534573-39-2

Usage

Molecular structure

1H-Indole-2-carboxamide, 1-[[5-(5-chloro-2-thienyl)-3-isoxazolyl]methyl]-N-[1-(1-methylethyl)-4-piperidinyl]is a complex organic compound with multiple functional groups and ring structures, including an indole core, an amide group, a piperidine ring, and a thienyl isoxazole moiety.

Indole core

The central structure of the compound is an indole, which is a bicyclic aromatic system with a benzene ring fused to a pyrrole ring.

Amide group

An amide group (-CONH2) is attached to the indole core, which is an important functional group that can participate in hydrogen bonding and coordinate with metal ions.

Piperidine ring

A piperidine ring (a six-membered nitrogen-containing heterocycle) is connected to the amide group. The presence of this ring contributes to the compound's structural complexity and may be involved in various non-covalent interactions.

Chlorine atom

A chlorine atom is present in the 5-position of the thienyl group, which may influence the compound's reactivity, polarity, and lipophilicity.

Isopropyl group

An isopropyl group (1-methylethyl) is part of the piperidine ring, adding to the structural complexity and potentially affecting the compound's solubility and interactions with biological targets.

Pharmacological or biological activities

Due to its intricate structure and the potential for interactions with biological targets, 1H-Indole-2-carboxamide, 1-[[5-(5-chloro-2-thienyl)-3-isoxazolyl]methyl]-N-[1-(1-methylethyl)-4-piperidinyl]may exhibit pharmacological or biological activities, making it a potential candidate for drug development or as a molecular probe in biological research.

Upstream product

• 754199-30-9 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-indole-2-carboxylic acid ethyl ester 
• 323594-71-4 ethyl 4-(5-chlorothiophen-2-yl)-2,4-dioxobutanoate 
• 323594-72-5 ethyl 5-(5-chlorothiophen-2-yl)isoxazole-3-carboxylate 
• 323594-73-6 (5-(5-chlorothiophen-2-yl)isoxazol-3-yl)methanol 
• 323594-39-4 3-(bromomethyl)-5-(5-chlorothiophen-2-yl)isoxazole 
• 73874-95-0 (piperidin-4-yl)carbamic acid tert-butyl ester 
• 6310-09-4 2-acetyl-5-chlorothiophene 
• 534595-41-0 1-[5-(5-chlorothiophen-2-yl)isoxazol-3-ylmethyl]-1H-indole-2-carboxylic acid methyl ester 
• 127285-08-9 4-amino-1-isopropylpiperidine 
• 534595-43-2 1-[5-(5-chlorothiophen-2-yl)isoxazol-3-ylmethyl]-1H-indole-2-carboxylic acid 
• 534595-37-4 (1-isopropylpiperidin-4-yl)carbamic acid tert-butyl ester 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 1477-50-5 Indole-2-carboxylic acid 

Relevant academic research and scientific papers

Probing the subpockets of factor Xa reveals two binding modes for inhibitors based on a 2-carboxyindole scaffold: A study combining structure-activity relationship and X-ray crystallography

Structure-activity relationships within a series of highly potent 2-carboxyindole-based factor Xa inhibitors incorporating a neutral P1 ligand are described with particular emphasis on the structural requirements for addressing subpockets of the factor Xa enzyme. Interactions with the subpockets were probed by systematic substitution of the 2-carboxyindole scaffold, in combination with privileged P1 and P4 substituents. Combining the most favorable substituents at the indole nucleus led to the discovery of a remarkably potent factor Xa inhibitor displaying a Ki value of 0.07 nM. X-ray crystallography of inhibitors bound to factor Xa revealed substituent-dependent switching of the inhibitor binding mode and provided a rationale for the SAR obtained. These results underscore the key role played by the P1 ligand not only in determining the binding affinity of the inhibitor by direct interaction but also in modifying the binding mode of the whole scaffold, resulting in a nonlinear SAR.

Factor Xa inhibitors based on a 2-carboxyindole scaffold: SAR of neutral P1 substituents

A series of novel, highly potent 2-carboxyindole-based factor Xa inhibitors is described. Structural requirements for neutral ligands, which bind in the S1 pocket of factor Xa were investigated with the 2-carboxyindole scaffold. This privileged fragment assembly approach yielded a set of equipotent, selective inhibitors with structurally diverse neutral P1 substituents.