Formaldehyde-Induced DNA Cross-Link of Indolizino[1,2-<i>b</i>]quinolines Derived from the A−D Rings of Camptothecin

Perzyna, Aurore; Marty, Carine; Facompré, Michaël; Goossens, Jean‐François; Pommery, Nicole; Colson, Pierre; Houssier, Claude; Houssin, Raymond; Hénichart, Jean‐Pierre; Bailly, Christian

doi:10.1021/jm020235g

Cited by 20 publications

(10 citation statements)

References 19 publications

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“…In Scheme , few synthetic applications of the known methodology are depicted. In particular, the Bechamp reduction is suitable for the reduction of nitroarenes a to give anilines b as starting building block for the synthesis of 9,11-dihydroindolizino[1,2- b ]quinolines c , which are biologically active compounds (Scheme a) . Indium was also used in the “all water” synthesis of substituted benzimidazoles d (Scheme b) .…”

Section: Metal Dissolving Reductionsmentioning

confidence: 99%

Recent Developments in the Reduction of Aromatic and Aliphatic Nitro Compounds to Amines

Orlandi

Brenna

Harms³

et al. 2016

Org. Process Res. Dev.

324

195

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The reduction of the nitro group represents a powerful and widely used transformation that allows to introducing an amino group in the molecule. New synthetic strategies for complex functionalized molecular architectures are deeply needed, including highly efficient and selective nitro reduction methods, tolerant of a diverse array of functional moieties and protecting groups. Since chiral amino groups are ubiquitous in a variety of bioactive molecules such as alkaloids, natural products, drugs, and medical agents, the development of reliable catalytic methodologies for the nitro group reduction is attracting an increasing interest also in the preparation of enantiomerically pure amines. In this context, the modern reduction methods should be chemoselective and respectful of the stereochemical integrity of the stereogenic elements of the molecule. The review will offer an overview of the different possible methodologies available for this fundamental transformation, with special attention on the most recent contributions in the field, especially in the last ten years: hydrogenations, metal dissolving and hydride transfer reductions, catalytic transfer hydrogenations, and metal-free reductions. The main advantages or limitations for the proposed methods will be briefly discussed, highlighting in some cases the most important features of the presented reduction methodologies from an industrial point of view. ■ CONTENTSAuthor Information 444 Corresponding Authors 444 Notes 444 Acknowledgments 444 References 444

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Section: Metal Dissolving Reductionsmentioning

confidence: 99%

Recent Developments in the Reduction of Aromatic and Aliphatic Nitro Compounds to Amines

Orlandi

Brenna

Harms³

et al. 2016

Org. Process Res. Dev.

324

195

View full text Add to dashboard Cite

show abstract

“…Quinoline | 639 ROMERO Et al. alkaloids derived from plants, animals, and micro-organisms have showed remarkable antitumor activity against different cancer cells (Jain, Chandra, Jain, Pathak, & Vaidya, 2016). Also, several examples of synthetic quinolines have been reported by multiple research groups worldwide as promising anticancer agents (Beauchard et al, 2009;Czoch, Pognan, Kaczmarek, & Boraty, 1994;Ferlin, Gatto, Chiarelotto, & Palumbo, 2001;Gamal, Khan, Maksoud, El-Din, & Oh, 2014;Heiniger, Gakhar, Prasain, Hua, & Nguyen, 2010;Kim et al, 2001;Martirosyan, Rahim-Bata, Freeman, Clarke, & Howard, 2004;Perzyna et al, 2002;Tseng, Chen, Lu, Yang, & Tzeng, 2008;Tseng et al, 2009Tseng et al, , 2010Utsugi et al, 1997). In particular, compounds based on 4-aminoquinolines have received largely attention by its significant anticancer activity (Chen, Chen, Wang, Han, & Tzeng, 2005;Chen, Chung, Chen, Chen, & Jeng, 2002;Chen et al, 2006Chen et al, , 2011Kakadiya et al, 2010;Lee et al, 2004;Lu et al, 2010;Mejía et al, 2009;Sanchez et al, 2011;Su et al, 1995;Via, Gia, Gasparotto, & Ferlin, 2008).…”

