84-26-4Relevant articles and documents
Cytotoxic hybrids between the aromatic alkaloids bauerine C and rutaecarpine
Huber, Kilian,Bracher, Franz
, p. 1313 - 1316 (2007)
Two hybrids between the alkaloids bauerine C and rutaecarpine were prepared. Screening for cytotoxic activity revealed that introduction of two chlorine substituents to the quinazolinocarboline core of rutaecarpine strongly enhances cytotoxic activity, wh
Sequential sonagashira and larock indole synthesis reactions in a general strategy to prepare biologically active β-carboline-containing alkaloids
Pan, Xiaohong,Bannister, Thomas D.
, p. 6124 - 6127 (2014)
A general synthetic approach to β-carboline-containing alkaloids was developed. Two consecutive palladium-mediated processes, a Sonagashira coupling and a Larock indole annulation reaction, are central to the method. The scope of the approach was investigated and found to be amenable for constructing a variety of biologically significant natural products and also for preparing substituted analogues for optimization and analysis of their biological properties.
Synthesis of 1-Thio-Substituted Isoquinoline Derivatives by Tandem Cyclization of Isothiocyanates
Wen, Li-Rong,Dou, Qian,Wang, Yuan-Chao,Zhang, Jin-Wei,Guo, Wei-Si,Li, Ming
, p. 1428 - 1436 (2017)
A copper-catalyzed tandem arylation-cyclization process to access 1-(arylthio)isoquinolines from isothiocyanates and diaryliodonium salts is described. It is the first general method to construct the potentially useful 1-(arylthio)isoquinoline derivatives. Moreover, 1-(methylthio)isoquinoline derivatives were also achieved successfully with MeOTf instead of diaryliodonium salts under metal-free conditions. Mechanistic studies reveal that these two processes proceed in different routes. This method has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.
Preparation method of 2-trifluoromethyl substituted quinazolinone compound and application of 2-trifluoromethyl substituted quinazolinone compound in synthesis of pharmaceutical molecules
-
Paragraph 0042; 0045, (2021/07/01)
The invention discloses a preparation method of a 2-trifluoromethyl substituted quinazolinone compound. The preparation method comprises the following steps: adding a palladium catalyst, a ligand, a carbon monoxide substitute, an additive, trifluoroethylimido acyl chloride and amine into an organic solvent, reacting at 110 DEG C for 16-30 hours, and after the reaction is completed, carrying out post-treatment to obtain the 2-trifluoromethyl substituted quinazolinone compound. The preparation method has the advantages of simple operation, cheap and easily available initial raw materials, high reaction efficiency, good substrate compatibility, synthesis of trifluoromethyl quinazolinone compounds substituted by different groups through substrate design, convenient operation, and broadening of the practicality of the method. The method is also successfully applied to the high-yield synthesis of the drug molecule Rutaecarpine.
Metal-Free Annulation of 2-Nitrobenzyl Alcohols and Tetrahydroisoquinolines toward the Divergent Synthesis of Quinazolinones and Quinazolinethiones
Le, Nhan T. H.,Ly, Duc,Nguyen, Khang X.,Nguyen, Thao T.,Nguyen, Tung T.,Nguyen, Vy P. T.,Pham, Phuc H.,Phan, Nam T. S.,Tran, Cam T. H.
, (2022/01/03)
A simple metal-free method for the synthesis of quinazolinones from commercially available 2-nitrobenzyl alcohols and tetrahydroisoquinolines is developed. The reaction conditions were tolerant of an array of functionalities such as halogen, tertiary amine, protected alcohol, and ester groups. Under nearly identical conditions, quinazolinethiones were obtained in the presence of elemental sulfur and suitable mediators.
Copper-catalyzed synthesis of pyrido-fused quinazolinones from 2-aminoarylmethanols and isoquinolines or tetrahydroisoquinolines
Ly, Duc,Nguyen, Duyen K.,Nguyen, Khang X.,Nguyen, Khoa D.,Nguyen, Thao T.,Nguyen, Tung T.,Pham, Phuc H.,Phan, Nam T. S.
supporting information, p. 4726 - 4732 (2021/06/09)
Pyrido-fused quinazolinones were synthesizedviacopper-catalyzed cascade C(sp2)-H amination and annulation of 2-aminoarylmethanols with isoquinolines or pyridines. The transformation proceeded readily in the presence of a commercially available CuCl2catalyst with molecular oxygen as a green oxidant. Moreover, the dehydrogenative cross-coupling of 2-aminoarylmethanols with tetrahydroisoquinolines was explored, in which CuBr exhibited higher catalytic activity than CuCl2. Broad substrate scope with good tolerance of functionalities was observed under the optimized reaction conditions. The bioactive naturally occurring alkaloid rutaecarpine could be obtained by this strategy. The remarkable feature of this protocol is that complicated heterocyclic structures are readily achieved in a single synthetic step from easily accessible reactants and catalysts. This pathway to pyrido-fused quinazolinones would be complementary to existing protocols.
Visible-Light-Mediated Synthesis of Rutaecarpine Alkaloids through C-N Cross-Coupling Reaction
Chen, Dong,Li, Shiqing,Wang, Jinhua,Gou, Tiantian,Zhang, Linfeng,Wang, Guixia,Kong, Xiangfei
, p. 987 - 992 (2021/04/21)
A visible-light-initiated cross-dehydrogenative-coupling amination is described, featuring metal- and photocatalyst-free, at room temperature, and using air as an oxidant. The reaction provides a facile approach for the synthesis of rutaecarpine and its derivatives. The substrates with electron-withdrawing groups give higher yields than those with electron-donating groups, but the substituent position has a negligible influence on the yield. Using binaphthyl-diyl hydrogen phosphate and dibenzyl phosphate as catalysts both deliver satisfying yields. This straightforward light-driven strategy might be applicable to the synthesis of quinazolinone derivatives.
Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family
Afanasyev, Oleg I.,Podyacheva, Evgeniya,Rudenko, Alexander,Tsygankov, Alexey A.,Makarova, Maria,Chusov, Denis
, p. 9347 - 9360 (2020/08/14)
A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.
Novel PDE5 inhibitors derived from rutaecarpine for the treatment of Alzheimer's disease
Dong, Yan-Hua,Huang, Xian-Feng,Ke, Heng-Ming,Song, Guo-Qiang,Wang, Jin-Hui,Xu, De-Feng
supporting information, (2020/03/23)
A series of novel rutaecarpine derivatives were synthesized and subjected to pharmacological evaluation as PDE5 inhibitors. The structure–activity relationships were discussed and their binding conformation and simultaneous interaction mode were further clarified by the molecular docking studies. Among the 25 analogues, compound 8i exhibited most potent PDE5 inhibition with IC50 values about 0.086 μM. Moreover, it also produced good effects against scopolamine-induced cognitive impairment in vivo. These results might bring significant instruction for further development of potential PDE5 inhibitors derived from rutaecarpine as a good candidate drug for the treatment of Alzheimer's disease.
Electrosynthesis of polycyclic quinazolinones and rutaecarpine from isatoic anhydrides and cyclic amines
Chen, Xingyu,Lu, Sixian,Sun, Peng,Zhang, Xing
, p. 44382 - 44386 (2020/12/25)
A direct decarboxylative cyclization between readily available isatoic anhydrides and cyclic amines was established to construct polycyclic fused quinazolinones employing electrochemical methods. This procedure was performed in an undivided cell without the use of a transition-metal-catalyst and external oxidant. A broad scope of polycyclic fused quinazolinones were obtained in moderate to good yields. Additionally, rutaecarpine was also prepared through our method in one step in good yield. This journal is
