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:
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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
Nasser S A M Khalil
European journal of medicinal chemistry, 42(9), 1193-1199 (2007-04-06)
First synthesis of N- and S-alpha-l-arabinopyranosyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles is described. Antimicrobial screening of two selected regioisomeric compounds against Aspergillus fumigatus, Penicillium italicum, Syncephalastrum racemosum, Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis and Escherichia coli are compared.
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
Vinod Mathew et al.
European journal of medicinal chemistry, 42(6), 823-840 (2007-03-03)
Several 3,6-disubstituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole and their dihydro analogues were synthesized from hetero aromatic acids and hetero aromatic aldehydes, respectively, by microwave-assisted dry media and conventional methods. Elemental analysis, IR, (1)H NMR, (13)C NMR and mass spectral data elucidated the structures of all
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
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