47136-65-2Relevant academic research and scientific papers
Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans
Xu, You-Kai,Yang, Lin,Liao, Shang-Gao,Cao, Pei,Wu, Bin,Hu, Hua-Bin,Guo, Juan,Zhang, Ping
, p. 1511 - 1517 (2015)
Nine new alkaloids of the koumine (1-4), humantenine (5-7), and yohimbane (8, 9) types as well as 12 known analogues were isolated from the leaves and vine stems of Gelsemium elegans. Compound 1 is the first N-4-demethyl alkaloid of the koumine type, compound 7 is the first nor-humantenine alkaloid, and compounds 8 and 9 are the first N-1-oxide and the first seco-E-ring alkaloids, respectively, of the yohimbane type. Compounds 1 and 7 exhibited moderate cytotoxicity against five human tumor cell lines with IC50 values in the range 4.6-9.3 μM. (Figure Presented)
Synthesis of Sempervirine, a Pentacyclic Anhydronium Indole Alkaloid
Chatterjee,Sahu,Saha,Banerji
, p. 1259 - 1262 (1996)
Sempervirine (2,3,4,13-tetrahydro-1H-benz[g]indolo[2,3-a]quinolizin-6-ium, 1) the pentacyclic anhydronium indole alkaloid of Gelsemium sempervirens Ait. f. (Loganiaceae), has been synthesized in three steps from hexahydroisochroman-3-one(6) and N-2-(3-ind
Microwave assisted Westphal condensation and its application to synthesis of sempervirine and related compounds
Chinta Rao,Saha, Sanjay,Raolji, Gajendra B.,Patro, Balaram,Risbood, Prabhaker,Difilippantonio, Michael J.,Tomaszewski, Joseph E.,Malhotra, Sanjay V.
, p. 487 - 490 (2013/02/25)
A concise synthesis of a potent lead in anticancer therapeutics, sempervirine, was achieved by one pot Westphal condensation, ester hydrolysis, and decarboxylation under microwave irradiation. The method was extended to the synthesis of several similar he
A DIRECTED METALATION ROUTE TO THE ZWITTERIONIC INDOLE ALKALOIDS. SYNTHESIS OF SEMPERVIRINE
Gribble, Gordon W.,Barden, Timothy C.,Johnson, David A.
, p. 3195 - 3202 (2007/10/02)
A synthesis protocol involving beta-lithiation of 2-(2-pyridinyl)indoles(45) and subsequent reaction with bromoacetaldehyde leads to the indoloquinolizine (1) ring system.Application of this methodology to 2-(2-pyridinyl)indole 17, which is prepared via Taylor-Boger triazine Diels-Alder annulation chemistry, affords the zwitterionic indole alkaloid sempervirine (3).
