A new approach to the synthesis of benzofuro[3,2‐b]quinolines, benzothieno[3,2‐b]quinolines and indolo[3,2‐b]quinolines

Rádl, S.; Konvička, Petr; Váchal, Petr

doi:10.1002/jhet.5570370430

Cited by 34 publications

(18 citation statements)

References 36 publications

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“…Radl and co-workers [106] reported the synthesis of quindoline 4 via intermediate 149 by treating anthranilonitrilo derivative 147 with phenacyl bromide 148 in presence of K 2 CO 3 (Scheme 34).…”

Section: Other Miscellaneous Methodsmentioning

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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Section: Other Miscellaneous Methodsmentioning

confidence: 99%

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

Parvatkar¹,

Parameswaran²,

Tilve

2011

COC

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“…In another synthetic procedure reported by Radl and co-workers [25], 2-nitro phenacyl bromide (25) was reacted with ethyl-2-cyanophenylcarbamate (26) under basic conditions to yield compound 27. Using the nitro group as a leaving group, cyclization of 27 under basic conditions yielded quindolinone (19) which can be converted to quindoline, as shown in Scheme 7.…”

Section: Methods Of Chemical Syntheses Of Indolo[32-b]quinoline (Quimentioning

confidence: 99%

Indolo[3,2-b]quinolines: Synthesis, Biological Evaluation and Structure Activity-Relationships

Kumar¹,

Etukala²,

Ablordeppey³

2008

MRMC

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The tetracyclic indolo[3,2-b]quinoline ring system constitutes an important structural moiety in natural products exhibiting numerous biological activities. In particular, indolo [3, 2-b]quinoline, commonly known as linear quindoline is of particular interest, because of its rigid structure and scope of derivatization. Although the core linear quindoline skeleton shows little or no activity in several biological systems, introduction of a methyl group on the N-5 atom leading to cryptolepine induces remarkable activity against a broad spectrum of biological targets. A number of analogs of quindoline and cryptolepine have been synthesized, incorporating various functional groups on the core quindoline skeleton leading to improved biological activities. In this review, we describe various synthetic methodologies leading to the quindoline scaffold, the biological activities and the structure activity relationships (SAR) of quindoline derivatives toward different disease states to give a better picture of the importance of this moiety in medicinal chemistry.

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“…The fact that compound 32 series had been shown to be highly active against chloroquine-sensitive P. berghei strains but not so active against chloroquine and mefloquine resistant strains, led to the suggestion that this class of compounds may share a common mode of action with the quinoline-like antimalarials. Additionally, Koh and co-workers showed that the differences in the planarity between 3-chloro-8-methoxy-11H-indolo[3,2-c]quindolines (31) and amodiaquine have little effect on activity, but the distance between quinolinic nitrogen and side chain nitrogen is determinant to activity [95][96]. To better understand the structure-activity relationships of these compounds and following their previous work, Go et al synthesized in 1998 a series of 3-chloro-8-methoxy-11H-indolo[3,2-c]quindolines with a basic side-chain at position 9 of the planar indoloquinoline ring (33) [97].…”

Section: Antiprotozoal Activitymentioning

confidence: 98%

Indoloquinolines as Scaffolds for Drug Discovery

Lavrado¹,

Moreira²,

Paulo

2010

CMC

162

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Traditional medicines have contributed greatly over the centuries to the discovery and development of new therapeutic agents and indoloquinoline alkaloids may represent a new class of drug leads. Cryptolepine (5-methyl-5Hindolo[3,2-b]quinoline), neocryptolepine (5-methyl-5H-indolo[2,3-b]quinoline), isocryptolepine (5-methyl-5H-indolo[3,2-c]quinoline, extracted from the African medicinal plant Cryptolepis sanguinolenta, and isoneocryptolepine (5-methyl-5Hindolo[2,3-c]quinoline), which has never been found in nature, are isomeric tetracyclic compounds of particular interest due to their broad spectrum of biological activities including antiparasitic, antifungal, antibacterial, cytotoxic, anti-inflammatory and antihyperglycaemic. As a result, in the last 30 years hundreds of indoloquinoline analogues were synthesized and their biological activities evaluated. In this paper, we present an overview of the potential of indoloquinolines as scaffolds in drug discovery by reviewing the in vitro and in vivo biological activities of natural and synthetic analogues, as well as the proposed mechanisms of action and structure-activity relationships.

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A new approach to the synthesis of benzofuro[3,2‐b]quinolines, benzothieno[3,2‐b]quinolines and indolo[3,2‐b]quinolines

Cited by 34 publications

References 36 publications

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

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

Indolo[3,2-b]quinolines: Synthesis, Biological Evaluation and Structure Activity-Relationships

Indoloquinolines as Scaffolds for Drug Discovery

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