20357-24-8

Usage

Uses

Used in Pharmaceutical Industry:
5-Methoxy-2-nitrobenzaldehyde is used as a starting material for the synthesis of a novel class of cis-locked combretastatins, known as combretabenzodiazepines. These compounds exhibit cytotoxic and antitubulin activity, which makes them promising candidates for the development of new anticancer drugs. The unique structure of combretabenzodiazepines allows them to target and disrupt the microtubules in cancer cells, thereby inhibiting their growth and proliferation.
In addition to its role in the synthesis of combretabenzodiazepines, 5-Methoxy-2-nitrobenzaldehyde may also be utilized in the development of other pharmaceutical compounds with potential therapeutic applications. Its reactivity and structural diversity make it a valuable tool in the design and synthesis of new molecules with specific biological activities.
Used in Chemical Research:
5-Methoxy-2-nitrobenzaldehyde can be employed as a research tool in various fields of chemistry, including organic synthesis, medicinal chemistry, and materials science. Its unique structure and reactivity make it an attractive candidate for the development of new synthetic methods, as well as for the study of reaction mechanisms and the exploration of novel chemical transformations.
In the field of materials science, 5-Methoxy-2-nitrobenzaldehyde may be used to develop new materials with specific properties, such as optical, electronic, or magnetic characteristics. Its incorporation into polymers or other molecular structures could lead to the creation of advanced materials with potential applications in various industries, including electronics, energy, and environmental protection.

InChI:InChI=1/C8H7NO4/c1-13-7-2-3-8(9(11)12)6(4-7)5-10/h2-5H,1H3

Upstream product

• 42454-06-8 2-nitro-5-hydroxybenzaldehyde 
• 591-31-1 3-methoxy-benzaldehyde 
• 77-78-1 dimethyl sulfate 
• 109005-38-1 4-methoxy-2-<<(4-methylphenyl)sulfonyl>methyl>-1-nitrobenzene 
• 74-88-4 methyl iodide 
• 7697-37-2 nitric acid 
• 63932-00-3 5-methoxy-2-nitrobenzoyl chloride 
• 5367-32-8 5-methoxy-2-nitrotoluene 
• 446-33-3 5-Fluoro-2-nitrotoluene 
• 454466-57-0 methyl 3-formylphenyl carbonate 
• 96042-30-7 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 
• 100-83-4 meta-hydroxybenzaldehyde 
• 1882-69-5 5-methoxy-2-nitro-benzoic acid 
• 879-55-0 (5-methoxy-2'-nitrophenyl)methanol 

Downstream Products

• 10226-40-1 5-methoxy-2-nitrocinnamic acid 
• 39755-95-8 5-methoxyisatine 
• 1882-69-5 5-methoxy-2-nitro-benzoic acid 
• 10202-94-5 3-methoxy-2,6-dinitrobenzaldehyde 
• 860243-67-0 5-methoxy-2,4-dinitrobenzaldehyde 
• 26831-52-7 2-amino-5-methoxybenzaldehyde 
• 21857-40-9 4-(5-methoxy-2-nitro-benzylidene)-2-methyl-4H-oxazol-5-one 
• 162927-72-2 1-(5-Methoxy-2-nitro-phenyl)-prop-2-en-1-ol 
• 156785-62-5 1-(5-methoxy-2-nitrophenyl)ethanol 
• 109133-78-0 5-[1-(5-Methoxy-2-nitro-phenyl)-meth-(Z)-ylidene]-1-methyl-imidazolidine-2,4-dione 
• 146233-06-9 5-Benzoylamino-2-[(E)-2-(5-methoxy-2-nitro-phenyl)-vinyl]-6-oxo-6H-pyran-3-carboxylic acid ethyl ester 
• 129841-08-3 C₈H₇⁽¹⁸⁾FO₂ 
• 73428-02-1 5-methoxy-2-nitrobenzaldehyde ethylene acetal 
• 55149-73-0 (E)-2-Cyano-3-(5-methoxy-2-nitro-phenyl)-acrylamide 

Relevant academic research and scientific papers

Synthesis of 5,10,15,20-tetrakis(2-amino-5-methoxyphenyl)-porphyrin: A versatile building block for porphyrin face selection

A new bis-faced substituted porphyrin has been prepared. The four hydroxyl groups on one side as well as the four amino functions on the other one allow at will, a different functionalization of each face of the macrocycle. The usefulness of this synthon is illustrated.

Iron-Catalyzed Reductive Cyclization by Hydromagnesiation: A Modular Strategy Towards N-Heterocycles

A reductive cyclization to prepare a variety of N-heterocycles, through the use of ortho-vinylanilides, is reported. The reaction is catalyzed by an inexpensive and bench-stable iron complex and generally occurs at ambient temperature. The transformation likely proceeds through hydromagnesiation of the vinyl group, and trapping of the in situ generated benzylic anion by an intramolecular electrophile to form the heterocycle. This iron-catalyzed strategy was shown to be broadly applicable and was utilized in the synthesis of substituted indoles, oxindoles and tetrahydrobenzoazepinoindolone derivatives. Mechanistic studies indicated that the reversibility of the hydride transfer step depends on the reactivity of the tethered electrophile. The synthetic utility of our approach was further demonstrated by the formal synthesis of a reported bioactive compound and a family of natural products.

Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer

Evodiamine (Evo) is a quinazolinocarboline alkaloid found in Evodia rutaecarpa and exhibits moderate antiproliferative activity. Herein, we report using a scaffold-hopping approach to identify a series of novel polycyclic heterocyclic derivatives based on Evo as the topoisomerase I (Top1) inhibitor for the treatment of triple-negative breast cancer (TNBC), which is an aggressive subtype of breast cancer with limited treatment options. The most potent compound 7f inhibited cell growth in a human breast carcinoma cell line (MDA-MB-231) with an IC50 value of 0.36 μM. Further studies revealed that Top1 was the target of 7f, which directly induced irreversible Top1-DNA covalent complex formation or induced an oxidative DNA lesion through an indirect mechanism mediated by reactive oxygen species. More importantly, in vivo studies showed that 7f exhibited potent antitumor activity in a TNBC-patient-derived tumor xenograft model. These results suggest that compound 7f deserves further investigation as a promising candidate for the treatment of TNBC.

Ursolic acid quinolinyl hydrazide derivative with anti-tumor activity as well as preparation method and application thereof

The invention discloses an ursolic acid quinolinyl hydrazide derivative with anti-tumor activity as well as a preparation method and application thereof. The invention provides an ursolic acid quinolinyl hydrazide heterocyclic derivative with a structure shown as a general formula I and pharmaceutically acceptable salt thereof: the formula I is shown in the description, wherein I-a: R1 is equal to H and R2 is equal to CH3; I-b: R1 is equal to OMe and R2 is equal to CH3; I-c: R1 is equal to F and R2 is equal to CH3; I-d: R1 is equal to C1 and R2 is equal to CH3; I-e: R1 is equal to H1 and R2 is equal to n-C4H9; I-f: R1 is equal to OMe and R2 is equal to n-C4H9; I-g: R1 is equal to F and R2 is equal to n-C4H9; I-h: R1 is equal to C1 and R2 is equal to n-C4H9. The ursolic acid quinolinyl hydrazide heterocyclic derivative and the pharmaceutically acceptable salt thereof, provided by the invention, have the remarkable anti-tumor activity; a pharmacology experiment shows that the ursolic acid quinolinyl hydrazide derivative disclosed by the invention has a remarkable inhibition effect on human breast cancer cells MDA-MB-231, human cervical cancer cells HeLa and human hepatoma cells SMMC-7721, has low toxicity on human normal epithelial cells QSG-7701 and has a potential of being used for developing anti-tumor drugs.

N, N ′-Disubstituted thiourea and urea derivatives: Design, synthesis, docking studies and biological evaluation against nitric oxide synthase

The synthesis and biological evaluation of new types of N,N′-disubstituted thiourea and urea derivatives as inhibitors of both neuronal nitric oxide synthase (nNOS) and inducible nitric oxide synthase (iNOS) are described. These compounds have been designed by reduction of the carbonyl group in the thiourea and urea kynurenamine derivatives 3 previously synthesized by our research group. The synthetic route performed to this new family also allows us to obtain the molecules 3 with less synthetic steps and higher global yield. Regarding the biological results, in general, the new derivatives 4a-q inhibit the neuronal NOS isoform better than the inducible one. Furthermore, thioureas exhibit higher inhibition than ureas for both isoenzymes. Among all the tested compounds, 4g shows significant nNOS (80.6%) and iNOS (76.6%) inhibition values without inhibiting eNOS. This molecule could be an interesting starting point for the design of new inhibitors with application in neurological disorders where both isoenzymes are implicated such as Parkinson's disease.

BIARYLTRIAZOLE INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR

The present disclosure describes biaryl triazole compounds, as well as their compositions and methods of use. The compounds inhibit the activity of macrophage migration inhibitory factor and are useful for the treatment of diseases, e.g., inflammatory dis

Heterobicyclic sphingosine 1-phosphate analogs

Compounds that have agonist activity at one or more of the S1P receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at S1P receptors.

S1P MODULATING AGENTS

Compounds of formula (I) or (II) can modulate the activity of SIP receptors.

SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS

Provided are compositions and methods useful for modulation of signaling through the Toll-like receptors TLR7 and/or TLR8. The compositions and methods have use in treating or preventing disease, including cancer, autoimmune disease, fibrotic disease, cardiovascular disease, infectious disease, inflammatory disorder, graft rejection, or graft-versus-host disease.

Design and synthesis of 6,6-fused heterocyclic amides as raf kinase inhibitors

Compounds belonging to several scaffolds-quinazolines, quinolines and quinoxalines-were designed and synthesized as Raf kinase inhibitors. Scaffolds were assessed for in vitro BrafV600E inhibition, and overall kinase selectivity. Pharmacokinetic parameters for one of the scaffolds were also determined.