111492-86-5Relevant articles and documents
A mild Bischler–Napieralski-type cyclization of trichloromethyl carbamates for the synthesis of β -carbolinones
Hirao, Seiya,Kitamori, Mayumi,Itoh, Tomoki,Chiba, Yuusuke,Abe, Takumi
, p. 235 - 250 (2020/02/11)
– A straightforward synthesis of β-carbolinones by the Bischler–Napieralski-type cyclization of the corresponding trichloromethyl carbamates, which does not require acids, bases, oxidants, or transition-metals to promote the cyclization, has been achieved.
Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones
Han, Hui,Xia, Ji-Bao,Yang, Shang-Dong
, p. 3357 - 3369 (2019/04/06)
The Pd/Cu cocatalyzed oxidative tandem C-H aminocarbonylation and dehydrogenation was developed, affording carbolinones with molecular oxygen as the terminal oxidant. Natural product strychnocarpine and its derivatives were prepared conveniently using this strategy.
Site-Selective Carbonylative Synthesis of Structurally Diverse Lactams from Heterocyclic Amines with TFBen as the CO Source
Ying, Jun,Gao, Qian,Wu, Xiao-Feng
, p. 14297 - 14305 (2019/11/03)
A palladium-catalyzed site-selective C-H carbonylation of heterocyclic amines for the synthesis of lactam motifs has been developed. The reaction of 3-thiophene methylamines, 2-thiophene methylamines, and tryptamines with benzene-1,3,5-triyl triformate (TFBen) as the CO source provides a series of structurally diverse lactams in moderate to high yields with excellent regioselectivities.
PIDA/I2-Mediated α- And β-C(sp3)-H Bond Dual Functionalization of Tertiary Amines
Zhu, Yu,Shao, Li-Dong,Deng, Zhen-Tao,Bao, Ying,Shi, Xin,Zhao, Qin-Shi
, p. 10166 - 10174 (2018/08/01)
The α,β-C(sp3)-H bond dual functionalization of tertiary amines is still a challenging task for both organic and medicinal chemists. Herein a direct, mild, metal-free, and site-specific method mediated by PIDA/I2 was developed for α,
Method for synthesizing tetrahydro beta-carboline-1-one compound through palladium catalysis
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Paragraph 0034; 0035; 0036, (2017/10/06)
The invention discloses a method for synthesizing a tetrahydro beta-carboline-1-one compound through palladium catalysis. According to the method, carbonic oxide is used as a carbonyl source; the carbonic oxide and a tryptamine type compound react at ordinary pressure for efficiently preparing the tetrahydro beta-carboline-1-one compound. The method has the advantages that the tetrahydro beta-carboline-1-one compound with great application prospects is effectively prepared by using the carbonic oxide at the ordinary pressure as the carbonyl source and using bivalent metal palladium as a catalyst. From the angle of production and economy, through being compared with high-pressure reaction, the method has the advantages that the reaction cost is greatly reduced through carbonic oxide gas at normal temperature, and the reaction operability is improved.
Design, synthesis, and biological evaluation of novel (1-thioxo-1,2,3,4- tetrahydro-β-carbolin-9-yl)acetic acids as selective inhibitors for AKR1B1
Minehira, Daisuke,Takeda, Daisuke,Urata, Hirokazu,Kato, Atsushi,Adachi, Isao,Wang, Xu,Matsuya, Yuji,Sugimoto, Kenji,Takemura, Mayuko,Endo, Satoshi,Matsunaga, Toshiyuki,Hara, Akira,Koseki, Jun,Narukawa, Kayo,Hirono, Shuichi,Toyooka, Naoki
scheme or table, p. 356 - 367 (2012/03/09)
New substituted (1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acids were designed as the inhibitor of AKR1B1 based upon the structure of rhetsinine, a minor alkaloidal component of Evodia rutaecarpa, and twenty derivatives were synthesized and evaluated. The most active compound of the series was (2-benzyl-6-methoxy-1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl) acetic acid (7m), which showed comparable inhibitory activity for AKR1B1 (IC50 = 0.15 μM) with clinically used epalrestat (IC50 = 0.1 μM). In the view of activity and selectivity, the most potent compound was (2-benzyl-6-carboxy-1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acid (7t), which showed strong inhibitory effect (IC50 = 0.17 μM) and very high selectivity for AKR1B1 against AKR1A1 (311:1) and AKR1B10 (253:1) compared with epalrestat.
An autoxidative approach to 1,2,3,4-tetrahydroisoquinolin-1-one and tetrahydro-β-carbolin-1-one
Bois-Choussy, Michèle,De Paolis, Micha?l,Zhu, Jieping
, p. 3427 - 3430 (2007/10/03)
Treatment of N-benzyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylate with sodium hydride in N,N-dimethylformamide gives the corresponding N-benzyl 1,2,3,4-tetrahydroisoquinolin-1-one in quantitative yield. The N-benzyl 1,2,3,4-tetrahydro-β-carbolin-1-one is prepared in a similar fashion. The N-deprotection occurred concomitantly with the oxidative decarboxylation when the nitrogen was benzyloxycarbonylated.
Synthesis and Serotonin-Receptor Activity of Substituted 1-Oxo-1,2,3,4-tetrahydro-&β-carbolines
Herdeis, Claus,Bissinger, Gerhard
, p. 785 - 790 (2007/10/02)
2,3-Dihydroxypyridine is used as a starting material for the synthesis of donor and acceptor substituted 1-oxo-1,2,3,4-tetrahydro-β-carbolines via Fisher indole cyclisation.An alkaloid from Alstonia venenata is prepared.All compounds inclusive strychnocarpine show low affinity to the serotonine receptor. - Key words: 3-Hydroxy-2-pyridone, Strychnocarpine Derivatives, 5-Hydroxytryptamine Receptor Stimulators
