SNF-4435C

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Category Antibiotics
Catalog number BBF-02477
CAS
Molecular Weight 477.5
Molecular Formula C28H31NO6

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Description

SNF-4435C is a nitrophenyl pyrone isolated from the culture broth of an actinomycete strain SNF4435. It is active against staphylococcus, mycobacteria, Candida albicans and Pyricularia oryzae. It shows a potent immunosuppressive activity in vitro and selectively suppresses B-cell proliferation induced by LPS versus T-cell proliferation induced by Con A.

Specification

Synonyms SNF4435C
IUPAC Name 2-methoxy-3,5-dimethyl-6-[(1R,2'R,6S,7S,8R)-1,3,5-trimethyl-8-(4-nitrophenyl)spiro[bicyclo[4.2.0]octa-2,4-diene-7,4'-oxolane]-2'-yl]pyran-4-one
Canonical SMILES CC1=CC(=CC2(C1C3(C2C4=CC=C(C=C4)[N+](=O)[O-])CC(OC3)C5=C(C(=O)C(=C(O5)OC)C)C)C)C
InChI InChI=1S/C28H31NO6/c1-15-11-16(2)24-27(5,12-15)25(19-7-9-20(10-8-19)29(31)32)28(24)13-21(34-14-28)23-17(3)22(30)18(4)26(33-6)35-23/h7-12,21,24-25H,13-14H2,1-6H3/t21-,24+,25-,27-,28+/m1/s1
InChI Key DXCYJJKWPZZHNZ-PAWAVCGOSA-N

Properties

Appearance Pale Yellow Powder
Antibiotic Activity Spectrum Gram-positive bacteria; neoplastics (Tumor); mycobacteria

Reference Reading

1. Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1
Tatsuro Kawamura, Takahiro Fujimaki, Natsuki Hamanaka, Kentaro Torii, Hiroki Kobayashi, Yoshikazu Takahashi, Masayuki Igarashi, Naoko Kinoshita, Yoshio Nishimura, Etsu Tashiro, Masaya Imoto J Antibiot (Tokyo). 2010 Oct;63(10):601-5. doi: 10.1038/ja.2010.98. Epub 2010 Aug 25.
In the course of screening for a new type of androgen receptor (AR) antagonist, we isolated a novel compound, arabilin, with two structural isomers, spectinabilin and SNF4435C, produced by Streptomyces sp. MK756-CF1. Structure elucidation on the basis of the spectroscopic properties showed that arabilin is a novel polypropionate-derived metabolite with a p-nitrophenyl group and a substituted γ-pyrone ring. Arabilin competitively blocked the binding of androgen to the ligand-binding domain of AR in vitro. In addition, arabilin inhibited androgen-induced prostate-specific antigen mRNA expression in prostate cancer LNCaP cells.
2. Total synthesis of (-)-SNF4435 C and (+)-SNF4435 D
Christopher M Beaudry, Dirk Trauner Org Lett. 2005 Sep 29;7(20):4475-7. doi: 10.1021/ol051790q.
[reaction: see text] A convergent, biomimetic total synthesis of the immunosuppressant polyketides SNF4435 C and D is described. The synthetic pathway features a stereo- and regioselective [3,3]-sigmatropic rearrangement as well as a high-yielding Stille coupling/8pi-6pi electrocyclization cascade.
3. The total synthesis of spectinabilin and its biomimetic conversion to SNF4435C and SNF4435D
Mikkel F Jacobsen, John E Moses, Robert M Adlington, Jack E Baldwin Org Lett. 2005 Jun 9;7(12):2473-6. doi: 10.1021/ol0507874.
[reaction: see text] A short synthesis of (+/-)-spectinabilin via a trans-selective Suzuki coupling and subsequent Negishi-type methylation, and its biomimetic conversion to (+/-)-SNF4435C and (+/-)-SNF4435D is described.

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