Synthesis and evaluation of 2-carboxy indole derivatives as potent and selective anti-leukemic agents

Cury, Nathália Moreno; Capitão, Rebeca Monique; Almeida, Renan do Canto Borges de; Artico, Leonardo Luís; Corrêa, Juliana Ronchi; Santos, Eric Francisco Simão dos; Yunes, José Andrés; Correia, Carlos Roque Duarte

doi:10.1016/j.ejmech.2019.111570

Cited by 16 publications

(9 citation statements)

References 41 publications

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“…We illustrated the synthetic relevance of alkylaryldiazenes in Scheme b by means of the straightforward conversion of diazenes 3ao , 3ac , 3af , and 4fa into the corresponding indoles 4ao , 4ac , 4af , and 4fa , that is, the Fischer indole synthesis. These newly formed heterocycles are representative compounds of an extensive class of bioactive molecules …”

Section: Resultsmentioning

confidence: 99%

Photoredox-Catalyzed Synthesis of Alkylaryldiazenes: Formal Deformylative C–N Bond Formation with Alkyl Radicals

et al. 2020

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Diazenes are valuable compounds that have found broad applicability because of their optical and biological properties. We report the synthesis of alkylaryldiazenes via formal, photoredox-catalyzed, deformylative C–N bond formation. The procedure employs dihydropyridines for the generation of alkyl radicals, which are then trapped by diazonium salts and reduced to the corresponding diazenes. Control experiments were performed to confirm the involvement of radicals in the mechanism. The reaction can be carried out at room temperature and employs readily available reagents; the mild conditions allowed the use of highly functionalized substrates. There was no observed tautomerization of the diazenes to the corresponding arylhydrazones.

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Section: Resultsmentioning

confidence: 99%

Photoredox-Catalyzed Synthesis of Alkylaryldiazenes: Formal Deformylative C–N Bond Formation with Alkyl Radicals

et al. 2020

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“…[39] In the same year, Moreno Cury and colleagues synthesized a novel series of potent 2-carboxy indole derivatives and elucidated their mechanism of action along with both in vitro and in vivo anti-leukemia potency. [40] The synthesis of these indole-based molecules (63, 65, 67) interestingly involved two Heck-Matsuda arylations to get disubstituted acrylates (62, 64, 66) followed by Cadogan-Sundberg reaction to afford the desired molecules (Scheme 15).…”

Section: Construction Of Indole Skeletonmentioning

confidence: 99%

“…The results showed compound 63 c to be tolerated well by mice during the complete experiment, revealing the significant prolonged overall survival of NOD/SCID mice used. [40] Thus, the evaluation of 63 c indicated it to be a promising lead for designing and developing new anti-leukemic agents.…”

Section: Construction Of Indole Skeletonmentioning

confidence: 99%

A Minireview on the Scope of Cadogan Cyclization Reactions Leading to Diverse Azaheterocycles

Kaur

Kumar

2022

Asian J Org Chem

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From the last two decades, Cadogan cyclization reaction is considered as one of the best routes for the preparation of various azaheterocycles comprising carbazoles, indoles, coumarins, carbolines, pyrazoloquinoxalines, S,N‐heterotetracenes from the nitro‐based substrates by using a variety of tetravalent phosphorus‐based reagents. To date the majority of Cadogan reactions are found to be intramolecular reactions, however, interestingly, a case of intermolecular Cadogan reaction is also reported, resulting in the widening of the reaction scope for futuristic perspectives. We report the Cadogan cyclization reactions for the synthesis of azaheterocycles from 2018 to present according to multiple classes of chemical frameworks including its scope (FDA approved drugs), along with the possibilities and mechanistic developments for unexpected products.

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“…Indoles can also exhibit strong anticancer activities as is shown in drugs such as Sunitinib, used for renal cell carcinoma, Osimertinib, used for the treatment of gastrointestinal stromal The derivatives showed selectivity and promising effectivity toward leukemia cells. 39 In addition, indoles have a wide range of applications including antimicrobial, antiemetic and migraine activities, among which "Triptans" were approved between 1992 and 2001 and contain an indole ring as their basic scaffold ( Fig. 4).…”

Section: Medicinal Applicationsmentioning

confidence: 99%

Benefits and applications of microwave-assisted synthesis of nitrogen containing heterocycles in medicinal chemistry

et al. 2020

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Synthesis and evaluation of 2-carboxy indole derivatives as potent and selective anti-leukemic agents

Cited by 16 publications

References 41 publications

Photoredox-Catalyzed Synthesis of Alkylaryldiazenes: Formal Deformylative C–N Bond Formation with Alkyl Radicals

Photoredox-Catalyzed Synthesis of Alkylaryldiazenes: Formal Deformylative C–N Bond Formation with Alkyl Radicals

A Minireview on the Scope of Cadogan Cyclization Reactions Leading to Diverse Azaheterocycles

Benefits and applications of microwave-assisted synthesis of nitrogen containing heterocycles in medicinal chemistry

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