109971-63-3

Basic information

• Product Name: COMBRETASTATIN A1
• Synonyms: COMBRETASTATIN A1;(Z)-3-Methoxy-6-(3,4,5-Trimethoxystyryl)Benzene-1,2-Diol;Combretastatin A1( 3-Methoxy-6-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-benzene-1,2-diol );(Z)-3,4,4',5-Tetramethoxy-2',3'-dihydroxystilbene;(Z)-3',4,4',5'-Tetramethoxystilbene-2,3-diol;3-Methoxy-6-[(Z)-3,4,5-trimethoxystyryl]-1,2-benzenediol
• CAS NO: 109971-63-3
• Molecular Formula: C₁₈H₂₀O₆
• Molecular Weight: 332.35
• Product Categories: Combretastatin
• Mol File: 109971-63-3.mol

Chemical Properties

• Melting Point: 113-115 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• Boiling Point: 528.4 °C at 760 mmHg
• Flash Point: 273.3 °C
• Appearance: /
• Density: 1.251 g/cm³
• Vapor Pressure: 8.82E-12mmHg at 25°C
• Refractive Index: 1.627
• PKA: 8.89±0.45(Predicted)
• CAS DataBase Reference: COMBRETASTATIN A1(CAS DataBase Reference)
• NIST Chemistry Reference: COMBRETASTATIN A1(109971-63-3)
• EPA Substance Registry System: COMBRETASTATIN A1(109971-63-3)

Safety Data

• Hazardous Substances Data: 109971-63-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H20O6/c1-21-13-8-7-12(16(19)17(13)20)6-5-11-9-14(22-2)18(24-4)15(10-11)23-3/h5-10,19-20H,1-4H3/b6-5+

Upstream product

• 444992-83-0 1-methoxy-2,3-bis(methoxymethoxy)-4-((3,4,5-trimethoxyphenyl)-ethynyl)benzene 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 53560-33-1 3,4,5-trimethoxyphenylacetylene 
• 108683-61-0 triphenyl(3,4,5-trimethoxybenzyl)phosphonium chloride 
• 3840-30-0 5-(chloromethyl)-1,2,3-trimethoxybenzene 
• 1400573-38-7 (Z)-1-[3',4',5'-trimethoxyphenyl]-2-[2'',3''-di[(isopropyl)oxy]-4''-methoxyphenyl]ethene 
• 1005788-31-7 C₃₀H₄₈O₆Si₂ 
• 290347-62-5 1-bromo-4-methoxy-2,3-bis(methoxymethoxy)-benzene 
• 878293-50-6 1-iodo-4-methoxy-2,3-bis(methoxymethoxy)benzene 
• 444992-85-2 C₂₂H₂₈O₈ 
• 109971-68-8 (Z)-1-[3',4',5'-trimethoxyphenyl]-2-[(2'',3''-di[(tert-butyldimethylsilyl)oxy]-4''-methoxy)phenyl]ethene 
• 61559-82-8 1-Bromo-2,3dihydroxy-4methoxy-benzene 
• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 109971-66-6 2,3-bis<(tert-butyldimethylsilyl)oxy>-4-methoxybenzaldehyde 

Downstream Products

• 192711-05-0 (Z)-3'-hydroxy-3,4,4',5-tetramethoxy-2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene 
• 192711-06-1 (Z)-2'-hydroxy-3,4,4',5-tetramethoxy-3'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene 
• 757996-09-1 3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)-Z-ethylene]-[1,2]benzoquinone 
• 313692-35-2 (Z)-1-[3',4',5'-trimethoxyphenyl]-2-[2'',3''-di[([bis[(benzyl)oxy]]phosphoryl)oxy]-4''-methoxyphenyl]ethene 

Related news

A validated HPLC method with fluorescence detection for the glucuronides of COMBRETASTATIN A1 (cas 109971-63-3) in human plasma, and studies on their cis–trans isomerisation07/30/2019

