Home Other Building Blocks Combretastatin A4

Combretastatin A4

CAS No.:
117048-59-6
Catalog Number:
AG000DMO
Molecular Formula:
C18H20O5
Molecular Weight:
316.3484
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
99%
1 week
United States
$140
- +
10mg
99%
1 week
United States
$190
- +
25mg
99%
1 week
United States
$357
- +
250mg
>98.0%(HPLC)
1 week
United States
$2085
- +
Product Description
Catalog Number:
AG000DMO
Chemical Name:
Combretastatin A4
CAS Number:
117048-59-6
Molecular Formula:
C18H20O5
Molecular Weight:
316.3484
MDL Number:
MFCD03453309
IUPAC Name:
2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
InChI:
InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
InChI Key:
HVXBOLULGPECHP-WAYWQWQTSA-N
SMILES:
COc1cc(/C=C\c2ccc(c(c2)O)OC)cc(c1OC)OC
UNII:
16U6OP69RQ
NSC Number:
613729
Properties
Complexity:
358  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
316.131g/mol
Formal Charge:
0
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
316.353g/mol
Monoisotopic Mass:
316.131g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
57.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.7  
Literature
Title Journal
3-(3-Hydroxy-4-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,2,5-selenadiazole (G-1103), a novel combretastatin A-4 analog, induces G2/M arrest and apoptosis by disrupting tubulin polymerization in human cervical HeLa cells and fibrosarcoma HT-1080 cells. Chemico-biological interactions 20150205
Autophagy blockade sensitizes the anticancer activity of CA-4 via JNK-Bcl-2 pathway. Toxicology and applied pharmacology 20140115
Structure-activity relationship and in vitro and in vivo evaluation of the potent cytotoxic anti-microtubule agent N-(4-methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride and its analogues as antitumor agents. Journal of medicinal chemistry 20130912
Synthesis and biological evaluation of novel heterocyclic derivatives of combretastatin A-4. Bioorganic & medicinal chemistry letters 20121201
The vascular-disrupting agent, combretastatin-A4-phosphate, enhances neurogenic vasoconstriction in rat small arteries. European journal of pharmacology 20121115
Novel cyanocombretastatins as potent tubulin polymerisation inhibitors. Bioorganic & medicinal chemistry letters 20121101
Spatiotemporally controlled co-delivery of anti-vasculature agent and cytotoxic drug by octreotide-modified stealth liposomes. Pharmaceutical research 20121001
The vascular targeting agent Combretastatin-A4 directly induces autophagy in adenocarcinoma-derived colon cancer cells. Biochemical pharmacology 20120901
Antihyperuricemic and nephroprotective effects of resveratrol and its analogues in hyperuricemic mice. Molecular nutrition & food research 20120901
Fluorescence lifetime imaging of E-combretastatin uptake and distribution in live mammalian cells. European journal of cancer (Oxford, England : 1990) 20120801
In vitro and in vivo biological evaluation of new 4,5-disubstituted 1,2,3-triazoles as cis-constrained analogs of combretastatin A4. European journal of medicinal chemistry 20120801
Colon tumor growth and antivascular treatment in mice: complementary assessment with MR elastography and diffusion-weighted MR imaging. Radiology 20120801
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Synthesis, biological evaluation, and structure-activity relationships of novel substituted N-phenyl ureidobenzenesulfonate derivatives blocking cell cycle progression in S-phase and inducing DNA double-strand breaks. Journal of medicinal chemistry 20120712
High-sensitivity in vivo imaging for tumors using a spectral up-conversion nanoparticle NaYF4: Yb3+, Er3+ in cooperation with a microtubulin inhibitor. Nanoscale 20120707
Synthesis and biological evaluation of 1-benzylidene-3,4-dihydronaphthalen-2-one as a new class of microtubule-targeting agents. Journal of medicinal chemistry 20120628
Phase I trial of combretastatin A4 phosphate (CA4P) in combination with bevacizumab in patients with advanced cancer. Clinical cancer research : an official journal of the American Association for Cancer Research 20120615
Discovery and optimization of a series of 2-aryl-4-amino-5-(3',4',5'-trimethoxybenzoyl)thiazoles as novel anticancer agents. Journal of medicinal chemistry 20120614
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Design, synthesis and biological evaluation of novel chalcone derivatives as antitubulin agents. Bioorganic & medicinal chemistry 20120515
Synthesis, biological evaluation, and molecular docking studies of 2,6-dinitro-4-(trifluoromethyl)phenoxysalicylaldoxime derivatives as novel antitubulin agents. Bioorganic & medicinal chemistry 20120515
Cholesterol superlattice modulates CA4P release from liposomes and CA4P cytotoxicity on mammary cancer cells. Biophysical journal 20120502
Discovery of small molecule inhibitors that interact with γ-tubulin. Chemical biology & drug design 20120501
