114778-46-0

Basic information

• Product Name: 3-AMINOOXY-N-PROPYL (DIMETHYL-T-BUTYLSILYL) ETHER
• Synonyms: 3-AMINOOXY-N-PROPYL (DIMETHYL-T-BUTYLSILYL) ETHER
• CAS NO: 114778-46-0
• Molecular Formula: C₉H₂₃NO₂Si
• Molecular Weight: 205.37
• Mol File: 114778-46-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-AMINOOXY-N-PROPYL (DIMETHYL-T-BUTYLSILYL) ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINOOXY-N-PROPYL (DIMETHYL-T-BUTYLSILYL) ETHER(114778-46-0)
• EPA Substance Registry System: 3-AMINOOXY-N-PROPYL (DIMETHYL-T-BUTYLSILYL) ETHER(114778-46-0)

Safety Data

• Hazardous Substances Data: 114778-46-0(Hazardous Substances Data)

Upstream product

• 73842-99-6 3-tert-butyldimethylsilyloxy-1-propanol 
• 114778-45-9 N-<3-<(tert-butyldimethylsilyl)oxy>propoxy>phthalimide 

Downstream Products

• 391212-50-3 N-[3-(tert-Butyl-dimethyl-silanyloxy)-propoxy]-4-fluoro-2-(4-iodo-2-methyl-phenylamino)-benzamide 
• 848852-42-6 5-{[2-(tert-butyl-dimethyl-silanyloxy)-ethoxyimino]-methyl}-N-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzamide 

Relevant articles and documents

OXIM DERIVATIVES AS HSP90 INHIBITORS

The invention relates to HSP90 inhibiting compounds consisting of the formula: (I) wherein the variables are as defined herein. The invention also relates to pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using said compounds.

Synthesis and anti-HIV-1 activity of a series of 1-alkoxy-5-alkyl-6- (arylthio)uracils

A series of 1-alkoxy-5-alkyl-6-(arylthio)uracils was synthesized and tested for their ability to inhibit HIV-1 replication. Treatment of 2-alkyl- 3,3-bis(methylthio)acryloyl chlorides (5a-e) with AgOCN in benzene followed by reaction of the resulting isocyanates 6a-e with an appropriate alkoxyamine gave N-alkoxy-N'-((2-alkyl-3,3-bis(methylthio)acryloyl)ureas (10a-z) in good to excellent yields. Cyclization of 10a-z in AcOH containing a catalytic amount of p-TsOH produced 1-alkoxy-5-alkyl-6-(methylthio)uracils (11a-z). Oxidation of 11a-z with 3-chloroperoxybenzoic acid in CH2Cl2 resulted in high yields of 1-alkoxy-5-alkyl-6-(methylsulfonyl)uracils (12a-x and 12z) and 1-(benzyloxy)-6-(methylsulfinyl)thymine (12y), which were subsequently reacted with an appropriate arenethiol in ethanolic NaOH solution to afford 1-alkoxy-5-alkyl-6-(arylthio)uracils (14-49). Substitution at the 3- and 5- positions of the C-6-(phenylthio) ring by two methyl groups significantly increased its original anti-HIV-1 activity (EC50: 6-((3,5- dimethylphenyl)thio)-5-isopropyl-1-propoxyuracil (18), 0.064 μM; 6-((3,5- dimethylphenyl)thio)-1-(3-hydroxypropoxy)-5-isopropyluracil (23), 0.19 μM). Among the various alkoxy substituents at the N-1, the propoxy group was the most beneficial for improving the anti-HIV-1 activity. The 1-propoxy derivative 18 proved to be the most potent inhibitor of HIV-1 replication, followed by the 1-(3-hydroxypropoxy) derivative 23. Introduction of an isopropyl group at C-5 of the uracil base also remarkably enhanced the activity. When compound 18 was incubated with a rat liver homogenate preparation, no metabolite was observed, thus confirming the metabolic stability of the N-O bond in these 1-alkoxyuracils.