15462-45-0

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxyquinoline-2-carboxylic Acid is used as an intermediate in the chromophore biosynthesis of quinomycin family antibiotics. These antibiotics are known for their potent antimicrobial and antitumor activities, making them valuable in the development of new drugs to combat resistant infections and cancer.
Used in Chemical Synthesis:
3-Hydroxyquinoline-2-carboxylic Acid is also utilized in the total synthesis of Echinomycin and its analogs. Echinomycin is a potent antitumor agent that has shown significant promise in the treatment of various types of cancer. The synthesis of these compounds is crucial for the development of novel therapeutic agents to improve patient outcomes and address the growing need for effective cancer treatments.

Synthesis Reference(s)

Tetrahedron, 61, p. 1407, 2005 DOI: 10.1016/j.tet.2004.12.011

InChI:InChI=1/C10H7NO3/c12-8-5-6-3-1-2-4-7(6)11-9(8)10(13)14/h1-5,12H,(H,13,14)

Upstream product

• 124-38-9 carbon dioxide 
• 177202-79-8 3-(methoxymethoxy)quinoline 
• 14370-68-4 ethyl 3-hydroxyquinoline-2-carboxylate 
• 62235-59-0 ethyl 3-amino-2-quinolinecarboxylate 
• 552-89-6 2-nitro-benzaldehyde 
• 2922-83-0 L-kynurenine 
• 33925-79-0 3-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylic acid 
• 110429-24-8 3-(benzyloxy)quinoline-2-carboxylic acid 
• 529-23-7 o-aminobenzaldehyde 
• 580-18-7 3-hydroxyquinoline 
• 847547-93-7 3-(methoxymethoxy)-2-methylquinoline 
• 171917-54-7 Methyl 3-(benzyloxy)quinoline-2-carboxylate 

Downstream Products

• 100940-65-6 sandramycin 

Relevant academic research and scientific papers

Synthesis and Antiproliferative Activity Evaluation of the Disulfide-Containing Cyclic Peptide Thiochondrilline C and Derivatives

Thiochondrilline C (4) was previously isolated from Verrucisispora sp. and reported to have moderate cytotoxicity against human lung adenocarcinoma cells. Herein, we report the synthesis of thiochondrilline C by N-terminal peptide extension, oxidative disulfide bond formation, and heterocycle installation as key steps. Antiproliferative activities for the prepared natural product and several derivatives against the NCI 60 cancer cell line panel are also described. Derivative 22 was identified as a moderately potent antiproliferative agent (50% growth inhibition (GI50) = 0.2-12.2 μM) with leukemia (average GI50 = 1.8 ± 0.1 μM) and colon (average GI50 = 2.4 ± 0.3 μM) cells being most sensitive.

Involvement of common intermediate 3-hydroxy-L-kynurenine in chromophore biosynthesis of quinomycin family antibiotics

Quinomycin antibiotics, represented by echinomycin, are an important class of antitumor antibiotics. We have recently succeeded in identification of biosynthetic gene clusters of echinomycin and SW-163D, and have achieved heterologous production of echinomycin in Escherichia coli. In addition, we have engineered echinomycin non-ribosomal peptide synthetase to generate echinomycin derivatives. However, the biosynthetic pathways of intercalative chromophores quinoxaline-2-carboxylic acid (QXC) and 3-hydroxyquinaldic acid (HQA), which are important for biological activity, were not fully elucidated. Here, we report experiments involving incorporation of a putative advanced precursor, (2S, 3R)-6′- 2 H-3-hydroxy-L-kynurenine, and functional analysis of the enzymes Swb1 and Swb2 responsible for late-stage biosynthesis of HQA. On the basis of these experimental results, we propose biosynthetic pathways for both QXC and HQA through the common intermediate 3-hydroxy-L-kynurenine.

A new approach to 3-hydroxyquinoline-2-carboxylic acid

Quinoline-2-carboxylic acid derivatives cap the N-terminal of several natural cyclic peptides with antitumoral activity. A new and convenient route for the preparation of 3-hydroxyquinoline-2-carboxylic acid is discussed. The preparation of the title compound is accomplished by a four-step procedure from 3-hydroxyquinoline via MOM protection of the hydroxyl group, followed by a 1,2-addition of methyllithium to the quinoline ring with concomitant oxidation, and, finally, a two-step oxidation procedure for the transformation of the methyl group to the carboxylic acid along with removal of the MOM group. Furthermore, different attempts to its preparation led to other interesting quinolines, such as 2-chloro-3-hydroxyquinoline-4-carboxylic acid and a protected 3,3′-dihydroxy-2,2′-biquinoline.