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Dehydrative fragmentation of 5-hydroxyalkyl-1H-tetrazoles: a mild route to alkylidenecarbenes. Organic letters 20120316
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Synthesis and biological evaluation of 1,4-diaryl-2-azetidinones as specific anticancer agents: activation of adenosine monophosphate activated protein kinase and induction of apoptosis. Journal of medicinal chemistry 20120308
Diffusion-weighted MR imaging allows monitoring the effect of combretastatin A4 phosphate on rabbit implanted VX2 tumor model: 12-day dynamic results. European journal of radiology 20120301
Increased endothelial cell selectivity of triazole-bridged dihalogenated A-ring analogues of combretastatin A-1. Bioorganic & medicinal chemistry 20120301
Synthesis and structure-activity relationship study of antimicrotubule agents phenylahistin derivatives with a didehydropiperazine-2,5-dione structure. Journal of medicinal chemistry 20120209
Synthesis, biological evaluation, and molecular docking studies of cinnamic acyl 1,3,4-thiadiazole amide derivatives as novel antitubulin agents. Bioorganic & medicinal chemistry 20120201
Design, synthesis, biological evaluation and molecular modeling of 1,3,4-oxadiazoline analogs of combretastatin-A4 as novel antitubulin agents. Bioorganic & medicinal chemistry 20120115
Synthesis and evaluation of 1,5-disubstituted tetrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative and antitumor activity. Journal of medicinal chemistry 20120112
Targeted delivery of a combination therapy consisting of combretastatin A4 and low-dose doxorubicin against tumor neovasculature. Nanomedicine : nanotechnology, biology, and medicine 20120101
Phase Ib trial of radiotherapy in combination with combretastatin-A4-phosphate in patients with non-small-cell lung cancer, prostate adenocarcinoma, and squamous cell carcinoma of the head and neck. Annals of oncology : official journal of the European Society for Medical Oncology 20120101
Comparison of two vascular-disrupting agents at a clinically relevant dose in rodent liver tumors with multiparametric magnetic resonance imaging biomarkers. Anti-cancer drugs 20120101
c-Jun N-terminal kinase mediates microtubule-depolymerizing agent-induced microtubule depolymerization and G2/M arrest in MCF-7 breast cancer cells. Anti-cancer drugs 20120101
Synthesis, biological evaluation and molecular modeling of 1,2,3-triazole analogs of combretastatin A-1. Bioorganic & medicinal chemistry 20120101
Vascular disrupting agent drug classes differ in effects on the cytoskeleton. PloS one 20120101
[Liposome formulations of combretastatin A4 and 4-arylcoumarin analog prodrugs: antitumor effect in the mouse model of breast cancer]. Biomeditsinskaia khimiia 20120101
Design and synthesis of 2-heterocyclyl-3-arylthio-1H-indoles as potent tubulin polymerization and cell growth inhibitors with improved metabolic stability. Journal of medicinal chemistry 20111222
5-Amino-2-aroylquinolines as highly potent tubulin polymerization inhibitors. Part 2. The impact of bridging groups at position C-2. Journal of medicinal chemistry 20111222
Patterning cells and shear flow conditions: convenient observation of endothelial cell remoulding, enhanced production of angiogenesis factors and drug response. Lab on a chip 20111221
Endostar enhances the antineoplastic effects of combretastatin A4 phosphate in an osteosarcoma xenograft. Cancer letters 20111215
One-pot synthesis and biological evaluation of 2-pyrrolidinyl-4-amino-5-(3',4',5'-trimethoxybenzoyl)thiazole: a unique, highly active antimicrotubule agent. European journal of medicinal chemistry 20111201
Substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamides as antimitotics. Antiproliferative, antiangiogenic and antitumoral activity, and quantitative structure-activity relationships. European journal of medicinal chemistry 20111101
1,1-Diarylalkenes as anticancer agents: dual inhibitors of tubulin polymerization and phosphodiesterase 4. Bioorganic & medicinal chemistry 20111101
Vascular effects dominate solid tumor response to treatment with combretastatin A-4-phosphate. International journal of cancer 20111015
The metabolic fate of isocombretastatin A-4 in human liver microsomes: identification, synthesis and biological evaluation of metabolites. ChemMedChem 20111004
Design, synthesis, and cytotoxicity of novel 3-arylidenones derived from alicyclic ketones. Chemical biology & drug design 20111001
Discovery of 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan (BNC105), a tubulin polymerization inhibitor with potent antiproliferative and tumor vascular disrupting properties. Journal of medicinal chemistry 20110908
Synthesis and biological activities of (R)- and (S)-N-(4-Methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride as potent cytotoxic antitubulin agents. Journal of medicinal chemistry 20110908
