549-92-8

Usage

InChI:InChI=1/C19H16N2/c1-2-6-14-12-21-10-9-16-15-7-3-4-8-17(15)20-19(16)18(21)11-13(14)5-1/h3-4,7-12H,1-2,5-6H2

Upstream product

• 110489-40-2 20α-yohimban; hydrochloride 
• 18335-58-5 trans-2,3-tetramethylene-δ-valerolactone 
• 117966-26-4 3-(1-(phenylsulfonyl)indol-2-yl)-1-methansulfonyl-5,6,7,8-tetrahydroisoquinoline 
• 17350-51-5 9H-2-Ethoxycarbonylmethyl-1-methylpyrido<3,4-b>indolium bromide 
• 765-87-7 cyclohexane-1,2-dione 
• 61-54-1 tryptamine 
• 2435-53-2 o-tetrachloroquinone 
• 117966-27-5 13-Benzenesulfonyl-8-hydroxy-2,3,4,7,8,13-hexahydro-1H-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-6-ylium; bromide 
• 26862-60-2 3-(indol-2-yl)-5,6,7,8-tetrahydroisoquinoline 
• 117966-20-8 1-phenylsulfonyl-2-(5,6,7,8-tetrahydroisoquinolin-3-yl)-1H-indole 

Downstream Products

• 574-60-7 3-(3-Ethylindol-2-yl)-5,6,7,8-tetrahydroisoquinoline 
• 69349-93-5 (+/-)-alloyahimbane 
• 483-25-0 dl-Epialloyohimbane 
• 17994-15-9 sempervirine nitrate 
• 525-15-5 Yobyrin 

Relevant academic research and scientific papers

Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans

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)

Microwave assisted Westphal condensation and its application to synthesis of sempervirine and related compounds

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

Synthesis of Sempervirine, a Pentacyclic Anhydronium Indole Alkaloid

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

A DIRECTED METALATION ROUTE TO THE ZWITTERIONIC INDOLE ALKALOIDS. SYNTHESIS OF SEMPERVIRINE

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).