Nigellicine是一种吲唑生物碱,也属于甜菜碱,化学式为C
13
H
14
N
2
O
3
。它最先是从家黑种草Nigella sativa)的种子里分离出来的[1],从中也能分离出结构类似的生物碱黑种草碱德语Nigeglanin[2]Nigellidin德语Nigellidin[3][4]2005年,Elliott等人发表了Nigellicin的首个全合成,由2-氯-5-甲基苯酚世界语2-Kloro-5-metilfenolo经14步反应产生:[5]

Nigellicine
IUPAC名
3-methyl-1-oxo-6,7,8,9-tetrahydropyridazino[1,2-a]indazole-11-carboxylic acid
3-甲基-1-羟基-6,7,8,9-四氢哒嗪并[1,2-a]吲唑-11-羧酸
英文名 Nigellicine
识别
CAS号 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
性质
化学式 C13H14N2O3
摩尔质量 246.26 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

参考资料

编辑
  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. ^ 李雅丽; 王增尚; 刘博; 陈望阳; 刘江云; 木胡牙提·乌拉斯汉. 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.