Synthesis and structure-activity relationships of constrained heterocyclic analogues of combretastatin A4. ChemMedChem 20110905
Microflow of fluorescently labelled red blood cells in tumours expressing single isoforms of VEGF and their response to vascular targeting agents. Medical engineering & physics 20110901
Phase II trial of combretastatin A4 phosphate, carboplatin, and paclitaxel in patients with platinum-resistant ovarian cancer. Annals of oncology : official journal of the European Society for Medical Oncology 20110901
Design, synthesis and antiproliferative activities of biarylolefins based on polyhydroxylated and carbohydrate scaffolds. European journal of medicinal chemistry 20110901
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Investigation of protein induction in tumour vascular targeted strategies by MALDI MSI. Methods (San Diego, Calif.) 20110801
Synthesis and biological evaluation of 4β-acrylamidopodophyllotoxin congeners as DNA damaging agents. Bioorganic & medicinal chemistry 20110801
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Regioselective synthesis of water-soluble monophosphate derivatives of combretastatin A-1. Journal of natural products 20110722
Design, synthesis, biological evaluation, and structure-activity relationships of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates as new tubulin inhibitors mimicking combretastatin A-4. Journal of medicinal chemistry 20110714
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In vivo near-infrared spectroscopy and magnetic resonance imaging monitoring of tumor response to combretastatin A-4-phosphate correlated with therapeutic outcome. International journal of radiation oncology, biology, physics 20110601
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Design, synthesis, and biological evaluation of novel γ-carboline ketones as anticancer agents. European journal of medicinal chemistry 20110401
Design and synthesis of novel enhanced water soluble hydroxyethyl analogs of combretastatin A-4. Bioorganic & medicinal chemistry letters 20110401
Acetyl analogs of combretastatin A-4: synthesis and biological studies. Bioorganic & medicinal chemistry 20110401
Synthesis and cytotoxic evaluation of N-(4-methoxy-1H-benzo[d]imidazol-7-yl)-arylsulfonamide and N-aryl-(4-methoxy-1H-benzo[d]imidazol)-7-sulfonamide analogs of combretastatin A-4. Journal of Asian natural products research 20110401
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Synthesis, molecular modeling and biological evaluation of guanidine derivatives as novel antitubulin agents. Bioorganic & medicinal chemistry 20101201
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The vascular targeting agent combretastatin-A4 and a novel cis-Restricted {beta}-Lactam Analogue, CA-432, induce apoptosis in human chronic myeloid leukemia cells and ex vivo patient samples including those displaying multidrug resistance. The Journal of pharmacology and experimental therapeutics 20101101
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1,2,3-triazole analogs of combretastatin A-4 as potential microtubule-binding agents. Bioorganic & medicinal chemistry 20100915
Identification of CKD-516: a potent tubulin polymerization inhibitor with marked antitumor activity against murine and human solid tumors. Journal of medicinal chemistry 20100909
Structure-activity relationships of indole compounds derived from combretastatin A4: synthesis and biological screening of 5-phenylpyrrolo[3,4-a]carbazole-1,3-diones as potential antivascular agents. European journal of medicinal chemistry 20100901
Design, synthesis and biological evaluation of 3,5-diaryl-isoxazoline/isoxazole-pyrrolobenzodiazepine conjugates as potential anticancer agents. European journal of medicinal chemistry 20100901
Targeted polymeric micelle system for delivery of combretastatin A4 to tumor vasculature in vitro. Pharmaceutical research 20100901
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Regioselective hydrostannation of diarylalkynes directed by a labile ortho bromine atom: an easy access to stereodefined triarylolefins, hybrids of combretastatin A-4 and isocombretastatin A-4. European journal of medicinal chemistry 20100901
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Novel combretastatin A-4 derivative XN0502 induces cell cycle arrest and apoptosis in A549 cells. Investigational new drugs 20100801
Combretastatin A-4 inhibits cell growth and metastasis in bladder cancer cells and retards tumour growth in a murine orthotopic bladder tumour model. British journal of pharmacology 20100801
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Antitumor agents 273. Design and synthesis of N-alkyl-thiocolchicinoids as potential antitumor agents. Bioorganic & medicinal chemistry letters 20100715
