Magnesium → HCID 15632080, compound

HRID 48904Notes

Reaction equation

HRID 48904 reaction equation
C1([C:11]2[CH:12]=[CH:13][N:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[C:16]([C:21]([OH:23])=[O:22])[C:15]3=[O:24])C2C(=CC=CC=2)C=CC=1.O1C(C2C=CN3C(C=2)=CC=C(C(O)=O)C3=O)=CC2C=CC=CC1=2.[Mg]>>[O:24]=[C:15]1[N:14]2[C:19]([CH:20]=[CH:11][CH:12]=[CH:13]2)=[CH:18][CH:17]=[C:16]1[C:21]([OH:23])=[O:22]

Participants

4

Reactant 3

HCID 5462224MagnesiumHCID 98795398-(benzo[b]furyl)-4-oxo-4H-quinolizine-3-carboxylic acidHCID 99014398-(naphth-1-yl)-4-oxo-4H-quinolizine-3-carboxylic acid

Product 1

HCID 15632080HCID 15632080, compound

Procedure

Fluorophores [6,7]-benzo-4-oxo-4H-quinolizine-3-carboxylic acid (3a) (FIG. 16), 1-[N,N-di(carboxymethyl)]-4-oxo-4H-quinolizine-3-carboxylic acid (11a) (FIG. 17), 8-(naphth-1-yl)-4-oxo-4H-quinolizine-3-carboxylic acid (23a) and 8-(benzo[b]furyl)-4-oxo-4H-quinolizine-3-carboxylic acid (24a), show an increase of the fluorescence emission when binding to Mg2+, and are sensitive to changing Mg2+ levels. The triacid 1-[N,N-di(carboxymethyl)]-4-oxo-4H-quinolizine-3-carboxylic acid (11a) exhibits a fluorescence maximum at 552 nm, making this compound an attractive fluorescent magnesium indicator. The presence of the amino group at the 1-position gave a hypsochromic shift of 117 nm with respect to 4-oxo-4H-quinolizine-3-carboxylic acid (1a). The introduction of an aromatic moiety at the 8-position (e.g., 8-(4-methoxyphenyl)-4-oxo-4H-quinolizine-3-carboxylic acid [22a]; 8-(naphth-1-yl)-4-oxo-4H-quinolizine-3-carboxylic acid [23a]; and 8-(benzo[b]furyl)-4-oxo-4H-quinolizine-3-carboxylic acid [24a]), or extension of the 7-system as in [6,7]-benzo-4-oxo-4H-quinolizine-3-carboxylic acid (3a) are believed to result in a hypsochromic shift to longer wavelengths, although it is not necessary to understand the mechanism in order to practice the present invention and it is not intended that the present invention be so limited. However, the hypsochromic shifts of these compounds are smaller in comparison to the hypsochromic shift exhibited by 1-[N,N-di(carboxymethyl)]-4-oxo-4H-quinolizine-3-carboxylic acid (11a).

Workup

  1. temperaturean increase of the fluorescence emission when binding to Mg2+

Sources & evidence

ORD record
ord-d38677251dc040b68267a1a46ff41261
Source dataset
uspto-grants-2004_03
Patent number
US06706528B2

Reaction notes

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