132209-79-1

Basic information

• Product Name: 1,8-Naphthyridine-3-carboxylic acid, 2-chloro-, ethyl ester
• CAS NO: 132209-79-1
• Molecular Formula: C11H9ClN2O2
• Molecular Weight: 236.658
• Mol File: 132209-79-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,8-Naphthyridine-3-carboxylic acid, 2-chloro-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-Naphthyridine-3-carboxylic acid, 2-chloro-, ethyl ester(132209-79-1)
• EPA Substance Registry System: 1,8-Naphthyridine-3-carboxylic acid, 2-chloro-, ethyl ester(132209-79-1)

Safety Data

• Hazardous Substances Data: 132209-79-1(Hazardous Substances Data)

Usage

Chemical class

Naphthyridine carboxylic acids

Physical appearance

White powder

Molecular weight

252.66 g/mol

Uses

a. Synthesis of pharmaceuticals and agrochemicals
b. Intermediate for the production of dyes and pigments

Solubility

Soluble in organic solvents

Stability

Enhanced stability due to ethyl ester functionality

Industrial applications

Versatile chemical with various uses in organic synthesis and chemical production

Upstream product

• 105-53-3 diethyl malonate 
• 5174-90-3 1,8-naphthyridin-2(1H)-on-3-carboxylic acid ethyl ester 
• 7521-27-9 2-(3-pyridyl)-1,3,8-triazanaphthalene 
• 7521-41-7 2-Aminonicotinaldehyde 
• 98-92-0 nicotinamide 

Relevant articles and documents

Design, Synthesis, and Pharmacological Evaluation of Novel 2-(4-substituted piperazin-1-yl)1, 8 Naphthyridine 3-Carboxylic Acids as 5-HT3 Receptor Antagonists for the Management of Depression

1, 8-naphthyridine-3-carboxylic acid analogs were synthesized and found to possess potential 5-HT3 receptor antagonism as well as antidepressant-like activity. Initially, 5-HT3 receptor antagonism of all the compounds was determined in the form of pA2 value against agonist 2-methyl 5-HT in longitudinal muscle-myenteric plexus preparation from Guinea-pig ileum. Among all the compounds tested, compound 7a demonstrated most promising pA2 value of 7.6. Subsequently, all the compounds were evaluated for antidepressant activity using forced swim test and tail suspension test in mice. Compounds 7a, 7d, 7f, 7h, and 7i exhibited significant (p 0.05) antidepressant-like activity as compound to vehicle-treated group. Importantly, none of the tested compound affected locomotor activity of mice at tested dose levels.

NOVEL BRONCHODILATING DIAZAHETEROARYLS

The invention relates to novel compounds having the general formula (I), and which compounds are useful to treat a disorder or disease characterized by bronchoconstriction, e.g. COPD and asthma.

Synthesis of some novel azetidino[2,3-b][1,8]naphthyridin-2(1H)-ones and 1,2,4-triazolo [4,3-a][1,8] naphthyridines

Ethyl 1.8-naphthyridin-2-one-3-carboxylate 1 on fusion with different anilines at 200°C affords N-aryl-1,8-naphthyridin-2-one-3-carboxamides 2, which undergo smooth cyclization with POCl3 yielding 1-arylazetidino [2,3-b][1,8]naphthyridin-2(1H)-ones 3. Compound 1 on treatment with POCl 3 yield ethyl 2-chloro-1,8-naphthyridine-3-carboxylate 4, which on reaction with aromatic acid hydrazides in methanol furnishes respective N-aroyl-N'-(3-carbethoxy-1,8-naphthyridin-2-yl) hydrazines 5. Cyclization of 5 with POCl3 under reflux result in the formation of 1-aryl-4-carbethoxy-1,2,4-triazol [4,3-a][1,8]naphthyridines 6. Compounds 3 and 6 have been evaluated for their antibacterial activity using streptomycin as a reference compound.