Synthesis and Potent Antimalarial Activity of Kalihinol B
Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kali...
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| Vydané v: | Journal of the American Chemical Society Ročník 137; číslo 15; s. 4912 - 4915 |
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WASHINGTON
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22.04.2015
Amer Chemical Soc |
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| ISSN: | 0002-7863, 1520-5126, 1520-5126 |
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| Abstract | Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of kalihinol A (a tetrahydropyran). Kalihinol B shows similarly high potency against chloroquine-resistant Plasmodium falciparum. |
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| AbstractList | Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of kalihinol A (a tetrahydropyran). Kalihinol B shows similarly high potency against chloroquine-resistant Plasmodium falciparum. Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of kalihinol A (a tetrahydropyran). Kalihinol B shows similarly high potency against chloroquine-resistant Plasmodium falciparum.Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of kalihinol A (a tetrahydropyran). Kalihinol B shows similarly high potency against chloroquine-resistant Plasmodium falciparum. |
| Author | Prudhomme, Jacques Daub, Mary Elisabeth Le Roch, Karine Vanderwal, Christopher D |
| AuthorAffiliation | Department of Chemistry Department of Cell Biology and Neuroscience University of California, Irvine University of California, Riverside |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: University of California, Riverside – name: University of California, Irvine – name: Department of Cell Biology and Neuroscience |
| Author_xml | – sequence: 1 givenname: Mary Elisabeth surname: Daub fullname: Daub, Mary Elisabeth – sequence: 2 givenname: Jacques surname: Prudhomme fullname: Prudhomme, Jacques – sequence: 3 givenname: Karine surname: Le Roch fullname: Le Roch, Karine – sequence: 4 givenname: Christopher D surname: Vanderwal fullname: Vanderwal, Christopher D email: cdv@uci.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25815413$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/ja802730a 10.1016/j.tet.2012.01.084 10.1016/j.tet.2010.02.088 10.1002/chem.201104029 10.1021/jo0522862 10.1371/journal.pone.0002335 10.1021/jo026837p 10.1039/c4np00109e 10.1021/ja310129b 10.1021/ol049918b 10.1016/j.tet.2003.08.082 10.1038/nature12472 10.1021/ol0517729 10.1021/ol2027587 10.1056/NEJMoa1314981 10.1039/c1cc16468f 10.1021/ol301874x |
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| References | CHANG, CWJ (WOS:A1987K315400035) 1987; 109 ANGERHOFER, CK (WOS:A1992KD08600014) 1992; 55 MIYASHITA, K (WOS:A1993KU36900009) 1993; 41 Miyaoka, H (WOS:000174742700024) 2002; 43 White, RD (WOS:000220508600014) 2004; 6 Miyaoka, H (WOS:000308284100021) 2012; 60 Miyaoka, H (WOS:000076411000011) 1998; 54 Xu, Y (WOS:000301964700016) 2012; 68 Chen, K (WOS:000278947200009) 2010; 66 McGarraugh, PG (WOS:000307387300033) 2012; 18 RODRIGUEZ, J (WOS:A1994PG67500001) 1994; 50 Surendra, K (WOS:000257358300052) 2008; 130 Hirota, H (WOS:A1996TV12800011) 1996; 52 Pronin, SV (WOS:000324244900035) 2013; 501 Clark, RJ (WOS:000086769200020) 2000; 56 BRAEKMAN, JC (WOS:A1994PP36900003) 1994; 103 Keaney, G. F. (000353606700010.15) 2005 Turschner, S (WOS:000263977200006) 2009; 9 Wright, AD (WOS:A1996UZ99400020) 1996; 59 Shimomura, M (WOS:000083266300035) 1999; 40 Bugni, TS (WOS:000223009800003) 2004; 60 White, RD (WOS:000169247100011) 2001; 3 Pronin, SV (WOS:000311869600027) 2012; 134 