Isonipecotamide

Chemical properties

WHITE TO LIGHT YELLOW CRYSTALLINE POWDER

The Uses of Isonipecotamide

Anesthetic, analgesic, antimicrobial and cooling agent for prevention or treatment of skin irritation.

The Uses of Isonipecotamide

Reactant for synthesis of:• ;Survival motor neuron (SMN) protein modulators1• ;Diaminotriazine hNav1.7 inhibitors2• ;Heteroalicyclic carboxamidines as inhibitors of inducible nitric oxide synthase3• ;Orally available naphthyridine protein kinase D inhibitors4• ;Phosphodiesterase 5 inhibitors5Reactant for identification of small molecular inhibitors of importin-β mediated nublear import6

The Uses of Isonipecotamide

Isonipecotamide is used as a reactant for the preparation of Survival motor neuron (SMN) protein modulators, orally available naphthyridine protein kinase D inhibitors and heteroalicyclic carboxamidines as inhibitors of inducible nitric oxide synthase. It is also used to prepare phosphodiesterase 5 inhibitors. It is also used as a reactant for identification of small molecular inhibitors of importin-beta mediated nuclear import. It is also used as a fluorenylmethyloxycarbonyl - deprotection agent in organic synthesis.

Definition

ChEBI: 4-Piperidine carboxamide is a piperidinecarboxamide.

What are the applications of Application

Isonipecotamide is an important substrate for organic synthesis reactions and can be used to prepare a wide range of inhibitors:
(1) Dual inhibitors of thrombin and cholinesterase with therapeutic potential for Alzheimer's disease^[1].
(2) 5-HT receptor inhibitors, based on Isonipecotamide synthesised piperidine carboxamide derivatives showing signs of decreasing 5-HT levels alone while increasing dopamine levels, with antidepressant drug effects^[2].
(3) Reversible inhibitors of coagulation factor Xa (fXa) and thrombin (thr) (cmpds 1-3), which have the ability to impede the infection of VERO cells with SARS-CoV-2, with cmpds3 showing a significant inhibitory effect on SARS-CoV-2 infection (~30%) at lower concentrations (3-50 μM)^[3].

References

[1] ROSA PURGATORIO. First-in-Class Isonipecotamide-Based Thrombin and Cholinesterase Dual Inhibitors with Potential for Alzheimer Disease.[J]. Molecules, 2021. DOI:10.3390/molecules26175208.
[2] SHAMIM AKHTAR. Behavioral and neurochemical profile of some novel phenacyl based isonipecotamide derivatives.[J]. Pakistan journal of pharmaceutical sciences, 2012.
[3] FLAVIO DE MAIO. Evaluation of Novel Guanidino-Containing Isonipecotamide Inhibitors of Blood Coagulation Factors against SARS-CoV-2 Virus Infection.[J]. Viruses-Basel, 2022. DOI:10.3390/v14081730.