A Convenient Synthesis of Two New Indoloquinoline Alkaloids

Timári, Géza; Soós, Tibor; Hajós, György

doi:10.1055/s-1997-1523

Cited by 86 publications

(37 citation statements)

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“…Then, the − OTs anion attacks intermediate 1 a“ , and target product 3 a is obtained through nucleophilic substitution of − OTs and dissociation of the LaCl 3 complex in the presence of K 2 CO 3 . On the other hand, rearrangement of 1 a into 1 c can occur through the assistance of p ‐tolylsulfonyl chloride –. The existence of intermediate 1 c has been confirmed by 1 H NMR and 13 C NMR spectroscopy, as shown in the Supporting Information.…”

Section: Figurementioning

confidence: 99%

Catalyst‐Controlled Selectivity in the Synthesis of C2‐ and C3‐Sulfonate Esters from Quinoline N‐Oxides and Aryl Sulfonyl Chlorides

et al. 2016

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The first example of the catalyst‐controlled selective synthesis of C2‐ and C3‐sulfonate‐ester‐substituted quinolines was developed by employing LaCl3 and chitosan@CuI catalysts, respectively. This protocol provides an expeditious route to an important class of quinoline derivatives frequently found in many biologically active compounds and features good practicality, high efficiency, and environmental friendliness. In addition, the easily recoverable chitosan@copper catalysts can be recycled five times without significant loss of catalytic performance.

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Section: Figurementioning

confidence: 99%

Catalyst‐Controlled Selectivity in the Synthesis of C2‐ and C3‐Sulfonate Esters from Quinoline N‐Oxides and Aryl Sulfonyl Chlorides

et al. 2016

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“…Timari et al [44] reported the synthesis of isocryptolepine and neocryptolepine using Suzuki procedure (Schemes 1 & 2).…”

Section: Palladium-catalyzed Coupling Reactionmentioning

confidence: 99%

Isolation, Biological Activities and Synthesis of Indoloquinoline Alkaloids: Cryptolepine, Isocryptolepine and Neocryptolepine

Parvatkar¹,

Parameswaran²,

Tilve

2011

COC

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The tetracyclic heteroaromatic compounds cryptolepine, isocryptolepine and neocryptolepine are all naturally occurring indoloquinoline alkaloids isolated from the shrub Cryptolepis sanguinolenta and are important due to their wide spectrum of biological properties. This review describes the isolation, brief biological activities and various synthetic methodologies developed during recent years for the preparation of this important class of alkaloids, with special emphasis on preparation and properties of cryptolepine 1, isocryptolepine 2 and neocryptolepine 3.Pd 2 (dba) 3 (2.5 mol%), P(tBu) 3 (10 mol%) K 3 PO 4 , dioxane pressure tube 120 0 C, 3h, 95% CH 3 I, DMF, 80 0 C, 1 h r.t., overnight 75% 33 34 35 16 2 Scheme 7.

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“…A series of studies addressed the synthesis of the g-carboline alkaloid isocryptolepine (5-methyl-5H-indolo[3, 2-c]quinoline) (53) using azides 52 [108,109] and 54 [110,111] as starting materials. Refluxing 52 in o-xylene followed by reduction using sodium bis(2-methoxyethoxy)aluminum hydride gave 53.…”

Section: Scheme 12mentioning

confidence: 99%

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

Smirnova¹,

Golovko²,

Граник³

2011

Pharm Chem J

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The main trends in the development of the chemistry of a-, g-, and d-carbolines are generalized. Syntheses of carbolines based on pyridine derivatives (including the Fischer synthesis, Graebe-Ullmann reaction, thermal decomposition of azides, photochemical cyclization of anilinopyridines, arylation of substituted pyridines and piperidones, etc.) and based on indole derivatives are described. Published data about the biological activity of compounds belonging to these series are summarized.Four classes of pyridoindoles, i.e., carbolines (1 -4), are known. Of these, b-carbolines (2) have been studied most completely. Numerous studies, including several reviews [1 -3], have addressed the synthesis and various properties of this class of compounds. The properties of the other carbolines have been studied in less detail, e.g., their syntheses and chemical and physicochemical properties have not yet been discussed and compared in the literature.A detailed comparison seems especially important because precisely such an analysis can expose the basic features that make these classes chemically and biologically significant. This is especially important during research directed at the discovery of new biologically active compounds. Because the large volume of literature dedicated to b-carbolines makes it practically impossible to discuss it in a single review, the present review is limited to a comparison of the other carbolines only, the syntheses of which have been discussed much less in the literature. We intend to discuss the main trends in the development of the chemistry of a-, g-, and d-carbolines without pretending to include all literature in its entirety in order to compare the potential of finding novel effective drugs in these series. We discuss first reviews dedicated to pyridoindoles [2 -5], including a rather recent review of g-carbolines [6]. Then we switch to chemical approaches to the synthesis of selected carboline derivatives, noting briefly publications on their biological properties.Pyridoindoles (carbolines), including pyrido[4,3-b]indoles (g-carbolines), some of which exhibit a broad spectrum of biological activity, are definitely interesting. Drugs of this class already exist, e.g., neuroleptic carbidine 5 (Carbidinum or Stobadine) and dimebon antihistamine drugs 6 (Dimebonum) and diazoline 7 (Diazolinum or Omeril) [7,8]. Furthermore, dimebon exhibited pronounced anti-NMDA (N-methyl-D-asparate, ED 50 = 42 mg/kg i.p.) and anticalcium activity (blocks calcium channels, IC 50 = 57 mM) and inhibited acetylcholinesterase (ACE) and butyrylcholinesterase (BuCE) (IC 50 = 42 and 7.9 mM, respectively) in in vitro tests. It also had pronounced cognitive-stimulant properties in in vivo tests for a neurotoxic 654 0091-150X/11/4412-0654

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A Convenient Synthesis of Two New Indoloquinoline Alkaloids

Cited by 86 publications

References 0 publications

Catalyst‐Controlled Selectivity in the Synthesis of C2‐ and C3‐Sulfonate Esters from Quinoline N‐Oxides and Aryl Sulfonyl Chlorides

Catalyst‐Controlled Selectivity in the Synthesis of C2‐ and C3‐Sulfonate Esters from Quinoline N‐Oxides and Aryl Sulfonyl Chlorides

Isolation, Biological Activities and Synthesis of Indoloquinoline Alkaloids: Cryptolepine, Isocryptolepine and Neocryptolepine

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

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