54997-91-0

Upstream product

• 2189-60-8 Octylbenzene 
• 6149-03-7 sodium p-(n-octyl)benzene sulphonate 
• 72978-95-1 8-chloro-octan-2-one 
• 71-43-2 benzene 

Downstream Products

• 4527-48-4 p-n-octylbenzenethiol 
• 1191951-80-0 4-octyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide 
• 1352144-06-9 (S)-3-(4'-octylbenzenesulfonylamino)-tetrahydropyridin-2-one 
• 1352144-05-8 (S)-3-(4'-octylbenzenesulfonylamino)-azepan-2-one 
• 1352144-07-0 (R)-(4'-octylbenzenesulfonylamino)-tetrahydropyridin-2-one 
• 54997-34-1 [2-(4-Octyl-phenylsulfanyl)-phenyl]-acetic acid 
• 54997-19-2 2-(4-Octyl-phenylsulfanyl)-benzoic acid 
• 54997-26-1 C₂₁H₂₇ClS 
• 54997-22-7 2-(4-n-Octylphenylthio)benzylalkohol 

Relevant academic research and scientific papers

Expanding the structural diversity of hydrophobic ionic liquids: physicochemical properties and toxicity of Gemini ionic liquids

Ionic liquids (ILs) have been labeled as a promising green alternative to traditional materials; however, many ILs have been discovered to be toxic, especially hydrophobic ILs (HILs). HILs are limited in their structural diversity as most are composed of heteroaromatic cations with long alkyl chains and paired with [BF4], [PF6], or [NTf2] anions. This study aims to diversify HILs by synthesizing two sets of HILs with unique cations and anions. The first set of HILs contain cholinium- and dicholinium-based cations paired with the [NTf2] anion. The [DC-ether] cation is identified as a promising cation and is paired with an array of asymmetric bis(sulfonyl)amide anions to form the second set of HILs. In total, twenty HILs are synthesized. Each HIL is characterized using traditional physicochemical techniques and is evaluted for toxicity usingin vitroandin vivomethods.

Synthesis and Biological Evaluation of Endocannabinoid Uptake Inhibitors Derived from WOBE437

WOBE437 ((2E,4E)-N-(3,4-dimethoxyphenethyl)dodeca-2,4-dienamide, 1) is a natural product-derived, highly potent inhibitor of endocannabinoid reuptake. In this study, we synthesized almost 80 analogues of 1 with different types of modifications in the dodecadienoyl domain as well as the dimethoxyphenylethyl head group, and we investigated their effects on anandamide uptake into U937 cells. Intriguingly, none of these analogues was a more potent inhibitor of anandamide uptake than WOBE437 (1). At the same time, a number of WOBE437 variants exhibited potencies in the sub-100 nM range, with high selectivity over inhibition of the endocannabinoid-degrading enzyme fatty acid amide hydrolase; two compounds were virtually equipotent with 1. Interestingly, profound activity differences were observed between analogues in which either of the two methoxy substituents in the head group had been replaced by the same bulkier alkoxy group. Some of the compounds described here could be interesting departure points for the development of potent endocannabinoid uptake inhibitors with more drug-like properties.

Effects of lipophilicity, protecting group and stereochemistry on the antimalarial activity of carbohydrate-derived thiochromans

A series of novel carbohydrate-derived thiochromans has been successfully synthesized in order to investigate the influence of alkyl substituents on the aromatic ring of the thiophenol moiety in addition to the effect of protecting groups and stereochemistry on the sugar component of the target molecules. Results from the evaluation of the thiochromans for their antimalarial activity against the chloroquine-sensitive (3D7) strain of Plasmodium falciparum suggest that the presence of short chain alkyl substituents, a benzyl ether protecting group and equatorial orientation of the C-4 substituent on the sugar moiety are crucial structural features that impart high antimalarial activity.

Development of sulfonamide AKT PH domain inhibitors

Disruption of the phosphatidylinositol 3-kinase/AKT signaling pathway can lead to apoptosis in cancer cells. Previously we identified a lead sulfonamide that selectively bound to the pleckstrin homology (PH) domain of AKT and induced apoptosis when present at low micromolar concentrations. To examine the effects of structural modification, a set of sulfonamides related to the lead compound was designed, synthesized, and tested for binding to the expressed PH domain of AKT using a surface plasmon resonance-based competitive binding assay. Cellular activity was determined by means of an assay for pAKT production and a cell killing assay using BxPC-3 cells. The most active compounds in the set are lipophilic and possess an aliphatic chain of the proper length. Results were interpreted with the aid of computational modeling. This paper represents the first structure-activity relationship (SAR) study of a large family of AKT PH domain inhibitors. Information obtained will be used in the design of the next generation of inhibitors of AKT PH domain function.

SMALL MOLECULE INHIBITORS OF THE PLECKSTRIN HOMOLOGY DOMAIN AND METHODS FOR USING SAME

Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein.