo-addition of elementary iodine to aliphatic olefins. Bridged iodoalkyl radicals
76. Angiogenesis in rheumatoid arthritis: Pathogenic and clinical significance
77. Clotrimazole, an imidazole antimycotic, is a potent inhibitor of angiogenesis
78. 1,8-Diazabicyclo[5.4.0]undecene mediated transesterification of p-nitrophenyl phosphonates: A novel route to phosphono esters
79. Synthesis, bioactivation and anti-HIV activity of the bis(4-acyloxybenzyl) and mono(4-acyloxybenzyl) esters of the 5'-monophosphate of AZT
80. Calcium antagonists: Some chemical pharmacologic aspects
81. Acute toxicity and general pharmacologic properties of 1,5-dimorpholino-3-(1-naphthyl)-pentane: DA 1686
82. Novel water-soluble phosphate prodrugs of Taxol possessing in vivo antitumor activity
83. N,N-Dialkyldiamide-type phosphate protecting groups for Fmoc synthesis of phosphotyrosine-containing peptides
84. Total synthesis of d,i-methylnolide, sulfur removal and remote stereo control
85. Synthesis and antitumor evaluation of water soluble Taxol phosphate
86. Photoisomerization dynamics of stilbenes
87. Regression of established tumors expressing P-glyco-protein by combinations of adriamycin, cyclosporin derivatives, and MRK-16 antibodies
88. Ergonovine testing to detect spontaneous remissions of variant angina during long-term treatment with calcium antagonist drugs
89. The reaction of L-ascorbic acid and D-isoascorbic acid with nicotinic acid and its amide
90. A marine animal product, patellamide D, reverses multidrug resistance in a human leukemic cell line
91. A nuclear magnetic resonance investigation of the iodination of 1,2-disubstituted ethylenes. Evidence for a trans addition-cis elimination