20357-25-9

Basic information

• Product Name: 6-Nitroveratraldehyde
• Synonyms: TIMTEC-BB SBB000505;ASISCHEM R27925;DMNB;6-NITROVERATRALDEHYDE;4,5-DIMETHOXY-2-NITROBENZALDEHYDE;3,4-DIMETHOXY-6-NITROBENZALDEHYDE;2-Nitro-4,5-dimethoxybenzaldehyde;2-NITRO-4,5-BIS(METHYLOXY)BENZALDEHYDE
• CAS NO: 20357-25-9
• Molecular Formula: C₉H₉NO₅
• Molecular Weight: 211.17
• EINECS: 243-762-1
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Aldehydes;C9;Carbonyl Compounds
• Mol File: 20357-25-9.mol
• Article Data: 35

Chemical Properties

• Melting Point: 133.2-134.5 °C
• Boiling Point: 350.84°C (rough estimate)
• Flash Point: 194.3 °C
• Appearance: yellow/solid
• Density: 1.4194 (rough estimate)
• Vapor Pressure: 2.59E-06mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO: 22 mg/mL
• Water Solubility: Insoluble in water. Soluble to 25 mM in ethanol with gentle warming and to 100 mM in DMSO.
• Sensitive: Air & Light Sensitive
• BRN: 395599
• CAS DataBase Reference: 6-Nitroveratraldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Nitroveratraldehyde(20357-25-9)
• EPA Substance Registry System: 6-Nitroveratraldehyde(20357-25-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: GY8410000
• HazardClass: IRRITANT
• Hazardous Substances Data: 20357-25-9(Hazardous Substances Data)

Usage

Chemical Properties

yellow fluffy powder

Uses

6-Nitroveratraldehyde has been used in the preparation of no-carrier-added 6-18F-fluoro-L-dopa, fundamental tracer for cerebral positron emission tomography studies of dopaminergic system in humans and o-nitroaryl-bis(5-methylfur-2-yl)methanes, versatile synthons for the synthesis of nitrogen-containing heterocycles. DMNB is also an enzyme involved in the non-homologous end-joining (NHEJ) pathway of double-stranded DNA break (DSB) repair. It is also used for synthesizing analogs of alpha-asarone.

General Description

A cell-permeable vanillin derivative that acts as a potent and selective inhibitor of DNA-dependent protein kinase (DNA-PK) activity (IC50 = 15 μM) and DNA-PK-mediated double strand break (DSB) DNA repair by non-homologous DNA-end-joining (NHEJ). Reported to effectively sensitize cells to Cisplatin (Cat. No. 232120). Does not affect the activities of PKC or Chk2.

Biological Activity

Inhibitor of DNA-dependent protein kinase (DNA-PK) (IC 50 = 15 μ M), an enzyme involved in the non-homologous end-joining (NHEJ) pathway of double-stranded DNA break (DSB) repair in human cells. Displays 100-fold higher potency than its analog vanillin and does not affect PKC activity. Produces lethal effects on cisplatin-treated D5037 cells upon continuous exposure.

Biochem/physiol Actions

Cell permeable: yes

Purification Methods

The aldehyde is purified by dissolving 9g in 200mL of boiling 95% EtOH, and set aside overnight to crystallise. It is then dried in vacuo at 50o and recrystallised from 110mL of 95% EtOH to give 6-7g of aldehyde with m 132-133o. Crystallisation from aqueous EtOH provides light yellow needles. It is light sensitive and should be stored in the dark [Fetscher Org Synth Coll Vol 4 735 1963]. [Beilstein 8 H 262, 8 I 610, 8 II 290, 6 III 2065, 6 IV 1785.]

InChI:InChI=1/C9H9NO5/c1-14-8-3-6(5-11)7(10(12)13)4-9(8)15-2/h3-5H,1-2H3

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 7697-37-2 nitric acid 
• 121-33-5 vanillin 
• 53413-67-5 6-nitroveratrylbromide 
• 1246852-94-7 2-(4-((4-(4,5-dimethoxy-2-nitrobenzyloxy)phenyl)(cyclohexylidene)methyl)phenoxy)-N,N-dimethylethanamine 
• 1023316-08-6 4,5-dimethoxy-2-nitrobenzyl benzoate 
• 876497-48-2 5-methoxy-2-nitro-4-(2-nitro-benzyloxy)-benzaldehyde 
• 81307-10-0 5-methoxy-2-nitro-4-(4-nitro-benzyloxy)-benzaldehyde 
• 81307-09-7 3-methoxy-4-[(4-nitrophenyl)methoxy]benzaldehyde 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 76936-55-5 4-allyl-1,2-dimethoxy-5-nitrobenzene 
• 74-88-4 methyl iodide 
• 77376-02-4 acetic acid 4,5-dimethoxy-2-nitrobenzyl ester 
• 123330-75-6 N-(4,5-Dimethoxy-2-nitro-benzyl)-acetamide 

