10022-79-4Relevant academic research and scientific papers
Discovery of 3,3′-pyrrolidinyl-spirooxindoles as cardioprotectant prohibitin ligands
Elderwish, Sabria,Audebrand, Ana?s,Nebigil, Canan G.,Désaubry, Laurent
, (2020)
The scaffold proteins prohibitins-1 and 2 (PHB1/2) play many important roles in coordinating many cell signaling pathways and represent emerging targets in cardiology and oncology. We previously reported that a family of natural products derivatives, flavaglines, binds to PHB1/2 to exert cardioprotectant and anti-cancer effects. However, flavaglines also target the initiation factor of translation eIF4A, which doesn't contribute to cardioprotection and may even induce some adverse effects. Herein, we report the development of a convenient and robust synthesis of the new PHB2 ligand 2′-phenylpyrrolidinyl-spirooxindole, and its analogues. We discovered that these compounds displays cardioprotective effect against doxorubicin mediated cardiotoxicity and uncovered the structural requirement for this activity. We identified in particular some analogues that are more cardioprotectant than flavaglines. Pull-down experiments demonstrated that these compounds bind not only to PHB2 but also PHB1. These novel PHB ligands may provide the basis for the development of new drugs candidates to protect the heart against the adverse effects of anticancer treatments.
Asymmetric transfer hydrogenation of imines and iminiums catalyzed by a water-soluble catalyst in water
Wu, Jiashou,Wang, Fei,Ma, Yaping,Cui, Xin,Cun, Linfeng,Zhu, Jin,Deng, Jingen,Yu, Bangliang
, p. 1766 - 1768 (2006)
The first asymmetric transfer hydrogenation of cyclic imines and iminiums in water was successfully performed in high yields and enantioselectivities with sodium formate as the hydrogen source and CTAB as an additive catalyzed by a water-soluble and recyc
A simple method for the synthesis of 1-substituted β-carboline derivatives from tryptamine and carboxylic acids in polyphosphoric acid
Ivanov, Iliyan,Nikolova, Stoyanka,Statkova-Abeghe, Stela
, p. 2483 - 2492 (2005)
A number of 1-substituted 3,4-dihydro-9H-β-carboline derivatives (4) with high purity and yields have been synthesized by treating of tryptamine (1) with carboxylic acids (2) in polyphosphoric acid. 3,4-Dihydro-9H-β-carbolines (4) were successfully transformed to 1,2,3,4-tetrahydro-9H-β-carbolines (5) and 9H-β-carbolines (6).{A figure is presented}.
IBX-mediated oxidative addition of isocyanides to cyclic secondary amines: Total syntheses of alangiobussine and alangiobussinine
Ambule, Mayur D.,Tripathi, Shashank,Ghoshal, Anirban,Srivastava, Ajay K.
, p. 10872 - 10875 (2019)
The present study describes a robust and general method for the synthesis of C(1)-carboxamides through IBX-mediated oxidative addition of isocyanides to tryptolines and 1,2,3,4-tetrahydroisoquinolines. In this transformation, IBX plays a dual role of an oxidant and Lewis acid to activate imine facilitating isocyanide addition. Detailed mechanistic investigations were performed by isotopic labeling and real-time NMR experiments. The method was utilized for the gram scale syntheses of two alkaloids alangiobussine and alangiobussinine in 63% and 45% overall yield, respectively.
