6938-27-8

Basic information

• Product Name: 5-nitro-1H-quinolin-2-one
• Synonyms: 5-nitro-1H-quinolin-2-one;5-nitroquinolin-2(1H)-one;5-Nitrocarbostyril;NSC 53940
• CAS NO: 6938-27-8
• Molecular Formula: C9H6N2O3
• Molecular Weight: 190.1555
• Mol File: 6938-27-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 245-247℃
• Boiling Point: 422.1 °C at 760 mmHg
• Flash Point: 209.1 °C
• Appearance: /
• Density: 1.419
• Vapor Pressure: 8.67E-07mmHg at 25°C
• Refractive Index: 1.589
• Solubility: Methanol, Ethyl Acetate
• CAS DataBase Reference: 5-nitro-1H-quinolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-nitro-1H-quinolin-2-one(6938-27-8)
• EPA Substance Registry System: 5-nitro-1H-quinolin-2-one(6938-27-8)

Safety Data

• Hazardous Substances Data: 6938-27-8(Hazardous Substances Data)

Usage

Description

5-Nitro-1H-quinolin-2-one is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and chemical compounds. It is characterized by its quinoline core structure, which is fused to a pyridine ring, and the presence of a nitro group at the 5-position. 5-nitro-1H-quinolin-2-one is known for its potential applications in medicinal chemistry, particularly in the development of new drugs and therapeutic agents.

Uses

Used in Pharmaceutical Industry:
5-Nitro-1H-quinolin-2-one is used as a synthetic intermediate for the preparation of novel antileishmanial agents targeting Leishmania donovani promastigotes. These agents are crucial in the development of treatments for leishmaniasis, a vector-borne disease caused by protozoan parasites of the genus Leishmania. 5-nitro-1H-quinolin-2-one's unique structure and properties make it a valuable building block in the synthesis of new drugs with potential therapeutic benefits.

InChI:InChI=1/C14H10ClNO3/c1-9-7-12(17)5-6-13(9)16-19-14(18)10-3-2-4-11(15)8-10/h2-8H,1H3

Upstream product

• 607-34-1 5-nitroquinoline 
• 13067-94-2 2-chloro-5-nitroquinoline 
• 116632-28-1 2-bromo-5-nitroquinoline 
• 91-22-5 quinoline 
• 612-62-4 2-Chloroquinoline 
• 2005-43-8 2-bromoquinoline 
• 59-31-4 2-hydroxyquinoline 
• 7613-19-6 5-nitro-quinoline-1-oxide 
• 1116137-62-2 2-chloro-5-nitro-1,2-dihydroquinoline 

Downstream Products

• 61317-32-6 5-amino-quinolin-2-ol 
• 13067-94-2 2-chloro-5-nitroquinoline 
• 77738-80-8 2-methoxy-5-nitroquinoline 
• 61317-32-6 5-aminoquinolin-2(1H)-one 
• 58130-38-4 5-amino-3,4-dihydro-1H-quinolin-2-one 
• 607377-99-1 2-chloro-5-aminoquinoline 

Relevant articles and documents

Discovery of Benzopyridone-Based Transient Receptor Potential Vanilloid 1 Agonists and Antagonists and the Structural Elucidation of Their Activity Shift

Among a series of benzopyridone-based scaffolds investigated as human transient receptor potential vanilloid 1 (TRPV1) ligands, two isomeric benzopyridone scaffolds demonstrated a consistent and distinctive functional profile in which 2-oxo-1,2-dihydroquinolin-5-yl analogues (e.g., 2) displayed high affinity and potent antagonism, whereas 1-oxo-1,2-dihydroisoquinolin-5-yl analogues (e.g., 3) showed full agonism with high potency. Our computational models provide insight into the agonist-antagonist boundary of the analogues suggesting that the Arg557 residue in the S4-S5 linker might be important for sensing the agonist binding and transmitting signals. These results provide structural insights into the TRPV1 and the protein-ligand interactions at a molecular level.

Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study

To study the antiparasitic 8-nitroquinolin-2(1H)-one pharmacophore, a series of 31 derivatives was synthesized in 1–5 steps and evaluated in vitro against both Leishmania infantum and Trypanosoma brucei brucei. In parallel, the reduction potential of all molecules was measured by cyclic voltammetry. Structure-activity relationships first indicated that antileishmanial activity depends on an intramolecular hydrogen bond (described by X-ray diffraction) between the lactam function and the nitro group, which is responsible for an important shift of the redox potential (+0.3 V in comparison with 8-nitroquinoline). With the assistance of computational chemistry, a set of derivatives presenting a large range of redox potentials (from ?1.1 to ?0.45 V) was designed and provided a list of suitable molecules to be synthesized and tested. This approach highlighted that, in this series, only substrates with a redox potential above ?0.6 V display activity toward L. infantum. Nevertheless, such relation between redox potentials and in vitro antiparasitic activities was not observed in T. b. brucei. Compound 22 is a new hit compound in the series, displaying both antileishmanial and antitrypanosomal activity along with a low cytotoxicity on the human HepG2 cell line. Compound 22 is selectively bioactivated by the type 1 nitroreductases (NTR1) of L. donovani and T. brucei brucei. Moreover, despite being mutagenic in the Ames test, as most of nitroaromatic derivatives, compound 22 was not genotoxic in the comet assay. Preliminary in vitro pharmacokinetic parameters were finally determined and pointed out a good in vitro microsomal stability (half-life > 40 min) and a 92% binding to human albumin.

Discovery of a new antileishmanial hit in 8-nitroquinoline series

A series of nitrated 2-substituted-quinolines was synthesized and evaluated in vitro toward Leishmania donovani promastigotes. In parallel, the in vitro cytotoxicity of these molecules was assessed on the murine J774 and human HepG2 cell lines. Thus, a very promising antileishmanial hit molecule was identified (compound 21), displaying an IC50 value of 6.6 μM and CC 50 values ≥ 100 μM, conferring quite good selectivity index to this molecule, in comparison with 3 drug-compounds of reference (amphotericin B, miltefosine and pentamidine). Compound 21 also appears as an efficient in vitro antileishmanial molecule against both Leishmania infantum promastigotes and the intracellular L. donovani amastigotes (respective IC50 = 7.6 and 6.5 μM). Moreover, hit quinoline 21 does not show neither significant antiplasmodial nor antitoxoplasmic in vitro activity and though, presents a selective antileishmanial activity. Finally, a structure-activity relationships study enabled to define precisely the antileishmanial pharmacophore based on this nitroquinoline scaffold: 2-hydroxy-8-nitroquinoline.