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Identification of the human UDP-glucuronosyltransferases involved in the glucuronidation of combretastatin A-4. Drug metabolism and disposition: the biological fate of chemicals 20100701
Structural determinants of resveratrol for cell proliferation inhibition potency: experimental and docking studies of new analogs. European journal of medicinal chemistry 20100701
Regio- and stereospecific synthesis of mono-beta-d-glucuronic acid derivatives of combretastatin A-1. Journal of natural products 20100625
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Highly chemo- and stereoselective palladium-catalyzed transfer semihydrogenation of internal alkynes affording cis-alkenes. The Journal of organic chemistry 20100507
Synthesis and biological evaluation of combretastatin analogs as cell cycle inhibitors of the G1 to S transition in Saccharomyces cerevisiae. Bioorganic & medicinal chemistry letters 20100501
A Phase Ib trial of CA4P (combretastatin A-4 phosphate), carboplatin, and paclitaxel in patients with advanced cancer. British journal of cancer 20100427
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate. Journal of medicinal chemistry 20100408
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Lead identification of conformationally restricted benzoxepin type combretastatin analogs: synthesis, antiproliferative activity, and tubulin effects. Journal of enzyme inhibition and medicinal chemistry 20100401
Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies. Bioorganic & medicinal chemistry 20100401
An efficient synthetic strategy for obtaining 4-methoxy carbon isotope labeled combretastatin A-4 phosphate and other Z-combretastatins. Journal of natural products 20100326
Targeted delivery of RGD-modified liposomes encapsulating both combretastatin A-4 and doxorubicin for tumor therapy: in vitro and in vivo studies. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20100301
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Exploring the effect of 2,3,4-trimethoxy-phenyl moiety as a component of indolephenstatins. European journal of medicinal chemistry 20100201
A boronic acid chalcone analog of combretastatin A-4 as a potent anti-proliferation agent. Bioorganic & medicinal chemistry 20100115
Design, synthesis, and biological evaluations of 2,5-diaryl-2,3-dihydro-1,3,4-oxadiazoline analogs of combretastatin-A4. Journal of medicinal chemistry 20100114
Novel hybrids from lamellarin D and combretastatin A 4 as cytotoxic agents. European journal of medicinal chemistry 20100101
Synthesis and antitumor-evaluation of cyclopropyl-containing combretastatin analogs. Bioorganic & medicinal chemistry letters 20091215
Vascular disrupting activity of tubulin-binding 1,5-diaryl-1H-imidazoles. Journal of medicinal chemistry 20091210
Development of a rapid and sensitive LC-MS/MS assay for the determination of combretastatin A4 phosphate, combretastatin A4 and combretastatin A4 glucuronide in beagle dog plasma and its application to a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20091115
Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: synthesis and biological evaluation of antivascular activity. Bioorganic & medicinal chemistry 20091115
Combretastatin-like chalcones as inhibitors of microtubule polymerisation. Part 2: Structure-based discovery of alpha-aryl chalcones. Bioorganic & medicinal chemistry 20091115
Reproducibility and changes in the apparent diffusion coefficients of solid tumours treated with combretastatin A4 phosphate and bevacizumab in a two-centre phase I clinical trial. European radiology 20091101
Synthesis, biological evaluation of 1,1-diarylethylenes as a novel class of antimitotic agents. ChemMedChem 20091101
Application of the McMurry coupling reaction in the synthesis of tri- and tetra-arylethylene analogues as potential cancer chemotherapeutic agents. Bioorganic & medicinal chemistry 20091001
Design, synthesis and structure-activity relationship of 2-(3',4',5'-trimethoxybenzoyl)-benzo[b]furan derivatives as a novel class of inhibitors of tubulin polymerization. Bioorganic & medicinal chemistry 20091001
Contribution of granulocyte colony-stimulating factor to the acute mobilization of endothelial precursor cells by vascular disrupting agents. Cancer research 20091001
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Antineoplastic agents. 579. Synthesis and cancer cell growth evaluation of E-stilstatin 3: a resveratrol structural modification. Journal of natural products 20090901
Design and synthesis of 2-(3-benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one analogues as potent antitumor agents that inhibit tubulin assembly. Journal of medicinal chemistry 20090813
Isocombretastatins a versus combretastatins a: the forgotten isoCA-4 isomer as a highly promising cytotoxic and antitubulin agent. Journal of medicinal chemistry 20090723
