70972-99-5

Upstream product

• 4885-02-3 Dichloromethyl methyl ether 
• 104-72-3 decylbenzene 
• 578027-26-6 4-dec-1-ynylbenzaldehyde 
• 108-48-5 2,6-dimethylpyridine 
• 54256-43-8 4-decylbenzoyl chloride 
• 82532-71-6 methyl p-n-decylbenzoate 
• 7408-29-9 4-decylphenylmethanol 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 202259-08-3 9-decyl-9-borabicyclo[3.3.1]nonane 
• 872-05-9 1-Decene 
• 1122-91-4 4-bromo-benzaldehyde 
• 764-93-2 1-decyne 
• 100-97-0 hexamethylenetetramine 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 110683-37-9 p-decylcinnamic acid 
• 38300-04-8 4-decylbenzoic acid 
• 7408-29-9 4-decylphenylmethanol 
• 918500-17-1 (4-allylphenyl)-(4-decylphenyl)-methanol 
• 864447-23-4 C₈₈H₉₂Cl₂N₈O₂₈ 
• 1353054-46-2 (4-decylphenyl)(4-(2-(triisopropylsilyloxy)ethyl)phenyl)methanol 
• 1353054-41-7 2-(4-((4-decylphenyl)(hydroxy)methyl)phenyl)ethanol 
• 1353054-50-8 (S)-2-(tert-butoxycarbonylamino)-3-(2-(4-(4-decylbenzoyl)phenyl)acetamido)propanoic acid 
• 1353054-51-9 (S)-tert-butyl 3-(2-(4-(4-decylbenzoyl)phenyl)acetamido)-1-(hexadecylamino)-1-oxo-propan-2-ylcarbamate 
• 1353054-52-0 (S)-2-amino-3-(2-(4-(4-decylbenzoyl)phenyl)acetamido)-N-hexadecylpropanamide 
• 1353054-45-1 C₃₀H₄₄O₃ 
• 1449766-09-9 (E)-methyl 3-(4-decylphenyl)acrylate 
• 1449766-10-2 (E)-3-(4-decylphenyl)prop-2-en-1-ol 
• 1449766-11-3 (E)-4-(4-decylphenyl)but-3-enenitrile 

Relevant academic research and scientific papers

Lipophilic tail modifications of 2-(hydroxymethyl)pyrrolidine scaffold reveal dual sphingosine kinase 1 and 2 inhibitors

The sphingosine 1-phosphate (S1P) signaling pathway is an attractive target for pharmacological manipulation due to its involvement in cancer progression and immune cell chemotaxis. The synthesis of S1P is catalyzed by the action of sphingosine kinase 1 or 2 (SphK1 or SphK2) on sphingosine and ATP. While potent and selective inhibitors of SphK1 or SphK2 have been reported, development of potent dual SphK1/SphK2 inhibitors are still needed. Towards this end, we report the structure–activity relationship profiling of 2-(hydroxymethyl)pyrrolidine-based inhibitors with 22d being the most potent dual SphK1/SphK2 inhibitor (SphK1 Ki = 0.679 μM, SphK2 Ki = 0.951 μM) reported in this series. 22d inhibited the growth of engineered Saccharomyces cerevisiae and decreased S1P levels in histiocytic lymphoma myeloid cell line (U937 cells), demonstrating inhibition of SphK1 and 2 in vitro. Molecular modeling studies of 22d docked inside the Sph binding pocket of both SphK1 and SphK2 indicate essential hydrogen bond between the 2-(hydroxymethyl)pyrrolidine head to interact with aspartic acid and serine residues near the ATP binding pocket, which provide the basis for dual inhibition. In addition, the dodecyl tail adopts a “J-shape” conformation found in crystal structure of sphingosine bound to SphK1. Collectively, these studies provide insight into the intermolecular interactions in the SphK1 and 2 active sites to achieve maximal dual inhibitory activity.

