4394-09-6

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-methoxy-anilino)-nicotinic acid is used as a therapeutic agent for the treatment of cancer and other conditions involving dysregulated tissue remodeling. Its ability to inhibit TIMP1 can potentially impact cellular processes such as cell proliferation, migration, and invasion, making it a valuable compound for the development of targeted therapies.
Used in Research Applications:
2-(4-methoxy-anilino)-nicotinic acid is used as a research tool for studying the role of TIMP1 and MMPs in tissue remodeling and degradation. Its potent and selective inhibition of TIMP1 allows researchers to investigate the underlying mechanisms of tissue remodeling and the potential therapeutic effects of TIMP1 inhibition in various diseases.
Used in Drug Development:
2-(4-methoxy-anilino)-nicotinic acid is used as a lead compound in the development of new drugs targeting TIMP1 and MMPs. Its potent and selective inhibition of TIMP1 makes it a valuable starting point for the design and synthesis of novel compounds with improved pharmacological properties and therapeutic potential.
Used in Diagnostic Applications:
2-(4-methoxy-anilino)-nicotinic acid can be used as a diagnostic agent to assess the activity of TIMP1 and MMPs in various conditions. Its ability to selectively inhibit TIMP1 can help in the identification of dysregulated tissue remodeling processes and the evaluation of the efficacy of therapeutic interventions targeting these enzymes.

Upstream product

• 2942-59-8 2-chloronicotinic acid 
• 104-94-9 4-methoxy-aniline 
• 95774-49-5 ethyl 2-((4-methoxyphenyl)amino)nicotinate 
• 1452-94-4 ethyl 2-chloronicotinate 

Downstream Products

• 1350515-54-6 N₃-[6-(methyloxy)-1,3-benzothiazol-2-yl]-2-[4-(methyloxy)phenyl]amino-3-pyridinecarboxamide 
• 1350515-62-6 N-3-(6-nitro-1,3-benzothiazol-2-yl)-2-(4-methoxyanilino)nicotinamide 
• 1350515-69-3 2-[2-(4-methoxyanilino)-3-pyridyl]-10-methyl-5,10-dihydro-5λ6-benzo[e][1,2,4]triazolo[1,5-b][1,2,4]thiadiazine-5,5-dione 
• 1531604-35-9 N-(6-fluorobenzo[d]thiazol-2-yl)-2-((4-methoxyphenyl)amino)nicotinamide 
• 41010-72-4 3-(4-methoxyphenyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel 4-(pyrrolo[2,3-d]pyrimidine-4-yloxy)benzamide derivatives as potential antitumor agents

Cancer is a major cause of death worldwide. Small molecule inhibitors have become a major therapeutic treatment for cancer. In this study, a series of novel 4-(pyrrolo[2,3-d]pyrimidine-4-yloxy)benzamide derivatives were designed, synthesized and evaluated

FUSED CYCLIC UREA DERIVATIVES AS CRHR2 ANTAGONIST

The present invention relates to fused cyclic urea derivatives which have antagonistic activities against CRHR1 and/or CRHR2, and which are useful in the treatment or prevention of disorders and diseases in which CRHR1 and/or CRHR2 is involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CRHR1 and/or CRHR2 is involved.

Synthesis and antiproliferative activity of pyrrolo[2,3-b]pyridine derivatives bearing the 1,8-naphthyridin-2-one moiety

A series of pyrrolo[2,3-b]pyridine derivatives bearing the 1,8-naphthyridin-2-one moiety were synthesized, and evaluated for their antiproliferative activity against four cancer cell lines (HT-29, A549, H460, and U87MG) and six tyrosine kinases (c-Met, Flt-3, PDGFR-β VEGFR-2, EGFR, and c-Kit) inhibitory activities in vitro. Most compounds showed moderate to excellent potency, with the most promising analogue 32 showing Flt-3/c-Met IC50 value of 1.16/1.92 nM. Structure-activity relationship studies indicated that the hydrogen atom served as R1 group was benefited to the potency, and mono-electron-withdrawing groups (mono-EWGs) on the phenyl ring (such as R3 = 4-F) showed a higher preference for antiproliferative activity.

