13100-00-0Relevant articles and documents
Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement
Nachtigall, Fabiane M.,Santos, Leonardo S.,Sathish, Manda
, p. 38672 - 38677 (2020/11/05)
Tetrahydro-β-carboline (THBC) is a tricyclic ring system that can be found in a large number of bioactive alkaloids. Herein, we report a simple and efficient method for the synthesis of enantiopure THBCs through a chiral thiosquaramide (11b) catalyzed imine reduction of dihydro-β-carbolines (17a-f). The in situ generated Pd-H employed as hydride source in the reaction of differently substituted chiral THBCs (18a-f) afforded high selectivities (R isomers, up to 96% ee) and good isolated yields (up to 88%). Moreover, the chiral thiosquaramide used also afforded exceptional catalyst activity in the syntheses of (-)-coerulescine (5) and (-)-horsfiline (6) with excellent enantioselectivities up to 98% and 93% ee, respectively, via an enantioselective oxidative rearrangement approach.
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.
RhII2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides
Pumphrey, Ashley L.,Dong, Huijun,Driver, Tom G.
, p. 5920 - 5923 (2012/08/07)
Approaching all isomers: A range of α-, β- and δ-carbolinium ions are readily available from ortho-substituted aryl azides using a rhodium(II) carboxylate catalyst (see scheme). The carbolinium ions are readily reduced to afford tryptolines or deprotonated to access pyridoindoles. This [RhII2]-catalyzed C-H bond amination was used in the synthesis of (±)-horsfiline and neocryptolepine. esp=α,α,α',α'- tetramethyl-1,3-benzenedipropionate. Copyright
Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; Synthesis of dimebolin
Dong, Huijun,Latka, Regina T.,Driver, Tom G.
, p. 2726 - 2729 (2011/06/28)
A range of γ-carbolines were produced stereoselectively from ruthenium(III)-catalyzed reactions of 3-pyridyl substituted aryl azides. Other catalysts and conditions were neither as selective nor as high-yielding. This method was used to synthesize dimebolin in a concise and efficient manner.
HDAC INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
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Page/Page column 49-50, (2011/02/24)
Histone deacetylases inhibitors (HDACIs) and compositions containing the same are disclosed. Methods of treating diseases and conditions wherein inhibition of HDAC provides a benefit, like a cancer, a neurodegenerative disorder, a neurological disease, traumatic brain injury, stroke, malaria, an autoimmune disease, autism, and inflammation, also are disclosed.
Rational design and simple chemistry yield a superior, neuroprotective HDAC6 inhibitor, tubastatin A
Butler, Kyle V.,Kalin, Jay,Brochier, Camille,Vistoli, Guilio,Langley, Brett,Kozikowski, Alan P.
supporting information; experimental part, p. 10842 - 10846 (2010/09/16)
Structure-based drug design combined with homology modeling techniques were used to develop potent inhibitors of HDAC6 that display superior selectivity for the HDAC6 isozyme compared to other inhibitors. These inhibitors can be assembled in a few synthetic steps, and thus are readily scaled up for in vivo studies. An optimized compound from this series, designated Tubastatin A, was tested in primary cortical neuron cultures in which it was found to induce elevated levels of acetylated α-tubulin, but not histone, consistent with its HDAC6 selectivity. Tubastatin A also conferred dose-dependent protection in primary cortical neuron cultures against glutathione depletion-induced oxidative stress. Importantly, when given alone at all concentrations tested, this hydroxamate-containing HDAC6-selective compound displayed no neuronal toxicity, thus, forecasting the potential application of this agent and its analogues to neurodegenerative conditions.
Tandem intramolecular photocycloaddition-retro-mannich fragmentation as a route to spiro[pyrrolidine-3,3′-oxindoles]. Total synthesis of (±)-coerulescine, (±)-horsfiline, (±)-elacomine, and (±)-6-deoxyelacomine
White, James D.,Li, Yang,Ihle, David C.
experimental part, p. 3569 - 3577 (2010/07/04)
Figure presented Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-M
Facile synthesis of 1,2,3,4-tetrahydro-carbolines by one-pot domino three-component indole formation and nucleophilic cyclization
Ohta, Yusuke,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
supporting information; experimental part, p. 1979 - 1982 (2009/09/08)
Two direct synthetic methods of 1,2,3,4-tetrahydro-/?-carboline derivatives have been developed. After initial indole formation by copper- catalyzed domino three-component coupling-cyclization using an appropriate ethynylaniline, aldehyde, and a secondary
On the rearrangement of an azaspiroindolenine to a precursor to phalarine: Mechanistic insights
Li, Chaomin,Chan, Collin,Heimann, Annekatrin C.,Danishefsky, Samuel J.
, p. 1444 - 1447 (2008/03/15)
(Chemical Equation Presented) An interesting rearrangement: Management of functional groups in derivatives of indoles enables a rearrangement to take place which provides the pentacyclic ring system found in phalarine (see scheme, CSA = camphorsulfonic ac
Studies on semirigid tricyclic analogues of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Booth,Trevor,Singer,Castagnoli Jr.
, p. 473 - 477 (2007/10/02)
The tetrahydro β-carboline derived from the condensation of N-methyltryptamine and formaldehyde, a semirigid tricyclic analogue of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) that has been detected in the brains of normal laboratory rats, is biotr