Section: Introductionmentioning

confidence: 99%

“…Specifically, antimalarial drugs such as chloroquine, hidroxychloroquine, mefloquine, quinine, and quinacrine have demonstrated an appreciable antiproliferative effect against different cancer cells, exhibiting sub-micromolar IC 50 values (Choi, Kim, Woo, Kim, & Yoon, 2016;Grimaldi et al, 2015;Maes, Kuchnio, Carmeliet, & Agostinis, 2016;Preet et al, 2012;Salentin et al, 2017;Verbaanderd et al, 2017;Yan et al, 2013). In general, most of the anticancer quinolines are targeted to tyrosine kinase enzymes, proteasome, tubuline polymerization, topoisomerase, or DNA repair (Beauchard et al, 2009;Czoch et al, 1994;Ferlin et al, 2001;Gamal et al, 2014;Heiniger et al, 2010;Kim et al, 2001;Martirosyan et al, 2004;Perzyna et al, 2002;Tseng et al, 2008Tseng et al, , 2009Tseng et al, , 2010Utsugi et al, 1997). Modulation of the large-conductance calcium-activated potassium (BK) channels also has been identified as target for 4-substituted quinolines and 4-substituted quinolin-2-ones, representing an attractive target for the 4-aminoquinolines tested in this investigation (Dinsmore & Bergman, 2003;Hewawasam, Sit, & Starrett, 2003;Hewawasam, Starrett, & Swartz, 1997;Kang et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

Identification of dehydroxy isoquine and isotebuquine as promising anticancer agents targeting K+ channel

et al. 2019

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Traditional antimalarial drugs based on 4‐aminoquinolines have exhibited good antiproliferative activities against human tumor cells; however, their low relative efficacy has limited their corresponding clinical uses. In order to identify new potent anticancer agents based on 4‐aminoquinoline, we evaluated the antiproliferative activity of a series of dehydroxy isoquines and isotebuquines against five human cancer lines. HeLa and SKBr3 were significantly more sensitive to the action of tested quinolines than the A549, MCF‐7, and PC‐3 cancer lines. Compound 2h was by far the most potent derivative against four of the tested lines (except to PC3 line), exhibiting low micromolar or nanomolar IC50 values superior to adriamycin reference, low toxicities on dermis human fibroblasts (LD50 > 250 μM), and excellent selectivity indexes against the mentioned cancer cells. A structure–activity relationship analysis put in evidence that a pyrrolidine or morpholine moiety as N‐alkyl terminal substitution and the incorporation of the extra phenyl attached to aniline ring are pharmacophore essentials for improvement the anticancer activity of the studied dehydroxy isoquines and isotebuquines. From the results, compound 2h emerged as a promising anticancer candidate for further in vitro assays against resistant‐strain and in vivo studies as well as pharmacokinetic and genotoxicity studies. Mechanistic assays suggested that the most active quinoline 2h act as calcium‐activated potassium channel activator.

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“…Subsequent investigation and modification of CPT brought fruits with two antitumor agents approved by the FDA: topotecan for small-cell lung cancer and irinotecan for refractory colorectum cancer . Further study showed that the ABCD rings of CPT function as the pharmacophore responsible for binding to DNA . Thus, developing practical and efficient strategies for acquiring different substituted indolizino[1,2- b ]quinolin-9(11 H )-ones has great significance to improve the clinical application of the camptothecin family.…”

Section: Introductionmentioning

confidence: 99%

Visible-Light-Induced Radical Cascade Cyclization: Synthesis of the ABCD Ring Cores of Camptothecins

et al. 2018

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A new strategy for constructing indolizino[1,2-b]quinolin-9(11H)-ones (ring cores of camptothecins) from readily available isocyanoarenes and N-(alkyl-2-yn-1-yl)pyridin-2(1H)-ones has been developed through a visible-light-induced radical cascade cyclization process. The reaction proceeds under mild conditions with fair to excellent yields. The easy introduction of substituents for both reactants and the broad functional group tolerance of the reaction make it a straightforward route to the cores of the marketed camptothecins and their derivatives.

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Formaldehyde-Induced DNA Cross-Link of Indolizino[1,2-b]quinolines Derived from the A−D Rings of Camptothecin

Cited by 20 publications

References 19 publications

Recent Developments in the Reduction of Aromatic and Aliphatic Nitro Compounds to Amines

Recent Developments in the Reduction of Aromatic and Aliphatic Nitro Compounds to Amines

Identification of dehydroxy isoquine and isotebuquine as promising anticancer agents targeting K+ channel

Visible-Light-Induced Radical Cascade Cyclization: Synthesis of the ABCD Ring Cores of Camptothecins

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