Selectivity-tunable oxidation of tetrahydro-β-carboline over an OMS-2 composite catalyst: preparation and catalytic performance
Bi, Xiuru,Tao, Luyao,Yao, Nan,Gou, Mingxia,Chen, Gexin,Meng, Xu,Zhao, Peiqing
, p. 3682 - 3692 (2021)
Controlling the reaction selectivity of organic transformations without losing high conversion is always a challenge in catalytic processes. In this work, a H3PO4·12WO3/OMS-2 nanocomposite catalyst ([PW]-OMS-2) was prepared through the oxidation of a Mn(ii) salt with sodium phosphotungstate by KMnO4. Comprehensive characterization indicates that different Mn2+precursors significantly affected the crystalline phase and morphology of the as-synthesized catalysts and only MnSO4·H2O as the precursor could lead to a cryptomelane phase. Moreover, [PW]-OMS-2 demonstrated excellent catalytic activity toward aerobic oxidative dehydrogenation of tetrahydro-β-carbolines due to mixed crystalline phases, enhanced surface areas, rich surface oxygen vacancies and labile lattice oxygen species. In particular, β-carbolines and 3,4-dihydro-β-carbolines could be obtained from tetrahydro-β-carbolines with very high selectivity (up to 99%) over [PW]-OMS-2viatuning the reaction solvent and temperature. Under the present catalytic system, scalable synthesis of a β-carboline was achieved and the composite catalyst showed good stability and recyclability. This work not only clarified the structure-activity relationship of the catalyst, but also provided a practical pathway to achieve flexible, controllable synthesis of functional N-heterocycles.
1-Benzyl-1,2,3,4-Tetrahydro-β-Carboline as Channel Blocker of N-Methyl-d-Aspartate Receptors
Espinoza-Moraga, Marlene,Caballero, Julio,Gaube, Friedemann,Winckler, Thomas,Santos, Leonardo S.
, p. 594 - 599 (2012)
N-methyl-d-aspartate (NMDA) receptors belong to the family of ligand-gated ion channels and are important for synaptic plasticity and memory function. The NMDA receptor consists of a voltage-dependent channel permeable to Ca2+ and Na+/sup
The synthesis of 1,1-disubstituted tetrahydro-β-carbolines induced by iodine
Lingam,Rao, D. Muralimohan,Bhowmik, Dipal R.,Santu, Pachore Sharad,Rao, K. Raghavendra,Islam, Aminul
, p. 7243 - 7245 (2007)
A mild access to 1,1-disubstituted tetrahydro-β-carbolines is described. Tryptamine is subjected to Pictet-Spengler cyclization with various ketones using iodine.
Stereoselective bioreduction of β-carboline imines through cell-free extracts from earthworms (Eisenia foetida)
Mirabal-Gallardo, Yaneris,Soriano, Maria Del Pilar C.,Santos, Leonardo S.
, p. 440 - 443 (2013)
Although remarkable advances have been made over the last decade in organic synthesis, catalysis, and biotechnology, there is still a need to introduce and develop new processes for chemical production to achieve sustainable and cleaner approaches to support the increasing global pharmaceutical/chemical industry. There is a growing need to produce optically active compounds in high yields to maintain and support areas such as pharmaceutical and natural product synthesis. Thus, chemists today are looking for alternative reactions carried out under green conditions. In this context, we describe β-carboline imine reductions employing cell-free extracts from red Californian earthworms (Eisenia foetida) in high yields and enantiomeric excesses. The enantiomeric excess values of the bioreduction showed no dependence on the imine 1a-g substituents to afford amines with an (R)-configuration. Based on these data, a model for the cell-free extract from the earthworm is proposed.
A highly enantioselective access to tetrahydroisoquinoline and β-carboline alkaloids with simple noyori-type catalysts in aqueous media
Evanno, Laurent,Ormala, Joel,Pihko, Petri M.
, p. 12963 - 12967 (2009)
Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme). The protocol was used in a very short synthesis of the alkaloids (S)-harmicine and (S)-crispine.
Synthetic study on the T3P-promoted one-pot preparation of 1-substituted-3,4-dihydro-β-carbolines by the reaction of tryptamine with carboxylic acids
ábrányi-Balogh, Péter,F?ldesi, Tamás,Grün, Alajos,Volk, Balázs,Keglevich, Gy?rgy,Milen, Mátyás
, p. 1953 - 1957 (2016)
A novel and efficient one-pot method has been developed for the synthesis of 1-substituted-3,4-dihydro-β-carbolines from tryptamine and a wide variety of carboxylic acids. The reaction was successfully applied to the synthesis of an important alkaloid har
