1190087-42-3

Basic information

• Product Name: 4-(n-hexyl)-N’-hydroxybenzimidamide
• Synonyms: 4-(n-hexyl)-N’-hydroxybenzimidamide
• CAS NO: 1190087-42-3
• Molecular Weight: 248.368
• Mol File: 1190087-42-3.mol

Chemical Properties

• CAS DataBase Reference: 4-(n-hexyl)-N’-hydroxybenzimidamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(n-hexyl)-N’-hydroxybenzimidamide(1190087-42-3)
• EPA Substance Registry System: 4-(n-hexyl)-N’-hydroxybenzimidamide(1190087-42-3)

Safety Data

• Hazardous Substances Data: 1190087-42-3(Hazardous Substances Data)

Upstream product

• 111-66-0 oct-1-ene 
• 3058-39-7 4-iodobenzonitrile 
• 60484-67-5 4-heptylbenzenecarbonitrile 

Downstream Products

• 1190087-43-4 C₂₇H₄₃N₃O₅ 
• 1215027-89-6 C₂₇H₄₃N₃O₅ 
• 1218817-68-5 (3-(4-heptylphenyl)-1,2,4-oxadiazol-5-yl)methyl ethanoate 
• 1449767-51-4 tert-butyl ((3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)methyl)carbamate 
• 1449767-48-9 (S)-tert-butyl (1-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-ethyl)carbamate 
• 1449767-45-6 (S)-tert-butyl (2-methyl-1-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)propyl)carbamate 
• 1449767-38-7 tert-butyl (1-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-cyclopropyl)carbamate 
• 1449767-55-8 (S)-tert-butyl 2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-pyrrolidine-1-carboxylate 
• 1449767-58-1 (R)-tert-butyl 2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-pyrrolidine-1-carboxylate 
• 1449767-92-3 (S)-tert-butyl 2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-azetidine-1-carboxylate 
• 1449768-01-7 (R)-tert-butyl 3-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-pyrrolidine-1-carboxylate 

Relevant articles and documents

Structure-activity relationship studies and in vivo activity of guanidine-based sphingosine kinase inhibitors: Discovery of SphK1- and SphK2-selective inhibitors

Sphingosine 1-phosphate (S1P) is a pleiotropic signaling molecule that acts as a ligand for five G-protein coupled receptors (S1P1-5) whose downstream effects are implicated in a variety of important pathologies including sickle cell disease, cancer, inflammation, and fibrosis. The synthesis of S1P is catalyzed by sphingosine kinase (SphK) isoforms 1 and 2, and hence, inhibitors of this phosphorylation step are pivotal in understanding the physiological functions of SphKs. To date, SphK1 and 2 inhibitors with the potency, selectivity, and in vivo stability necessary to determine the potential of these kinases as therapeutic targets are lacking. Herein, we report the design, synthesis, and structure-activity relationship studies of guanidine-based SphK inhibitors bearing an oxadiazole ring in the scaffold. Our studies demonstrate that SLP120701, a SphK2-selective inhibitor (Ki = 1 μM), decreases S1P levels in histiocytic lymphoma (U937) cells. Surprisingly, homologation with a single methylene unit between the oxadiazole and heterocyclic ring afforded a SphK1-selective inhibitor in SLP7111228 (Ki = 48 nM), which also decreased S1P levels in cultured U937 cells. In vivo application of both compounds, however, resulted in contrasting effect in circulating levels of S1P. Administration of SLP7111228 depressed blood S1P levels while SLP120701 increased levels of S1P. Taken together, these compounds provide an in vivo chemical toolkit to interrogate the effect of increasing or decreasing S1P levels and whether such a maneuver can have implications in disease states.

LONG CHAIN BASE SPHINGOSINE KINASE INHIBITORS

The invention relates to inhibitors of sphingosine kinase enzymatic activity, compounds and pharmaceutical compositions that inhibit sphingosine kinase 1 and sphingosine kinase 2 (SphK1 and SphK2) enzymes and further relates to methods of treating diseases and disorders mediated by sphingosine 1 phosphate activity, comprising administering an effective amount of sphingosine kinase inhibitors.

INHIBITORS OF SPHINGOSINE KINASE 1

The invention relates to compounds of Formula (I). Compounds of the present invention are inliibitors of sphingosine kinase 3, and are useful in the treatment of various disorders and conditions, such as inflammatory disorders

Synthesis and biological evaluation of sphingosine kinase substrates as sphingosine-1-phosphate receptor prodrugs

In the search for bioactive sphingosine 1-phosphate (S1P) receptor ligands, a series of 2-amino-2-heterocyclic-propanols were synthesized. These molecules were discovered to be substrates of human-sphingosine kinases 1 and 2 (SPHK1 and SPHK2). When phosphorylated, the resultant phosphates showed varied activities at the five sphingosine-1-phosphate (S1P) receptors (S1P1-5). Agonism at S1P1 was displayed in vivo by induction of lymphopenia. A stereochemical preference of the quaternary carbon was crucial for phosphorylation by the kinases and alters binding affinities at the S1P receptors. Oxazole and oxadiazole compounds are superior kinase substrates to FTY720, the prototypical prodrug immunomodulator, fingolimod (FTY720). The oxazole-derived structure was the most active for human SPHK2. Imidazole analogues were less active substrates for SPHKs, but more potent and selective agonists of the S1P1 receptor; additionally, the imidazole class of compounds rendered mice lymphopenic.