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A68203

Sigma-Aldrich

6-Aminonicotinamide

99%

Synonym(s):

6AN, 6-Aminopyridine-3-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C6H7N3O
CAS Number:
329-89-5
Molecular Weight:
137.14
Beilstein:
116042
EC Number:
206-349-7
MDL number:
MFCD00006327
UNSPSC Code:
12352100
PubChem Substance ID:
24891142
NACRES:
NA.22

Assay

99%

form

powder

mp

245-248 °C (lit.)

SMILES string

NC(=O)c1ccc(N)nc1

InChI

1S/C6H7N3O/c7-5-2-1-4(3-9-5)6(8)10/h1-3H,(H2,7,9)(H2,8,10)

InChI key

ZLWYEPMDOUQDBW-UHFFFAOYSA-N

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General description

6-Aminonicotinamide is an aminopyridine, which is a specific pentose inhibitor and thus inhibits the NADP production.

Application

6-Aminonicotinamide can be used as a reactant:
  • For the synthesis of 6-substituted imidazo[1,2-a]pyridines with potential application as chemotherapeutic drugs.
  • In the dehydrative N-monobenzylation.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360FD

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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L Poulain et al.
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Alterations in metabolic activities are cancer hallmarks that offer a wide range of new therapeutic opportunities. Here we decipher the interplay between mTORC1 activity and glucose metabolism in acute myeloid leukemia (AML). We show that mTORC1 signaling that is constantly
A borrowing hydrogen methodology: palladium-catalyzed dehydrative N-benzylation of 2-aminopyridines in water.
Hikawa H, et al.
Green Chemistry, 20(13), 3044-3049 (2018)
Jorge Domínguez-Andrés et al.
PLoS pathogens, 13(9), e1006632-e1006632 (2017-09-19)
Monocytes are innate immune cells that play a pivotal role in antifungal immunity, but little is known regarding the cellular metabolic events that regulate their function during infection. Using complementary transcriptomic and immunological studies in human primary monocytes, we show
6-Substituted imidazo [1, 2-a] pyridines: Synthesis and biological activity against colon cancer cell lines HT-29 and Caco-2.
Dahan-Farkas N, et al.
European Journal of Medicinal Chemistry, 46(9), 4573-4583 (2011)
Sachin A Gupte et al.
Journal of molecular and cellular cardiology, 41(2), 340-349 (2006-07-11)
In the failing heart, NADPH oxidase and uncoupled NO synthase utilize cytosolic NADPH to form superoxide. NADPH is supplied principally by the pentose phosphate pathway, whose rate-limiting enzyme is glucose 6-phosphate dehydrogenase (G6PD). Therefore, we hypothesized that cardiac G6PD activation
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