Irofulven - CAS 158440-71-2

Irofulven - CAS 158440-71-2 Catalog number: BADC-00330

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Irofulven is a semisynthetic sesquiterpene derivative of illudin S, a natural toxin isolated from the fungus Omphalotus illudens. Irofulven alkylates DNA and protein macromolecules, forms adducts, and arrests cells in the S-phase of the cell cycle.

General Information

Category
ADCs Cytotoxin
Product Name
Irofulven
CAS
158440-71-2
Catalog Number
BADC-00330
Molecular Formula
C15H18O3
Molecular Weight
246.12

Chemical Structure

  • Irofulven

Ordering Information

Catalog Number Size Price Stock Quantity
BADC-00330 5 mg $1490 In stock
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Purity
≥95%
Appearance
Soild powder
Synonyms
6-hydroxymethylacylfulvene; hydroxymethylacylfulvene; MGI 114; MGI-114; MGI114
Canonical SMILES
CC1=C(C2=C(C3(CC3)C(C(=O)C2=C1)(C)O)C)CO
InChI Key
NICJCIQSJJKZAH-AWEZNQCLSA-N
InChI
InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3/t14-/m0/s1
Current Developer
MGI PHARMA
1. Natural sesquiterpenoids
Braulio M. Fraga. Nat. Prod. Rep., 2004, 21, 669–693
A formal synthesis of7-protoilludene has been described. The distribution of ptaquiloside has been studied in four Danish bracken populations in order to evaluate the transfer of this carcinogenic sesquiterpene from ferns to the soil. An approach to the synthesis of pteridanone, the aglycone of the glucoside pteridanoside, has been reported. Studies on the structure–activity relationship of illudin analogues possessing a spiro-cyclobutane ring have been carried out. Illudin S has been identified as the sole antiviral compound present in an extract of mature fruiting bodies ofOmphalotus illudens. A library of forty-nine illudinoids has been preparedvia a three-step synthesis and tested against three cancer cell lines. The reaction of the antitumour agent irofulven with zinc and acetic acid led to a series of compounds, which present a more reduced toxicity to human leukaemia than irofulven. Synthetic studies towards the framework construction of the fomannosane sesquiterpene illudosin have been reported.
2. Recent advances in the use of temporary silicon tethers in metal-mediated reactions
Sonia Bracegirdle and Edward A. Anderson*. Chem. Soc. Rev.,2010,39, 4114–4129
Finally, an equally impressive example of enyne RCM in total synthesis is illustrated by the Movassaghi group’s preparation of (-)-acylfulvene (51, Scheme 10) and (-)-irofulven, two members of the cytotoxic illudin family. Preparation of the disiloxane52was readily achievedviaunion of an appropriate alkyne and aldehyde, followed by silylation. This substrate is designed with great care, as TST ring-closing enyne metathesis must be achieved in the presence of an additional ‘spectator’ trisubstituted alkene, and for this the phenyl substituent proved crucial as a protecting group. Thus, initiation of the cascade cyclisation at the mono-substituted alkene was followed by dienyne RCM, terminating on the 1,1-disubstituted alkene, which afforded the 7,6-bicycle53in an outstanding 79% yield; notably, the use of less bulky or non-conjugated blocking groups on the trisubstituted alkene led to competing metathesis side-reactions.

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