Fumarranol

Fumarranol
Identifiers
	IUPAC name (1S,5S)-5-(hydroxymethyl)-1-methoxy-6-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]bicyclo[3.1.0]hexan-2-one;
CAS Number	912569-37-0;
PubChem CID	44416119;
Chemical and physical data
Formula	C16H24O4
Molar mass	280.364 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=CC[C@@H]1[C@@](O1)(C)C2[C@]3([C@@]2(C(=O)CC3)OC)CO)C;
	InChI InChI=1S/C16H24O4/c1-10(2)5-6-12-14(3,20-12)13-15(9-17)8-7-11(18)16(13,15)19-4/h5,12-13,17H,6-9H2,1-4H3/t12-,13?,14+,15-,16+/m1/s1; Key:CANZHCRPLGNWCR-LMINUHAASA-N;

Fumarranol is a drug which acts as an inhibitor of the type 2 methionine aminopeptidase enzyme METAP2. It was derived by structural modification of the natural product fumagillin. It was originally developed as an anti-angiogenesis drug for the treatment of cancer,^[1] but it was subsequently found to bind with high affinity to the METAP2 enzyme in malaria parasites and has been investigated as a potential treatment for malaria.^[2]^[3]

References

^ Lu J, Chong CR, Hu X, Liu JO (September 2006). "Fumarranol, a rearranged fumagillin analogue that inhibits angiogenesis in vivo". Journal of Medicinal Chemistry. 49 (19): 5645–8. doi:10.1021/jm060559v. PMID 16970390.
^ Chen X, Xie S, Bhat S, Kumar N, Shapiro TA, Liu JO (February 2009). "Fumagillin and fumarranol interact with P. falciparum methionine aminopeptidase 2 and inhibit malaria parasite growth in vitro and in vivo". Chemistry & Biology. 16 (2): 193–202. doi:10.1016/j.chembiol.2009.01.006. PMID 19246010.
^ Deu E (August 2017). "Proteases as antimalarial targets: strategies for genetic, chemical, and therapeutic validation". The FEBS Journal. 284 (16): 2604–2628. doi:10.1111/febs.14130. PMC 5575534. PMID 28599096.

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[1] Lu J, Chong CR, Hu X, Liu JO (September 2006). "Fumarranol, a rearranged fumagillin analogue that inhibits angiogenesis in vivo". Journal of Medicinal Chemistry. 49 (19): 5645–8. doi:10.1021/jm060559v. PMID 16970390.

[2] Chen X, Xie S, Bhat S, Kumar N, Shapiro TA, Liu JO (February 2009). "Fumagillin and fumarranol interact with P. falciparum methionine aminopeptidase 2 and inhibit malaria parasite growth in vitro and in vivo". Chemistry & Biology. 16 (2): 193–202. doi:10.1016/j.chembiol.2009.01.006. PMID 19246010.

[pmid28599096-3] Deu E (August 2017). "Proteases as antimalarial targets: strategies for genetic, chemical, and therapeutic validation". The FEBS Journal. 284 (16): 2604–2628. doi:10.1111/febs.14130. PMC 5575534. PMID 28599096.

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[2]

[3]

Identifiers

IUPAC name (1S,5S)-5-(hydroxymethyl)-1-methoxy-6-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]bicyclo[3.1.0]hexan-2-one
CAS Number	912569-37-0
PubChem CID	44416119
Chemical and physical data
Formula	C₁₆H₂₄O₄
Molar mass	280.364 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=CC[C@@H]1[C@@](O1)(C)C2[C@]3([C@@]2(C(=O)CC3)OC)CO)C
InChI InChI=1S/C16H24O4/c1-10(2)5-6-12-14(3,20-12)13-15(9-17)8-7-11(18)16(13,15)19-4/h5,12-13,17H,6-9H2,1-4H3/t12-,13?,14+,15-,16+/m1/s1 Key:CANZHCRPLGNWCR-LMINUHAASA-N

Fumarranol

See also

References