Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA018921
PROPERTIES
| NPAID | NPA018921 |
|---|---|
| CLUSTER ID | 6150 |
| NODE ID | 4293 |
| NAME | Largazole |
| FORMULA | C29H42N4O5S3 |
| MOLECULAR WEIGHT (Da) | 622.8790 |
| ACCURATE MASS (Da) | 622.2317 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Symploca |
| ORIGIN SPECIES | sp. |
| InChIKey | AXESYCSCGBQJBL-SZPBEECKSA-N |
| InChI | InChI=1S/C29H42N4O5S3/c1-5-6-7-8-9-13-24(35)39-14-11-10-12-20-15-22(34)30-16-23-31-21(17-40-23)26-33-29(4,18-41-26)28(37)32-25(19(2)3)27(36)38-20/h10,12,17,19-20,25H,5-9,11,13-16,18H2,1-4H3,(H,30,34)(H,32,37)/b12-10+/t20-,25+,29+/m1/s1 |
| SMILES | CCCCCCCC(=O)SCC/C=C/[C@@H]1CC(=O)NCC2=NC(=CS2)C3=N[C@@](CS3)(C(=O)N[C@H](C(=O)O1)C(C)C)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Taori, Kanchan; Paul, Valerie J.; Luesch, Hendrik Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp Journal of the American Chemical Society 2008 130 (6) 1806-1807. | ||
|---|---|---|---|
| DOI | 10.1021/ja7110064 | PMID | 18205365 |
SYNTHESES
| CITATION 1 | Benelkebir H; Marie S; Hayden AL; Lyle J; Loadman PM; Crabb SJ; Packham G; Ganesan A Total synthesis of largazole and analogues: HDAC inhibition, antiproliferative activity and metabolic stability. Bioorganic and Medicinal Chemistry 2011 19 (12) 3650-3658. DOI: 10.1016/j.bmc.2011.02.024 PMID: 21420302 | ||
|---|---|---|---|
| CITATION 2 | Zeng X; Yin B; Hu Z; Liao C; Liu J; Li S; Li Z; Nicklaus MC; Zhou G; Jiang S Total synthesis and biological evaluation of largazole and derivatives with promising selectivity for cancers cells. Organic Letters 2010 12 (6) 1368-1371. DOI: 10.1021/ol100308a PMID: 20184338 | ||
| CITATION 3 | Ying Y; Taori K; Kim H; Hong J; Luesch H Total synthesis and molecular target of largazole, a histone deacetylase inhibitor. Journal of the American Chemical Society 2008 130 (26) 8455-8459. DOI: 10.1021/ja8013727 PMID: 18507379 | ||
| CITATION 4 | Ghosh AK; Kulkarni S Enantioselective total synthesis of (+)-largazole, a potent inhibitor of histone deacetylase. Organic Letters 2008 10 (17) 3907-3909. DOI: 10.1021/ol8014623 PMID: 18662003 | ||
| CITATION 5 | Nasveschuk CG; Ungermannova D; Liu X; Phillips AJ A concise total synthesis of largazole, solution structure, and some preliminary structure activity relationships. Organic Letters 2008 10 (16) 3595-3598. DOI: 10.1021/ol8013478 PMID: 18616341 | ||
| CITATION 6 | Bowers A; West N; Taunton J; Schreiber SL; Bradner JE; Williams RM Total synthesis and biological mode of action of largazole: a potent class I histone deacetylase inhibitor. Journal of the American Chemical Society 2008 130 (33) 11219-11222. DOI: 10.1021/ja8033763 PMID: 18642817 | ||
| CITATION 7 | Xiao Q; Wang LP; Jiao XZ; Liu XY; Wu Q; Xie P Concise total synthesis of largazole. Journal of Asian Natural Products Research 2010 12 (11) 940-949. DOI: 10.1080/10286020.2010.510114 PMID: 21061215 | ||
