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518654

Sigma-Aldrich

4-Amino-2-chloro-6,7-dimethoxyquinazoline

95%

Synonym(s):

2-Chloro-6,7-dimethoxy-4-quinazolinamine

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About This Item

Empirical Formula (Hill Notation):
C10H10ClN3O2
CAS Number:
23680-84-4
Molecular Weight:
239.66
Beilstein/REAXYS Number:
747463
EC Number:
245-821-7
MDL number:
MFCD00051734
UNSPSC Code:
12352100
PubChem Substance ID:
24874035
NACRES:
NA.22

Quality Level

100

assay

95%

mp

262-268 °C (dec.) (lit.)

SMILES string

COc1cc2nc(Cl)nc(N)c2cc1OC

InChI

1S/C10H10ClN3O2/c1-15-7-3-5-6(4-8(7)16-2)13-10(11)14-9(5)12/h3-4H,1-2H3,(H2,12,13,14)

InChI key

HWIIAAVGRHKSOJ-UHFFFAOYSA-N

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pictograms

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GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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S F Campbell et al.
Journal of medicinal chemistry, 30(10), 1794-1798 (1987-10-01)
A series of 4-amino-6,7-dimethoxy-2(4-heterocyclylpiperazin-1-yl)quinazolines (3) was prepared and screened for alpha-adrenoceptor affinity and antihypertensive activity. These quinazoline derivatives showed high binding affinity (ca. 10(-10) M) and selectivity (greater than 10,000) for alpha 1-adrenoceptors in vitro, with no relevant activity at
V A Alabaster et al.
Journal of medicinal chemistry, 30(6), 999-1003 (1987-06-01)
A series of 4-amino-2-(4-carbamoylpiperidino)-6,7-dimethoxyquinazolines (2) were synthesized and evaluated for alpha-adrenoceptor affinity and antihypertensive activity. These compounds displayed high binding affinity (Ki, 10(-9)-10(-10) M) and selectivity for alpha 1-adrenoceptors in vitro, and 12, 14, 21-26, and 29 showed similar potency
A Leonardi et al.
Journal of medicinal chemistry, 42(3), 427-437 (1999-02-13)
A new series of novel piperazine and non-piperazine derivatives of 2, 4-diamino-6,7-dimethoxyquinazoline was synthesized and evaluated for binding affinity toward alpha1-adrenergic and other G-protein-coupled aminergic receptors. The alpha1-adrenoceptor (AR) subtype selectivity was also investigated for the most interesting compounds. Only
D Giardinà et al.
Journal of medicinal chemistry, 39(23), 4602-4607 (1996-11-08)
The enantiomers of [4-(4-amino-6, 7-dimethoxyquinazolin-2-yl)-cis-octahydroquinoxalin-1-yl]-fu ran- 2-ylmethanone (cyclazosin, 1) were synthesized from the chiral furan-2-yl(cis-octahydroquinoxalin-1-yl)methanone [(+)-2 and (-)-2], which were obtained by resolution of the racemic amine with (S)-(+)- and (R)-(-)-mandelic acid. The binding profile of the enantiomers of 1

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