186413-77-4

Basic information

• Product Name: 6-chloro-2-isopropoxy-3-nitropyridine
• Synonyms: 6-chloro-2-isopropoxy-3-nitropyridine
• CAS NO: 186413-77-4
• Molecular Formula: C8H9ClN2O3
• Molecular Weight: 216.62
• Mol File: 186413-77-4.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: 6-chloro-2-isopropoxy-3-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-2-isopropoxy-3-nitropyridine(186413-77-4)
• EPA Substance Registry System: 6-chloro-2-isopropoxy-3-nitropyridine(186413-77-4)

Safety Data

• Hazardous Substances Data: 186413-77-4(Hazardous Substances Data)

Usage

Chemical Structure

nitro-pyridine derivative with a chlorine atom at the 6th position and an isopropoxy group at the 2nd position

Uses

Commonly used in pharmaceutical and agrochemical industries as a building block for synthesis of biologically active molecules
Potential antimicrobial and anti-inflammatory properties
Intermediate in production of pesticides, herbicides, and insecticides

Upstream product

• 16013-85-7 2,6-dicholoro-3-nitropyridine 
• 67-63-0 isopropyl alcohol 
• 75-30-9 2-iodo-propane 
• 27048-04-0 2-amino-6-chloro-3-nitropyridine 
• 92138-35-7 6-chloro-3-nitro-1H-pyridin-2-one 

Downstream Products

• 1373319-36-8 5-(5-(4-amino-3-isopropoxybenzamido)-6-isopropoxypicolinamido)-6-isopropoxypicolinic acid 
• 1373319-35-7 4-(5-(4-amino-3-isopropoxybenzamido)-6-isopropoxypicolinamido)-3-isopropoxybenzoic acid 
• 1373319-34-6 4-(5-(5-amino-6-isopropoxypicolinamido)-6-isopropoxypicolinamido)-3-isopropoxybenzoic acid 
• 1373319-33-5 4-(4-(5-amino-6-isopropoxypicolinamido)-3-isopropoxybenzamido)-3-isopropoxybenzoic acid 
• 1373319-48-2 methyl 5-(5-(4-amino-3-isopropoxybenzamido)-6-isopropoxypicolinamido)-6-isopropoxypicolinate 
• 1373319-47-1 methyl 4-(5-(4-amino-3-isopropoxybenzamido)-6-isopropoxypicolinamido)-3-isopropoxybenzoate 
• 1373319-46-0 methyl 4-(5-(5-amino-6-isopropoxypicolinamido)-6-isopropoxypicolinamido)-3-isopropoxybenzoate 
• 1373319-45-9 methyl 4-(4-(5-amino-6-isopropoxypicolinamido)-3-isopropoxybenzamido)-3-isopropoxybenzoate 
• 1373319-39-1 methyl 4-(5-amino-6-isopropoxypicolinamido)-3-isopropoxybenzoate 
• 1373319-44-8 methyl 6-isopropoxy-5-(6-isopropoxy-5-(3-isopropoxy-4-nitrobenzamido)picolinamido)picolinate 
• 1373319-43-7 methyl 3-isopropoxy-4-(6-isopropoxy-5-(3-isopropoxy-4-nitrobenzamido)picolinamido)benzoate 
• 1373319-42-6 methyl 3-isopropoxy-4-(6-isopropoxy-5-(6-isopropoxy-5-nitropicolinamido)picolinamido)benzoate 
• 1373319-41-5 methyl 3-isopropoxy-4-(3-isopropoxy-4-(6-isopropoxy-5-nitropicolinamido)benzamido)benzoate 
• 1373319-37-9 methyl 3-isopropoxy-4-(6-isopropoxy-5-nitropicolinamido)benzoate 

Relevant articles and documents

INDOLE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS

Provided herein are compounds of formula (V) that bind to BF3 of an androgen receptor (AR), which can modulate the AR for the treatment of Kennedy's disease.

Flupirtine and retigabine as templates for ligand-based drug design of KV7.2/3 activators

Drug induced liver injury (DILI) and tissue discoloration led to the recent discontinuation of the therapeutic use of the closely related drugs flupirtine and retigabine, respectively. Experience gained with these drugs strongly suggests that heterotetramer, voltage-gated potassium channels 2 and 3 (KV7.2/3) are valid targets for effective treatment of pain and epilepsy. Because the adverse effects are not related to the mechanism of action, it appears promising to investigate chemical modifications of these clinically validated, drug-like leads. In the present retro-metabolic drug design study, a series of 43 compounds were synthesized and characterized with regard to KV7.2/3 opening activity and efficacy. The most active compound 22d displays excellent potency (EC50 = 4 nM) and efficacy (154%) as a KV7.2/3 opener. Limited aqueous solubility hampered toxicity testing at concentrations higher than 63 μM, but this concentration was nontoxic to two hepatocellular cell lines (HEP-G2 and TAMH) in culture. The slightly less active but more soluble compound 25b (EC50 = 11 nM, efficacy 111%) showed an improved toxicity/activity ratio compared to flupirtine by three orders of magnitude and represents an attractive lead structure for the development of safer analgesics and antiepileptics.

Dual potent ALK and ROS1 inhibitors combating drug-resistant mutants: Synthesis and biological evaluation of aminopyridine-containing diarylaminopyrimidine derivatives

To identify ALK and ROS1 dual inhibitors conferring resistance to ALK secondary mutations, especially ‘gatekeeper’ L1196 M and the most predominant ceritinib-resistant G1202R mutations, a series of novel 2,4-diarylaminopyrimidine analogues were designed and synthesized by incorporating 2-alkoxy-6-alicyclic aminopyridinyl motifs. The biological evaluations on cellular and enzymatic assays led to identification of compound F-1, which turned out to be effective against ALKWT, ROS1WT, ALKL1196M and ALKG1202R kinases with IC50 of 2.1 nM, 2.3 nM, 1.3 nM and 3.9 nM, respectively, superior to crizotinib and ceritinib. Moreover, F-1 exhibited significant cytotoxicity on ALK-addicted Karpas299, H2228, and Ba/F3 cell expressing G1202R mutant, as well as ROS1-positive HCC78 cell with IC50 values ranging from 10 nM to 43 nM. Notably, F-1 was capable of suppressing phospho-ALK and its relative downstream signaling pathways, and eventually, inducing cell apoptosis in a dose-dependent manner in Karpas-299 cell. Together, F-1 is validated as a promising ALK/ROS1 dual inhibitor great potential for G1202R ALK mutation cancers.