Two monoglucuronides (CA1G1 and CA1G2) of the catecholic cis-stilbene Combretastatin A1 (CA1, OXi4500), have been identified in a clinical trial of the bisphosphate prodrug of OXi4500, OXi4503. A validated assay for the two glucuronides in human plasma using HPLC with fluorescence detection afte...detailed

Relevant articles and documents

Bioreductively Activatable Prodrug Conjugates of Combretastatin A-1 and Combretastatin A-4 as Anticancer Agents Targeted toward Tumor-Associated Hypoxia

The natural products combretastatin A-1 (CA1) and combretastatin A-4 (CA4) function as potent inhibitors of tubulin polymerization and as selective vascular disrupting agents (VDAs) in tumors. Bioreductively activatable prodrug conjugates (BAPCs) can enha

Synthesis and biological evaluation of combretastatin analogs as cell cycle inhibitors of the G1 to S transition in Saccharomyces cerevisiae

A series of Z and E combretastatin A-4 analogs bearing different substituents (OH, F, NO2, NH2, B(OH)2) in the 3′ position were synthesized. These derivatives and Z and E combretastatin A-1 were analysed by monitoring their ability to inhibit cell growth in Saccharomyces cerevisiae. Combretastatin A-1 (2a), A-4 (2b) and compound 2c were found to inhibit yeast growth. Moreover, combretatstatin A-4 (2b) and compound 2c induced a G1 arrest by affecting the synthesis of Clb5 protein, the principal S-phase cyclin. The G1 arrest is coincident with the activation of the stress activated kinase Snf1.

Development of synthetic methodology suitable for the radiosynthesis of combretastatin A-1 (CA1) and its corresponding prodrug CA1P

Synthetic methodology has been established suitable for the preparation of combretastatin A-1 (CA1) and its corresponding phosphate prodrug salt (CA1P) in high specific activity radiolabeled form. Judicious selection of appropriate phenolic protecting groups to distinguish positions on the A-ring from the B-ring of the stilbenoid was paramount for the success of this project. Methylation of the C-4' phenolic moiety by removal of the tert- butyldimethylsilyl protecting group in the presence of methyl iodide was accomplished in excellent yield without significant Z to E isomerization. This step (carried out with 12C-methyl iodide as proof of concept in this study) represents the process in which a 14C radioisotope could be incorporated in an actual radiosynthesis. CA1 is a natural product isolated from the African bush willow tree (Combretum caffrum) that has important medicinal value due, in part, to its ability to inhibit tubulin assembly. As a prodrug, CA1P (OXi4503) is in human clinical trials as a vascular disrupting agent.

Synthesis of combretastatins A-1 and B-1

Combretastatins A-1 and B-1 have been synthesized by coupling MOM-protected p-iodomethoxycatechol with 3,4,5-trimethoxyphenylacetylene in a Sonogashira reaction.

Direct biooxidation of arenes to corresponding catechols with E. coli JM109 (pDTG602). Application to synthesis of combretastatins A-1 and B-1

Convergent syntheses of combretastatins A-1 and B-1 were accomplished via coupling of biocatalytically generated p-bromomethoxycatechol with trimethoxyphenylacetylene.

Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)

(E)-3-(β-D-Glucopyranosyloxy)-4',5-dihydroxystilbene (resveratrol 3-β-D-glucoside, piceid), (Z)-2',3'-dihydroxy-3,4,4',5-tetramethoxystilbene (combretastatin A-1), (Z)-3'-hydroxy-3,4,4', 5-tetramethoxystilbene (combretastatin A-4), (Z)-2'-hydroxy-3,4,4',5-tetramethoxystilbene (combretastatin iso-A-4), α,β-dihydro-2',3'-dihydroxy-3,4,4',5-tetramethoxystilbene (combretastatin B-1), the corresponding glucosides, and related compounds have been synthesized via Wittig reactions followed by,glucosylation under phase-transfer catalysis. Most of the compounds synthesized have been tested with respect to biological activity (cytostatic, cytotoxic, antimitotic, neurotoxic, antiplatelet aggregation activity).