127472-41-7

Usage

General Description

1H-Indazole-3-carboxylic acid, 1-ethyl- is a chemical compound with the formula C11H10N2O2. It belongs to the indazole class of organic compounds and is characterized by its indazole ring structure and carboxylic acid functional group. 1H-Indazole-3-carboxylic acid, 1-ethyl- is commonly used in pharmaceutical research and drug development due to its potential pharmacological properties, such as anti-inflammatory and anticancer activities. It has shown promise in targeting specific biological pathways and has the potential to be used as a building block for the synthesis of novel drug candidates. Additionally, it has been studied for its potential application in the field of materials science, specifically in the development of novel polymers and materials with unique properties. Overall, 1H-Indazole-3-carboxylic acid, 1-ethyl- is a versatile compound with potential applications in both pharmaceutical and materials science research.

Upstream product

• 173599-97-8 methyl 1-ethyl-1H-indazole-3-carboxylate 
• 75-03-6 ethyl iodide 
• 4498-68-4 ethyl 1H-indazole-3-carboxylate 
• 43120-28-1 methyl 1H-indazole-3-carboxylate 
• 4498-67-3 1H-Indazole-3-carboxylic acid 

Downstream Products

• 129294-66-2 N-(1-benzyl-4-methylhexahydro-1H-1,4-diazepin-6-yl)-1-ethyl-1H-indazole-3-carboxamide 

Relevant academic research and scientific papers

Sulfocoumarin-, Coumarin-, 4-Sulfamoylphenyl-Bearing Indazole-3-carboxamide Hybrids: Synthesis and Selective Inhibition of Tumor-Associated Carbonic Anhydrase Isozymes IX and XII

A series of sulfocoumarin-, coumarin-, and 4-sulfamoylphenyl-bearing indazole-3-carboxamide hybrids were synthesized and investigated as inhibitors of the human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I and II (cytosolic isozymes), as well as hCA IX and XII (transmembrane, tumor-associated enzymes). Compounds 6 a–g (amide derivatives) and 7 a–h (triazoles) act as “prodrugs”, and their hydrolysis products are the de facto CA inhibitors. These compounds displayed sub-micromolar to high-nanomolar inhibitory activity against hCA isoforms IX and XII, which were recently validated as antitumor drug targets. Moreover, no inhibition of the off-target hCA I and II isoforms was observed. Compounds 8 a–f (another set of triazoles) exhibited nanomolar inhibition against hCA isoforms I, II, IX and XII, among which compounds 8 c, 8 d, and 8 f were found to inhibit the tumor-associated hypoxia-induced hCA isoform IX with Ki values of 1.8, 2.3, and 2.0 nm respectively. Further exploration of these compounds could be useful for the development of novel antitumor agents with selective mechanisms of CA inhibitory action.

Indazole derivatives having monocyclic amine

An indazole compound having the formula (I): wherein: R1 is hydrogen, C1 -C6 alkyl, C3 -C6 alkenyl or C3 -C6 cycloalkyl; Q is carbonyl, thiocarbonyl or methylene; and R2 is a group of the formula (II) or (IV); STR1 wherein R1 is C1 -C6 alkyl, C3 -C6 alkenyl or benzyl, of which a phenyl group thereof is optionally mono- or di-substituted by the same or different halogen or methoxy; m is 0 to 2; n and o is 1 or 2. The compound exhibits 5-HT4 receptor agonist activity.

Development of potent serotonin-3 (5-HT3) receptor antagonists. II. Structure-activity relationships of N-(1-benzyl-4-methylhexahydro-1H-1,4- diazepin-6-yl)carboxamides

Our studies on 4-amino-5-chloro-2-ethoxybenzamides led to the discovery that the N-(1,4-dimethylhexahydro-1H-1,4-diazepin-6-yl)benzamide 9 and the 1- benzyl-4-methylhexahydro-1H-1,4-diazepine analogue 10 are potent serotonin-3 (5-HT3) receptor antagonists. Structure-activity relationship (SAR) studies on the influence of the aromatic nucleus of 9 and 10 upon inhibition of the von Bezold-Jarisch reflex in rats are described. Heteroaromatic rings such as pyrrole, thiophene, furan, pyridine, pyridaziae, 1,2-benzisoxazole, indole, quinoline, and isoquinoline rings showed weak 5-HT3 receptor antagonistic activity. Within this series, use of the 1H-indazole ring as an aromatic moiety led to a substantial increase of the activity; the 1H- indazolylcarboxamides 54, 57, 97, and 102 showed potent 5-HT3 receptor antagonistic activity. The optimal compound identified via extensive SAR studies was N-(1-benzyl-4-methylhexahydro-1H-1,4-diazepin-6-yl)-1H-indazole- 3-carboxamide (54), whose effect was superior to that of the corresponding benzamide 10 and essentially equipotent to those of ondansetron (1) and granisetron (4).