22027-96-9

Basic information

• Product Name: 3,4-DIMETHOXY-5-NITRO-BENZALDEHYDE
• Synonyms: 3,4-DIMETHOXY-5-NITRO-BENZALDEHYDE;3,4-Dimethoxy-5-nitro-benazldehyde;nitroveratraldehyde
• CAS NO: 22027-96-9
• Molecular Formula: C₉H₉NO₅
• Molecular Weight: 211.17
• Mol File: 22027-96-9.mol

Chemical Properties

• Boiling Point: 389.7 °C at 760 mmHg
• Flash Point: 193.7 °C
• Appearance: /
• Density: 1.312g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,4-DIMETHOXY-5-NITRO-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHOXY-5-NITRO-BENZALDEHYDE(22027-96-9)
• EPA Substance Registry System: 3,4-DIMETHOXY-5-NITRO-BENZALDEHYDE(22027-96-9)

Safety Data

• Hazardous Substances Data: 22027-96-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-DIMETHOXY-5-NITRO-BENZALDEHYDE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form complex molecules with therapeutic properties.
Used in Organic Chemistry:
It serves as a versatile building block in organic chemistry, facilitating the creation of a wide range of organic compounds due to its reactive functional groups.
Used as a Flavoring Agent in the Food Industry:
3,4-DIMETHOXY-5-NITRO-BENZALDEHYDE is utilized for its distinctive strong odor, contributing unique flavor profiles to food products.
Used in Biological and Pharmacological Research:
3,4-DIMETHOXY-5-NITRO-BENZALDEHYDE is studied for its potential as an anti-inflammatory and anti-cancer agent, indicating its use in research and development for novel therapeutic applications.

Upstream product

• 121-33-5 vanillin 
• 116313-85-0 3,4-dihydroxy-5-nitrobenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 22027-95-8 5-Nitro-vanillin-dimethylacetal 
• 6635-20-7 isonitrovanillin 

Downstream Products

• 120314-19-4 3,4-dimethoxy-5-nitrostyrene 
• 64838-05-7 1-phenyl-5-(3,4-dimethoxy-5-nitrophenyl)-1,4-pentadiene-3-one 
• 17418-07-4 1,2-dimethoxy-3,4,5-trinitrobenzene 
• 872283-58-4 3,4-dimethoxy-5-nitrobenzaldehyde oxime 
• 1609084-42-5 (3,4-dimethoxy-5-nitrophenyl)(3,4,5-trimethoxyphenyl)methanol 
• 1609084-43-6 C₁₈H₁₉NO₈ 
• 1609084-44-7 (3-amino-4,5-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)methanone 
• 1609084-33-4 (E)-N-(2,3-dimethoxy-5-(3,4,5-trimethoxybenzoyl)phenyl)-3-(3,4,5-trimethoxyphenyl)acrylamide 
• 1609084-34-5 (E)-N-(2,3-dimethoxy-5-(3,4,5-trimethoxybenzoyl)phenyl)-3-(3,4-dimethoxyphenyl)acrylamide 
• 1609084-35-6 (E)-N-(2,3-dimethoxy-5-(3,4,5-trimethoxybenzoyl)phenyl)-3-(4-methoxyphenyl)acrylamide 
• 1609084-36-7 (E)-N-(2,3-dimethoxy-5-(3,4,5-trimethoxybenzoyl)phenyl)-3-(3-methoxyphenyl)acrylamide 
• 1609084-38-9 (E)-N-(2,3-dimethoxy-5-(3,4,5-trimethoxybenzoyl)phenyl)-3-(3-(prop-2-ynyloxy)phenyl)acrylamide 
• 1609084-39-0 (E)-N-(2,3-dimethoxy-5-(3,4,5-trimethoxybenzoyl)phenyl)-3-(4-fluorophenyl)acrylamide 
• 1609084-40-3 (E)-N-(2,3-dimethoxy-5-(3,4,5-trimethoxybenzoyl)phenyl)-3-(4-(trifluoromethyl)phenyl)acrylamide 

Relevant articles and documents

Aminobenzoic acid derivative and preparation method and application thereof

The invention relates to an aminobenzoic acid derivative and a preparation method and application thereof, and belongs to the field of medicinal chemistry, and the structural formula of the aminobenzoic acid derivative is shown in the specification, R is alkyl, substituted phenyl, heteroaromatic ring group or substituted styryl; R is alkyl; R is alkyl, substituted phenyl or benzyl; R is alkyl; R is guanidyl; and R is alkyl. The preparation method is simple and high in yield. Most compounds of the invention have good influenza virus neuraminidase inhibition activity.

Synthesis and biological evaluation of cinnamido linked benzophenone hybrids as tubulin polymerization inhibitors and apoptosis inducing agents

A new class of hybrid molecules containing cinnamide subunit linked to benzophenone as inhibitors of tubulin polymerization were synthesized and evaluated for their anticancer potential. These hybrids exhibit anticancer activity with IC50 values ranging from 0.06 to 16.3 μM. Compounds 4f and 4g possessing fluoro and trifluoromethyl on the cinnamido subunit showed significant cytotoxic activity with IC50 values 0.06 and 0.09 μM against HeLa cell line, respectively. These compounds showed cell cycle arrest at G2/M phase of the cell cycle and inhibited tubulin polymerization followed by activation of caspase-3 activity and apoptotic cell death. Further in vitro tubulin polymerization assay showed that the level of tubulin inhibition was comparable to that of 2a for the compounds 4f and 4g. Moreover, Hoechst 33258 staining and DNA fragmentation assay suggested that these compounds induce cell death by apoptosis. Overall, the current study demonstrates that the synthesis of benzophenone linked cinnamide subunit conjugates as promising anticancer agents with G2/M arrest and apoptotic-inducing ability via targeting tubulin.