Downstream Products

• 10234-92-1 4-(4.5-Dimethoxy-2-nitro-benzyliden)-3-methyl-1-phenyl-2-pyrazolin-5-on 
• 21873-14-3 4-(4,5-dimethoxy-2-nitro-benzylidene)-2-phenyl-4H-oxazol-5-one 
• 21873-14-3 4-((Z)-4,5-dimethoxy-2-nitro-benzylidene)-2-phenyl-4H-oxazol-5-one 
• 68742-13-2 (2E)-3-(4,5-dimethoxy-2-nitrophenyl)-2-(4-methoxyphenyl)prop-2-enoic acid 
• 68742-14-3 (2Z)-3-(4,5-dimethoxy-2-nitrophenyl)-2-(4-methoxyphenyl)prop-2-enoic acid 
• 118509-95-8 (E)-1,2-dimethoxy-4-nitro-5-(2-nitroethenyl)benzene 
• 20567-38-8 6-nitro-3,4-dimethoxycinnamic acid 
• 93316-93-9 3-(4,5-dimethoxy-2-nitro-phenyl)-2-phenyl-acrylic acid 
• 18505-71-0 6-(p-tolylaminomethylidene)-3,4-dimethoxynitrobenzene 
• 51813-42-4 2-[4,5-dimethoxy-2-nitro-benzylidene-(seqtrans)]-indan-1-one 
• 93729-81-8 2-benzo[1,3]dioxol-5-yl-3t-(4,5-dimethoxy-2-nitro-phenyl)-acrylic acid 
• 63190-11-4 (3,4-dimethoxy-6-nitro-benzyliden)-aniline 
• 337472-04-5 N-(4,5-dimethoxy-2-nitro-benzylidene)-o-toluidine 
• 24844-72-2 (4,5-dimethoxy-2-nitro-benzylidene)-malonic acid diethyl ester 

Relevant articles and documents

Highly Efficient Supramolecular Catalysis by Endowing the Reaction Intermediate with Adaptive Reactivity

A new strategy of highly efficient supramolecular catalysis is developed by endowing the reaction intermediate with adaptive reactivity. The supramolecular catalyst, prepared by host–guest complexation between 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) and cucurbit[7]uril (CB[7]), was used for biphasic oxidation of alcohols. Cationic TEMPO+, the key intermediate, was stabilized by the electrostatic effect of CB[7] in aqueous phase, thus promoting the formation of TEMPO+ and inhibiting side reactions. Moreover, through the migration into the organic phase, TEMPO+ was separated from CB[7] and recovered the high reactivity to drive a fast oxidation of substrates. The adaptive reactivity of TEMPO+ induced an integral optimization of the catalytic cycle and greatly improved the conversion of the reaction. This work highlights the unique advantages of dynamic noncovalent interactions on modulating the activity of reaction intermediates, which may open new horizons for supramolecular catalysis.

Polymer-supported IBX-amide reagents: Significant role of spacer and additive in alcohol oxidation

We found that the spacer and additive play a significant role in the oxidation of alkyl alcohols using polymer-supported IBX-amide reagents. The introduction of the spacer between the polymer support and IBX-amide group improved the initial conversion rate (up to 60% conversion). Furthermore, various alcohol compounds, when reacted with IBX-amide resin in the presence of BF3·OEt2, were effectively converted into the corresponding aldehydes or ketones within 5-30 minutes in high purities (>94%) at room temperature. Georg Thieme Verlag Stuttgart.

Non-alkylator anti-glioblastoma agents induced cell cycle G2/M arrest and apoptosis: Design, in silico physicochemical and SAR studies of 2-aminoquinoline-3-carboxamides

Malignant gliomas are the most common brain tumors, with generally dismal prognosis, early clinical deterioration and high mortality. Recently, 2-aminoquinoline scaffold derivatives have shown pronounced activity in central nervous system disorders. We herein reported a series of 2-aminoquinoline-3-carboxamides as novel non-alkylator anti-glioblastoma agents. The synthesized compounds showed comparable activity to cisplatin against glioblastoma cell line U87 MG in vitro. Among them, we found that 6a displayed good inhibitory activity against A172 and U118 MG glioblastoma cell lines and induced cell cycle arrest in the G2/M phase and apoptosis in U87 MG by flow cytometry analysis. Additionally, 6a displayed low cytotoxicity to several normal human cell lines. In silico study showed 6a had promising physicochemical properties and was predicted to cross the blood–brain barrier. Moreover, preliminary structure–activity relationships are also investigated, shedding light on further modifications towards more potent agents on this series of compounds. Our results suggest this compound has a promising potential as an anti-glioblastoma agent with a differential effect between tumor and non-malignant cells.

A preparation method of gefitinib (by machine translation)

The present invention relates to organic chemical and medical technology field, in particular relates to a preparation method of gefitinib. The present invention provides a preparation method of gefitinib, obtained by formula I compounds, the formula I compound preparation method comprises the following steps: nitration reaction, oxidation reaction, selective demethylation reaction, reduction reaction, a cyclization reaction, phenolic hydroxyl acetylation reaction. The present invention provides a preparation method can at the same time reducing the cost, it is easy for the refined purification, easy preparation and control of related impurities, the overall preparation process routes are greatly optimized, is suitable for industrial scale production. (by machine translation)