ALVI, KA (WOS:A1991FD07600002) 1991; 54 Chi, YG (WOS:000231858100048) 2005; 7 PIERS, E (WOS:A1988M249500015) 1988; 60 Overman, LE (WOS:000087789600009) 2000; 78 PATRA, A (WOS:A1984TW47400061) 1984; 106 OMAR, S (WOS:A1988R349100034) 1988; 53 Overman, LE (WOS:000235453900036) 2006; 71 TRIMURTULU, G (WOS:A1994NL79700009) 1994; 57 IMI, K (WOS:A1987G479300008) 1987; 52 McGarraugh, PG (WOS:000297717800034) 2011; 13 Melchiorre, P (WOS:000183066100003) 2003; 68 Miyaoka, H (WOS:000299589700036) 2012; 48 Wang, ZX (WOS:000073505600056) 1998; 63 Wolf, D (WOS:000077879700015) 1998; 61 Prudhomme, J (WOS:000262614300030) 2008; 3 FUSETANI, N (WOS:A1990DL19400021) 1990; 31 Houjeiry, TI (WOS:000308390000025) 2012; 14 OKINO, T (WOS:A1995TF21000030) 1995; 36 Ashley, EA (WOS:000339556900006) 2014; 371 CHANG, CWJ (WOS:A1984TD41000073) 1984; 106 Schnermann, MJ (WOS:000351710900003) 2015; 32 |
| References_xml | – volume: 57 start-page: 501 year: 1994 ident: WOS:A1994NL79700009 article-title: 6 NEW DITERPENE ISONITRILES FROM THE SPONGE ACANTHELLA-CAVERNOSA publication-title: JOURNAL OF NATURAL PRODUCTS – volume: 52 start-page: 1013 year: 1987 ident: WOS:A1987G479300008 article-title: REACTION OF CYANOTRIMETHYLSILANE WITH OXIRANES - EFFECTS OF CATALYSTS OR MEDIATORS ON REGIOSELECTIVITY AND AMBIDENT CHARACTER publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 60 start-page: 1224 year: 2012 ident: WOS:000308284100021 article-title: Synthesis of Marine Diterpene Isocyanide (-)-Kalihinol Y and Diterpene Isothiocyanate (-)-10-Epi-kalihinol I publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN – volume: 63 start-page: 3099 year: 1998 ident: WOS:000073505600056 article-title: A pH study on the chiral ketone catalyzed asymmetric epoxidation of hydroxyalkenes publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 130 start-page: 8865 year: 2008 ident: WOS:000257358300052 article-title: Rapid and enantioselective synthetic approaches to germanicol and other pentacyclic triterpenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja802730a – volume: 68 start-page: 2876 year: 2012 ident: WOS:000301964700016 article-title: Antifouling and cytotoxic constituents from the South China Sea sponge Acanthella cavernosa publication-title: TETRAHEDRON doi: 10.1016/j.tet.2012.01.084 – volume: 36 start-page: 8637 year: 1995 ident: WOS:A1995TF21000030 article-title: ANTIFOULING KALIHINENES FROM THE MARINE SPONGE ACANTHELLA-CAVERNOSA publication-title: TETRAHEDRON LETTERS – volume: 52 start-page: 2359 year: 1996 ident: WOS:A1996TV12800011 article-title: Terpenoids with antifouling activity against barnacle larvae from the marine sponge Acanthella cavernosa publication-title: TETRAHEDRON – volume: 66 start-page: 4738 year: 2010 ident: WOS:000278947200009 article-title: Total synthesis of eudesmane terpenes: cyclase phase publication-title: TETRAHEDRON doi: 10.1016/j.tet.2010.02.088 – volume: 18 start-page: 10742 year: 2012 ident: WOS:000307387300033 article-title: Organocatalytic Kinetic Resolution Cascade Reactions: New Mechanistic and Stereochemical Manifold in Diphenyl Prolinol Silyl Ether Catalysis publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201104029 – volume: 3 start-page: 1825 year: 2001 ident: WOS:000169247100011 article-title: Progress toward the total synthesis of kalihinane diterpenoids publication-title: ORGANIC LETTERS – volume: 103 start-page: 187 year: 1994 ident: WOS:A1994PP36900003 article-title: 2 NEW KALIHINENES FROM THE MARINE SPONGE ACANTHELLA-CAVERNOSA publication-title: BULLETIN DES SOCIETES CHIMIQUES BELGES – volume: 106 start-page: 7981 year: 1984 ident: WOS:A1984TW47400061 article-title: AN UNPRECEDENTED TRIISOCYANO