Discovery of novel 2-substituted-4-phenoxypyridine derivatives as potential antitumor agents

A series of 2-substituted-4-phenoxypyridine derivatives were designed, synthesized, and evaluated for their antiproliferative activity against 4 cancer cell lines (A549, HT-29, H460, and U87MG) in vitro. Most compounds showed moderate to excellent potency. Nine tyrosine kinases (c-Met, Flt-3, ALK, VEGFR-2, VEGFR-3, PDGFR-α PDGFR-β c-Kit, and EGFR) were used to evaluate the inhibitory activities with the most promising analogue 39, which showed the Flt-3/c-Met IC50 values of 2.18/2.61 nM. Structure-activity relationship studies indicated that n-Pr served as R1 group showed a higher preference, and stronger mono-EWGs on the phenyl ring (such as R2 = 4-F) was benefited to the potency.

Synthesis and antiproliferative activity of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 1,8-naphthyridin-2-one moiety

A series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 1,8-naphthyridin-2-one moiety were designed, synthesized and evaluated for their biological activities. The target compounds exhibited moderate to high antiproliferative activity against three cancer cell lines (A549, HepG2 and MCF-7) and several compounds (25, 27, 33, 37, 41, 43, 49 and 53) were evaluated for the activity against c-Met kinase. The most promising compound 33 (IC50 c-Met = 2.36 nM) showed excellent activity against A549, HepG2 and MCF-7 cell lines with IC50 values of 0.23 μM, 0.42 μM and 0.21 μM, respectively, which was 1.5–2.1 times of the positive control. Furthermore, compound 33 was evaluated for the activity against Flt3, PDGFR-α PDGFR-β c-Kit, Flt4, ALK and EGFR kinase. Structure activity relationship studies indicated that mono-EWGs (such as R2 = F) at 4-position of moiety C was a key factor in improving the antitumor activity. In addition, further research on compound 33 was mainly including concentration dependence, apoptosis (acridine orange staining), apoptosis result analyzing and molecular docking.

Synthesis and mechanistic aspects of 2-anilinonicotinyl-pyrazolo[1,5-a]pyrimidine conjugates that regulate cell proliferation in MCF-7 cells via estrogen signaling

A series of anilinonicotinyl linked pyrazolo[1,5-a]pyrimidine conjugates (6a-x) were synthesized and evaluated for their antiproliferative activity. Some of these conjugates exhibited promising cytotoxic effects in the MCF-7 cell line and among these 6a a

Synthesis and anticancer potential of benzothiazole linked phenylpyridopyrimidinones and their diones as mitochondrial apoptotic inducers

A series of benzothiazole linked phenylpyridopyrimidinones (8a-g) and their diones (9a-g) have been designed, synthesized and evaluated for their anticancer activity. Among the series one of the conjugate 8b showed significant cytotoxicity against human cervical cancer cell line ME-180 with IC 50 value of 4.01 μM. This compound was tested on the cell cycle perturbations and DNA damage. Flow cytometry analysis revealed that the compound 8b showed drastic cell cycle perturbations due to concentration dependent increase in the sub-G0 phase in ME-180 cell line. DNA fragmentation and Hoechst staining reveals that this compound induced cell death by apoptosis. Further caspase-3 and loss of mitochondrial membrane potential suggested that the compound induces cell death by apoptosis.

Synthesis of 2-anilinopyridine dimers as microtubule targeting and apoptosis inducing agents

A series of 2-anilinopyridine dimers have been synthesized and evaluated for their anticancer potential. Most of the compounds have showed significant growth inhibition of the cell lines tested and compound 4d was most effective amongst the series display

2-ANILINO NICOTINYL LINKED 2-AMINO BENZOTHIAZOLE CONJUGATES AND PROCESS FOR THE PREPARATION THEREOF

The present invention provides compounds of general formula A useful as potential anticancer agents against human cancer cell lines and apoptosis inducers. The present invention further provides a process for the preparation of 2-anilino nicotinyl linked 2-amino benzothiazole conjugates of general formula (A), wherein R1═H or CI; R2═H, OCH3 or F; R3═H, OCH3, F or CI; R4═H, OCH3 or F and X═OCH3, F or N02.

2-ANILINO NICOTINYL LINKED 2-AMINO BENZOTHIAZOLE CONJUGATES AND PROCESS FOR THE PREPARATION THEREOF

The present invention provides compounds of general formula A useful as potential anticancer agents against human cancer cell lines and apoptosis inducers. The present invention further provides a process for the preparation of 2-anilino nicotinyl linked 2-amino benzothiazole conjugates of general formula (A), wherein R1 = H or CI; R2 = H, OCH3 or F; R3 = H, OCH3, F or CI; R4=H, OCH3 or F and X= OCH3, F or N02.