6284-92-0

Basic information

• Product Name: 3-HYDROXY-4-METHOXY-2-NITRO-BENZALDEHYDE
• Synonyms: 3-HYDROXY-4-METHOXY-2-NITRO-BENZALDEHYDE;2-(2-Oxo-pyrrolidin-1-yl)-but-2-enoic acid aMide;NSC 5399
• CAS NO: 6284-92-0
• Molecular Formula: C₈H₇NO₅
• Molecular Weight: 197.14488
• Mol File: 6284-92-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 147-148℃
• Boiling Point: 343.1 °C at 760 mmHg
• Flash Point: 161.3 °C
• Appearance: /
• Density: 1.456
• Vapor Pressure: 3.63E-05mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.03±0.31(Predicted)
• CAS DataBase Reference: 3-HYDROXY-4-METHOXY-2-NITRO-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-4-METHOXY-2-NITRO-BENZALDEHYDE(6284-92-0)
• EPA Substance Registry System: 3-HYDROXY-4-METHOXY-2-NITRO-BENZALDEHYDE(6284-92-0)

Safety Data

• Hazardous Substances Data: 6284-92-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 49, p. 2022, 2006 DOI: 10.1021/jm050879z

InChI:InChI=1/C8H7NO5/c1-14-6-3-2-5(4-10)7(8(6)11)9(12)13/h2-4,11H,1H3

Upstream product

• 621-59-0 isovanillin 

Downstream Products

• 886442-71-3 (Z)-2-(2'-nitro-3'-tert-butyldimethylsilyloxy-4'-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene 

Relevant articles and documents

Synthesis and Biochemical Evaluation of 3-Phenoxy-1,4-diarylazetidin-2-ones as Tubulin-Targeting Antitumor Agents

Structure-activity relationships for a series of 3-phenoxy-1,4-diarylazetidin-2-ones were investigated, leading to the discovery of a number of potent antiproliferative compounds, including trans-4-(3-hydroxy-4-methoxyphenyl)-3-phenoxy-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (78b) and trans-4-(3-amino-4-methoxyphenyl)-3-phenoxy-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (90b). X-ray crystallography studies indicate the potential importance of the torsional angle between the 1-phenyl A ring and 4-phenyl B ring for potent antiproliferative activity and that a trans configuration between the 3-phenoxy and 4-phenyl rings is generally optimal. These compounds displayed IC50 values of 38 and 19 nM, respectively, in MCF-7 breast cancer cells, inhibited the polymerization of isolated tubulin in vitro, disrupted the microtubular structure in MCF-7 cells as visualized by confocal microscopy, and caused G2/M arrest and apoptosis. Compound 90b possessed a mean GI50 value of 22 nM in the NCI60 cell line screen, displayed minimal cytotoxicity, and was shown to interact at the colchicine-binding site on β-tubulin. Phosphate and amino acid prodrugs of both 78b and 90b were synthesized, of which the alanine amide 102b retained potency and is a promising candidate for further clinical development.

COMPOUND OF CAMPTOTHECIN AND PREPARATION AND USE THEREOF

The present disclosure relates to a compound of formula I, a pharmaceutical composition thereof and the use thereof as an anti-tumor drug.

Design and Synthesis of Aminostilbene-Arylpropenones as Tubulin Polymerization Inhibitors

A series of aminostilbene - arylpropenones were designed and synthesized by Michael addition and were investigated for their cytotoxic activity against various human cancer cell lines. Some of the investigated compounds exhibited significant antiproliferative activity against a panel of 60 human cancer cell lines of the US National Cancer Institute, with 50% growth inhibition (GI50) values in the range from 50 value of 50) values ranging from 0.011 to 8.56μM. A cell cycle assay revealed that these compounds arrested the G2/M phase of the cell cycle. Two compounds exhibited strong inhibitory effects on tubulin assembly with IC50 values of 0.71 and 0.79μM. Moreover, dot-blot analysis of cyclinB1 demonstrated that some of the congeners strongly induced cyclinB1 protein levels. Molecular docking studies indicated that these compounds occupy the colchicine binding site of tubulin.