16344-24-4

Basic information

• Product Name: 2-ANILINONICOTINIC ACID
• Synonyms: 2-ANILINONICOTINIC ACID;2-(Phenylamino)-3-pyridinecarboxylic acid;2-(phenylamino)nicotinic acid
• CAS NO: 16344-24-4
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• Mol File: 16344-24-4.mol

Chemical Properties

• Boiling Point: 391.4 °C at 760 mmHg
• Flash Point: 190.5 °C
• Appearance: /
• Density: 1.328 g/cm³
• Vapor Pressure: 7.94E-07mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2-ANILINONICOTINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ANILINONICOTINIC ACID(16344-24-4)
• EPA Substance Registry System: 2-ANILINONICOTINIC ACID(16344-24-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 16344-24-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Anilinonicotinic acid is used as a pharmaceutical intermediate for the development of new drugs for the treatment of certain medical conditions. Its unique molecular structure and biological activities make it a promising candidate for the creation of novel therapeutic agents.
Used in Medicinal Chemistry Research:
2-Anilinonicotinic acid is used as a research compound in medicinal chemistry to explore its potential applications in the treatment of various diseases and disorders. Its anti-inflammatory and analgesic properties are of particular interest, as they may contribute to the development of new treatments for pain and inflammation-related conditions.

InChI:InChI=1/C12H10N2O2/c15-12(16)10-7-4-8-13-11(10)14-9-5-2-1-3-6-9/h1-8H,(H,13,14)(H,15,16)/p-1

Upstream product

• 2942-59-8 2-chloronicotinic acid 
• 62-53-3 aniline 
• 5345-47-1 2-aminopyridin-3-carboxylic acid 
• 108-86-1 bromobenzene 
• 141-97-9 ethyl acetoacetate 
• 17758-13-3 1-phenyl-2(1H)-pyrimidinone 
• 1452-94-4 ethyl 2-chloronicotinate 
• 115891-18-4 ethyl 2-(phenylamino)pyridine-3-carboxylate 
• 446-26-4 methyl 2-fluoro-3-pyridinecarboxylate 
• 6042-35-9 2-iodonicotinic acid 

Downstream Products

• 6631-37-4 2-(phenylamino)pyridine 
• 28907-30-4 5-oxo-5,10-dihydrobenzo<1,8>naphthiridine 
• 108409-21-8 10-phenyl-2,3-dihydroimidazol<1,2-a>pyrido<2,3-d>pyrimidin-5(10H)-one 
• 21093-54-9 2-Phenylamino-3-hydroxymethylpyridine 
• 89109-17-1 4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one 
• 583031-58-7 4-chloro-1-phenyl-1,8-naphthyridin-2(1H)-one 
• 128271-31-8 (3-Methylsulfanylmethyl-pyridin-2-yl)-phenyl-amine 
• 127555-82-2 1,3-Dihydro-3-methyl-1-phenyl-2H-pyrrolo[2,3-b]pyridin-2-one 
• 127555-25-3 1,3-dihydro-3,3-dimethyl-1-phenyl-2H-pyrrolo<2,3-b>pyridin-2-one 
• 128271-21-6 3-Methylsulfanyl-1-phenyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one 
• 128271-24-9 3-Ethyl-3-methyl-1-phenyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one 
• 127555-34-4 3,3-Diethyl-1-phenyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one 
• 127555-60-6 1,3-dihydro-3-methyl-3-(methylthio)-1-phenyl-2H-pyrrolo[2,3-b]pyridin-2-one 
• 128271-32-9 Phenyl-(3-phenylsulfanylmethyl-pyridin-2-yl)-amine 

Relevant articles and documents

A convenient synthesis of 4-aryl-1,8-naphthyridin-2(1H)-ones by the Suzuki coupling

4-Halo-1,8-naphthyridin-2(1H)-ones readily available from 2-chloronicotinic acid were subjected to the Suzuki coupling reaction with arylboronic acids to give a diversity of 4-aryl-1,8-naphthyridin-2(1H)-ones.

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

Design, synthesis and biological evaluation of anthranilamide derivatives as potent SMO inhibitors

A series of anthranilamide derivatives were designed and synthesized as novel smoothened (SMO) inhibitors based on the SMO inhibitor taladegib (LY2940680), which can also inhibit the SMO-D473H mutant, via a ring-opening strategy. The phthalazine core in LY2940680 was replaced with anthranilamide, which retained the inhibitory activity towards the hedgehog (Hh) signaling pathway as evidenced by a dual luciferase reporter gene assay. Compound 12a displayed the best inhibitory activity against the Hh signaling pathway with IC50 value of 34.09 nM, and exhibited better proliferation inhibitory activity towards the Daoy cell line (IC50 = 0.48 μM) than LY2940680 (IC50 = 0.79 μM).

Nicotinic acid ester compound and preparation method and application thereof

The invention discloses a nicotinic acid ester compound shown as a general formula (I) (please see the specifications for the general formula). All substituent groups are seen in a specification. Theinvention further discloses a preparation method and app

Preparation and application of 2-carbamoyl-4-heteroaromatic pyridine compounds

The invention provides 2-carbamoyl-4-heteroaromatic pyridine derivatives and pharmaceutically acceptable salts, hydrates, solvates and prodrugs thereof. The substituent groups R1, R2 and Y have definitions in the specification. The invention further relates to compounds with a general formula I having strong effects of inhibiting c-Met kinase, and also relates to an application of the compounds and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of medicines for treating diseases caused by abnormal high expression of the c-Met kinase, particularly an application in preparation of medicines for treating and/or preventing cancers.

Preparation and application of 6,7-disubstituted-4-aromatic quinoline compound

The invention relates to a 6,7-disubstituted-4-aromatic quinoline derivative shown as a general formula I as well as pharmaceutically-acceptable salt, a hydrate, a solvate and pro-drug thereof, wherein substituents R1, X and Y have meanings given in the description. The invention further relates to a compound with a strong effect on inhibiting c-Met kinase shown as the general formula I and further relates to application of the compound and pharmaceutically-acceptable salt, a hydrate, a solvate and pro-drug thereof to preparation of a drug for treating a disease caused by the abnormally-high expression of the c-Met kinase, in particular to application to preparation of a drug for treating and/or preventing a cancer.

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.

Pyrrolo-pyridine compound containing naphthyridinone structure and application of pyrrolo-pyridine compound

The invention discloses a pyrrolo-pyridine compound containing a naphthyridinone structure, a geometric isomer and pharmaceutically acceptable salt, hydrate, solvate or prodrug of the pyrrolo-pyridine compound, and a preparation method of the pyrrolo-pyridine compound. The pyrrolo-pyridine compound containing the naphthyridinone structure, the pharmaceutically acceptable salt, the hydrate or the solvate of the pyrrolo-pyridine compound are used as active components and are mixed with a pharmaceutically acceptable carrier or an excipient to prepare a composition and the composition is prepared into a clinically acceptable preparation. The invention provides application of the compound provided by the invention to preparation of a medicine for treating and/or preventing proliferative diseases, application of the compound to preparation of a medicine for treating and/or preventing cancers, and application of the compound to preparation of a medicine for treating and/or preventing lung cancer, liver cancer, stomach cancer, colon cancer and breast cancer. (A formula (I) is shown in the description.).