DITERPENOID ANTIBIOTIC FROM A SPONGE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 53 start-page: 5971 year: 1988 ident: WOS:A1988R349100034 article-title: POLYFUNCTIONAL DITERPENE ISONITRILES FROM MARINE SPONGE ACANTHELLA-CARVENOSA publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 55 start-page: 1787 year: 1992 ident: WOS:A1992KD08600014 article-title: ANTIMALARIAL ACTIVITY OF SESQUITERPENES FROM THE MARINE SPONGE ACANTHELLA-KLETHRA publication-title: JOURNAL OF NATURAL PRODUCTS – volume: 71 start-page: 1581 year: 2006 ident: WOS:000235453900036 article-title: Scope and facial selectivity of the prins-pinacol synthesis of attached rings publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0522862 – volume: 3 start-page: ARTN e2335 year: 2008 ident: WOS:000262614300030 article-title: Marine Actinomycetes: A New Source of Compounds against the Human Malaria Parasite publication-title: PLOS ONE doi: 10.1371/journal.pone.0002335 – volume: 78 start-page: 732 year: 2000 ident: WOS:000087789600009 article-title: A new strategy for synthesis of attached rings publication-title: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE – volume: 40 start-page: 8015 year: 1999 ident: WOS:000083266300035 article-title: Absolute configuration of marine diterpenoid kalihinol A publication-title: TETRAHEDRON LETTERS – volume: 60 start-page: 107 year: 1988 ident: WOS:A1988M249500015 article-title: THE USE OF SOME BIFUNCTIONAL REAGENTS IN ORGANIC-SYNTHESIS publication-title: PURE AND APPLIED CHEMISTRY – volume: 9 start-page: 206 year: 2009 ident: WOS:000263977200006 article-title: Drug Resistance in Plasmodium: Natural Products in the Fight Against Malaria publication-title: MINI-REVIEWS IN MEDICINAL CHEMISTRY – volume: 109 start-page: 6119 year: 1987 ident: WOS:A1987K315400035 article-title: KALIHINOLS, MULTIFUNCTIONAL DITERPENOID ANTIBIOTICS FROM MARINE SPONGES ACANTHELLA SPP publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 68 start-page: 4151 year: 2003 ident: WOS:000183066100003 article-title: Direct enantioselective Michael addition of aldehydes to vinyl ketones catalyzed by chiral amines publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo026837p – volume: 32 start-page: 543 year: 2015 ident: WOS:000351710900003 article-title: Syntheses and biological studies of marine terpenoids derived from inorganic cyanide publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/c4np00109e – volume: 134 start-page: 19604 year: 2012 ident: WOS:000311869600027 article-title: Synthesis of a Potent Antimalarial Amphilectene publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja310129b – volume: 54 start-page: 71 year: 1991 ident: WOS:A1991FD07600002 article-title: ANTHELMINTIC POLYFUNCTIONAL NITROGEN-CONTAINING TERPENOIDS FROM MARINE SPONGES publication-title: JOURNAL OF NATURAL PRODUCTS – volume: 56 start-page: 3071 year: 2000 ident: WOS:000086769200020 article-title: New isocyano and isothiocyanato terpene metabolites from the tropical marine sponge Acanthella cavernosa publication-title: TETRAHEDRON – volume: 6 start-page: 1123 year: 2004 ident: WOS:000220508600014 article-title: Total synthesis of (+/-)-kalihinol C publication-title: ORGANIC LETTERS doi: 10.1021/ol049918b – volume: 60 start-page: 6981 year: 2004 ident: WOS:000223009800003 article-title: Kalihinols from two Acanthella cavernosa sponges: inhibitors of bacterial folate biosynthesis publication-title: TETRAHEDRON doi: 10.1016/j.tet.2003.08.082 – volume: 501 start-page: 195 year: 2013 ident: WOS:000324244900035 article-title: Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines publication-title: NATURE doi: 10.1038/nature12472 – volume: 