17952-82-8Relevant academic research and scientific papers
First total synthesis of the proposed structures of orisuaveolines A and B
Zhang, Jie,Da, Shijun,Feng, Xiaolin,Chen, Xiaoyi,Jiang, Jianhui,Li, Ying
, p. 123 - 126 (2013)
First total synthesis of the proposed structures of β- indoloquinazoline alkaloids orisuaveolines A and B is reported. The key steps of the synthesis included a Pictet-Spengler reaction to build a six-member lactam which further transformed into target molecular by a one-pot condensation. This synthesis provided an access to the proposed structures of orisuaveolines A and B in a short and convenient manner from inexpensive, commercially available starting materials. The structures of our synthesized products were confirmed by 2D-NMR experiments. First total synthesis of the proposed structures of β-indoloquinazoline alkaloids orisuaveolines A and B is reported. The key steps of the synthesis included a Pictet-Spengler reaction to build a six-member lactam which further transformed into target molecular by a one-pot condensation. The structures of our synthesized products were confirmed by 2D-NMR experiments. Copyright
Access to substituted thiapyrrolizidinones and fused pyridones using the domino N-acyliminium-thionium equilibrium/1,3-dipolar cycloaddition/desulfurization cyclization cascade
Hamid, Abdulkareem,Oulyadi, Hassan,Da?ch, Adam
, p. 6398 - 6404 (2006)
Substituted thiapyrrolizidinones and fused pyridones, and quinolizinones were reported efficaciously from suitable thioamides in yields ranging from 30% to 65%. The reaction proceeded in a one-pot procedure as cascade process by the intramolecular 1,3-dip
Investigation into the stability and reactivity of the pentacyclic alkaloid dehydroevodiamine and the benz-analog thereof
Wehle, Sarah,Espargaró, Alba,Sabaté, Raimon,Decker, Michael
, p. 2535 - 2543 (2016/04/26)
Limited synthetic approaches to obtain the biologically active alkaloid dehydroevodiamine (DHED) are known to date. Undesired demethylation in the most widely applied route was found to be a hampering side reaction for the benz-DHED derivative leading to a quinazolinone, which represents a benz-rutaecarpine derivative. For rutaecarpine, a related plant alkaloid, many different synthetic approaches have been described. Alternative reaction procedures to obtain DHED such as methylation of rutaecarpine and oxidation of evodiamine were investigated to make DHED more easily accessible and the latter method proved to be the most successful one. Furthermore, the remarkable equilibrium between the ring closed quinazolinium and the ring open form of the compounds was systematically investigated by UV-vis measurements. The ring open form and the quinazolinium salt, form the same species when incubated in buffer solution for 24 h. A better soluble form, i.e., 'hydroxyevodiamine', seems to represent the biologically active form that has not yet been described.
Optical evodiamine derivatives: Asymmetric synthesis and antitumor activity
Li, Zhen-Gang,Dong, Guo-Qiang,Wang, Sheng-Zheng,Miao, Zhen-Yuan,Yao, Jian-Zhong,Zhang, Wan-Nian,Sheng, Chun-Quan
, p. 267 - 271 (2015/04/14)
Evodiamine and its derivatives have an asymmetric center at the C13b position. Herein, isomers of evodiamine derivatives 2 and 3 were obtained by straightforward asymmetric total synthesis. Their inhibitory activities toward topoisomerases I and II and th
Fischer Reaction with 2-Perfluoroalkylated Cyclic Imines - An Efficient Route to 2-Perfluoroalkyl-Substituted Tryptamines and Their Derivatives and Homologues
Shmatova, Olga I.,Shevchenko, Nikolay E.,Nenajdenko, Valentine G.
supporting information, p. 6479 - 6488 (2015/10/19)
The reaction of 2-perfluoroalkyl-substituted cyclic imines with arylhydrazines was investigated. We found that 2-perfluoroalkylated cyclic imines are highly reactive electrophiles that form, through ring opening, the corresponding hydrazones bearing an amine group at the end of the alkyl chain. Subsequent acidic treatment resulted in a Fischer rearrangement. Thus, a new synthesis of 2-perfluoroalkylated tryptamines and their homologues through a Fischer reaction was developed. The possibility of modification of the indole core of the 2-CF3-substituted tryptamine products was demonstrated, and various 2-trifluoromethylated tryptamines substituted at the 5-position were prepared. An efficient method for the synthesis of CF3-substituted tryptamines was developed based on the Fischer reaction of perfluoroalkyl-substituted cyclic imines with arylhydrazines. A 5-bromotryptamine was also transformed into further derivatives.
17a-HYDROXYLASE/C17,20-LYASE INHIBITORS
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, (2014/03/21)
The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.
Efficient synthesis of eudistomin U and evaluation of its cytotoxicity
Roggero, Chad M.,Giulietti, Jennifer M.,Mulcahy, Seann P.
supporting information, p. 3549 - 3551 (2014/07/22)
Eudistomin U is a member of a subclass of naturally occurring indole alkaloids known as β-carbolines. These molecules are reported to have diverse biological activity and high binding affinity to DNA, which make them attractive targets for total synthesis
Efficient synthesis of eudistomin U and evaluation of its cytotoxicity
Roggero, Chad M.,Giulietti, Jennifer M.,Mulcahy, Seann P.
supporting information, p. 3549 - 3551 (2015/02/19)
Eudistomin U is a member of a subclass of naturally occurring indole alkaloids known as β-carbolines. These molecules are reported to have diverse biological activity and high binding affinity to DNA, which make them attractive targets for total synthesis
An expedient protecting-group-free total synthesis of (±)- dievodiamine
Unsworth, William P.,Kitsiou, Christiana,Taylor, Richard J. K.
supporting information, p. 3302 - 3305 (2013/07/26)
The first total synthesis of the Evodia rutaecarpa derived natural product dievodiamine is described. The convergent synthesis was performed without protecting groups, delivering a route that is short and high yielding and uses limited chromatography. Key
Synthesis of 3,4-dihydroisoquinolin-1-ones from N-Boc-(β-Arylethyl) carbamates via isocyanate intermediates
In, Jinkyung,Hwang, Soonho,Kim, Changhun,Seo, Jae Hong,Kim, Sanghee
, p. 965 - 971 (2013/03/14)
Mild reaction conditions for the regioselective synthesis of isoquinolin-1-ones and related fused-ring heterocycles from N-Boc-protected (β-arylethyl)carbamates are described. The reactions involved the use of Tf2O and 2-chloropyridine and isocyanates are likely to be key intermediates. The method was extended to substrates bearing less nucleophilic aryl moieties by using Lewis acid additives, such as BF3· Et2O, to enhance the Friedel-Crafts-type cyclization of the isocyanate intermediates. This method allowed the synthesis of various substituted isoquinolin-1-ones, β-carbolines, thiophene-fused ring systems and tetrahydrobenzoazepin-1-ones in good yields and with high regioselectivities. Copyright