1,4-Diamino-2,3-dicyano-1,4-bis(methylthio)butadiene (U0126) enhances the cytotoxicity of combretastatin A4 independently of mitogen-activated protein kinase kinase. The Journal of pharmacology and experimental therapeutics 20090701
Anticancer strategies involving the vasculature. Nature reviews. Clinical oncology 20090701
A phase I trial of radioimmunotherapy with 131I-A5B7 anti-CEA antibody in combination with combretastatin-A4-phosphate in advanced gastrointestinal carcinomas. Clinical cancer research : an official journal of the American Association for Cancer Research 20090701
A diaryl sulfide, sulfoxide, and sulfone bearing structural similarities to combretastatin A-4. European journal of medicinal chemistry 20090601
Targeted treatment of choroidal neovascularization using integrin-mediated sterically stabilized liposomes loaded with combretastatin A4. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20090601
Nitric oxide synthase inhibition enhances the tumor vascular-damaging effects of combretastatin a-4 3-o-phosphate at clinically relevant doses. Clinical cancer research : an official journal of the American Association for Cancer Research 20090601
Vascular disrupting agents: a novel mechanism of action in the battle against non-small cell lung cancer. The oncologist 20090601
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Preclinical evaluation of vascular-disrupting agents in Ewing's sarcoma family of tumours. European journal of cancer (Oxford, England : 1990) 20090301
Synthesis and biological evaluation of cis-locked vinylogous combretastatin-A4 analogues: derivatives with a cyclopropyl-vinyl or a cyclopropyl-amide bridge. Bioorganic & medicinal chemistry letters 20090301
Diffusion-weighted MRI of hepatic tumor in rats: comparison between in vivo and postmortem imaging acquisitions. Journal of magnetic resonance imaging : JMRI 20090301
A phase II trial of fosbretabulin in advanced anaplastic thyroid carcinoma and correlation of baseline serum-soluble intracellular adhesion molecule-1 with outcome. Thyroid : official journal of the American Thyroid Association 20090301
Up-regulation of connective tissue growth factor in endothelial cells by the microtubule-destabilizing agent combretastatin A-4. Molecular cancer research : MCR 20090201
A review and update of the current status of the vasculature-disabling agent combretastatin-A4 phosphate (CA4P). Expert opinion on investigational drugs 20090201
In vitro and in vivo phase II metabolism of combretastatin A-4: evidence for the formation of a sulphate conjugate metabolite. Xenobiotica; the fate of foreign compounds in biological systems 20090201
Pt(II) complexes of a combretastatin A-4 analogous chalcone: effects of conjugation on cytotoxicity, tumor specificity, and long-term tumor growth suppression. Journal of medicinal chemistry 20090122
Design, synthesis and biological evaluation of novel stilbene-based antitumor agents. Bioorganic & medicinal chemistry 20090115
Treatment of rodent liver tumor with combretastatin a4 phosphate: noninvasive therapeutic evaluation using multiparametric magnetic resonance imaging in correlation with microangiography and histology. Investigative radiology 20090101
Combination of combretastatin A4 phosphate and doxorubicin-containing liposomes affects growth of B16-F10 tumors. Acta biochimica Polonica 20090101
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Design, synthesis, and biological evaluation of thiophene analogues of chalcones. Bioorganic & medicinal chemistry 20080515
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Assessment of tumor response to the vascular disrupting agents 5,6-dimethylxanthenone-4-acetic acid or combretastatin-A4-phosphate by intrinsic susceptibility magnetic resonance imaging. International journal of radiation oncology, biology, physics 20071115
Replacement of the lactone moiety on podophyllotoxin and steganacin analogues with a 1,5-disubstituted 1,2,3-triazole via ruthenium-catalyzed click chemistry. Bioorganic & medicinal chemistry 20071101
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Novel potent antimitotic heterocyclic ketones: synthesis, antiproliferative activity, and structure-activity relationships. Bioorganic & medicinal chemistry letters 20070701
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The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4. Bioorganic & medicinal chemistry 20070501
Characterizing the tumor response to treatment with combretastatin A4 phosphate. International journal of radiation oncology, biology, physics 20070501
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Evaluation of the vascular targeting agent combretastatin a-4 prodrug on retinal neovascularization in the galactose-fed dog. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20070401
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Properties