Synthesis and antitumor activity of feruloyl and caffeoyl derivatives This paper is dedicated to Prof. Wei-xiao Hu for his lifelong commitment to mentoring graduate students

We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg-1.

SUBSTITUTED ISOQUINOLINES AND THEIR USE AS TUBULIN POLYMERIZATION INHIBITORS

The present invention relates generally to substituted isoquinolines and their use as tubulin polymerization inhibitors. In particular, the invention relates to substituted isoquinolines which possess useful therapeutic activity, use of these compounds in methods of therapy and the manufacture of medicaments as well as compositions containing these compounds

4-(3-Halo/amino-4,5-dimethoxyphenyl)-5-aryloxazoles and-N-methylimidazoles That Are cytotoxic against combretastatin a resistant tumor cells and vascular disrupting in a cisplatin resistant germ cell tumor model

New combretastatin A analogues featuring oxazole or N-methylimidazole bridged Z-alkenes and halo-or amino-substituted A-rings were tested against various cancer cell lines and in testicular germ cell tumor xenografts in mice. Imidazoles with 3-halo-4,5-dimethoxy substituted A-rings and 3-amino-4-methoxy substituted B-rings (7b and 8b) were efficacious at nanomolar concentrations against cells of combretastatin A refractory HT-29 colon carcinoma, multidrug-resistant MCF-7/Topo breast carcinoma, and cisplatin-resistant 1411HP testicular germ cell tumor. They induced apoptosis and inhibited tubulin polymerization. While well tolerated by mice at high doses, these imidazoles initiated extensive intratumoral hemorrhage and regressions of highly vascularized 1411HP xenografts.

Discovery of a long-acting, peripherally selective inhibitor of catechol- O -methyltransferase

Novel nitrocatechol-substituted heterocycles were designed and evaluated for their ability to inhibit catechol-O-methyltransferase (COMT). Replacement of the pyrazole core of the initial hit 4 with a 1,2,4-oxadiazole ring resulted in a series of compounds endowed with longer duration of COMT inhibition. Incorporation of a pyridine N-oxide residue at position 3 of the 1,2,4-oxadiazole ring led to analogue 37f, which was found to possess activity comparable to entacapone and lower toxicity in comparison to tolcapone. Lead structure 37f was systematically modified in order to improve selectivity and duration of COMT inhibition as well as to minimize toxicity. Oxadiazole 37d (2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4, 6-dimethylpyridine 1-oxide (BIA 9-1067)) was identified as a long-acting, purely peripheral inhibitor, which is currently under clinical evaluation as an adjunct to l-Dopa therapy of Parkinson's disease.

Synthesis and evaluation of bifunctional nitrocatechol inhibitors of pig liver catechol-O-methyltransferase

Bifunctional compounds were tested in vitro as potential inhibitors of pig liver catechol-O-methyltransferase (COMT) with respect to the catechol substrate 4-[(3,4-dihydroxyphenyl)azo]benzenesulfonate. The bifunctional compounds were a composite of either two nitrocatechols or one nitrocatechol and one phenol, linked by amide bonds to a spacer unit comprising two to five methylene groups. The unsymmetrical compounds N-[2-(4-hydroxybenzoylamine)ethyl]-3,4-dihydroxy-5- nitrobenzamide], N-[3-(4-hydroxybenzoyl-amine)propyl]-3,4-dihydroxy-5- nitrobenzamide] and N-[5-(4-hydroxybenzoylamine)pentyl]-3,4-dihydroxy-5- nitrobenzamide] demonstrated strong inhibitory action against COMT with K i values in the 100 nM range. In comparison, the monofunctional nitrocatechol analogues of these compounds had Ki values that were significantly higher.

Further naphthylcombretastatins. An investigation on the role of the naphthalene moiety

By synthesis and biological studies of new naphthalene analogues of combretastatins, we have found that the naphthalene is a good surrogate for the isovanillin moiety (3-hydroxy-4-methoxyphenyl) of combretastatin A-4, always generating highly cytotoxic analogues when combined with the 3,4,5-trimethoxyphenyl or related systems. On the other hand, when the naphthalene replaces the 3,4,5-trimethoxyphenyl moiety, the cytotoxic activity is largely decreased. The most cytotoxic naphthalene analogues of combretastatins, which also produce inhibition of tubulin polymerization, exerted their antimitotic effects through microtubule network disruption and subsequent G2/M arrest of the cell cycle in human cancer cells.

Benzoxazepinones and their use as squalene synthase inhibitors

There is disclosed a compound represented by the formula [I]: wherein R1 is optionally substituted 1-carboxyethyl group, optionally substituted alkyl-sulfonyl group, optionally substituted (carboxy-cycloalkyl)-alkyl group, -X1-X2-Ar-X3-X4-COOH (wherein X1 and X4 are a bond or alkylene group, X2 and X3 are a bond, -O-, -S-, Ar is divalent aromatic group etc.), R2 is alkyl group optionally substituted with alkanoyloxy group and/or hydroxy group, R3 is alkyl group, and W is halogen atom, etc., or a salt thereof. The compound has the cholesterol lowering activity and the triglyceride lowering activity and is useful for preventing and/or treating hyperlipidemia.