Benzophenone-containing fatty acids and their related photosensitive fluorescent new probes: Design, physico-chemical properties and preliminary functional investigations

Hydrophobic photoaffinity labeling is a powerful strategy to identify hydrophobic segments within molecules, in particular membrane proteins. Here we report the design and synthesis of a novel family of fluorescent and photosensitive lipid tools, which have a common amino acid scaffold functionalized by three groups: (i) a first fatty acid chain grafted with a photoactivatable benzophenone moiety (Fatty Acid BenzoPhenone, FABP), (ii) a second fatty acid chain to ensure anchoring into a half-bilayer or hydrophobic environment, and (iii) a fluorescent carboxytetramethylrhodamine headgroup (CTMR) to detect the photolabeled compound. We present data of the synthesis and characterization of three lipid tools whose benzophenone ring is situated at various distances from the central scaffold. We could therefore establish structure/properties relationships dependent upon the depth of insertion of benzophenone into the membrane. Our lipid tools were extensively characterized both physico- and bio-chemically, and we assessed their functionality in vitro using bacterioRhodopsin (bR). We thus provide the scientific community with novel and reliable tools for the identification and study of hydrophobic regions in proteins.

Synthesis of benzophenone-containing fatty acids

(Chemical Equation Presented) Syntheses of new benzophenone-containing fatty acids (FABPs) 1, 5, and 6 and a new route to FABP 3 are described. Combined with the known 2 and 4, these FABPs comprise a set of photoactivatable fatty acid analogues with the crosslinking site at defined distances from the carboxylic acid hydroxyl group oxygen atoms ranging from 7.9 to 25.0 A.

Synthesis and immunosuppressive activity of 2-substituted 2- aminopropane-1,3-diols and 2-aminoethanols

A series of 2-substituted 2-aminopropane-1,3-diols was synthesized and evaluated for their lymphocyte-decreasing effect and immunosuppressive effect on rat skin allograft. A phenyl ring was introduced into the alkyl chain of the lead compound 3, which is an immunosuppressive agent structurally simplified from myriocin (1, ISP-I) via compound 2. The potency of the various compounds was dependent upon the position of the phenyl ring within the alkyl side chain. The most suitable length between the quaternary carbon atom and the phenyl ring was two carbon atoms. 2-Substituted 2-aminoethanols were successively synthesized and evaluated for their T-cell-decreasing effect and immunosuppressive effect using a popliteal lymph node gain assay in rats. The absolute configuration at the quaternary carbon affected the activity, and the (pro-S)-hydroxymethyl group of compound 6 was essential for potent immunosuppressive activity. Favorable substituents for the (pro-R)- hydroxymethyl group of 6 were hydroxyalkyl (hydroxyethyl and hydroxypropyl) or lower alkyl (methyl and ethyl) groups. 2-Amino-2-[2-(4- octylphenyl)ethyl]propane-1,3-diol hydrochloride (6, FTY720) was found to possess considerable activity and is expected to be useful as an immunosuppressive drug for organ transplantation.

Phenyl acetylenic acetals

Phenyl acetylenic acetals and thioacetals and their use in the treatment of allergy, asthma, inflammation, arthritis, hyperproliferative skin disease, psoriasis or contact dermatitis are disclosed. Also disclosed are intermediates useful for producing sai

New potent antagonists of leukotrienes C4 and D4. 1. Synthesis and structure-activity relationships

(p-Amylcinnamoyl)anthranilic acid (3a) had moderate antagonist activities against LTD4-induced smooth muscle contraction on guinea pig ileum and LTC4-induced bronchoconstriction in anesthetized guinea pigs. Modifications were made in the hydrophobic part (cinnamoyl moiety) and the hydrophilic part (anthranilate moiety) of 3a. A series of 8-(benzoylamino)-2-tetrazol-5-yl-1,4-benzodioxans and 8-(benzoylamino)-2-tetrazol-5-yl-4-oxo-4H-1-benzopyrans were revealed to be potent antagonists of leukotrienes C4 and D4. Among both series, ONO-RS-347 (18k) and ONO-RS411 (19h) were the most potent and orally active antagonists, respectively. Structure-activity relationships are discussed.

Synthesis of Unbranched 4-Alkylbenzaldehydes

The preparation of unbranched 4-alkylbenzaldehydes free of positional and branched-chain isomers by different methods is described.A one-step preparation of the aldehydes is reported which involves the direct hydrogenation of a Friedel-Craft's complex in the presence of Pd/C catalyst.