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372714

Sigma-Aldrich

2,6-Dimethoxypyridine-3-carboxylic acid

99%

Synonym(s):

2,6-Dimethoxynicotinic acid

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About This Item

Empirical Formula (Hill Notation):
C8H9NO4
CAS Number:
16727-43-8
Molecular Weight:
183.16
MDL number:
MFCD00075582
UNSPSC Code:
12352100
PubChem Substance ID:
24863158

assay

99%

mp

140-144 °C (lit.)

SMILES string

COc1ccc(C(O)=O)c(OC)n1

InChI

1S/C8H9NO4/c1-12-6-4-3-5(8(10)11)7(9-6)13-2/h3-4H,1-2H3,(H,10,11)

InChI key

SDJQZCSCHUIITF-UHFFFAOYSA-N

General description

2,6-Dimethoxypyridine-3-carboxylic acid (2,6-Dimethoxynicotinic acid, DMNIH) is a piperidine derivative. It forms various organotin(IV) complexes and their antiproliferative action against pancreatic carcinoma (PANC-1), erythroleukemia (K562), and two glioblastoma multiform (U87 and LN-229) human cell lines has been evaluated.

Application

2,6-Dimethoxypyridine-3-carboxylic acid (2,6-Dimethoxynicotinic acid, DMNIH) may be used in the preparation of the following organotin(IV) complexes (DMNIH=2,6-dimethoxynicotinic acid, BZDOH=1,4-benzodioxane-6-carboxylic acid, DMFUH=2,5-dimethyl-3-furoic acid and Cy=cyclohexyl):
  • [SnCy3-(DMNI)]
  • [SnCy3(BZDO)]
  • [SnCy3(DMFU)]
  • [SnPh2-(BZDO)2]
2,6-Dimethoxypyridine-3-carboxylic acid (2,6-dimethoxynicotinic acid, DMPH) may be used in the preparation of novel benzothiazolo naphthyridone carboxylic acid derivatives. It may be used in the preparation of following complexes, via reaction with different precursors [Ti(η5-C5H5)2Cl2], [Ti(η5-C5H4Me)2Cl2], [Ti(η5-C5H4SiMe3)(η5-C5H5)Cl2], [Ti(η5-C5Me5)Cl3], SnMe3Cl and GatBu3:
  • [Ti(η5-C5H5)2(DMP-κO)2]
  • [Ti(η5-C5H4Me)2(DMP-κO)2]
  • [Ti(η5-C5H4SiMe3)(η5-C5H5)(DMP-κO)2
  • [Ti(η5-C5Me5)(DMP-κ2O,O′)3]
  • [SnMe3(μ-DMP-κO:κO′)]∞
  • [GatBu2(μ-DMP-κO:κO′)]2

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Murugesan Dinakaran et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 63(1), 11-18 (2007-12-15)
Sixteen novel 3-nitro-2-(sub)-5,12-dihydro-5-oxobenzothiazolo[3,2-a]-1,8-naphthyridine-6-carboxylic acids were synthesized from 2,6-dimethoxynicotinic acid and 2-aminothiophenol and evaluated for their antitubercular activities in vitro and in vivo against Mycobacterium tuberculosis H(37) Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among the synthesized compounds, 2-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-3-nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]-1,8-naphthyridine-6-carboxylic acid
One ligand different metal complexes: Biological studies of titanium (IV), tin (IV) and gallium (III) derivatives with the 2, 6-dimethoxypyridine-3-carboxylato ligand.
Gomez-Ruiz S, et al.
Journal of Organometallic Chemistry, 696(20), 3206-3213 (2011)
Lourdes Rocamora-Reverte et al.
ChemMedChem, 7(2), 301-310 (2011-12-16)
A group of organotin(IV) complexes were prepared: [SnCy3 (DMNI)] (1), [SnCy3 (BZDO)] (2), [SnCy3 (DMFU)] (3), and [SnPh2 (BZDO)2 ] (4), for which DMNIH=2,6-dimethoxynicotinic acid, BZDOH=1,4-benzodioxane-6-carboxylic acid, and DMFUH=2,5-dimethyl-3-furoic acid. The cytotoxic activities of compounds 1-4 were tested against pancreatic

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