529509-59-9

Basic information

• Product Name: 6,6-difluoro-1,4-bis[(4-methylbenzene)sulfonyl]-1,4-diazepane
• Synonyms: 6,6-difluoro-1,4-bis[(4-methylbenzene)sulfonyl]-1,4-diazepane
• CAS NO: 529509-59-9
• Molecular Weight: 444.523
• Mol File: 529509-59-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6,6-difluoro-1,4-bis[(4-methylbenzene)sulfonyl]-1,4-diazepane(CAS DataBase Reference)
• NIST Chemistry Reference: 6,6-difluoro-1,4-bis[(4-methylbenzene)sulfonyl]-1,4-diazepane(529509-59-9)
• EPA Substance Registry System: 6,6-difluoro-1,4-bis[(4-methylbenzene)sulfonyl]-1,4-diazepane(529509-59-9)

Safety Data

• Hazardous Substances Data: 529509-59-9(Hazardous Substances Data)

Upstream product

• 203722-04-7 1,4-bis(toluene-4-sulfonyl)-[1,4]diazepan-6-one 
• 28860-33-5 1,4-bis[(4-methylbenzene)sulfonyl]-1,4-diazepan-6-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 4403-78-5 ditosylethylenediamine 

Downstream Products

• 529509-58-8 6,6-difluoro-[1,4]diazepane 

Relevant articles and documents

Identification of 2,4-Disubstituted Imidazopyridines as Hemozoin Formation Inhibitors with Fast-Killing Kinetics and in Vivo Efficacy in the Plasmodium falciparum NSG Mouse Model

A series of 2,4-disubstituted imidazopyridines, originating from a SoftFocus Kinase library, was identified from a high throughput phenotypic screen against the human malaria parasite Plasmodium falciparum. Hit compounds showed moderate asexual blood stage activity. During lead optimization, several issues were flagged such as cross-resistance against the multidrug-resistant K1 strain, in vitro cytotoxicity, and cardiotoxicity and were addressed through structure-Activity and structure-property relationship studies. Pharmacokinetic properties were assessed in mice for compounds showing desirable in vitro activity, a selectivity window over cytotoxicity, and microsomal metabolic stability. Frontrunner compound 37 showed good exposure in mice combined with good in vitro activity against the malaria parasite, which translated into in vivo efficacy in the P. falciparum NOD-scid IL-2Rnull (NSG) mouse model. Preliminary mechanistic studies suggest inhibition of hemozoin formation as a contributing mode of action.

Synthesis of 6,6-difluorohomopiperazines via microwave-assisted detosylation

[1,4]-Diazepan-6-ols are easily oxidized to ketones using Swern or Dess-Martin oxidation conditions. The fluorination of these [1,4]-diazepanones with diethylaminosulfur trifluoride (DAST) affords gem-difluorohomopiperazines. Detosylation under microwave conditions represents a rapid method to access the corresponding amines in high yields.