Nigellicine是一種吲唑生物鹼,也屬於甜菜鹼,化學式為C
13
H
14
N
2
O
3
。它最先是從家黑種草Nigella sativa)的種子裡分離出來的[1],從中也能分離出結構類似的生物鹼黑種草鹼德語Nigeglanin[2]Nigellidin德語Nigellidin[3][4]2005年,Elliott等人發表了Nigellicin的首個全合成,由2-氯-5-甲基苯酚世界語2-Kloro-5-metilfenolo經14步反應產生:[5]

Nigellicine
IUPAC名
3-methyl-1-oxo-6,7,8,9-tetrahydropyridazino[1,2-a]indazole-11-carboxylic acid
3-甲基-1-羥基-6,7,8,9-四氫噠嗪並[1,2-a]吲唑-11-羧酸
英文名 Nigellicine
識別
CAS號 98063-20-8
PubChem 11402337
ChemSpider 9577233
SMILES
 
  • O=C(O)C1=C2C(=O)C=C(C=C2N3N1CCCC3)C
InChI
 
  • 1S/C13H14N2O3/c1-8-6-9-11(10(16)7-8)12(13(17)18)15-5-3-2-4-14(9)15/h6-7H,2-5H2,1H3,(H,17,18)
InChIKey FEJTUHSIRAJLOJ-UHFFFAOYSA-N
性質
化學式 C13H14N2O3
摩爾質量 246.26 g·mol−1
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

參考資料

編輯
  1. ^ Atta-ur-Rahman; Malik, Sohail; Cun-heng, He; Clardy, Jon. Isolation and structure determination of nigellicine, a novel alkaloid from the seeds of nigella sativa. Tetrahedron Letters. 1985, 26 (23): 2759–2762. doi:10.1016/S0040-4039(00)94904-9. 
  2. ^ 李雅麗; 王增尚; 劉博; 陳望陽; 劉江雲; 木胡牙提·烏拉斯漢. 黑种草子化学成分和药理研究进展. 2016-08-22. doi:10.11669/cpj.2016.14.001. 
  3. ^ Liu, Yu-Ming; Yang, Jun-Shan; Liu, Qing-Hua. A New Alkaloid and Its Artificial Derivative with an Indazole Ring from Nigella glandulifera. Chemical and Pharmaceutical Bulletin. 2004, 52 (4): 454–455. ISSN 0009-2363. doi:10.1248/cpb.52.454. 
  4. ^ Atta-ur-Rahman; Malik, Sohail; Hasan, S.Sadiq; Choudhary, M.Iqbal; Ni, Chao-Zhou; Clardy, Jon. Nigellidine — A new indazole alkaloid from the seeds of Nigella sativa. Tetrahedron Letters. 1995, 36 (12): 1993–1996. doi:10.1016/0040-4039(95)00210-4. 
  5. ^ Elliott, Eric L.; Bushell, Simon M.; Cavero, Marta; Tolan, Brian; Kelly, T. Ross. Total Synthesis of Nigellicine and Nigeglanine Hydrobromide. Organic Letters. 2005-06-01, 7 (12): 2449–2451. ISSN 1523-7060. doi:10.1021/ol050769m.