Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA011049
PROPERTIES
| NPAID | NPA011049 |
|---|---|
| CLUSTER ID | 4324 |
| NODE ID | 11 |
| NAME | Calothrixin B |
| FORMULA | C19H10N2O2 |
| MOLECULAR WEIGHT (Da) | 298.3010 |
| ACCURATE MASS (Da) | 298.0742 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Calothrix |
| ORIGIN SPECIES | sp. |
| InChIKey | CCPDIHKLISWESE-UHFFFAOYSA-N |
| InChI | InChI=1S/C19H10N2O2/c22-18-12-9-20-13-7-3-1-5-10(13)15(12)19(23)17-16(18)11-6-2-4-8-14(11)21-17/h1-9,21H |
| SMILES | C1=CC=C2C(=C1)C3=C(N2)C(=O)C4=C(C3=O)C=NC5=CC=CC=C54 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Rickards, Rodney W.; Rothschild, Jennifer M.; Willis, Anthony C.; Chazal, Nola M. de; Kirk, Julie; Kirk, Kiaran; Saliba, Kevin J.; Smith, Geoffrey D. Calothrixins A and B, novel pentacyclic metabolites from Calothrix cyanobacteria with potent activity against malaria parasites and human cancer cells Tetrahedron 1999 55 (47) 13513-13520. | ||
|---|---|---|---|
| DOI | 10.1016/s0040-4020(99)00833-9 | PMID | - |
SYNTHESES
| CITATION 1 | Ramkumar N; Nagarajan R Total synthesis of Calothrixin A and B via C-H activation. Journal of Organic Chemistry 2013 78 (6) 2802-7. DOI: 10.1021/jo302821v PMID: 23421392 | ||
|---|---|---|---|
| CITATION 2 | Ramkumar N; Nagarajan R Total synthesis of ellipticine quinones, olivacine, and calothrixin B. Journal of Organic Chemistry 2014 79 (2) 736-41. DOI: 10.1021/jo402593w PMID: 24372379 | ||
| CITATION 3 | Ramkumar N; Nagarajan R Total synthesis of calothrixin B via sequential Sonogashira coupling/copper-catalyzed oxidative cyclization. Organic & Biomolecular Chemistry 2015 13 (45) 11046-51. DOI: 10.1039/c5ob01766a PMID: 26395099 | ||
| CITATION 4 | Mori-Quiroz LM; Dekarske MM; Prinkki AB; Clift MD Exploiting Alkylquinone Tautomerization for the Total Synthesis of Calothrixin A and B. Journal of Organic Chemistry 2017 82 (23) 12257-12266. DOI: 10.1021/acs.joc.7b02101 PMID: 29086565 | ||
| CITATION 5 | Singh S; Samineni R; Pabbaraja S; Mehta G A General Carbazole Synthesis via Stitching of Indole-Ynones with Nitromethanes: Application to Total Synthesis of Carbazomycin A, Calothrixin B, and Staurosporinone. Organic Letters 2019 21 (9) 3372-3376. DOI: 10.1021/acs.orglett.9b01111 PMID: 31013110 | ||