54 start-page: 13467 year: 1998 ident: WOS:000076411000011 article-title: Antimalarial activity of kalihinol A and new relative diterpenoids from the Okinawan sponge, Acanthella sp. publication-title: TETRAHEDRON – volume: 61 start-page: 1524 year: 1998 ident: WOS:000077879700015 article-title: New diterpene isonitriles from the sponge Phakellia pulcherrima publication-title: JOURNAL OF NATURAL PRODUCTS – volume: 7 start-page: 4253 year: 2005 ident: WOS:000231858100048 article-title: Diphenylprolinol methyl ether: A highly enantioselective catalyst for Michael addition of aldehydes to simple enones publication-title: ORGANIC LETTERS doi: 10.1021/ol0517729 – volume: 13 start-page: 6460 year: 2011 ident: WOS:000297717800034 article-title: An Organocascade Kinetic Resolution publication-title: ORGANIC LETTERS doi: 10.1021/ol2027587 – volume: 43 start-page: 2227 year: 2002 ident: WOS:000174742700024 article-title: Total synthesis of marine diterpenoid kalihinene X publication-title: TETRAHEDRON LETTERS – year: 2005 ident: 000353606700010.15 publication-title: THESEIS YALE U NEW H – volume: 371 start-page: 411 year: 2014 ident: WOS:000339556900006 article-title: Spread of Artemisinin Resistance in Plasmodium falciparum Malaria publication-title: NEW ENGLAND JOURNAL OF MEDICINE doi: 10.1056/NEJMoa1314981 – volume: 106 start-page: 4644 year: 1984 ident: WOS:A1984TD41000073 article-title: KALIHINOL-A, A HIGHLY FUNCTIONALIZED DIISOCYANO DITERPENOID ANTIBIOTIC FROM A SPONGE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 48 start-page: 901 year: 2012 ident: WOS:000299589700036 article-title: Total synthesis of antimalarial diterpenoid (+)-kalihinol A publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c1cc16468f – volume: 50 start-page: 11079 year: 1994 ident: WOS:A1994PG67500001 article-title: VARIATION AMONG KNOWN KALIHINOL AND NEW KALIHINENE DITERPENES FROM THE SPONGE ACANTHELLA-CAVERNOSA publication-title: TETRAHEDRON – volume: 14 start-page: 4394 year: 2012 ident: WOS:000308390000025 article-title: Synthesis of Optically Active 4-Substituted 2-Cyclohexenones publication-title: ORGANIC LETTERS doi: 10.1021/ol301874x – volume: 59 start-page: 710 year: 1996 ident: WOS:A1996UZ99400020 article-title: Antimalarial activity: The search for marine-derived natural products with selective antimalarial activity publication-title: JOURNAL OF NATURAL PRODUCTS – volume: 41 start-page: 465 year: 1993 ident: WOS:A1993KU36900009 article-title: AN APPROACH TO THE STEREOSELECTIVE SYNTHESIS OF NIDIFOCENE .3. TOTAL SYNTHESES OF THE STEREOISOMERS OF (+/-)-NIDIFOCENE FROM (+/-)-DEHALOGENONIDIFOCENE publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN – volume: 31 start-page: 3599 year: 1990 ident: WOS:A1990DL19400021 article-title: KALIHINENE AND ISOKALIHINOL-B, CYTOTOXIC DITERPENE ISONITRILES FROM THE MARINE SPONGE ACANTHELLA-KLETHRA publication-title: TETRAHEDRON LETTERS |
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| SubjectTerms | Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Chemistry Chemistry, Multidisciplinary Chloroquine - pharmacology Diterpenes - chemical synthesis Diterpenes - chemistry Diterpenes - pharmacology Drug Resistance - drug effects Molecular Structure Parasitic Sensitivity Tests Physical Sciences Plasmodium falciparum - drug effects Science & Technology |
| Title | Synthesis and Potent Antimalarial Activity of Kalihinol B |
| URI | http://dx.doi.org/10.1021/jacs.5b01152 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000353606700010 https://www.ncbi.nlm.nih.gov/pubmed/25815413 https://www.proquest.com/docview/1675169371 |
| Volume | 137 |
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