856444
(+)-Griseofulvin
Synonym(s):
(2S)-trans-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro(benzofuran-2[3H],1′-[2]cyclohexene)-3,4′-dione, Griseofulvin
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About This Item
Empirical Formula (Hill Notation):
C17H17ClO6
CAS Number:
Molecular Weight:
352.77
UNSPSC Code:
12352103
EC Number:
204-767-4
Beilstein/REAXYS Number:
95226
MDL number:
SMILES string
COc1cc(OC)c2C(=O)[C@]3(Oc2c1Cl)[C@H](C)CC(=O)C=C3OC
optical activity
[α]17/D +370°, c = 1 in chloroform
mp
218-220 °C (lit.)
Features and Benefits
Antimitotic.
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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
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
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
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).
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
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