Abstract
Nα-Urocanylhistamine and two related compounds were synthesized by using PyBOP coupling protocols. These compounds represent naturally occurring histamine derivatives.
Highlights
Nα-Urocanylhistamine (1) was reported in 1973 as being naturally occurring in neogastropod mollusks [1]. It is one of several natural histamine derivatives known [2], little information exists about the possible role of this compound in the living systems where it is found
In the case of DCC, a reagent that has been previously used for the synthesis of amide derivatives of histamine [3], only an O→N-acyl rearrangement product and starting materials were present after 24 h
The coupling reagent PyBOP proves to be useful for the synthesis of amide derivatives of histamine providing good yields to purified products
Summary
Nα-Urocanylhistamine (1) was reported in 1973 as being naturally occurring in neogastropod mollusks [1] It is one of several natural histamine derivatives known [2], little information exists about the possible role of this compound in the living systems where it is found. We report the synthesis of 1-3, work that was initially undertaken as part of a project to discover new classes of histamine H2 receptor agonists. These compounds are structurally related to compounds that have proven to be useful in metal complexation [3] and non-enzymatic catalysis [4]
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