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7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

CAS Number 100361-18-0

Chemistry Building Blocks, Fluorinated Building Blocks, Heterocyclic Building Blocks, Materials, Monomers

Product Code B1791-25g
Price £115 ex. VAT

A fluorinated heterocyclic building block

Used as a synthesis intermediate for APIs in application of drug discovery

Specifications | MSDS | Literature and Reviews

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (CAS number 100361-18-0) is derived from naphthyridine, a bicyclic heterocyclic, bearing a chlorine (7-position), a fluorine (6-position), a cyclopropyl (1-position), a carbonyl (4-position) and a carboxylic acid (3-position). 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid is an important intermediate for synthesizing Gemifloxacin, a quinolone antibiotic. It is also a molecular scaffold for many other active pharmaceutical ingredients (APIs) of anticancer and anti-inflammatory activities.

Chemical structure of Gemifloxacin
Chemical structure of Gemifloxacin, an antibiotic

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid has multiple metal-binding sides. The ketone and carboxylic acid form a 1,3-diketone moiety which binds transition metals to produce metal complexes. The drug-metal complexes show enhanced biological activity. The amines (1,8-position) in 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid can also chelate to metal centres yielding complexes for APIs.

Multiple functional groups

Multiple functional groups

For facile synthesis

Fluorinated building block

Fluorinated naphthyridine building block

For drug discovery, medicinal chemistry, and biochemistry research

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High purity 100361-18-0

High purity

>98% High purity

General Information

CAS Number 100361-18-0
Chemical Formula C12H18ClFN2O3
Full Name 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
Molecular Weight 282.65 g/mol
Synonyms 1-Cyclopropyl-6-fluoro-7-chloride-4-oxo-1,4-dihydro-1,8-napthyridine-3-carboxylic acid
Classification / Family Fluorinated building block, Heterocyclic building block, APIs, Antibiotics

Chemical Structure

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid chemical structure, CAS 100361-18-0
7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid chemical structure, CAS 100361-18-0

Product Details

Purity >98%
Melting Point Tm = 224 °C
Appearance Off-white powder

MSDS Documentation

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid MSDS Sheet7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid MSDS Sheet

Literature and Reviews

  1. 1,8-Naphthyridine derivatives: a review of multiple biological activities, A. Madaan et al., Arch. Pharm. Chem. Life Sci., 348, 837–860(2015); DOI: DOI 10.1002/ardp.201500237.
  2. 1,8-Naphthyridine revisited: applications dimetal chemistry, J. Bera et al., Eur. J. Inorg. Chem. 2009(27), 4023–4038(2009); DOI: 10.1002/ejic.200900312.
  3. 1,8-Naphthyridine-3-carboxamide derivatives with anticancer and anti-inflammatory activity, V. Kumar et al., Eur. J. Med. Chem., 44(8), 3356–3362(2009); DOI: 10.1016/j.ejmech.2009.03.015.

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