Altemicidin: Difference between revisions

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{{Chembox
| ImageFile = Altemicidin.pngsvg
| ImageSize = 150px
| ImageAlt =
| IUPACName = (4aR,6S,7R,7aS)-4-carbamoyl-6-hydroxy-2-methyl-7-(2-sulfamoylacetamido)-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylic acid
| IUPACName =
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 125399-82-8
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 159572
| SMILESUNII = }}39E2X82JVD
| PubChem = 15957211036174
| Section2 = {{Chembox Properties
| FormulaChemSpiderID = 9211348
| SMILES = O=S(=O)(N)CC(=O)N[C@@]2(C(=O)O)[C@@H](O)C[C@H]1C(=C/N(C[C@H]12)C)\C(=O)N
| MolarMass =
| InChI = 1/C13H20N4O7S/c1-17-3-7(11(14)20)6-2-9(18)13(12(21)22,8(6)4-17)16-10(19)5-25(15,23)24/h3,6,8-9,18H,2,4-5H2,1H3,(H2,14,20)(H,16,19)(H,21,22)(H2,15,23,24)/t6-,8+,9-,13+/m0/s1
| Appearance =
| InChIKey = VZRFZUPFQKSXPV-VPFIQFBEBF
| Density =
| StdInChI = 1S/C13H20N4O7S/c1-17-3-7(11(14)20)6-2-9(18)13(12(21)22,8(6)4-17)16-10(19)5-25(15,23)24/h3,6,8-9,18H,2,4-5H2,1H3,(H2,14,20)(H,16,19)(H,21,22)(H2,15,23,24)/t6-,8+,9-,13+/m0/s1
| MeltingPt =
| StdInChIKey = VZRFZUPFQKSXPV-VPFIQFBESA-N}}
| BoilingPt =
| Section2 = {{Chembox Properties
| Solubility = }}
| Formula = C<sub>13</sub>H<sub>20</sub>N<sub>4</sub>O<sub>7</sub>S
| Section3 = {{Chembox Hazards
| MainHazardsMolarMass = 376.39
| FlashPtAppearance =
| AutoignitionDensity = }}
| MeltingPt =
| BoilingPt =
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
 
'''Altemicidin''' is [[monoterpene]] [[alkaloid]] first identified in isolates from marine [[actinomycetes]] (specifically [[Streptomyces sioyaensis]]) in 1989.<ref name="TakahashiKurasawa1989">{{cite journal|last1=Takahashi|first1=Atsushi|last2=Kurasawa|first2=Shogo|last3=Ikeda|first3=Daishiro|last4=Okami|first4=Yoshiro|last5=Takeuchi|first5=Tomio|title=Altemicidin, a new acaricidal and antitumor substance. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties.|journal=The Journal of Antibiotics|volume=42|issue=11|year=1989|pages=1556–1561|issn=0021-8820|doi=10.7164/antibiotics.42.1556|doi-access=free|pmid=2584137 }}</ref><ref name="TakahashiIkeda1989">{{cite journal|last1=Takahashi|first1=Atsushi|last2=Ikeda|first2=Daishiro|last3=Nakamura|first3=Hikaru|last4=Naganawa|first4=Hiroshi|last5=Kurasawa|first5=Shogo|last6=Okami|first6=Yoshiro|last7=Takeuchi|first7=Tomio|last8=Iitaka|first8=Yoichi|title=Altemicidin, a new acaricidal and antitumor substance. II. Structure determination.|journal=The Journal of Antibiotics|volume=42|issue=11|year=1989|pages=1562–1566|issn=0021-8820|doi=10.7164/antibiotics.42.1562|doi-access=free|pmid=2584138 }}</ref> It may also be produced synthetically.<ref name="KendeLiu1995">{{cite journal|last1=Kende|first1=Andrew S.|last2=Liu|first2=Kun|last3=Jos Brands|first3=K. M.|title=Total Synthesis of (-)-Altemicidin: A Novel Exploitation of the Potier-Polonovski Rearrangement|journal=Journal of the American Chemical Society|volume=117|issue=42|year=1995|pages=10597–10598|issn=0002-7863|doi=10.1021/ja00147a032}}</ref><ref name="KanKawamoto2008">{{cite journal|last1=Kan|first1=Toshiyuki|last2=Kawamoto|first2=Yuichiro|last3=Asakawa|first3=Tomohiro|last4=Furuta|first4=Takumi|last5=Fukuyama|first5=Tohru|title=Synthetic Studies on Altemicidin: Stereocontrolled Construction of the Core Framework|journal=Organic Letters|volume=10|issue=2|year=2008|pages=169–171|issn=1523-7060|doi=10.1021/ol701940f|pmid=18081299}}</ref>
'''Altemicidin''' is an anticancer alkaloid isolated from marine [[actinomycetes]].
Altemicidin displays both [[acaricidal]] and antitumor activity.<ref name="TakahashiKurasawa1989"/>
 
==External linksReferences==
{{Reflist}}
*[http://www.ncbi.nlm.nih.gov/pubmed/2584138 Altemicidin, a new acaricidal and antitumor substance. II. Structure determination]
*[http://www.ncbi.nlm.nih.gov/pubmed/7710421 Bioactive compounds from marine actinomycetes]
 
[[Category:Alkaloids]]
[[Category:Sulfonamides]]
 
 
{{organic-chemalkaloid-stub}}
 
 
 
{{organic-chem-stub}}