115891-18-4

Basic information

• Product Name: 3-Pyridinecarboxylic acid, 2-(phenylaMino)-, ethyl ester
• Synonyms: 3-Pyridinecarboxylic acid, 2-(phenylaMino)-, ethyl ester;Ethyl 2-(phenylamino)nicotinate
• CAS NO: 115891-18-4
• Molecular Formula: C₁₄H₁₄N₂O₂
• Molecular Weight: 242.27316
• EINECS: -0
• Mol File: 115891-18-4.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Pyridinecarboxylic acid, 2-(phenylaMino)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarboxylic acid, 2-(phenylaMino)-, ethyl ester(115891-18-4)
• EPA Substance Registry System: 3-Pyridinecarboxylic acid, 2-(phenylaMino)-, ethyl ester(115891-18-4)

Safety Data

• Hazardous Substances Data: 115891-18-4(Hazardous Substances Data)

Upstream product

• 53087-78-8 Ethyl 2-bromo-3-pyridinecarboxylate 
• 62-53-3 aniline 
• 2942-59-8 2-chloronicotinic acid 
• 1452-94-4 ethyl 2-chloronicotinate 

Downstream Products

• 113256-66-9 2-phenylamino-3-pyridinecarboxaldehyde 
• 21093-54-9 2-Phenylamino-3-hydroxymethylpyridine 
• 16344-24-4 2-(phenylamino)nicotinic acid 
• 1350515-76-2 2-(2-anilino-3-pyridyl)-10-phenyl-5,10-dihydro-5λ6-benzo[e][1,2,4]triazolo[1,5-b][1,2,4]thiadiazine-5,5-dione 
• 1350515-71-7 2-(2-anilino-3-pyridyl)-10-methyl-5,10-dihydro-5λ6-benzo[e][1,2,4]triazolo[1,5-b][1,2,4]thiadiazine-5,5-dione 
• 1350515-64-8 N-3-(6-nitro-1,3-benzothiazol-2-yl)-2-(phenylamino)-3-pyridinecarboxamide 
• 1350515-57-9 N₃-[6-(methyloxy)-1,3-benzothiazol-2-yl]-2(phenylamino)-3-pyridinecarboxamide 
• 120137-15-7 2-(phenylamino)pyridine-3-carbohydrazide 

Relevant articles and documents

Synthesis of 2-anilinopyridyl linked benzothiazole hydrazones as apoptosis inducing cytotoxic agents

A series of 2-anilinopyridyl linked benzothiazole-hydrazone conjugates (5a-aa) were designed, synthesized and evaluated for their in vitro cytotoxic potency against a panel of cancer cell lines like mouse skin melanoma (B16F10), lung adenocarcinoma (A549), breast adenocarcinoma (MCF-7), triple negative breast cancer (MDA-MB-231) and normal lung epithelial (L132) cell lines. Preliminary screening results revealed that some of these conjugates like 5i and 5l exhibited a significant antiproliferative effect against human breast cancer (MCF-7) with IC50 values of 1.03 and 1.69 μM respectively. Further, detailed biological studies of this promising conjugate (5i) were carried out on MCF-7 cells. The flow cytometric analysis revealed that this conjugate induces cell-cycle arrest in the G2/M phase in a dose dependent manner. Furthermore, in order to determine the effect of the conjugate on cell viability, various cell based assays such as clonogenic assay, ethidium bromide staining, Hoechst staining, detection of ROS generation and annexin V-FITC/PI assays were performed. In these studies, apoptotic features were clearly observed indicating that this conjugate inhibited cell proliferation by apoptosis.

Synthesis of 2-anilinopyridine-arylpropenone conjugates as tubulin inhibitors and apoptotic inducers

A series of new (Z)-3-(arylamino)-1-(2-(arylamino)pyridin-3-yl)prop-2-en-1-one conjugates 9a-p were synthesized and evaluated for their cytotoxic activity against some human cancer cell lines. Some of the treated compounds like 9a, 9g and 9j showed significant activity with IC50 values ranging from 0.51 to 1.29 μM. Flow cytometry results revealed that for A549 cells these compounds caused accumulation of cells in the G2/M phase. Interestingly, compound 9a demonstrated a considerable inhibitory effect on tubulin polymerization and showed significant inhibition of tubulin polymerization with an IC50 value of 1.34 μM, whereas nocodazole showed antitubulin activity with an IC50 value 2.64 μM. Further, Hoechst staining and activation of caspase-3 suggested that these conjugates induced cell death by apoptosis. Fluorescence based competitive colchicine binding assay and docking studies suggest that these conjugates 9a and 9g bind to the tubulin perfectly at the colchicine binding site.

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.