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Merck
CN

50872

Griseofulvin

from Penicillium griseofulvum, ≥95% (HPLC)

Synonym(s):

(2S)-trans-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro(benzofuran-2[3H],1′-[2]cyclohexene)-3,4′-dione

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About This Item

Empirical Formula (Hill Notation):
C17H17ClO6
CAS Number:
126-07-8
Molecular Weight:
352.77
EC Number:
204-767-4
UNSPSC Code:
12352200
MDL number:
MFCD00082343
Beilstein/REAXYS Number:
95226

Key Documents

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InChI

1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1

InChI key

DDUHZTYCFQRHIY-RBHXEPJQSA-N

SMILES string

ClC1=C(O[C@@]2(C(OC)=CC(C[C@H]2C)=O)C3=O)C3=C(OC)C=C1OC

biological source

Penicillium griseofulvum

assay

≥95% (HPLC)

optical activity

[α]20/D +355±5°, c = 1% in DMF(lit.)

mp

216-220 °C

antibiotic activity spectrum

fungi

storage temp.

−20°C

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pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Carc. 2 - Repr. 1B - Skin Sens. 1

Storage Class

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

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Nida N Farshori et al.
Bioorganic & medicinal chemistry letters, 20(6), 1933-1938 (2010-02-23)
The long-chain alkenoic acid hydrazides (1a-d) on reaction with phenylisocyanate and phenylthiocyanate gave their corresponding semicarbazides (2a-d) and thiosemicarbazides (4a-d), which on further refluxing with POCl(3) and Ac(2)O yielded corresponding 1,3,4-oxadiazoles (3a-d) and thiadiazoles (5a-d), respectively. The structure elucidation of
Mads H Rønnest et al.
Journal of medicinal chemistry, 52(10), 3342-3347 (2009-05-01)
Griseofulvin was identified as an inhibitor of centrosomal clustering in a recently developed assay. Centrosomal clustering is an important cellular event that enables bipolar mitosis for cancer cell lines harboring supernumerary centrosomes. We report herein the synthesis and SAR of
Hatem A Abdel-Aziz et al.
European journal of medicinal chemistry, 44(12), 4985-4997 (2009-09-29)
The reaction of 2-oxo-N-arylpropanehydrazonoyl chlorides 3a-e with 3-methyl-2-benzofurancarboxylic acid hydrazide (7) furnished N-(aryl)propanehydrazonoyl chlorides 8a-e. X-Ray of 8c revealed the (1Z,2E) configuration of structure 8. Nucleophilic substitution reaction of 8a or 8d with piperidine resulted in the formation of 1-(piperidin-1-yl)-N(2)-arylamidrazones
Mari Sithambaram Karthikeyan et al.
European journal of medicinal chemistry, 43(1), 25-31 (2007-05-25)
A series of 2,4-dichloro-5-fluorophenyl containing 1,3,4-oxadiazoles (10 and 11) were synthesized by POCl3 cyclization of 2,4-dichloro-5-fluorobenzoyl hydrazide (4) and 2-(2,4-dichloro-5-fluorophenyl)cinchoninyl hydrazide (8) with aryloxyacetic acids (9). The structures of newly synthesized compounds were characterized by spectral and elemental analyses. All
Paul Klausmeyer et al.
Journal of natural products, 68(8), 1300-1302 (2005-08-30)
Dereplication of the antifungal extracts of Aspergillus flavus indicated that the primary antifungal compound present was the known aspirochlorine (1). Preparative isolation work resulted in the identification of the new compounds tetrathioaspirochlorine (2) and cyclo(D-N-methyl-Leu-L-Trp) (3).
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