1398331-98-0

Basic information

• Product Name: 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutanol
• Synonyms: 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutanol
• CAS NO: 1398331-98-0
• Molecular Weight: 274.168
• Mol File: 1398331-98-0.mol

Chemical Properties

• CAS DataBase Reference: 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutanol(1398331-98-0)
• EPA Substance Registry System: 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutanol(1398331-98-0)

Safety Data

• Hazardous Substances Data: 1398331-98-0(Hazardous Substances Data)

Usage

Chemical class

Cyclobutanol compounds

Structural features

Contains a cyclobutanol ring and a phenyl group, with a dioxaborolane moiety attached to the phenyl ring

Common use

Organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds

Reagent in

Suzuki-Miyaura cross-coupling reaction

Applications

Synthesis of pharmaceuticals, agrochemicals, and materials

Potential

Development of new drugs and materials due to unique structural features and reactivity

Upstream product

• 19936-14-2 1-(4-bromophenyl)cyclobutan-1-ol 
• 73183-34-3 bis(pinacol)diborane 
• 589-87-7 1,4-bromoiodobenzene 
• 106-37-6 1.4-dibromobenzene 

Downstream Products

• 1467062-11-8 [4-(1-hydroxycyclobutyl)phenyl]boronic acid 
• 1467059-92-2 methyl 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate 
• 1467057-23-3 6-chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carboxylic acid 
• 1467059-95-5 6-fluoro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carbaldehyde 

Relevant articles and documents

Compound with AMPK agonistic activity and preparation and application of prodrug thereof

The invention relates to a compound with AMPK agonistic activity and a prodrug thereof, and as well as a preparation method and medical application of a prodrug thereof. The compound has the structure shown in the formula (I), and the prodrug of the compound has the structure shown in the formula (II), wherein each group and the substituent are as defined in the specification. The invention discloses a preparation method of the compound and application of the compound in prevention and treatment AMPK related diseases, and the AMPK related diseases include, but are not limited to, energy metabolism abnormality related diseases. Neurodegenerative diseases and inflammation-related diseases and the like.

Evolution of the Synthesis of AMPK Activators for the Treatment of Diabetic Nephropathy: From Three Preclinical Candidates to the Investigational New Drug PF-06409577

Indole acids 1, 2, and 3 are potent 5′-adenosine monophosphate-activated protein kinase (AMPK) activators for the potential treatment of diabetic nephropathy. Compounds 1-3 were scaled to supply material for preclinical studies, and indole 3 was selected for advancement to first-in-human clinical trials and scaled to kilogram quantities. The progression of the synthesis strategy for these AMPK activators is described, as routes were selected for efficient structure-activity relationship generation and then improved for larger scales. The developed sequences employed practical isolations of intermediates and APIs, reproducible cross-coupling, hydrolysis, and other transformations, and enhanced safety and purity profiles and led to the production of 40-50 g of 1 and 2 and 2.4 kg of 3. Multiple polymorphs of 3 were observed, and conditions for the reproducible formation of crystalline material suitable for clinical development were identified.

QUINOLINONE DERIVATIVES

The present invention relates to compounds of the formula (I), salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds as activators of AMPK.