91013-21-7

Basic information

• Product Name: Isonicotinic acid, 2-ethoxy-6-hydroxy-, ethyl ester (7CI)
• Synonyms: Isonicotinic acid, 2-ethoxy-6-hydroxy-, ethyl ester (7CI)
• CAS NO: 91013-21-7
• Molecular Formula: C10H13NO4
• Molecular Weight: 211.21452
• Product Categories: ETHOXY
• Mol File: 91013-21-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Isonicotinic acid, 2-ethoxy-6-hydroxy-, ethyl ester (7CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Isonicotinic acid, 2-ethoxy-6-hydroxy-, ethyl ester (7CI)(91013-21-7)
• EPA Substance Registry System: Isonicotinic acid, 2-ethoxy-6-hydroxy-, ethyl ester (7CI)(91013-21-7)

Safety Data

• Hazardous Substances Data: 91013-21-7(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 99-11-6 citrazinic acid 

Relevant articles and documents

Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology

Analogues of the anti-tuberculosis drug bedaquiline, bearing a 3,5-dimethoxy-4-pyridyl C-unit, retain high anti-bacterial potency yet exert less inhibition of the hERG potassium channel, in vitro, than the parent compound. Two of these analogues (TBAJ-587 and TBAJ-876) are now in preclinical development. The present study further explores structure-activity relationships across a range of related 3,5-disubstituted-4-pyridyl C-unit bedaquiline analogues of greatly varying lipophilicity (clogP from 8.16 to 1.89). This broader class shows similar properties to the 3,5-dimethoxy-4-pyridyl series, being substantially more potent in vitro and equally active in an in vivo (mouse) model than bedaquiline, while retaining a lower cardiovascular risk profile through greatly attenuated hERG inhibition.

Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles

Replacing the naphthalene C-unit of the anti-tuberculosis drug bedaquiline with a range of bicyclic heterocycles of widely differing lipophilicity gave analogs with a 4.5-fold range in clogP values. The biological results for these compounds indicate on average a lower clogP limit of about 5.0 in this series for retention of potent inhibitory activity (MIC90s) against M.tb in culture. Some of the compounds also showed a significant reduction in inhibition of hERG channel potassium current compared with bedaquiline, but there was no common structural feature that distinguished these.