Compounds
COMPOUND NPA000031
PROPERTIES
| NPAID | NPA000031 |
|---|---|
| CLUSTER ID | 30 |
| NODE ID | 29 |
| NAME | Quinine |
| FORMULA | C20H24N2O2 |
| MOLECULAR WEIGHT (Da) | 324.4240 |
| ACCURATE MASS (Da) | 324.1838 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Diaporthe |
| ORIGIN SPECIES | sp. |
| InChIKey | LOUPRKONTZGTKE-WZBLMQSHSA-N |
| InChI | InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1 |
| SMILES | COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Maehara, Shoji; Simanjuntak, Partomuan; Kitamura, Chinami; Ohashi, Kazuyoshi; Shibuya, Hirotaka Cinchona alkaloids are also produced by an endophytic filamentous fungus living in cinchona plant Chemical and Pharmaceutical Bulletin 2011 59 (8) 1073-1074. | ||
|---|---|---|---|
| DOI | 10.1248/cpb.59.1073 | PMID | 21804259 |
SYNTHESES
| CITATION 1 | Friestad GK; Ji A; Korapala CS; Qin J Intermolecular radical addition to N-acylhydrazones as a stereocontrol strategy for alkaloid synthesis: formal synthesis of quinine. Organic & Biomolecular Chemistry 2011 9 (11) 4039-4043. DOI: 10.1039/c1ob05219e PMID: 21537510 | ||
|---|---|---|---|
| CITATION 2 | Gutzwiller J; Uskoković M Total synthesis of quinine and quinidine. II. Journal of the American Chemical Society 1970 92 (1) 204-205. DOI: 10.1021/ja00704a037 PMID: 5410108 | ||
| CITATION 3 | Uskoković M; Gutzwiller J; Henderson T Total synthesis of quinine and quinidine. I. Journal of the American Chemical Society 1970 92 (1) 203-204. DOI: 10.1021/ja00704a036 PMID: 5410107 | ||
| CITATION 4 | Webber P; Krische MJ Concise stereocontrolled formal synthesis of (+/-)-quinine and total synthesis of (+/-)-7- hydroxyquinine via merged Morita-Baylis-Hillman-Tsuji-Trost cyclization. Journal of Organic Chemistry 2008 73 (23) 9379-9387. DOI: 10.1021/jo802165k PMID: 18989927 | ||
| CITATION 5 | O' Donovan DH; Aillard P; Berger M; de la Torre A; Petkova D; Knittl-Frank C; Geerdink D; Kaiser M; Maulide N C-H Activation Enables a Concise Total Synthesis of Quinine and Analogues with Enhanced Antimalarial Activity. Angewandte Chemie International Edition 2018 57 (33) 10737-10741. DOI: 10.1002/anie.201804551 PMID: 29761878 | ||
| CITATION 6 | Stork G; Niu D; Fujimoto RA; Koft ER; Balkovec JM; Tata JR; Dake GR; Fujimoto A The first stereoselective total synthesis of quinine. Journal of the American Chemical Society 2001 123 (14) 3239-3242. DOI: 10.1021/ja004325r PMID: 11457058 | ||
| CITATION 7 | Lee J; Chen DY A Local-Desymmetrization-Based Divergent Synthesis of Quinine and Quinidine. Angewandte Chemie International Edition 2019 58 (2) 488-493. DOI: 10.1002/anie.201811530 PMID: 30394634 | ||
