906067-45-6Relevant academic research and scientific papers
Preparation method of 1-carbonyl-beta-carboline compound
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Paragraph 0053-0055, (2017/06/13)
The invention discloses a preparation method of a 1-carbonyl-beta-carboline compound. The preparation method comprises the following step: in an air or oxygen atmosphere, in the presence of an additive and under the condition of illumination, performing oxidation reaction on tetrahydrocarboline compound as shown in a formula II to obtain the 1-carbonyl-beta-carboline compound as shown in a formula I, wherein the additive is tetrabutyl quaternary ammonium salt selected from any one of tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium chloride, tetrabutylammonium acetate and tetrabutylammonium fluoride; and the molar ratio of the tetrahydrocarboline compound as shown in the formula II to the additive is 1:(0.2-2). The preparation method provided by the invention is high in yield, wherein most of the yield is between 60% and 90%. When R3 is an aromatic group, the variety and the position of a substituent group on an aromatic ring do not have substantial influence on the yield of the reaction. In addition, the R3 group has wider applicability and also comprises an alkyl R3 group besides the aromatic R3 group, and in this aspect, the preparation method provided by the invention is substantially improved compared with the existing synthesis.
Iodine-mediated oxidative Pictet-Spengler reaction using terminal alkyne as the 2-oxoaldehyde surrogate for the synthesis of 1-aroyl-β-carbolines and fused-nitrogen heterocycles
Dighe, Shashikant U.,Samanta, Surya K.,Kolle, Shivalinga,Batra, Sanjay
, p. 2455 - 2467 (2017/04/03)
An efficient iodine-mediated oxidative Pictet-Spengler reaction in dimethyl sulphoxide (DMSO) using terminal alkynes as the 2-oxoaldehyde surrogate for the synthesis of aryl (9H-pyrido[3,4-b]indol-1-yl)methanones is described. The scope of the protocol includes the total synthesis of Fascaplysin, Eudistomins Y1 and Y2. The methodology is extended for preparing pyrrolo[1,2-a]-quinoxaline and indolo[1,5-a]quinoxaline derivatives. The utility of 1-aroyl-β-carbolines was demonstrated by performing palladium-catalyzed β-carboline directed ortho-C(sp2)-H functionalization of the phenyl ring with thiomethyl (SMe) group using DMSO as source and for accessing 4-aryl-canthin-6-ones.
A cascade coupling strategy for one-pot total synthesis of β-carboline and isoquinoline-containing natural products and derivatives
Zhu, Yan-Ping,Liu, Mei-Cai,Cai, Qun,Jia, Feng-Cheng,Wu, An-Xin
supporting information, p. 10132 - 10137 (2013/09/02)
Multi-birds with one stone: A cascade coupling strategy was developed for the synthesis of β-carbolines. The method can direct the synthesis of β-carboline and isoquinoline-containing natural products with high yields. Moreover, this protocol can also be further applied towards the total synthesis of natural products fascaplysin and papaverin (see scheme). Copyright
Synthesis, in vitro anti-inflammatory and cytotoxic evaluation, and mechanism of action studies of 1-benzoyl-β-carboline and 1-benzoyl-3-carboxy-β-carboline derivatives
Yang, Mei-Lin,Kuo, Ping-Chung,Hwang, Tsong-Long,Chiou, Wen-Fei,Qian, Keduo,Lai, Chin-Yu,Lee, Kuo-Hsiung,Wu, Tian-Shung
experimental part, p. 1674 - 1682 (2011/04/16)
In the present study, various 1-substituted and 1,3-disubstituted β-carboline derivatives were synthesized by a modified single-step Pictet-Spengler reaction. The compounds were examined for cytotoxicity and anti-inflammatory activity, as measured by the
Regioselective photo-oxidation of 1-benzyl-4,9-dihydro-3H-β-carbolines
Garcia, Marcos D.,Wilson, A. James,Emmerson, Daniel P. G.,Jenkins, Paul R.
, p. 2586 - 2588 (2008/03/31)
The synthesis of a series of β-carboline-based analogues of the natural product fascaplysin is presented; the compounds were produced using a novel photo-oxidation reaction of 1-benzyl-4,9-dihydro-3H-β-carbolines as the key step. The Royal Society of Chemistry 2006.
Synthesis, crystal structure and biological activity of β-carboline based selective CDK4-cyclin D1 inhibitors
Garcia, Marcos D.,Wilson, A. James,Emmerson, Daniel P.G.,Jenkins, Paul R.,Mahale, Sachin,Chaudhuri, Bhabatosh
, p. 4478 - 4484 (2008/09/19)
The design, synthesis and biological activity of a series of non-planar dihydro-β-carboline and β-carboline-based derivatives of the toxic anticancer agent fascaplysin is presented. We show these compounds to be selective inhibitors of CDK4 over CDK2 with an IC50 (CDK4-cyclin D1) = 11 mol for the best compound in the series 4d. The crystallographic analysis of some of the compounds synthesised (3b/d and 4a-d) was carried out, in an effort to estimate the structural similarities between the designed inhibitors and the model compound fascaplysin. The Royal Society of Chemistry.
A versatile route to the synthesis of 1-substituted β-carbolines by a single step Pictet-Spengler cyclization
Yang, Mei-Lin,Kuo, Ping-Chung,Damu, Amooru G.,Chang, Ren-Jie,Chiou, Wen-Fei,Wu, Tian-Shung
, p. 10900 - 10906 (2007/10/03)
A one-step conversion of l-tryptophan and activated aldehydes (1,2-dicarbonyl compounds) directly to 1-substituted β-carbolines without formation of the tetrahydro derivatives under modified Pictet-Spengler conditions was described. Moreover, a practical
