Rocaglamide: Difference between revisions

Rocaglamide
Names
	IUPAC name (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
Identifiers
CAS Number	84573-16-0;
3D model (JSmol)	Interactive image;
ChemSpider	293974;
PubChem CID	331783;
CompTox Dashboard (EPA)	DTXSID101004852 ;
	InChI InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1 Key: DAPAQENNNINUPW-IDAMAFBJSA-N; InChI=1/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1 Key: DAPAQENNNINUPW-IDAMAFBJBD;
	SMILES CN(C)C(=O)[C@@H]1[C@H]([C@]2([C@@]([C@@H]1O)(C3=C(C=C(C=C3O2)OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5;
Properties
Chemical formula	C29H31NO7
Molar mass	505.6 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Revision as of 14:33, 17 April 2012

Rocaglamide is an anticancer natural product, which belongs to a class of molecules called flavaglines.^[1]^[2] This compound was isolated in 1982 by King and colleagues based on its antileukemic activity.^[3] Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities.

Rocaglamide was first synthesized by Barry Trost in 1990.^[4] Although other syntheses have been described since, Trost’s remains the only one to afford rocaglamide in an enantio-specific manner.

References

^ Ebada SS, Lajkiewicz N, Porco JA, Li-Weber M, Proksch P (2011). "Chemistry and biology of rocaglamides (= flavaglines) and related derivatives from aglaia species (meliaceae)". Fortschr Chem Org Naturst. 94: 1–58. doi:10.1007/978-3-7091-0748-5_1. PMID 21833837.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Ribeiro N, Thuaud F, Nebigil C, Désaubry L (2012). "Recent advances in the biology and chemistry of the flavaglines". Bioorg. Med. Chem. 20 (6): 1857–64. doi:10.1016/j.bmc.2011.10.048. PMID 22071525. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ King M.L., Chiang C.C., Ling H.C., Fujita E., Ochiai M., McPhail A.T. (1992). "X-Ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from Aglaia elliptifolia". Chem. Commun.: 1150–1.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Trost, B.M., Greenspan, P.D., Yang, B.V., Saulnier M.G. (1990). "An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (-)-rocaglamide". J. Am. Chem. Soc. 112 (24): 9022–4. doi:10.1021/ja00180a081. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

[1] Ebada SS, Lajkiewicz N, Porco JA, Li-Weber M, Proksch P (2011). "Chemistry and biology of rocaglamides (= flavaglines) and related derivatives from aglaia species (meliaceae)". Fortschr Chem Org Naturst. 94: 1–58. doi:10.1007/978-3-7091-0748-5_1. PMID 21833837.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[2] Ribeiro N, Thuaud F, Nebigil C, Désaubry L (2012). "Recent advances in the biology and chemistry of the flavaglines". Bioorg. Med. Chem. 20 (6): 1857–64. doi:10.1016/j.bmc.2011.10.048. PMID 22071525. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[3] King M.L., Chiang C.C., Ling H.C., Fujita E., Ochiai M., McPhail A.T. (1992). "X-Ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from Aglaia elliptifolia". Chem. Commun.: 1150–1.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[4] Trost, B.M., Greenspan, P.D., Yang, B.V., Saulnier M.G. (1990). "An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (-)-rocaglamide". J. Am. Chem. Soc. 112 (24): 9022–4. doi:10.1021/ja00180a081. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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@@ Line 21: / Line 21: @@
 }}
 | Section2 = {{Chembox Properties
+|  C=29 |H=31 |N=1 |O=7
-|  Formula =C<sub>29</sub>H<sub>31</sub>NO<sub>7</sub>
 |  MolarMass =505.6 g/mol
 |  Appearance =
@@ Line 34: / Line 34: @@
 }}
-'''Rocaglamide''' is an [[anticarcinogen|anticancer]] natural product, which belongs to a class of molecules called [[flavaglines]].<ref>Ebada S.S., Lajkiewicz N., Porco J.A. Jr, Li-Weber M., Proksch P. Chemistry and biology of rocaglamides (= flavaglines) and related derivatives from aglaia species (meliaceae). Fortschr Chem. Org. Naturst. 94:1-58 (2011).</ref><ref>Ribeiro N., Thuaud F., Nebigil C., Désaubry L. Recent advances in the biology and chemistry of the flavaglines. Bioorg. Med. Chem. Lett. 21 (in press, 2012).</ref> This compound was isolated in 1982 by King and colleagues based on its antileukemic activity.<ref>King M. L., Chiang C. C., Ling H. C., Fujita E., Ochiai M., McPhail A. T. X-Ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from Aglaia elliptifolia. Chem. Commun. 1150-51 (1992).</ref>  Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities.
+'''Rocaglamide''' is an [[anticarcinogen|anticancer]] natural product, which belongs to a class of molecules called [[flavaglines]].<ref>{{cite journal |author=Ebada SS, Lajkiewicz N, Porco JA, Li-Weber M, Proksch P |title=Chemistry and biology of rocaglamides (&#61; flavaglines) and related derivatives from aglaia species (meliaceae) |journal=Fortschr Chem Org Naturst |volume=94 |issue= |pages=1–58 |year=2011 |pmid=21833837 |doi=10.1007/978-3-7091-0748-5_1 }}</ref><ref>{{cite journal |author=Ribeiro N, Thuaud F, Nebigil C, Désaubry L |title=Recent advances in the biology and chemistry of the flavaglines |journal=Bioorg. Med. Chem. |volume=20 |issue=6 |pages=1857–64 |year=2012 |month=March |pmid=22071525 |doi=10.1016/j.bmc.2011.10.048 |url=http://linkinghub.elsevier.com/retrieve/pii/S0968-0896(11)00857-1}}</ref> This compound was isolated in 1982 by King and colleagues based on its antileukemic activity.<ref>{{cite journal |author=King M.L., Chiang C.C., Ling H.C., Fujita E., Ochiai M., McPhail A.T. |title=X-Ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from ''Aglaia elliptifolia'' |journal=Chem. Commun. |volume= |issue= |pages=1150–1 |year=1992 }}</ref>  Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities.
-Rocaglamide was first synthesized by [[Barry Trost]] in 1990.<ref>Trost, B. M., Greenspan, P. D., Yang, B. V., Saulnier  M. G. An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (-)-rocaglamide. J. Am. Chem. Soc. 112, 9022-4 (1990).</ref> Although other syntheses have been described since, Trost’s remains the only one to afford rocaglamide in an [[enantiomer|enantio-specific]] manner.
+Rocaglamide was first synthesized by [[Barry Trost]] in 1990.<ref>{{cite journal |author=Trost, B.M., Greenspan, P.D., Yang, B.V., Saulnier  M.G. |title=An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (-)-rocaglamide |journal=J. Am. Chem. Soc. |volume=112 |issue=24 |pages=9022–4 |year=1990 |month=November |doi=10.1021/ja00180a081 |url=http://pubs.acs.org/doi/abs/10.1021/ja00180a081}}</ref> Although other syntheses have been described since, Trost’s remains the only one to afford rocaglamide in an [[enantiomer|enantio-specific]] manner.
 ==See also==
@@ Line 42: / Line 42: @@
 ==References==
+{{reflist}}
-<references />
 {{organic-compound-stub}}