Quality Control of 1-Bromoundecane. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 1-Bromoundecane, is researched, Molecular C11H23Br, CAS is 693-67-4, about Probing the substitution pattern of indole-based scaffold reveals potent and selective sphingosine kinase 2 inhibitors. Author is Congdon, Molly; Fritzemeier, Russell G.; Kharel, Yugesh; Brown, Anne M.; Serbulea, Vlad; Bevan, David R.; Lynch, Kevin R.; Santos, Webster L..
Elevated levels of sphingosine 1-phosphate (S1P) and increased expression of sphingosine kinase isoforms (SphK1 and SphK2) have been implicated in a variety of disease states including cancer, inflammation, and autoimmunity. Selective inhibition of either SphK1 or SphK2 has been demonstrated to be effective in modulating S1P levels in animal models. Previously, authors reported a SphK2 naphthalene-based selective inhibitor, (R)-2-(3-(7-(pentyloxy)naphthalen-2-yl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide hydrochloride, which displays approx. 7-fold selectivity for hSphK2 over hSphK1 and has a SphK2 Ki value of 1.0μM. To improve SphK2 potency and selectivity, author’s designed, synthesized, and evaluated a series of indole-based compounds derived from (R)-2-(3-(7-(pentyloxy)naphthalen-2-yl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide hydrochloride. After investigating substitution patterns around the indole ring, author’s discovered that 1,5-disubstitution promoted optimal binding in the SphK2 substrate binding site and subsequent inhibition of enzymic activity. Author’s studies led to the identification of I (SphK2 Ki = 90 nM, >110 fold selective for SphK2 over SphK1). Mol. modeling studies revealed key nonpolar interactions with Val308, Phe548, His556, and Cys533 and hydrogen bonds with both Asp211 and Asp308 as responsible for the high SphK2 inhibition and selectivity.
In addition to the literature in the link below, there is a lot of literature about this compound(1-Bromoundecane)Quality Control of 1-Bromoundecane, illustrating the importance and wide applicability of this compound(693-67-4).
Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem