Synthesis and biological evaluation of simplified mycothiazole analogues
New structurally mycothiazole analogues were synthesized and evaluated against HCT-15 colon tumor cells and L 4 larvae of Nippostrongylus brasiliensis. Thiazoline and oxazoline analogues of the natural product mycothiazole were synthesized from a common intermediate and evaluated in vitro against HC...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 16; no. 5; pp. 1309 - 1311 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Oxford
Elsevier Ltd
01.03.2006
Elsevier |
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| Abstract | New structurally mycothiazole analogues were synthesized and evaluated against HCT-15 colon tumor cells and L
4 larvae of
Nippostrongylus brasiliensis.
Thiazoline and oxazoline analogues of the natural product mycothiazole were synthesized from a common intermediate and evaluated in vitro against HCT-15 colon cancer cells and L
4 larvae of nematode
Nippostrongylus brasiliensis. The nature of the heterocyclic moiety seems to modulate the cytotoxic or anthelmintic activity. |
|---|---|
| AbstractList | Thiazoline and oxazoline analogues of the natural product mycothiazole were synthesized from a common intermediate and evaluated in vitro against HCT-15 colon cancer cells and L(4) larvae of nematode Nippostrongylus brasiliensis. The nature of the heterocyclic moiety seems to modulate the cytotoxic or anthelmintic activity. Thiazoline and oxazoline analogues of the natural product mycothiazole were synthesized from a common intermediate and evaluated in vitro against HCT-15 colon cancer cells and L sub(4) larvae of nematode Nippostrongylus brasiliensis. The nature of the heterocyclic moiety seems to modulate the cytotoxic or anthelmintic activity. New structurally mycothiazole analogues were synthesized and evaluated against HCT-15 colon tumor cells and L 4 larvae of Nippostrongylus brasiliensis. Thiazoline and oxazoline analogues of the natural product mycothiazole were synthesized from a common intermediate and evaluated in vitro against HCT-15 colon cancer cells and L 4 larvae of nematode Nippostrongylus brasiliensis. The nature of the heterocyclic moiety seems to modulate the cytotoxic or anthelmintic activity. |
| Author | Saldaña, Jenny Manta, Eduardo Mahler, Graciela Domínguez, Laura Dematteis, Sylvia Serra, Gloria |
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| Cites_doi | 10.1021/ja00466a066 10.1002/1099-0690(200102)2001:4<775::AID-EJOC775>3.0.CO;2-Z 10.1021/ol047603q 10.1081/SCC-200057988 10.1021/ol000128l 10.1158/1535-7163.333.4.2 10.1016/S0040-4020(03)01020-2 10.1039/a605539g 10.1016/S0040-4039(01)01759-2 10.3987/COM-98-8244 10.1021/ja00221a042 10.1016/S0040-4039(00)81416-1 10.1021/jm0105171 10.1021/ol005777b |
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| Keywords | Anthelmintic HTC-15 colon cells Mycothiazole Deoxo-Fluor Thiazolines Oxazolines Antineoplastic agent Five membered ring Thiazole derivatives Cytotoxicity Organic carbamate Nippostrongylus brasiliensis Structure activity relation Colon Secondary alcohol Chemical synthesis Nematoda Oxazole derivatives Tumor cell Oxygen nitrogen heterocycle Human Sulfur nitrogen heterocycle Aliphatic compound In vitro Cell line Larva Helmintha Parasiticide Nemathelminthia Invertebrata Ethylenic compound |
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| References_xml | – volume: 24 start-page: 391 year: 1983 ident: bib7 publication-title: Tetrahedron Lett. contributor: fullname: Hirao – volume: 2 start-page: 2149 year: 2000 ident: bib3 publication-title: Org. Lett. contributor: fullname: Cossy – ident: bib11 – volume: 45 start-page: 1901 year: 2002 ident: bib6 publication-title: J. Med. Chem. contributor: fullname: Day – volume: 2 start-page: 1165 year: 2000 ident: bib10 publication-title: Org. Lett. contributor: fullname: Williams – volume: 35 start-page: 1481 year: 2005 ident: bib5 publication-title: Synth. Commun. contributor: fullname: Manta – volume: 52 start-page: 603 year: 1997 ident: bib14 publication-title: Il Farmaco contributor: fullname: Suescum – start-page: 935 year: 1997 ident: bib9 publication-title: J. Chem. Soc., Perkin Trans. 1 contributor: fullname: Mesher – volume: 4 start-page: 333 year: 2005 ident: bib4 publication-title: Mol. Cancer Ther. contributor: fullname: Gerwick – volume: 110 start-page: 4365 year: 1988 ident: bib1 publication-title: J. Am. Chem. Soc. contributor: fullname: Riccio – volume: 50 start-page: 3317 year: 1965 ident: bib8 publication-title: J. Org. Chem. contributor: fullname: Sieck – volume: 99 start-page: 8078 year: 1977 ident: bib12 publication-title: J. Am. Chem. Soc. contributor: fullname: Hecht – volume: 99 start-page: 8078 year: 1977 ident: 10.1016/j.bmcl.2005.11.072_bib12 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00466a066 contributor: fullname: Minster – volume: 66 start-page: 775 year: 2001 ident: 10.1016/j.bmcl.2005.11.072_bib1b publication-title: Eur. J. Org. Chem. doi: 10.1002/1099-0690(200102)2001:4<775::AID-EJOC775>3.0.CO;2-Z contributor: fullname: Cutignano – ident: 10.1016/j.bmcl.2005.11.072_bib2 – volume: 7 start-page: 339 year: 2005 ident: 10.1016/j.bmcl.2005.11.072_bib3c publication-title: Org. Lett. doi: 10.1021/ol047603q contributor: fullname: Le Flohic – volume: 35 start-page: 1481 year: 2005 ident: 10.1016/j.bmcl.2005.11.072_bib5a publication-title: Synth. Commun. doi: 10.1081/SCC-200057988 contributor: fullname: Mahler – volume: 2 start-page: 2149 year: 2000 ident: 10.1016/j.bmcl.2005.11.072_bib3a publication-title: Org. Lett. doi: 10.1021/ol000128l contributor: fullname: Sugiyama – volume: 4 start-page: 333 year: 2005 ident: 10.1016/j.bmcl.2005.11.072_bib4 publication-title: Mol. Cancer Ther. doi: 10.1158/1535-7163.333.4.2 contributor: fullname: Simmons – volume: 59 start-page: 6579 year: 2003 ident: 10.1016/j.bmcl.2005.11.072_bib3b publication-title: Tetrahedron doi: 10.1016/S0040-4020(03)01020-2 contributor: fullname: Sugiyama – start-page: 935 year: 1997 ident: 10.1016/j.bmcl.2005.11.072_bib9 publication-title: J. Chem. Soc., Perkin Trans. 1 doi: 10.1039/a605539g contributor: fullname: Aitken – volume: 42 start-page: 8143 year: 2001 ident: 10.1016/j.bmcl.2005.11.072_bib5_2 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)01759-2 contributor: fullname: Mahler – volume: 48 start-page: 2035 year: 1998 ident: 10.1016/j.bmcl.2005.11.072_bib5_3 publication-title: Heterocycles doi: 10.3987/COM-98-8244 contributor: fullname: Serra – volume: 110 start-page: 4365 year: 1988 ident: 10.1016/j.bmcl.2005.11.072_bib1a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00221a042 contributor: fullname: Crews – volume: 24 start-page: 391 year: 1983 ident: 10.1016/j.bmcl.2005.11.072_bib7 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)81416-1 contributor: fullname: Yamaguchi – volume: 50 start-page: 3317 year: 1965 ident: 10.1016/j.bmcl.2005.11.072_bib8 publication-title: J. Org. Chem. contributor: fullname: Argabrigth – volume: 45 start-page: 1901 year: 2002 ident: 10.1016/j.bmcl.2005.11.072_bib6 publication-title: J. Med. Chem. doi: 10.1021/jm0105171 contributor: fullname: Wipf – ident: 10.1016/j.bmcl.2005.11.072_bib13 – volume: 52 start-page: 603 year: 1997 ident: 10.1016/j.bmcl.2005.11.072_bib14 publication-title: Il Farmaco contributor: fullname: Gordon – volume: 2 start-page: 1165 year: 2000 ident: 10.1016/j.bmcl.2005.11.072_bib10 publication-title: Org. Lett. doi: 10.1021/ol005777b contributor: fullname: Phillips |
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| Snippet | New structurally mycothiazole analogues were synthesized and evaluated against HCT-15 colon tumor cells and L
4 larvae of
Nippostrongylus brasiliensis.... Thiazoline and oxazoline analogues of the natural product mycothiazole were synthesized from a common intermediate and evaluated in vitro against HCT-15 colon... |
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| SubjectTerms | Animals Anthelmintic Anthelmintics - chemical synthesis Anthelmintics - chemistry Anthelmintics - pharmacology Anthelmintics - toxicity Antibiotics. Antiinfectious agents. Antiparasitic agents Antineoplastic agents Antiparasitic agents Biological and medical sciences Cell Line, Tumor Deoxo-Fluor General aspects HTC-15 colon cells Larva - drug effects Medical sciences Molecular Structure Mycothiazole Nematoda Nippostrongylus - drug effects Nippostrongylus brasiliensis Oxazolines Oxazolone - analogs & derivatives Oxazolone - chemical synthesis Oxazolone - chemistry Pharmacology. Drug treatments Structure-Activity Relationship Thiazoles - chemical synthesis Thiazoles - chemistry Thiazoles - pharmacology Thiazoles - toxicity Thiazolines |
| Title | Synthesis and biological evaluation of simplified mycothiazole analogues |
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